Full Disclosure: I built HealthScout, an app to help patients navigate our complex healthcare system.

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"Are you still on Vicodin?" asks an intake nurse for the umpteenth time. No, I’m not “on” Vicodin. It was prescribed after my gallbladder was removed in 2005. Why are they still asking about it 20 years later, and what does it mean for health AI?

Wrong Records Produce Wrong Answers

The healthcare industry has been working for decades on something called “the longitudinal record,” an initiative to provide access to all your health records from all your providers to you, the patient and (with your permission) your doctors. Real progress has been made, but what I found developing HealthScout is that most people’s health records are a mess: medications never marked as inactive, diagnoses that are now resolved, and typos. At some point someone typed in Rosuvastatin 5mg when in fact I’m on 40mg.

If you feed wrong information into an AI, it’s going to try to make the best sense of the information it has. So when I ask it for the history of my cholesterol numbers as compared to my statin medications, it struggles to make sense of a sudden “drop” in Rosuvastatin dosage.

Is that the AI hallucinating or just bad data?

What If You Could Just Fix the Record Yourself?

So HealthScout includes a feature called “My Added Records” that enables you to correct your health record. Now you can note when you stopped a medication or mark when a condition was resolved. Your correction takes priority over the healthcare provider records, so every answer HealthScout gives from that point forward reflects what’s true about your health today, not what was documented years ago.

No Health App Covers Every Provider. HealthScout Fixed That.

I have six healthcare providers. One of them, a specialist I see regularly, isn’t in the Apple Health network. For most health apps, that provider doesn’t exist.

This isn’t unusual. Smaller practices, independent specialists, and physical therapists often don’t participate in electronic health record networks. If any one of your providers falls into that category, a significant piece of your health story is missing.

With My Added Records, you can close that gap yourself. Securely upload whatever that provider has given you: a lab result they emailed, clinical notes from your visit, or an imaging report that came in the mail. You can even photograph a printed document or take a picture of a report on your computer screen. HealthScout reads it, incorporates it, and treats it the same as anything pulled from a connected provider.

The Stuff That Never Made It Into Any Record

Even if your healthcare provider records were complete and accurate, they would still be missing information never reported to your doctor.

Think about the last year. When did you come down with that terrible flu, January or February? When did you start taking fish oil supplements?

All those notes could be important, but none are documented in any medical record. They felt too minor to bring up to your doctor. Yet undocumented information like this can be critical if something serious pops up later.

Your doctors make decisions about your health based on the information they have. They take laborious histories to try and catch everything, but they can’t. Without a complete picture, medical professionals can’t make the best decisions. And if you ask an AI to analyze your incomplete records, it will miss things too.

But you know all of it. You lived it.

My Added Records is how you give that context to the AI. Log the gastrointestinal issue you had, your new supplements, or the exercise routine you started.

Every one of those entries becomes part of the picture HealthScout uses when you ask questions.

Patients Should Control Their Health Records

The healthcare industry is working on the serious problem of getting health records to move between systems. But if the original records are out-of-date or just plain wrong, then all these systems are synchronizing inaccurate records.

HealthScout is the only place where you can manage one complete health record that you own. And who cares more about your health than you?

HealthScout is available now on the App Store. No email required, no account. Start with one record to see how it works, or securely link your healthcare providers to get a complete picture.

Download HealthScout Free

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Full Disclosure: I built HealthScout, an app to help patients navigate our complex healthcare system.

I was reading OpenAI’s Health Privacy Notice to find out if a court ordered OpenAI to hand over user health data, could they comply? If they could, that would confirm health data is technically accessible to employees.

I never got to that question. Something stopped me on the way there.

The ChatGPT Health launch page says:

“Conversations in Health are not used to train our foundation models.”

But the actual legal document, the Health Privacy Notice, reads:

“By default, we do not use data in Health content to improve our foundational models.”

Then again, a few paragraphs later: “By default, we do not use content in Health to improve our foundational models.”

“By Default” = There’s a Hole in their Privacy Architecture

Saying “Conversations in Health are not used to train our foundation models” is a commitment. “By default, we do not use content in Health” is a policy, one that can be changed. Policies get updated all the time, often announced with an email that no one will read.

The difference between we don’t do this and we haven’t chosen to do this yet is everything when the data involved is your mental health history, your ED meds, or your colonoscopy results.

The privacy notice also confirms that even under current policy, “a limited number of authorized OpenAI personnel and trusted service providers might access Health content to improve model safety.”

This means people can reach ChatGPT Health data, already.

Therefore, using your data for training is not the only privacy risk. If employees can reach your health data, so can someone who phishes their way in, or an insider who decides their access is worth selling. And of course, the answer to my original question about a court order? Yes, OpenAI would be legally compelled to comply and share your health records.

Good Intentions Don’t Protect Your Data

To be fair, I think OpenAI is genuinely trying to build something useful. ChatGPT Health looks impressive, and the intent seems real.

But intentions don’t protect your data. Architecture does.

The difference is between “we’ve decided not to look at your data” and “we've built a system where we have nothing to hand over.” It’s privacy by policy versus privacy by design.

When we built HealthScout, we made privacy by design an architectural choice from day one, knowing it would constrain the business in some ways. HealthScout stores your health data encrypted using Apple’s highest-level encryption standard, Advanced Data Protection (ADP) Complete, where the keys are locked on your device behind hardware-based Face ID or Touch ID encryption. Apple doesn’t even have them.

In fact, the UK government demanded Apple create a backdoor to this data, and Apple’s response was to pull the feature from the UK entirely rather than comply. That’s the standard HealthScout is built on.

When you ask a question on HealthScout, a portion of your health data is encrypted, transmitted to our AI partners and deleted. Our AI partners are contractually prohibited from using any content from those queries. That’s a legal obligation between two companies that can be enforced in a court of law versus a policy that can flip with a privacy update email to unsuspecting users.

HealthScout also does not collect personally identifying information (PII). No email collection. No account creation. We can’t identify our users even if we wanted to. If HealthScout ever received a court order demanding user health data, we’d have no ability to hand anything over because we don’t have it.

Before you connect your medical records to any AI system, it’s worth asking one question: is this company choosing not to use my data, or have they built a system where they simply don’t have it?

One of those is a promise. The other is a fact.

If you want AI that protects your health records and doesn’t watch what you ask, HealthScout is on the App Store now. No email. No account. We can’t see what you ask.

Download it free.

Full Disclosure: I built HealthScout, an app to help patients navigate our complex healthcare system.

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In an Oxford AI health study, only 35% of the people asking health questions got the right answer. Not great.

In the same study, when the AI model was given clean, structured cases, it scored 95%. The main difference was context.

Much of the press generated from the study took the angle that AI doesn’t work for health. But that 60-point accuracy drop wasn’t because the AI didn’t work. The AI models were identical.

What changed was what the AI had to work with. Researchers gave the AI complete, organized information. Real patients couldn’t do that. They didn’t know what was relevant, and they didn’t have their health records handy.

My Labs Looked Normal. They Weren’t.

I saw the Oxford study's findings about health context play out in my own life before the study was even published.

During an annual physical, I complained to my doctor about my “old man pains” (knee, back, shoulder) that increasingly affected my ability to be active. The doctor recommended I try an over-the-counter NSAID (non-steroidal anti-inflammatory drug) called naproxen.

It was magical. After a few days taking it twice a day (as he suggested), I felt amazing. It worked so well that I eventually switched to a prescription NSAID called celecoxib, which studies show is easier on the stomach. I thought I'd done my homework.

A year later, at my next wellness check, my eGFR came back at 69.

My doctor scanned the results, saw nothing flagged as “High,” and moved on. I did too. With 30 minutes for a wellness check, you cover a lot of ground quickly.

Four months later, I started building HealthScout. My own health records were the only data I had to test with. As soon as a working version was running, I started asking it questions. One of my early test questions was:

“Do you see any trends that show a relationship between my medications and my lab results?”

To my surprise, HealthScout suggested that my “recent kidney function decline” could have something to do with my regular use of NSAIDs.

What recent kidney function decline? I had no idea what it was talking about.

As it turns out, my primary care doctor only had records from One Medical. HealthScout had records from three providers spanning over a decade.

With that full history, it could see that my steady-state eGFR was around 90. A drop to 69 in seven months isn’t “low-normal.” It’s a 30% decline, which with full context is at least a yellow flag. HealthScout also knew that while most primary care physicians use the standard eGFR threshold of 60 as the cutoff for concern, nephrologists use a more granular classification system where 69 is already approaching moderate kidney disease.

No single provider would have seen any of this. Each one only had their own slice of my history.

My eGFR dropped all the way to 50 on my next test, low enough that I was diagnosed with Chronic Kidney Disease Stage 3a. A biopsy confirmed the finding: the NSAIDs had caused the decline. The good news: I’m off them now, and my kidneys are slowly recovering.

The Context Gap Is Structural

My doctor is a good guy who was put into a difficult situation — not enough data and not enough time. The Oxford study confirmed what I experienced firsthand: more context produced better answers. Less of it produced dangerous ones.

HealthScout connects to over 10,000 healthcare systems through Apple Health, including Labcorp and Quest Diagnostics, where most Americans get their blood drawn. It also accepts uploaded documents: photos of lab printouts, PDFs of clinical notes, or even pictures of reports snapped from your computer screen. The AI works from your complete history, across providers, going back as far as your records exist.

Your actual health history exists. It's just in multiple systems that don't talk to each other. Do yourself a favor and put it all in one place.

HealthScout is available now on the App Store. No email required, no account needed. Connect your providers, upload a record, and ask your first question in under a minute.

Download HealthScout Free

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Full Disclosure: I built HealthScout, an app to help patients navigate our complex healthcare system.

I typed the same question into two AI apps: “I woke up with a headache. What should I do?”

ChatGPT went straight to a comprehensive six-step response. Drink water. Eat something light. Take a pain reliever. Stretch your neck. Get some fresh air. Try coffee.

HealthScout presented nine numbered scenarios and asked me to pick the ones that fit.

ChatGPT Suggested Taking a Drug That Would Hurt Me

ChatGPT’s third recommendation, right under “Take a Pain Reliever (if needed),” is ibuprofen.

I have chronic kidney disease. Ibuprofen accelerates kidney damage. It’s one of the first things a nephrologist tells you to avoid.

ChatGPT didn’t know I had CKD. It didn’t ask. So it handed me advice a doctor familiar with my history would never give.

This isn’t rare. The person asking about a headache might be on blood thinners, might be pregnant, or might be taking a medication that interacts badly with what’s being recommended. Generic AI can’t know any of that, because it doesn’t ask, and it doesn’t have your records.

What HealthScout Did Instead

Before answering anything, HealthScout gave me nine numbered scenarios and asked me to pick the ones that fit.

Each option covered a different angle: severity, context, medication status, specific health concern. I typed “1 and 8”, and it had what it needed.

Look at what option 8 actually said: “I’m concerned about what pain relief I can take because of my chronic kidney disease.”

HealthScout already knew I had CKD. It surfaced that scenario specifically because it was in my records. I didn’t explain my history. I just confirmed it.

Why Numbered Options Matter

Describing your headache in words takes effort, and most people don’t do it well. You leave things out. You don’t know what’s relevant.

Numbered scenarios covering distinct angles are faster and more accurate. You pick one or several, and the app has what it needs to give you something useful.

ChatGPT does eventually ask for clarification. If you scroll past the six steps, past the warning signs, past the “quick routine,” there’s a section at the very bottom: “if you want, tell me where the headache is and how strong it is.”

After the laundry list of advice. After the ibuprofen recommendation.

Then HealthScout Answered About Me

Once I replied with “1 and 8,” HealthScout pulled from what it already knew: my CKD diagnosis, my current medications, and my history. The response was about my headache, filtered through my health picture.

For a lot of questions, a wall of text is exactly what you want. For research or planning questions, a broad answer is fine. For health questions, it isn’t.

That’s what purpose-built means in practice. A system designed to understand your situation before drawing a conclusion, because the right answer for most people may be the wrong answer for you.

HealthScout is available now on the App Store. No email required, no account. Upload one record and ask your first question in under a minute.

Download HealthScout Free

Subscribe now

Full Disclosure: I built HealthScout, an app to help patients navigate our complex healthcare system.

The most common thing I hear when I tell people about HealthScout is some version of: “Why can’t I just paste my lab results into ChatGPT and get the same thing?”

It’s a fair question. ChatGPT is free, it’s fast, and if you paste in a PDF of your blood work, it will give you a detailed interpretation that sounds authoritative. For a single set of lab results, it might even be useful.

But the approach has a problem most people don’t think about: you’re deciding what’s relevant before you know the answer. You’re “pre-filtering” what the AI sees.

When you paste a lab result into ChatGPT, you’ve already made a choice. You included your CBC but not your metabolic panel from three months ago. You pasted today’s results but not last year’s, so there’s no trend to analyze. You mentioned your current medication but forgot the one you stopped in January.

A doctor reviewing your chart doesn’t ask you to decide which pages matter. They look at everything and make connections you wouldn’t think to flag.

That’s exactly what gets lost in the paste-it-in approach. You can’t include everything that’s relevant because you simply can’t know. How would you know the pattern between a medication one doctor prescribed and a lab result another doctor ordered? How might you know about a slow trend across years of results from two different providers?

ChatGPT’s memory feature might recall that you mentioned a kidney problem last month. But it won’t maintain your actual eGFR values, medication dosages, or lab trends over time. Remembering fragments from past conversations isn’t the same as holding your health record.

The pre-filtering problem is just one reason generic AI falls short for personal health questions. I spent over a year building HealthScout, an app designed specifically for this job, and in the process I found five more reasons using generic AI is unsafe for personal health.

Each one matters more than you’d expect.

1. Generic AI Recommended a Drug I Can’t Take.

I typed “I woke up with a headache. What should I do?” into both ChatGPT and HealthScout.

ChatGPT gave me six steps immediately. Drink water, eat something, take ibuprofen, stretch, get fresh air, try coffee. Confident and organized. Looks like good advice.

HealthScout didn’t answer. Instead it presented eight numbered scenarios that narrowed down the possible root causes of my headache before giving any information. All I had to do was type in the numbers that matched my situation to get to a relevant answer tailored to my specific health context.

That difference matters more than it seems.

ChatGPT’s third recommendation was ibuprofen. I have chronic kidney disease. Taking ibuprofen would accelerate damage to my kidneys. ChatGPT didn’t know that, because it didn’t ask.

The full article details why the difference between a purpose-built health AI and a generic AI is the difference between helpful advice and a recommendation your doctor would immediately shut down.

Full article coming March 24: Generic AI Recommended a Drug I Can’t Take

2. AI Without Your Health History Is Guessing

Forty percent of American adults have used AI for health questions. Most of them type something into a blank text box with zero context about who they are.

Think about that from the AI’s perspective. It has no idea whether you’re pregnant, whether you’re on blood thinners, whether you have a family history of heart disease, or whether the medication it’s about to recommend interacts with something you already take. It answers anyway, because that’s what it’s designed to do.

A good answer for most people can be a dangerous answer for you. The gap between generic advice and personalized guidance is where people get hurt, and that gap only closes when the AI actually knows your health history.

The full article walks through what a generic AI answer looks like versus one grounded in your actual health history, and why the difference between a generic answer and a personal one can change what you do next.

Full article coming March 31: AI Without Your Health History Is Guessing

3. ChatGPT Health Watches. OpenAI’s Fine Print Explains How.

When OpenAI launched ChatGPT Health, they made a big deal about privacy. Their launch page says conversations in Health are not used to train their models. Full stop.

Their actual legal document, the Health Privacy Notice, says something different. It uses the phrase “by default” twice. The difference between “we don’t do this” and “by default, we haven’t chosen to do this” is everything when the data involved is your mental health history, your fertility records, or your STD results.

And here’s a question worth sitting with: how did OpenAI know that 40 million people use ChatGPT for health questions every day? OpenAI looked inside those conversations and categorized them. They’re watching.

The full article breaks down exactly what OpenAI’s privacy policy does and doesn’t promise, and what to look for before you paste your lab results into any AI.

Full article coming April 7: ChatGPT Health Watches. OpenAI’s Fine Print Explains How.

4. Your Health Records Are Wrong

Government officials, academics, and health professionals have been talking about a unified health record for decades. They haven’t built one. If you want to transfer your records to a new doctor in 2026, they’ll most likely be faxed. And faxed records will most likely sit in a file folder somewhere, much less easy for your doctor to access than your records stored in their digital system.

Combining all your records from different providers and giving your doctor access would clearly make their care more effective. But there’s a deeper problem. Even if your records were all in one place, they’d still be wrong. Prescriptions show start dates but not stop dates. Resolved conditions stay listed as current problems. Records accumulate, but they rarely get cleaned up.

Wrong records produce wrong answers, whether the one reading them is a doctor or an AI. The patient is the only person who knows what’s actually true across their full health picture.

The full article shows how you can build the complete health record that no hospital, government agency, or tech company has been able to create.

Full article coming April 14: Your Health Records Are Wrong

5. AI Answers What You Ask. That’s the Problem.

Every year, roughly a million new peer-reviewed medical research articles are published. No doctor can track every development across every condition. While generic AI can process it all, it can’t connect any of it to you, because in order to pull out that relevant information, you have to know what to ask.

I have knee osteoarthritis. I’d done the research, found a specialist, and thought I knew all the treatment options available to me. I was wrong. There were treatments with real research behind them that I’d never heard of, because I hadn’t known to look for them.

The full article covers how HealthScout found treatments for my condition that my own specialist hadn’t heard of, and why an AI that only answers what you ask will never give you the full picture.

Full article coming April 28: AI Answers What You Ask. That’s the Problem.

The Common Thread

Each of these problems traces back to the same root cause: generic AI was not designed for health. The same system that writes marketing copy and debugs code is fielding questions about chest pain and drug interactions. A blank text box that handles everything handles nothing particularly well when the stakes are personal.

After building just the scaffolding of HealthScout, the app found a 30% decline in my kidney function that my doctor had missed because each individual lab value still fell within the “normal” range. The trend only became visible when AI could see across all my providers, over time.

That’s what purpose-built means in practice — a system designed from the ground up to understand your situation before drawing a conclusion.

HealthScout is available now on the App Store. No email required, no account. Upload one record and ask your first question in under a minute.

Download HealthScout Free

Diana* had been healthy her entire life. Then, in the span of just a few months, she found herself juggling appointments between her primary care physician and two specialists: a neurologist and a cardiologist.

“All of a sudden, having a neurologist and a cardiologist, it was just crazy to me,” Diana told me. “I don’t really know how to interact with them.”

It started with mysterious fainting episodes — first on a plane, then at a restaurant where she collapsed and vomited in front of other diners. What followed was the medical equivalent of a relay race where no one passed the baton.

The Specialist Shuffle Begins

Her cardiologist discovered SVT (a heart rhythm disorder) and possibly atrial fibrillation — conditions requiring treatment — but saw nothing that explained the fainting. Then she found that getting a neurology appointment with insurance would take nine months. So Diana searched outside her network and finally found a neurologist who would take her sooner.

The neurologist ordered comprehensive testing in an attempt to understand the fainting, including brain scans. The results came back quickly — weeks before her follow-up appointments. So Diana had the data but couldn’t understand it. Most patients would have just waited anxiously. But Diana realized the results were already synchronized with HealthScout.

Armed with Information

“I asked HealthScout: What does it make of these recent tests and what should I ask about when I meet my doctors,” Diana explained. “And it gave me this really fabulous writeup, by doctor practice, including what I should be discussing with each.”

HealthScout didn’t just analyze her test results — it helped her document symptoms she’d been dismissing as normal aging: chronic nasal problems, occasional unsteady steps, sleep issues, fatigue. Then it organized everything by specialist, creating targeted question lists for her neurologist, cardiologist, and general practitioner.

“Before HealthScout, I would have only been able to listen to what each specialist told me, and been overwhelmed with just understanding all the information,” Diana told me. “Then afterwards, I would think of questions I should have asked. That would take yet more doctor’s visits, weeks out.”

This systematic preparation transformed her from a passive patient, hoping doctors would figure things out, into an informed advocate for her own care.

The Professional Patient Advocate Problem

Diana’s experience highlighted something many patients don’t realize exists: professional patient advocates.

“People with grave conditions can hire someone at the hospital or a medical consultant to guide them every step of the way to simply remember what the doctor said and to make sure all the important questions get asked,” she observed.

But these advocates are expensive and rare. “I don’t have such a person.”

HealthScout filled that gap. It became her patient advocate — organizing information, suggesting questions, helping her remember what to discuss with each specialist.

The Results

Diana’s preparation paid off across all her appointments:

The neurologist delivered mostly good news: No predictive markers for Alzheimer’s — Diana’s biggest fear. And her brain volume ranked in the 90th percentile for women her age. “I am an overachiever, as I like to be, and that made me tremendously happy.”

However, the scans revealed white spots on her brain that shouldn’t be there, potentially related to sleep issues. This led to a home sleep study to investigate sleep apnea as a possible cause.

The cardiologist confirmed her heart condition wasn’t related to the neurological findings, and prescribed new medication to help manage it.

Her general practitioner addressed her chronic sinus problems — something Diana had never realized was worth mentioning. “I can actually, at the moment, breathe better than I have in a long time. I just didn’t know what normal breathing should feel like.”

The Bigger Picture

Diana hasn’t had a fainting spell since starting this chapter in her medical journey, and the cause of the fainting still hasn’t been 100% diagnosed. But Diana’s story isn’t about finding a hidden diagnosis or catching medical errors. It’s about successfully navigating an increasingly complex healthcare system when you’re not equipped for the journey.

“HealthScout just really helped me keep it all organized. It was just so overwhelming between cardiologist, neurologist, and the general practitioner. And because I was so tired all the time, I know I wouldn’t have asked all my questions.”

The transformation was remarkable. Instead of feeling lost in the medical system, Diana became an active participant in her care.

“I am just eternally grateful for HealthScout, just in time for my aging process,” she said.

The Patient Advocate We All Need

Diana’s experience reveals a fundamental truth: as we age and our healthcare becomes more complex, we all need patient advocates. But professional advocates are expensive and scarce.

HealthScout democratizes patient advocacy, giving everyone access to the kind of systematic preparation and organization that only the most resourced patients typically receive. In a system where specialists don’t coordinate, Diana became the one passing the baton between her disconnected doctors — and HealthScout gave her the confidence to do it effectively.

“It felt like having someone on my side,” Diana reflected. “HealthScout helped me feel so much more in control. I don’t mean in control of what the doctor does because in the end, the doctor should be in control of what they’re prescribing or telling me to do. But I felt in control of knowing what I should hear about and what questions I wanted to ask.”

That’s the power of having a patient advocate in your pocket — not to replace your doctors, but to help you get the most out of every appointment.

*Diana’s name has been changed to protect her privacy, but her story, quotes, and medical details are real.

HealthScout is an educational tool only and does not provide medical advice, diagnosis, or treatment. Always consult with qualified healthcare professionals for medical decisions.

Feeling overwhelmed by your healthcare journey? Get the patient advocate we all need, right in your pocket. Download HealthScout free in the App Store.

More stories of how HealthScout helped people with their healthcare

"You have two main options," the specialist explained matter-of-factly. "Fosamax, which is a weekly pill, or Reclast, an annual IV infusion. Both are effective treatments."

Then came the part that left Maya feeling adrift: "I'll let you decide which one you prefer."

No recommendation. No guidance about which might work better for her specific situation. Just two options and a decision that felt too important to make without more information.

The Friendship Network Investigation

What do you do when your doctor won't make a recommendation? Maya did what many of us do — she crowdsourced the decision.

"I wrote to my network of girlfriends, accumulating several dozen stories of what others had experienced," Maya told me. For weeks, she collected testimonials, experiences, and opinions from friends who had faced similar choices.

The pattern that emerged was telling. Several friends mentioned they had tried Fosamax but experienced stomach problems that forced them to switch treatments. These stories resonated with Maya — she remembered having gastrointestinal issues with other oral medications in the past, though they seemed minor and distant.

Based on these friendship consultations, Maya concluded that Reclast would be the safer choice. She could avoid the potential stomach issues that had plagued her friends and that she vaguely remembered experiencing herself.

It was solid reasoning, but it had taken weeks of research and dozens of conversations to reach that conclusion.

The Instant Answer

Then Maya got access to HealthScout during our beta testing phase.

Curious to validate her weeks of research, she asked a simple question: "Should I take Fosamax or Reclast to treat my osteoporosis?"

HealthScout's response was immediate and definitive: Given her documented history of GI problems with oral medications, Reclast would indeed be the better choice.

"HealthScout arrived at an answer within seconds that I had taken weeks to research," Maya marveled.

What Her Doctor Didn’t Consider

The key difference? HealthScout had access to Maya's complete medical history, including those "minor" GI issues from years past that her endocrinologist had never connected to her current treatment decision.

"My endocrinologist had not picked up this issue as it was minor and very far in my past," Maya explained. To be fair to the specialist, those old medication intolerances were buried somewhere in Maya's long medical history, and the endocrinologist was focused on treating osteoporosis, not excavating every past drug reaction.

But HealthScout could see the pattern instantly. It knew that patients with a history of GI problems with oral medications are better candidates for IV therapies when both options are clinically equivalent.

The Information Gap

Maya's experience highlights a crucial gap in how medical decisions get made. Her endocrinologist was perfectly qualified to treat osteoporosis and offered two excellent treatment options. But without the time or tools to synthesize Maya's complete medical history, the specialist couldn't provide the personalized guidance Maya needed.

This left Maya to conduct her own research through friendship networks — a common but inefficient approach many patients resort to when faced with medical decisions.

The Validation

But the real value wasn't just speed — it was confidence. Instead of relying on friends' anecdotal experiences, Maya now had an evidence-based recommendation rooted in her own medical history.

She could approach her next appointment knowing she had made the right choice for her specific situation, armed with the medical reasoning she needed to discuss with her endocrinologist.

The Bigger Picture

Maya's story illustrates how much medical decision-making happens in the gaps of our healthcare system. Specialists focus on their area of expertise but may not have the time or comprehensive view needed for fully personalized recommendations.

Patients are left to navigate complex treatment decisions with incomplete information, often turning to friends, family, or "Dr. Google" for guidance that may or may not apply to their specific medical situation.

HealthScout bridges this gap by giving patients access to their complete health story, enabling informed medical decisions based on their unique history rather than generic advice or anecdotal experiences.

What medical decisions might you be facing that could benefit from seeing your complete health picture?

Update September 17, 2025

HealthScout is now out of beta and available for iOS users in the US. Download it today to see what critical information your health records hold.

*Maya's name has been changed to protect her privacy, but her story, quotes, and medical details are real.

HealthScout is an educational tool only and does not provide medical advice, diagnosis, or treatment. Always consult with qualified healthcare professionals for medical decisions.

Mark* had been taking a statin for years when comprehensive blood testing revealed something his primary care doctor had never checked for: elevated Lp(a).

"I'd never even heard of it," Mark told me. "Turns out 10-15% of people have high Lp(a), but most doctors don't routinely test for it. This was my first time."

Lp(a) is a particularly dangerous marker for heart events that's almost entirely genetic. Unlike regular cholesterol that responds to diet and exercise, you're essentially stuck with whatever Lp(a) level you inherited. High levels dramatically increase cardiovascular risk, yet many physicians don’t regularly screen for it.

Mark's primary care doctor had never tested for Lp(a) and had never mentioned it, despite Mark having other cholesterol markers.

But the elevated Lp(a) meant Mark was at higher cardiovascular risk than anyone realized.

What His Doctor Missed

When Mark asked the HealthScout beta about his Lp(a) results, it recognized he was already on a statin, and then flagged something his doctor hadn't mentioned: Ezetimibe.

Mark: "HealthScout told me about this daily medication that works alongside statins to help lower LDL and ApoB levels — and might even help with Lp(a) marginally. I'd never heard of Ezetimibe before. I still can't pronounce it."

“HealthScout caught something that was right there in my results, but that neither my doctor nor I had noticed.”

HealthScout knew about research on treatment combinations for this specific risk factor, specifically studies on using Ezetimibe alongside statins for people with elevated Lp(a). While his primary care doctor focused only on the standard cholesterol markers that looked acceptable, HealthScout knew about treatment combinations and newer research protocols for this specific risk factor.

Mark: "The crazy thing is, when I looked back at my blood test interpretation, there was actually a reference to Ezetimibe buried in the fine print. HealthScout caught something that was right there in my results, but that neither my doctor nor I had noticed."

Armed with Information

When Mark brought HealthScout's findings to his doctor, everything changed. His physician looked at the evidence, agreed that Ezetimibe could help reduce Mark's cardiovascular risk, and prescribed it immediately.

"Go HealthScout!" Mark texted me after starting the medication. "Worth every penny of my subscription!"

Mark's experience demonstrates exactly how HealthScout is designed to work — not by replacing doctors, but by empowering patients with informed questions. His primary care doctor had the knowledge and willingness to prescribe combination therapy; he just hadn't initially considered this newer approach for Mark's specific risk profile.

The Bigger Picture

Mark's story reveals how much medical information can slip through the cracks of our healthcare system. His comprehensive blood panel contained the exact information needed to guide treatment decisions, but crucial details were buried in fine print that neither patient nor doctor initially caught.

This happens constantly in medicine. Test results arrive with pages of data, appointment times are limited, and doctors must process information for dozens of patients daily. Important treatment options — especially newer combination therapies — can easily be overlooked.

That's where HealthScout provides unique value. It has infinite patience to review every detail of your health records, cross-reference findings with current research, and may uncover treatment options to discuss with your doctor.

Update September 17, 2025

HealthScout is now out of beta and available for iOS users in the US. Download it today to see what treatment options might be hiding in your health records.

*Mark's name has been changed to protect his privacy, but his story, quotes, and medical details are real.

HealthScout is an educational tool only and does not provide medical advice, diagnosis, or treatment. Always consult with qualified healthcare professionals for medical decisions.

Lilo1 had always been fit, lean, and strong. She could eat whatever she wanted and maintain her athletic lifestyle without much thought. Then 2020 arrived, and everything changed.

It started with her clothes not fitting. Her middle was expanding despite her best efforts with diet and exercise. "It's menopause," her ob-gyn explained when she brought up the weight gain. "Middle section fat is part of the deal."

Then came the digestive issues — constant bloating and diarrhea that made her athletic activities uncomfortable. Her ob-gyn suggested this might be another menopause side effect.

But the problems kept multiplying.

The Specialist Shuffle

Her blood work started showing high cholesterol and concerning liver enzyme readings. Her primary care doctor did what primary care doctors do when faced with complex, interconnected symptoms: she referred Lilo to specialists.

Over the next five years, Lilo found herself in a medical pinball machine. GI specialist for the digestive issues. Liver specialist for the enzymes. Neurology for some symptoms. Sleep specialist for others. When she needed knee surgery for a torn meniscus, a hematologist had to clear her first due to her history of blood clots twenty years apart.

The hematologist found more concerning blood readings and sent her back to the GI and liver specialists for additional tests, then on to a vascular surgeon to investigate her clotting history. The vascular surgeon diagnosed thoracic outlet syndrome and recommended removing her top rib bone.

She had both surgeries - the knee and the rib removal - and recovered fully. But five years later, she was still dealing with the same core issues: unexplained weight gain, persistent bloating and diarrhea, high cholesterol, and elevated liver enzymes.

What Each Doctor Saw

Each specialist looked through their particular lens:

• The ob-gyn saw menopause

• The GI specialist saw digestive symptoms

• The liver specialist saw enzyme readings

• The hematologist saw clotting risk

• The vascular surgeon saw structural issues

Each treated their piece of the puzzle. None looked at the whole picture.

"The maddening part is that no doctor is looking at all of this holistically for me," Lilo told me. Her primary care doctor suggested a statin for the cholesterol but was nearly impossible to reach for follow-up appointments.

What HealthScout Saw

When Lilo got access to HealthScout during our beta test, she asked it to look at her complete health history across all these providers and symptoms.

HealthScout immediately flagged something none of her specialists had mentioned: her history of PCOS (polycystic ovary syndrome).

The AI pointed out that PCOS could be contributing to multiple issues her doctors were treating separately — the stubborn weight gain, the persistent bloating, and possibly even the liver enzyme readings. These weren't separate problems requiring separate specialists; they were potentially connected manifestations of an underlying condition.

HealthScout also analyzed her expensive cardiac CT scan results alongside her other tests and suggested she likely didn't need the statin her primary care doctor recommended. The imaging showed her actual cardiovascular risk might be lower than her cholesterol numbers suggested.

The Power of the Complete Picture

What made the difference? HealthScout had access to Lilo's complete health story, across providers, across years, across specialties. It could see patterns that individual doctors, each focused on their area of expertise and limited by 15-minute appointment slots, simply couldn't detect.

More importantly, it translated these connections into informed questions Lilo could bring back to her doctors. Instead of passively receiving fragmented care, she could now drive the conversation.

"All of the interaction with HealthScout has provided me with more informed questions I can ask my doctors and drive my care proactively," she explained.

The Broader Problem

Lilo's story illustrates a fundamental flaw in our healthcare system. It’s become so specialized that it has lost the ability to see patients as whole human beings with interconnected systems.

The irony is that Lilo had excellent medical care. She saw skilled specialists at reputable institutions. She received appropriate treatment for each individual issue. But no one was connecting the dots.

This isn't a failure of individual doctors. It's a systemic problem. Our healthcare system rewards specialization and volume over holistic thinking and pattern recognition. Doctors have neither the time nor the tools to synthesize information across multiple specialties and years of care.

That's where HealthScout comes in. It's not replacing doctors — it's empowering patients. Lilo's complete health story revealed patterns she and her doctors never knew existed.

What could yours reveal?

Update September 17, 2025

HealthScout is now out of beta and available for iOS users in the US.

HealthScout is an educational tool only and does not provide medical advice, diagnosis, or treatment. Always consult with qualified healthcare professionals for medical decisions.

True Story

While developing the app, I got to use it with my own health data, and was shocked that this combination of my health data plus AI revealed aspects of my health that neither my doctors nor I were aware of.

Patient (me):
Is there anything I can do about my worsening knee, back, and shoulder pain? Ibuprofen helps…but only for a few hours.

Primary Care Physician:
I’ve had many patients successfully use over-the-counter doses of naproxen (Aleve) with great results. Take one in the morning and one at night for three days and see how you feel.

Later…

Patient (me):
It's been a bit over three weeks and I have to say, [naproxen has] made a significant improvement to all my joint problems. I'm actually able to do things I wasn't able to just a month ago. Good news, thank you!

Questions: Am I on this forever now? Are there long term side effects?

Primary Care Physician:
I would say, take it for as long as you feel that you are getting benefit from it, and stop it periodically/regularly to see if you still need to be taking it. Many people take naproxen twice per day for decades.

So, I happily continued to take naproxen and later switched to a similar non-steroidal anti-inflammatory (NSAID) called celecoxib that clinical trials have shown to be easier on the stomach. I told friends of the miracle as well.

What My Doctor Saw

A year later at my next wellness check-up, my eGFR lab (a measure of kidney function) came back and looked like this.

On the lower end of Normal, is normal, right? My primary healthcare provider is One Medical, which allows doctors to spend a generous 30 minutes for wellness checks (many providers only allow 15 minutes). Still 30 minutes really isn’t that much time, so I’m guessing my doctor scanned my labs for “High” markers, and given the Labcorp generated chart above for my eGFR, he moved right past it.

I did too.

What HealthScout Saw

Four months later, when I started working on HealthScout, my own health records were the only data I could test with. As soon as it was hobbling, I excitedly started asking test questions of this fresh new AI model. One of my early questions to evaluate HealthScout’s analytical ability was:

Do you see any trends that show a relationship between my medications and my lab results?

To my surprise, HealthScout suggested that my recent kidney function decline could have something to do with my regular use of NSAIDs.

What???? What kidney function decline?!

I peppered HealthScout with lots of questions and learned exactly what it meant. Later I built this chart showing what HealthScout saw (HealthScout doesn’t have charting…yet).

Unlike my One Medical primary care physician, HealthScout had access to my entire health history across three providers over a decade.

With this historical context, HealthScout saw that my eGFR steady state was around 90, and when it dropped 30% in only seven months, that’s at least a yellow flag.

Further, while it seems many primary care physicians use the standard > 60 eGFR as “normal” measure as shown in the Labcorp chart, HealthScout knew about a more granular classification nephrologists (kidney doctors) use. Under this kidney health classification system, my 69 eGFR was not really “normal,” but rather quickly approaching “moderate” kidney disease as shown in the chart above.

Last, HealthScout recognized that I started on my NSAIDs in February 2024. It connected the dots and suggested that my NSAID use could have caused my kidney function to decline.

Wow.

What Are The Implications

Of course, HealthScout’s observation about my kidney health being related to NSAID use is correlation and not causation. It noted that many other factors could have caused my eGFR to be lower including being poorly hydrated on the day of the test, complications with other medications, eating too much protein, and sadly “age.”

I’m not confident HealthScout (or anyone) could answer definitively why my eGFR went down, but HealthScout was the first system to point out that it did go down in a concerning way.

This experience highlights how HealthScout can help:

• Identify patterns in your health data that individual doctors might miss

• Connect information across multiple healthcare providers and years of records

• Translate concerning trends into actionable questions for your next doctor visit

• Put you in control of your complete health story

Because of HealthScout, I'm now armed with intelligent questions for my doctor about my kidney health. That's the essence of how HealthScout can empower you.

Update September 17, 2025.

PostScript

After I wrote this original post, my kidney function worsened, I was referred to a nephrologist (kidney specialist), and ended up getting a biopsy, which confirmed that NSAIDs caused my kidney function decline.

The good news is that as long as I stay off NSAIDs, drink lots of water, and eat a healthy diet, my kidneys should heal.

HealthScout Now Available!

Even better news — the beta is over and HealthScout is now available. If you’re curious if your own health records contain hidden information, download HealthScout free from the App Store.

What I've discovered is a new approach that could help patients wrestle control of their medical journey from the healthcare system by empowering people with their own information. Information that is rightfully theirs but nearly impossible to acquire and often difficult to understand — a way of democratizing healthcare.

Book Launch Highlights

First, I want to thank every one of you who supported the book development and launch. The response has been incredible.

• Outsmart the Learning Curve reached #1 New Release in Amazon’s Business & Motivation category over Christmas 2024

• The audiobook version launched this month. Yes, I narrated it!

• We secured a Chinese language rights deal (简体中文 in 2026!)

• And I was honored to receive this incredible endorsement:

"Brilliantly captures how regular people transform obstacles into extraordinary outcomes. A compelling, insightful guide to accelerating your growth."

–Nir Eyal, bestselling author of Hooked and Indistractable

What’s Next: Solving Healthcare?

While celebrating this milestone, I found myself facing a different type of learning curve that millions of Americans struggle with daily: navigating our complex healthcare system.

After 45 years of pickup basketball, both knees staged a revolt. And the healthcare system left me with an ultimatum between full knee replacement (don’t image search that) or continuing to inadequately ease my suffering with physical therapy, ibuprofen, and rest.

Despite spending a lot of time with Dr. Google and AI chatbots, I found myself lost in a maze of medical terminology and conflicting recommendations. Further, my healthcare team was highly constrained by 1) time, 2) their speciality, and 3) the healthcare system itself.

Why “The System” Fails Patients

The U.S. healthcare system is complicated and often ineffective in part because it’s controlled by large, inflexible entities like insurance companies, the FDA, pharmaceuticals, and healthcare providers. While they are all trying to do good things, their siloed structure, bureaucratic red tape, and, sadly, a profit motive, often get in the way of providing great healthcare. Individual doctors and nurses are often heroic, but because of the controlling entities, most spend no more than 15 minutes on a patient, and few are able to see your whole health picture because of so much specialization and the fragmented nature of healthcare providers’ data systems.

Patients and their advocates often do have more of a whole health picture but need help remembering it, communicating it, and exploring it on their own. Patients themselves are often victims of the system and advocating for themselves takes energy…a lot of energy. Patients are often swimming upstream and lack the knowledge or stamina to challenge the system. They're at the mercy of “The System.”

Healthcare Information Gap

Part of the reason understanding and advocating for your own health journey is so difficult is that healthcare has arguably the largest information gap between any service and its customers.

Patients often don't know enough to ask the right questions or evaluate their options. This is made worse by the fact that the patient’s own data can sometimes inadvertently be held from them. When the information is provided, it uses cryptic language that keeps patients from truly understanding their own problems.

There’s essentially a language barrier between the medical world and its patients. If the patient doesn’t ask for clarifications and/or the doctor is too busy, the patient really can’t understand or help solve their own problem.

In addition, medical records are often scattered across multiple providers, which makes it nearly impossible for patients to maintain their comprehensive health history. It’s unlikely that any single doctor can access all this data, which is often critical.

Google and AI Chatbots Aren’t Good Enough

As I mentioned above, I used Google and AI chatbots to navigate alternatives for fixing my knees when cortisone shots wore out after six weeks. At first, the internet and AI were giving me the same generic advice I heard from my doctors. Why? Because:

• Google 1) gives you links to pages most likely to be clicked, not necessarily the best or latest information, and 2) Google doesn’t have the context of my personal medical history. You get generalized info.

• AI Chatbots can be fed more context, but it’s pretty near impossible to feed it ALL the context.

But I was desperate, so I started uploading all my MRIs, clinical notes, medications, and more into Anthropic’s Claude. To be fair, extracting all my data out of four different patient portals, squeezing it into a size that is acceptable to AI models, and uploading it in an AI-readable form was a ton of work — work that most people would not or could not do.

Once my health records were uploaded, I was able to question the AI more broadly and deeply about my options as well as explore alternatives that my doctors rolled their eyes at. I eventually found a treatment and provider that worked — on Friday I ran for the first time in six months!

Solving Healthcare from the Patient Perspective

This whole experience made me think that while solving our healthcare gridlock from the inside is an intractable problem, arming consumers with tools to help them navigate this complex system could be revolutionary.

Next week I’ll share more about the tool I’m building that empowers patients to navigate the healthcare system more easily.

In the meantime, what’s the most baffling healthcare moment you’ve faced? Comment below.

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The chapter “Get Help” describes why doing anything transformational by yourself is impossible. Writing this book proved that point. I'm deeply grateful to these amazing people who helped turn this vision into reality.

First, a heartfelt thank you to the courageous individuals who generously shared their stories:

• Martha Niño, who made the incredible journey from a silenced undocumented immigrant to a trusted Fortune 500 manager, published author, accomplished public speaker, and creator of her own foundation dedicated to giving hope to immigrant students.

• Helen Wells, who was dissuaded from following her passion for art at 17, was rejected from art school at 29, and after another decade, finally quit her day job to become a self-supporting artist.

• Jason Lee, whose parents drilled into him since early childhood that he would become a doctor. A struggle with organic chemistry coupled with a vision that came to him during a concert led to this 26 year-old running an eight-figure real estate business.

• Jeremy Schifeling, who went from a failing kindergarten teacher to a sought-after consultant at Harvard, Stanford, and nearly every top MBA program in the world.

• Chase Friedman, a buoyant 25 year-old who was paralyzed in a freak accident and stunned doctors with his amazing recovery.

• Jason Christie, a promising “golden child” of medical research who somehow failed on his first seven attempts to get NIH grant funding before making a career out of life-saving contributions to the field of lung transplantation.

I’m also incredibly thankful for the many people who supported me, cheered me on, and bravely gave me the cold, hard truth about my work as it progressed.

First, my patient, kind wife, Mary Sipher, who has the skill to switch careers and become a copy editor, if she only had a glimmer in that area. Next, a heartfelt thank-you to my daughter, Ali Sipher, who may have been my most valuable critic and confidant through this process. A special thank-you also to my sister, Lynn Sipher, who helped shape the book by applying her compassionate lens on the world to every word she reviewed. And, of course, I can’t forget my talented and supportive writing coach, Nicola Kraus, who guided me through every step of the publishing process.

A deep thank-you to all the people who reviewed early drafts, who were gracious enough with their time for interviews, or who collaborated on ideas and suggested potential subjects, including Michelle Azimov, Andrea Butter, Charles Cushing, Sarah Dobson, Amelia Duran-Stanton, Lee Epting, Irwin Epstein, Jonah Gutenberg, Bruce Jacobs, Jeremy Kahn, Randy Komisar, Ryan Lindner, Prashant Mahajan, Lori Mazan, Kathleen McShane, Lisa Morgan, Lori Pappas, Daniel Parris, Kate Purmal, Denise Robinson, Bill Rogers, Ari Roisman, Melina Schaefer, Daniel Sipher, Devan Sipher, Josh Sipher, Christine Tao, Laura Thompson, Ben Villagra, Madelaine Claire Weiss, Beth Wolff, David York, and Heather Yurovsky.

I think the book can help people struggling with their career or finding their way. Please take a look and share it with those you think might benefit.

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Is AI Causing the Sky to Fall?

Every week I meet with students and young professionals seeking career guidance, and lately our conversations inevitably turn to AI. The anxiety is palpable and understandable—hardly a day goes by without headlines about AI disrupting another industry or profession. But beneath the fear lies a more complex and ultimately more hopeful story.

Many of the worst scenarios assume that AI will continue to improve at an exponential pace until it gets to a magical point referred to as Artificial General Intelligence (AGI), when AI systems can match or exceed human-level performance. There’s a lot of debate over if and when we might reach AGI, but the most breathless optimists see it coming as soon as 2025!

But hold on. Let’s take a breath.

AI Progress May Be Plateauing

Maybe it’s a bandwagon thing or the echo chamber, but several analysts and news outlets ran stories in the last few weeks (Benedict Evans, Axios, The Independent) describing how the latest versions of the big AI models from OpenAI, Anthropic, and Google are not making the huge leaps they were just a year ago.

For example, the graphic below illustrates little improvement on language understanding for OpenAI’s GPT models over the last three iterations.

Whether this is a temporary blip or perhaps the end of dramatic improvements for a while is unclear. But the evidence is pretty compelling that AI may be hitting a wall.

Why Could AI Be Hitting a Wall?

Jeff Hawkins1 has spent the last 20 years studying intelligence at Numenta, his brain-inspired AI research and technology company. Hawkins is not only predicting that the current approach to AI will indeed plateau, he’s also describing why significant improvement will hit a wall.

Hawkins outlined his arguments in a recent Fast Company article saying the neural network-based approach used to build large language model (LLM) chatbots like ChatGPT simply won’t work to achieve AGI or “real intelligence.” His main points were:

• No Reality Check. Current AI models have no way to validate their output with the real world. That’s why your favorite chatbot will confidently state certain living authors have died or generate false citations to non-existent academic papers. Humans, on the other hand, can check official records or contact the authors; AI can only work with patterns in its training data.

• Weak Discovery Capability. While AI can predict protein structures from existing data (as Deepmind’s app AlphaFold does), it can't tell us if there's life on Mars. That requires actually going there and looking. No amount of training data can replace physical exploration.

• Language-Only Understanding. When an AI model generates a phrase like "soft cat fur," it’s just matching words. Unlike a human, who has felt cat fur and knows its texture, warmth, and how it differs from synthetic fur, current AI has no sensory experience to ground its output language.

Hawkins is not saying AGI won’t happen though. His point is that the language-based neural network path that the OpenAI, Google, and others are on will plateau, and we need to take a different approach to level up to AGI.

Hawkins's vision? Study the biology of the brain itself—the only truly intelligent object we know—and build on its fundamental principles to create intelligence. This is a distinct departure from current AI’s dependency on neural networks, which despite the name, are merely simplified mathematical approximations rather than anything close to simulations of biological processes.

Hawkins has spent the better part of his life pursuing this vision. But even if his path to AGI is correct, it’s not clear how long it will take to get there.

Can Today’s AI Replace Human Creativity?

Just as the reports of AI plateauing and Jeff Hawkins’s article came out, I stumbled on a video of Ben Affleck speaking quite confidently and eloquently about how and why AI will never get past a “craftsman” level of artistry for film. From the clip, it’s clear that he’s studied the topic and has a definitive point of view.

While Affleck acknowledges AI's impressive ability to imitate—like a craftsman learning techniques by watching others, he argues it fundamentally lacks the artistic discernment that elevates “craft” to “art.” His key observations about AI's limitations mirror Hawkins's points but from a creative industry perspective:

• No Reality Check in Art. Hawkins notes AI's inability to validate its conclusions against reality. Affleck makes the same point through an artistic lens, arguing that "knowing when to stop" and exercising taste requires a kind of judgment that "currently entirely eludes AI's capability."

• Weak on True Creativity. While AI can generate "excellent imitative verse," Affleck emphasizes it's just "cross pollinating things that exist. Nothing new is created." This directly parallels Hawkins's point about AI being limited to patterns in its training data, unable to discover genuinely new information.

• Language Only Limits. Where Hawkins points to AI's inability to understand "soft cat fur" without sensory experience, Affleck highlights how AI fails to capture the chemistry between actors that can elevate a scene. Both are describing AI's fundamental disconnect from real-world, physical interactions.

Affleck isn't a complete AI skeptic. He sees it revolutionizing the "laborious, less creative, and more costly aspects of filmmaking," particularly in visual effects. But for core creative functions? He believes film will be "one of the last things" to be fully replaced by AI—if it ever happens at all.

But Today’s AI Is Already Changing Everything

So what if AI never gets much better than it is right now. It’s already so powerful and effective that it’s replacing or reducing the scope of many jobs. The questions I’m getting from mentees are “What should I study to prepare for an AI-enabled job opportunity?” and “What career pivot is AI-proof?”

Frankly, there are no perfect answers to these questions because AI is so new, and people are still figuring out how to incorporate it into their workflows. However, a good starting point can be derived from Hawkins and Affleck’s arguments which define a boundary or edge between where AI excels and where it fails.

So what are job opportunities given the limitations of today’s AI?

• Direction Setters and Guardrails. While AI excels at execution, today it requires human guidance on what to create and, importantly, when to stop. So direction setters like creative directors, people managers, and product managers will continue to exist. In addition, those who set vision and boundaries like ethics or compliance officers will also continue to be important. Both of these role types require understanding AI capabilities and how AI meshes with business needs. AI could not have conjured the need for this article, let alone tie together timely news stories, a Fast Company article, and a relatively obscure YouTube video. I did that. While I used AI to help polish the language, the core insights and connections came from human judgment.

• Relationship Builders. Yes it’s possible to create a “relationship” with AI apps like character.ai. But my sense is that humans prefer to trust other human relationships when it comes to their health, their family, and their money. So healthcare providers, physical therapists, social workers, and skilled trade workers will remain valuable because they combine human sensory feedback with expert judgment. In addition, while I see ads for AI-based sales development representatives (SDRs) for the laborious lead generation part of sales, it’ll be a long time before anyone buys a complex software solution, an expensive piece of real estate, or a company from a bot. Relationships are about trust, and right now it’s very hard to build a trusting relationship with AI.

• Physical World Bridgers. The physical world's complexity demands professionals who can bridge AI's text-only understanding of the world with things only humans can touch and feel. For example, AIs alone can’t be field researchers digging for dinosaur bones, marine biologists looking for undiscovered species, or any kind of explorer who gathers real-world data. Nor can AI alone handle quality control for real-world products that you have to touch and feel.

• Reality Validators. Fact-checkers and research verification specialists will be crucial as AI continues generating plausible but potentially false information. Importantly, this role will be part of nearly every knowledge-based job. With AI’s incredible ability to write and mimic expertise, a valuable skill we should all be building is sniffing out truth from fiction no matter what the source.

IMPORTANT: The scope of all the above jobs will change and be enhanced by AI. In fact, the people who will succeed in the above jobs will be those using AI most effectively, and those who don’t will be left behind.

AI Is the Great Equalizer

I recommend to nearly everyone I talk to that they should be learning, embracing, and testing the edges of AI as their side gig. That’s what I’m doing. Even if today’s AI has reached its functional limit, its current ability to prompt and query a huge percentage of human knowledge is beyond incredible.

The good news is that AI’s power is empowering for the rest of us.

In his recent book, Co-Intelligence: Living and Working with AI, Wharton professor Ethan Mollick makes a compelling case that top writers, consultants, and students benefit less from AI than average performers.

For example, Mollick ran a study of nearly 800 Boston Consulting Group consultants randomized into two groups: an experimental group taught how to use GPT-4 to perform 18 consulting tasks, and a control group, which performed the tasks without AI help. The performance gap between the top and bottom consultants in the control group was 22%. But for the group who used GPT-4, the gap shrunk to just 4%. Conclusion? GPT-4 brought the lowest performers to nearly the same level of output as the top performers—truly leveling the field.

Embrace AI

No, AI isn’t causing the sky to fall. But we clearly all must adapt to our new AI-enhanced world. While current AI may be plateauing a bit short of human-level intelligence, its impact is already profound. And success in this new era won't come from ignoring or hiding from AI, but from understanding the edge between its limitations and its strengths.

Bottom line, I’m not afraid of AI becoming too powerful; I worry that too few people are embracing its current capabilities while either putting their head in the sand or waiting for a fearful future that may never arrive.

What do you think?

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I’m thrilled to announce that the Outsmart the Learning Curve book is now available for preorder!

The early reviews have been incredibly encouraging. Educators, therapists, career counselors, and mentors agree that the book delivers both inspiration and practical advice for a variety of readers including:

• Career changers ready to reinvent themselves

• Students who are unsure about their future paths

• Job seekers, especially those feeling disheartened by a challenging job market

Outsmart the Learning Curve would make a thoughtful gift for anyone on these paths and will be available December 10th, 2024.

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Outsmart the Learning Curve starts with the premise that success techniques that work for world-class people may not be helpful for the rest of us—that it’s more valuable and inspiring to understand how ordinary people can achieve extraordinary things versus studying the unreachable elite.

I’ve been working on this premise for the last two years, and last week, a gift fell into my lap confirming my point. A newsletter from AI answer tool Perplexity used the example query:

What are the key takeaways from Tim Ferriss’s book, Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers?

The book documents Ferriss’s interviews with dozens of billionaires, icons and world-class performers. Tim Ferriss is clearly a smart guy and has helped countless people with his books, blogs, and podcasts. However, many of the AI summarized takeaways1 reinforce that what works for billionaires, icons, or world-class people may not for us mere mortals.

Here’s a cherry-picked and categorized version of the Perplexity takeaway list followed by Outsmart the Learning Curve interpretations.

Takeaways 1 - Sensible Ideas for Billionaires

• Say "no" frequently - Being selective and saying no to most things allows you to focus on what's truly important.

• Focus on strengths - Rather than trying to fix weaknesses, most focused on leveraging and maximizing their natural strengths and talents.

• Surround yourself with great people - The people you spend time with have an enormous impact, so choose wisely.

Nonsense for the Rest of Us

If you look closely, the above takeaways are based on hidden advantages that most of us don't have and therefore shouldn’t be mirroring.

• Say Yes to Growth (versus the privileged “no”): Of course, successful billionaires should say “no” all the time—they are likely approached with so many opportunities, it would be impossible to say yes to everything. If you’re still working on yourself, undergoing a transformation, or trying to overcome an obstacle, saying “yes” more frequently might get you out of your rut or lead you down a new fruitful path. The rest of us should say “yes” more.

• Work on Strategic Weaknesses (versus a strength only focus): Many billionaires can focus on their strengths because they can outsource the things they’re not good at. The rest of us should selectively work on weaknesses that may be preventing success. Whether that’s increasing levels of openness, behaving more extraverted, or simply being more likable, improving on weaknesses can help ordinary people reach greater heights. The rest of us should work on select weaknesses.

• Build Your Network (versus using ready-made connections): I do try to seek out people I can learn from, but it’s much easier to surround yourself with great people if you run in elite circles as these billionaires do, or have access to the Harvard or Stanford alumni network. What about the rest of us who went to state schools or didn’t even go to college? Surrounding yourself with “great people” is definitely desirable. To do that well first concentrate on cultivating your network.

Takeaways 2 - Billionaire Habits

• Develop a consistent morning routine - Many high performers have a structured morning routine that includes things like meditation, journaling, exercise, and planning their day.

• Prioritize sleep - Getting adequate, high-quality sleep was emphasized by many top performers as critical to their success.

• Have clear goals - Setting specific, measurable goals and regularly reviewing them was a common practice.

Smart Habits May Correlate to World-Class Performance, But Aren’t Causal

It’s hard to argue with any of these practices, but it’s pretty clear that not everybody who has a consistent morning routine or sets clear goals becomes a billionaire, icon or world-class performer. Further accomplishing these habits for a billionaire, icon or world-class performance is often easier than it is for us regular people. We have to do it a bit differently.

• Morning Routines: Yes, Richard Branson wakes at 5 AM to exercise, and Jack Dorsey takes an HOUR to meditate each morning. But what they don't mention is they have personal chefs, housekeepers, and often zero commutes. For working parents juggling school drop offs or people working multiple jobs, an elaborate morning routine is more aspirational than practical. The good news? Real success often comes from small, consistent actions that work for your life—whether that's ten minutes of stretching while the coffee brews, listening to an audiobook during your commute, or doing a few minutes of planning over breakfast. Sometimes the humblest routines create the strongest foundations.

• Sleep Prioritization: When billionaires talk about prioritizing sleep, they're sleeping in custom-built bedrooms with $5,000 mattresses and perfect temperature control. For the average person dealing with noisy neighbors, night shifts, or crying babies, "just prioritize sleep" isn't actionable advice. The real win comes from finding creative ways to improve sleep quality within our constraints—whether that's using white noise apps, sleep masks, or smarter schedule adjustments that work with our real lives rather than against them.

• Clear Goals: When billionaires talk about "clear goals," they're operating with massive teams, unlimited resources, and safety nets that let them fail with little consequence. For the rest of us, goal-setting requires balancing immediate survival needs with long-term aspirations—a juggling act that looks nothing like a billionaire's singular focus on "disrupting industries" or "building global brands." Yet this constraint can actually lead to smarter, more sustainable progress as we learn to break down big dreams into achievable steps that build real momentum over time.

Takeaways 3 - Billionaires Use the Latest Thinking

• Cold exposure - Things like cold showers or ice baths were commonly used for health, recovery and mental toughness.

• Use intermittent fasting - Many practice some form of intermittent fasting or time-restricted eating for health and cognitive benefits.

Be Careful with Fads for Rich People

While there’s data supporting the value of cold exposure and intermittent fasting, let's not forget that previous billionaire health fads like the seemingly insane advice to drink “raw water” turned out to be dangerous nonsense. Further, if you do want to partake in the latest thinking, there is often a “regular” people option.

• Cold Exposure: While there's solid science behind cold therapy's benefits, billionaires are doing this in carefully controlled environments with $20,000 ice baths. But you don't need billionaire equipment to benefit from temperature stress. A minute of cold water at the end of your regular shower offers many of the same advantages. Sure, it's uncomfortable—that's actually the point—but it's also free, quick, and backed by research. The key difference? Billionaires turn this simple practice into an elaborate production while the rest of us can get similar benefits without the fancy gear.

• Intermittent Fasting: Maybe this is a good practice, but some smart people are starting to question the real world value versus downsides like muscle loss. Either way fasting is another causation vs correlation issue. I’ve skipped breakfast most of my life against my mother’s pleading, and look at me now—I’ve been intermittent fasting the whole time. Still waiting for my first billion to roll in though.

The Real Path Forward

While the practices of billionaires and world-class performers can certainly be inspiring, they often reflect privileges and circumstances that aren't readily available to most people.

The real challenge—and perhaps the more valuable insight—lies in understanding how ordinary people can create extraordinary success through accessible strategies and intelligent adaptation of their existing resources. That’s what Outsmart the Learning Curve is all about.

Success isn't about mimicking the elite; it's about finding your own path while working within your current reality to expand your possibilities.

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How much does what you think you can do affect what you can do? Pretty much everyone agrees “a lot.” But Harvard psychology researcher, Ellen Langer, set out to quantify just how much our expectations limit us. And the result of her study will challenge your understanding of human potential.

Turning Back the Clock

In 1979, Langer set up what she called the Counterclockwise study in which she offered a group of elderly men a one week retreat. Before the retreat the subjects were measured on physical dexterity, cognitive function, sensory acuity (both seeing and hearing), appearance, and psychological well-being. She split the subjects into two groups:

1. The control group, who spent an ordinary week in an ordinary resort-like setting and were told to reminisce about 1959.

2. The experimental group, who spent the week with the clock turned back 20 years.

The researchers set up the experimental group’s living space such that:

• Magazines and newspapers were from 1959.

• The furnishings and decor were unabashedly mid-century.

• Music and TV shows were from the 1950s.

In addition the researchers asked participants in the experimental group to speak about their lives in the present tense, as if it really was 1959. The researchers instructed:

We are not asking you to ‘act as if it is 1959’, but to let yourself be just who you were in 1959. We have good reason to believe that if you are successful at this, you will feel as well as you did in 1959.

The results were remarkable. After just one week, the group with the clock turned back showed measurable improvements in strength, dexterity, cognitive function, and even vision as compared to their baseline measurements. Some participants also appeared visibly younger in photographs taken after the experiment.

The implications of this experiment are profound. By simply reframing their context for a week, the men in the experimental group essentially became younger. They didn’t just behave younger, but their physical attributes and capabilities indicated that they were younger. This experiment is one of the starkest examples of the brain’s surprising power over the body.

If a week of thinking like it’s 20 years ago could have this powerful of an effect, think of that poor control group who just reminisced about 1959, but continued to feel like grumpy old men.

Oh wait a minute, we’re all in the control group!

The Power of Reframing

While we can't easily replicate Langer's experiment in our daily lives, the implications are clear: our mindset and expectations significantly affect our capabilities. In a sense, we're all living in a 'control group,' limited by our own perceptions of what's possible.

The forthcoming Outsmart the Learning Curve book includes several examples of how subjects in the book used reframing techniques that enabled incredible transformations or catalyzed overcoming crippling obstacles. Some of these reframing techniques include:

Reframing Stress

Conventional wisdom often portrays stress as entirely negative, but research suggests our perception of stress might be more important than the stress itself. A University of Wisconsin-Madison study found that people who experienced high stress and believed stress was harmful to their health (High Stress, High Perception group below) had a 43% higher risk of dying compared to those who experienced low stress and didn't view it as harmful.

Health psychologist Kelly McGonigal proposes that by reframing our perception of stress, we can turn it into an asset. It may be that the High Stress, Low Perception group above, having a 17% lower mortality rate than the baseline, are doing just that. The idea is that when you notice physical signs of stress like a racing heartbeat or quickened breath, you should recognize these as your body's natural fight-or-flight response—a reaction evolved to empower and protect you.

This stress response enriches your blood with oxygen, sharpens your brain, and prepares your muscles for action. In small doses, this bodily reaction can be helpful. By viewing stress this way, you're more likely to use it to your advantage during challenging moments and calm yourself when the stressful situation passes.

The key is to use controlled, empowering stress as a tool for resilience when facing difficulties, rather than allowing it to spiral into long-term, constant stress, which can indeed be harmful. Reframing stress in this manner can help you navigate the bumpy parts of any learning curve or challenging situation more effectively.

Reframing Failure

We've all experienced the sting of failure, but what’s now becoming clearer is that early failure is almost a requirement for success. A previous newsletter covered the fascinating research showing that NIH grant applicants who narrowly missed getting their first grant but persevered went on to outperform those who succeeded on their first try. These "near miss" researchers published more papers and conducted more impactful studies.

So remember, when you fail at something, it's simply a step toward getting better. By changing our perspective on failure, we can build resilience, learn faster, and ultimately achieve greater success.

Reframing Rejection

Getting rejected or ghosted is discouraging, but a simple shift in perspective can change how we view it. Instead of focusing on the rejection rate, try reframing it as a conversion rate. If you reach out to 100 people in your network and 10 respond positively, rather than seeing it as a 90% rejection rate, view it as a 10% conversion rate. This approach, commonly used in sales and marketing, focuses on successes rather than failures.

By adopting this mindset, you can approach networking and opportunity-seeking with more resilience and optimism. Each positive response becomes a win, rather than each non-response feeling like a loss. In many professional fields, a 10% success rate would be considered outstanding. Viewing your efforts through this lens can help you persist, learn from each interaction, and ultimately increase your chances of success.

Reframing Your Reality: The Key to Unleashing Your Potential

From Ellen Langer's Counterclockwise study to reframing stress, failure, and rejection, we've seen some examples of how dramatically our mindset influences our capabilities. The title of this essay "Doing the Best You Can? You're Not Even Close" isn't meant to discourage you—it's a challenge to reconsider what's possible. By reframing your context, you can unleash hidden potential you never knew existed.

What if you're capable of much more than you currently believe? What if the limitations you've accepted are actually flexible? By consciously challenging these self-imposed boundaries, you can continue to expand what "your best" means.

Have you ever surprised yourself by exceeding what you thought were your limits? How might you apply the concept of reframing to a current challenge in your life? Share your experiences and ideas in the comments below!

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Outsmart the Learning Curve is about how ordinary people can achieve extraordinary success. Gabby Thomas is pretty much the opposite of an ordinary person. She has multiple Olympic gold medals, a Harvard degree, and spokesmodel-like poise and beauty. She is an extraordinary human being.

One technique she uses to propel her success is visualization. In an interview with the Guardian a month before the Paris Olympics, Thomas describes what she does.

Part of my warm-up routine in every race is just visualizing success. But I also do it the night before. I’m seeing everything. I’m imagining who is lined up against me, everything from start to finish, and even how I’m going to celebrate at the end. Essentially, if you think about it enough and the mind starts believing it’s true, then the body does as well. The mind is really powerful. It’s insane how you can trick your brain into doing things and how your body follows.

The kind of visualization Gabby Thomas uses falls under the broader category of self-improvement tools I’ll call “mind over matter.” These techniques can be used by nearly anyone, and are so commonplace, they feel mundane. But if you think about it, the idea of using only brain power to change a physical outcome is truly astonishing.

Mind Over Matter Techniques Supported by Science

Over centuries of evolution, humans have cultivated a wide range of mind over matter techniques. Of course, various forms of meditation have been around for a long time. Here are a few of the better known techniques that various formal studies have shown to improve physical performance, alter health outcomes, and even boost career achievements:

• Visualization. My father used visualization back in the early 80’s to fight his cancer diagnosis. I remember thinking it was voodoo at the time, but he did live beyond the grim 3 to 5-year life expectancy doctors gave him. Multiple studies demonstrate that visualization can also be applied to various sports, from weightlifting to golf putting to free throw shooting. In addition, visualization has been shown to improve an incredible variety of health outcomes including pain management, wound healing, and fibromyalgia.

• Meditation. Former Michigan football star J.J. McCarthy meditates before every game. He started the practice after battling depression, but continues because he finds it “centering,” clearing his mind and enabling focus on the present. Studies show regular meditation practice is linked to reduced stress, improved focus, and better emotional regulation even for non-experienced meditators. In terms of physical health, meditation practice can lower blood pressure as well as improve immune function.

• Growth Mindset. Simply reorienting thinking from “this is how I am” to “I can grow and learn” has been studied mostly around school-age children. Research indicates that this simple shift in the way students think can improve academic achievement among lower-achieving students. Applying a growth mindset in work environments has also proven effective in improving both organizational development and leadership.

• Self-Talk. Watching the Olympics, I saw many athletes with words on their lips before their big event—there’s some prayer for sure, but likely a lot of positive self-talk too. And for good reason. Multiple studies suggest the idea that filling your brain with positive statements before an athletic event can improve performance. In addition, positive self-talk can help with non-athletic activities including leadership.

• Placebo Effect. The placebo effect is perhaps the most tested mind over matter technique we’ve come across. Nearly every medical study with a control group shows that a placebo works better than no treatment and often as well as actual medical interventions. When drugs fail in trials because they were “no better than a placebo,” it seems everyone forgets that the placebo, meaning your brain alone, is doing something amazing!

Look for a future newsletter on harnessing the placebo effect for self-improvement.

So these mind over matter techniques have been shown to increase performance for a broad range of activities and for ordinary people along with extraordinary ones. But how?

Beyond Belief: The Mechanisms of Mind Over Matter

When I was a kid, I watched a mysterious man named Uri Geller use only his mind to bend steel. I remember watching The Merv Griffin Show and being astonished that, by just thinking hard enough, Geller could make a metal spoon droopy and even fix long-broken watches. I ran to our silverware drawer and tried to bend one of our spoons myself and failed.

Of course this was magic.

While mind over matter techniques like visualization and meditation sound almost Uri Geller-like, they aren’t magic. Countless researchers and scientists cannot be fooled like a nine-year-old boy stuck at home watching daytime TV. But if using your mind to change physical bodily functions and health outcomes isn’t magic, what’s the underlying mechanism?

While not 100% settled science, researchers have made significant progress in understanding some of the underlying processes. Here's an overview of what we currently know:

• Neuroplasticity. One key concept in understanding how mind-over-matter techniques work is neuroplasticity—the brain's ability to reorganize itself by forming new neural connections. Techniques like visualization, meditation and having a growth mindset help create new neural pathways, essentially "rewiring" the brain to support new behaviors or thought patterns. Meditation has even been associated with increased gray matter density in areas associated with learning, memory, and emotional regulation.

• Epigenetic Changes. While your DNA is fixed from birth, which genes are active can change during your life. This is the study of epigenetics. Early research suggests that mind over matter practices may lead to epigenetic changes, potentially altering which genes are active or suppressed.

• Brain Chemical Regulation. Some studies suggest that positive thinking and visualization can influence the release of brain chemicals or neurotransmitters like serotonin and dopamine. These chemicals play crucial roles in mood regulation and pain perception.

• Stress Reduction. Many of these techniques have been shown to reduce stress. Lower stress levels can lead to bodily effects like decreased inflammation and improved immune function which lead to better overall health outcomes.

• Pain Perception. Techniques like visualization, meditation and the placebo effect can alter pain perception by changing how the brain processes pain signals. This doesn't necessarily change the source of the pain but can affect how it's experienced.

Your Brain Is Your Body

Bottom line, your mind is your brain, and your brain is part of your body. Just like exercising arms and legs can make physical changes to muscles and bones, exercising your brain can make physical changes to it, which in turn can produce magical results in athletic performance, health, and well-being.

From Olympic athletes to people battling illness to everyday people just trying to get better, the power of using brain techniques can be truly extraordinary. But it's not about bending spoons—it's about bending our own limitations. What mental, physical or career barriers are you ready to overcome? Share your thoughts, techniques, and skepticism in the comments below.

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I used to hate thanking people. As a kid my mother would nag me to send thank you notes or, God forbid, call relatives to thank them for a $10 birthday gift. The nine-year-old version of me thought the whole process was cringy and a complete waste of time. I clearly didn’t understand gratitude.

Of course, a “thank you” is meaningless unless true gratitude inspires it.

Today I feel real gratitude around my wonderful family, my health, and even truly thoughtful gifts.

But here’s a surprise: gratitude can make you more resilient.

Gratitude has been a part of the human condition since the beginning of time, but a quick look on trends.google.com shows the word has been consistently and continuously searched more frequently over the last twenty years, with spikes every November for Thanksgiving, and understandable dips in 2020 and 2021 likely due to COVID.

How Does Gratitude Make You Stronger?

COVID inadvertently created an amazing natural experiment to understand how gratitude affects people’s reactions to adversity. Researchers at the University of Nebraska asked over 200 college students to complete a standardized gratitude questionnaire assessing the subjects’ “appreciation of positive experiences in daily life.” The deadline to submit answers happened to be March 15, 2020. On March 16, COVID-19 restrictions were imposed on campus, so everyone in the study was simultaneously hit with an anxiety-provoking and confusing bump in the road.

The researchers repeated the gratitude questionnaire at the end of April 2020 when the news only continued to get worse, and the future was still quite unclear. The second survey included additional questions about how subjects were feeling about the COVID situation.

Surprisingly, the researchers found that those who scored higher on the gratitude scale on the first questionnaire were more resilient in their reaction to COVID-19. That is, they were more likely to report positive life changes due to the pandemic, including strengthened relationships, more free time, academic improvements, and better mental health indicators.

Conversely, those lower on the gratitude scale had a far more negative reaction to the pandemic including a higher preponderance of depressive symptoms, higher anxiety, and more negative outlooks.

The researchers discuss several theories about why those higher on the gratitude scale reacted so positively towards the COVID epidemic. The three concepts they describe include:

• The broaden-and-build theory which proposes that gratitude, as a positive emotion, may broaden one's thinking and build lasting personal resources that can be drawn upon during difficult times.

• The undoing hypothesis, which suggests that gratitude might counteract the effects of negative emotions.

• The incompatibility theory, that gratitude may be incompatible with negative states like depression and anxiety, potentially displacing these harmful thought patterns.

These theories suggest that by practicing gratitude, you can build lasting mental resources that can help you navigate future challenges more effectively. Cultivating gratitude builds resilience.

How to Cultivate Gratitude

Like most healthy practices (e.g., eating right or exercising), you can’t just start being grateful “when you need it.” Gratitude is a practice like yoga or meditation where the benefits build over time. By practicing gratitude daily, being truly thankful for your life situation, you should be in a better position to respond well to the next looming crisis. While I found a range of methods for cultivating gratitude, everything from “gratitude journaling” to a “gratitude jar,” here are three that feel pretty natural that I actually do:

• Express Gratitude While Walking Around. I walk pretty much everywhere and am lucky enough to be in beautiful cities or natural surroundings most of the time. I find myself consciously appreciating things like architecture, public art, or natural beauty and often take a moment to be grateful that I experience it.

• Reflect on Challenges. Sometimes I ruminate on problems or challenges. When I catch myself in negative self-talk, I stop and reflect on what I have learned or could learn from these things. I only figured this one out in the last few years.

• Sincerely Thank People. I’ve grown up quite a bit from that selfish nine-year-old and make a practice to authentically and sincerely thank people for everything from small acts of kindness to supportive phone calls to just being there for me.

How do you cultivate gratitude in your daily life?

Share your practices in the comments below—your idea might just help someone else build their resilience!

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Quitters are losers, right?

It’s not that simple. People who quit too early, before they give what they’re working on a chance to succeed, are making a mistake. And people who refuse to quit in the face of all evidence that what they’re working on will fail are also making a mistake.

People who know when to quit, they’re actually the winners.

Consider the “Sisyphus Revisited” graphic above as a metaphor for adversity. Unlike other Sisyphus depictions, this one can actually get to the top of the hill and let the boulder roll down the other side—the equivalent of “making it.”

On the arduous way up, Sisyphus cannot see the top of the hill—the boulder is in the way (a metaphor for the daily grind). He has no idea how long he will have to keep pushing until he finally reaches the top. Will it be on the next step or perhaps never?

When faced with these uncertainties, how do you know when it’s time to quit and let the boulder roll back to where you started, or if you’re so close you should keep pushing? This is a valid question whether your adversity is about a promotion, trying to learn a new complex skill, or working through a personal relationship. After a long, rough go of it, at some point you have to ask, “is it time to quit?”

Deciding When

In my experience, when people finally do quit, they often say they waited too long—stayed too long in that job, kept giving that underperforming employee too many chances, or stuck with a relationship beyond its expiration date. Can we get better at quitting? Yes!

In Quit: The Power of Knowing When to Walk Away, former world champion poker player and now executive coach and speaker, Annie Duke, provides empowering strategies about how and when to quit. First, she dispels the idea that quitting is a bad thing. If you’ve been reading Outsmart the Learning Curve, you might assume that I think quitting equals failing, and that I recommend only resilience and grit.

I don’t. Quitting an idea, a job, or even a partner can be the healthiest choice in the right circumstances, and enable the success you’re destined for.

When to quit is the hardest decision to make, especially if you’ve invested a long time in whatever you’re trying to accomplish. We humans are well known to fall prey to the sunk cost fallacy. That is, to continue investing in an activity simply because we have already spent time and resources on it, even when investing further brings little to no additional value. The logically-minded can look objectively at the costs and benefits going forward—without considering the previous investment—because, of course, you can’t change that.

Somehow our paleolithic brains aren’t great at that piece of logic, even if we understand the sunk cost fallacy academically. Nobel Prize winning behavioral economist, Richard Thaler, admitted even he fell victim to the sunk cost fallacy when he and a friend decided to go to a basketball game that neither really wanted to attend only because they had already paid for the tickets.

One More Thing

Similarly, the problem solvers among us struggle with the “one more thing” problem. That is, they see their failure as a puzzle and want to keep trying one more thing to see if they can fix it versus quitting and moving on.

Looking back on my product career, I made this mistake more than once—continuously adding just one more feature in hopes that it would transform a failed product into a successful one. Lately, I sense a lot of “but if we add some AI, this might work!” Most of the time, the additional features only make the product worse by either muddying the primary purpose of the product or simply making it harder to use.

But when you sense the promise that this new feature will be the difference maker, or, in a different quitting context, the hope that your boss won’t be a jerk after this last confidence killing episode, or the prospect that your underperforming employee will turn things around, it’s really hard to make the quit decision. That’s why Duke recommends deciding when to quit in advance.

Quit in Advance

The reality is that most times you don’t know for sure if the “one more thing” won’t be a tipping point that swings your activity from failure to success. But when you’re in a more rational state of mind, it may be easier to look at your future self and decide, “If I can’t figure this out by the end of the year, then I’ll move on to something else.” Duke calls this “quit criteria,” which you commit to, that is promise yourself, for some future date or attempt. Besides just picking a date, my earlier article on predicting success and failure suggests two more quit criteria: 1) seeing measurable improvement between attempts and 2) decreasing time between attempts. If you don’t see positive trends in those areas, you may be doomed to pushing the boulder up the hill forever.

Find a Quitting Coach

If your quit criteria aren’t met by your predetermined date, it’s time to move on. This is really hard in the real world. To give yourself more accountability, ask someone to be your “quitting coach” who will hold you to your promise to quit.

A quitting coach is a person you respect and trust to be honest with you even if they know their recommendations might hurt. It’s best to choose a quitting coach who will be objective as well as able to balance emotional intelligence with analytical skills. Without a quitting coach, people tend to cheat themselves and keep going for longer or come up with a new “one more thing.” If there really is a great “one more thing,” consult your quitting coach and maybe they’ll agree, but you should set another quit criterion in case that last attempt doesn’t work out either.

Outsmart the Learning Curve is not about politics, but when current events collide with techniques from this newsletter, I just can’t resist.

As of this writing, Joe Biden is staying in the 2024 race for President in the face of broad calls for him to quit. He gave himself a definitive quit date by saying he’s a “bridge” president back in March of 2020. Great! But clearly he’s intent on letting that quit date pass. And uncle Joe doesn’t seem to have an honest, objective quitting coach. As I write this in July, it’s pretty clear that other Democratic candidates are more fit to be president than he is now, let alone in four years when he’ll be 86.

President Biden, you’ve reached the top of your Sisyphean mountain. You made it to President of the United States, you served your country well, and you’ve achieved much of your agenda.

It’s a perfect time to quit.

Embracing the art of the quit can be transformative because it will redirect your energy from the futile to the new and exciting—perhaps the path you should have been on all along.

What’s your experience with quitting, and how has it shaped your path to success?

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This week instead of an excerpt from my upcoming book, I’m sharing Part II of my insights into the crazy world of book publishing. I suggest reading Part I first, though if you’re lazy like me, you can get the gist reading the recap below.

Demystifying Book Deals Part I Recap

Traditional publishing heavily favors celebrities and franchise authors, while self-publishing, through Amazon’s Kindle Direct Publishing (KDP), enables anyone to publish a book. But self-publishing requires significant author investment without controlling for quality.

Hybrid publishing has emerged as a middle ground, vetting submissions and ensuring quality, while offering higher royalties than traditional publishers. Because I was fortunate enough to receive six hybrid offers, I have a ton of data about the financial side of hybrid that doesn’t seem widely known.

As a courtesy, I won’t tie the names of hybrid publishers with their numbers except for the one I signed with, Koehler Books, whose royalties, costs and sample contract are transparently published right on their website.

Print Methodology Drives a Big Decision

Amazon created Kindle Direct Publishing (KDP) to build an ecosystem around its eBook reader. However, it was another technology, print-on-demand, that enabled the much larger paper side of the self-publishing business. Even today, physical books outsell digital formats 4 to 1.

With print-on-demand, the moment a customer places their order, the print job enters a queue, prints, and ships directly to the end customer. Traditional offset print technology requires forecasting runs of hundreds or thousands of books, which take weeks to complete. The resulting inventory of books needs to be warehoused like any other physical good. This includes fulfilling orders to online retailers like Amazon as well as brick and mortar stores like Barnes & Noble, airports, or thousands of independent bookstores.

Here’s a dirty little secret: While nearly all hybrid publishers will confirm that your book can be ordered by brick and mortar stores, it’s unlikely retailers like Barnes & Noble will keep a print-on-demand book in stock because retailers require return policies that traditional printing is well suited for. Perhaps you could walk into your local Barnes & Noble and convince the manager to order a few copies of your book for that store, but nationwide distribution requires an army of convincing salespeople, some evidence of traction elsewhere, and a 100% return policy. Oh and guess who gets stuck holding the proverbial bag on returns? Not the deep-pocketed retailers or publishers. It’s the poor author.

Besides returns, another reason getting into retail is so hard is that, in the physical world, space is limited. Stocking a new book requires removing an existing title off the shelf. Another little known secret, 86% of business book sales are from the “backlist” or books published years ago. More than once during the publisher discussions I heard something like:

Is your book going to replace Dale Carnegie’s “How To Win Friends and Influence People?”

For reference, as I write this in the summer of 2024, Carnegie’s 1936 book is ranked #5 in Amazon’s “Business and Money” top seller list.

Of the six hybrid publishers that offered me a deal, three used traditional offset printing and three used print-on-demand. For the chance to get my book into retail, I would have to choose one of the offset printing options along with taking the inventory risk.

Authors Must Pay to Play

Self-publishing is not free. Producing and marketing a decent quality book costs thousands. My estimate, detailed in Part 1 of this post and shown as $25,930 in the chart below, is a guess at the cost to produce a 200 page nonfiction book self-publishing with Kindle Direct Publishing (KDP). I suspect some will suggest this estimate is too low, others too high. But I’ll note it was my thoughtful guess because if my manuscript was rejected by all the publishers, I planned to self-publish.

Of course, hybrid publishing is not free either. It was difficult to normalize the various hybrid publisher proposals for the purposes of this exercise. Each used different terminology, provided different services, and sometimes didn’t include basics like production for the audio book. With that in mind I did the best I could to make sure the services and costs quoted were as equivalent as possible.

Topline findings include:

• The range is quite insane. For essentially the same thing, one hybrid publisher barely cost more than self-publishing, and another proposed more than 2.5x that, at over $66K or the price of a well-configured Tesla Model Y.

• The traditional offset printing hybrids are more expensive in part because they require printing minimum runs at author expense (a major component of “production” in the chart) and in part because they pass the cost of brick and mortar sales on to authors.

• The larger marketing budgets are mostly either strategic or administrative activities versus actual marketing spend. Some charge for mundane tasks like submitting your manuscript for reviews and awards that the author could easily do. To make the budgets apples-to-apples, in some cases, I had to level up marketing spend to match my spending forecast on the self-publishing option.

• Quality of work is not captured in the chart above. However, I did get samples from the publishers I was most serious about as well as conducted reference calls with a few of their authors. While each had strengths and weaknesses, I think I would have been happy with all of them quality wise.

Royalty Promises Are Tricky

Yes, of course, there’s upfront author investment, but don’t worry, you will earn it all back with royalties, right? The good news is that hybrid publishers offer between 50% and 85% royalties whereas traditional publishers only share 10% - 15% of the net price. But what does that all boil down to when you net out printing and distribution costs?

The only way to know is to stop talking percentages and calculate the per book unit economics. I calculated the hybrid royalties below based on a weighted average of a $29.99 hardback, $19.99 softback, $9.99 eBook, and $8.99 Audible. With all the other data provided in their contracts, the per book royalty for hybrids all came out to around $4.00, while KDP was nearly double that.

Why Self-Publishing with KDP Yields Higher Royalties

Why is KDP’s royalty so much higher than the hybrid publishers? The answer lies in the way retail sales has worked since the beginning of time. Retailers buy books at wholesale prices, which in the case of book publishing is half the retail price of any book sold. So if your hardcover book is $29.99, about $15 goes to whatever store sells that book to the end customer, whether it be Amazon, Barnes & Noble or an independent book shop. After accounting for the price of the book and distribution costs, you and the publisher carve up the rest according to that royalty rate. Another way to think about it is there are two tiers of distribution: the retailer and the publisher. Each needs to get a piece of the pie.

In the case of KDP, Amazon serves as both the publisher and the retailer, so there’s only one tier of distribution to pay. Note, if you are a KDP author and want to sell your books at Target, Walmart, or Barnes & Noble, you’ll have a similar two-tier distribution and the royalties for those sales will be much lower.

The reality is that most people buy their books on Amazon these days. If you use a publisher other than Amazon, you have to pay that publisher and Amazon’s retail margin. Savvy business people call what Amazon has created a “moat,” but those on the outside of the moat looking in call it a monopoly.

Royalty Rates Can Be Deceiving

Among the six offers I received, the advertised royalty rates ranged from 60% to 85%, yet the range in hard dollar royalty per book followed a much narrower band. How could that be? The answer is that there are shell games built into some of these offers.

For example, one of these publishers quoted a $5.00 cost to print the paperback version. Since all the other offers quoted an exact printing cost of say $4.28 for a paperback, I asked if the $5.00 was just an estimate, assuming I’d be charged the true cost. Silence. When I asked whether we could change the terms of the contract such that I pay for the exact printing cost, the publisher representative, a little flustered, said no author had ever asked for that, and he’d have to get back to me. When your average royalty is in the $4.00 range, and $0.72 gets skimmed off the top, it’s kind of a big deal. I didn’t select that publisher.

Breakeven

Divide the numbers in the blue Author Investment chart by those in the yellow Royalty per Book chart and you get how many books you need to sell to make up for that initial investment, your breakeven. Anything over this breakeven number of sales, and you start actually making money as an author.

When I first started seeing these numbers, I thought “doable.” I’ve been in businesses that sold millions of far more expensive items than books. A few thousand should be child’s play, right? When I mentioned these numbers to an author friend, he told me that 10,000 books was considered a “hit.”

After I signed the deal with Koehler, I learned that 96% of new books never sell more than 1,000 copies. So even the seemingly tiny 3,317 units sold to break even on KDP appear to be a high hill to climb.

How I Decided

This post is all about money, but I never intended to make money from writing this book. I’m writing Outsmart the Learning Curve because I reached a point in my career where it’s time to give back—to inspire, encourage, and teach the next generation. Plus I saw a real need for a book that speaks to “regular people” who want to improve or make a transformation versus using the top 0.1% as examples.

So my primary objective is to get the book in as many hands as possible. I just don’t want to completely devastate my bank account while doing it.

I also want to produce a quality book. While it’s absolutely possible to produce a beautiful, well-written self-published book, there are no shortcuts. Even if you start with a brilliant manuscript, you also need a great editor, a talented cover designer, an expert book layout person, a savvy book marketer, and a detail-oriented project manager.

When I realized how difficult it would be to hire each of those people individually or do all that myself, it was clear that having an established publishing team, who had my back throughout the process, was the right choice for me.

Which Hybrid Publisher and Why

Once I realized how relatively few books get sold through retail and my chances, as a first-time author, of getting carried in retail were slim, I decided to go the print-on-demand route. This decision also relieved me from carrying inventory risk. Just to put it in real terms, if I ordered 3,000 too many $4 books, that’s $12,000 sitting in a warehouse.

Between the three print-on-demand publishers, Koehler required the lowest upfront investment and for a really good reason. They explicitly admitted they weren’t going to pretend to do the marketing and charged basically nothing for it. They offer great marketing resources and guidance free, and even one-on-one sessions with the publisher himself, John Koehler, but their proposal was not weighed down by hand-wavy strategic or administrative marketing costs.

Of course, my book publishing journey is far from over. The manuscript is basically done and is deep into edit as this post goes live. The current schedule makes the title available for pre-order in October and the book goes on sale December 10th, just in time for the holidays.

Sometime next year, I’ll write a follow up to share what really happened.

More from Outsmart the Learning Curve

How Does a Nobody Like Me Get a Book Deal?

Celebrities like Britney Spears, Michelle Obama, and Matthew McConaughey command multi-million dollar advances to write their books. Of course, these people are outliers in many ways.

Erik Hoel’s clever analysis makes the case that there are approximately the same number of self-made billionaires in the US as there are non-celebrity authors who make a humble living. By Hoel’s calculations there are about 585 non-celebrity self-supporting authors versus 515 self-made billionaires.

To be fair, that 585 number doesn’t consider those who self-publish. But I’m getting ahead of myself. Here’s a simplified primer on today’s complex book publishing landscape.

Traditional Publishing

Not long ago, there was essentially one way to get a book published if you weren’t famous, or “have a platform” as they say in the publishing industry. With exceptions, the general order of operations for regular people is:

1. Pour your soul into a manuscript which often takes years. It’s possible to go to step 2 with an idea or a chapter, but without a “platform” your chances aren’t great.

2. Query agents. This means sending your manuscript to as many as 100 agents who seemingly aren’t great communicators. Many have adopted a "NO RESPONSE MEANS NO" policy…nice.

3. If you’re lucky enough to get a deal in step 2, your agent pitches your manuscript to publishers. Of course, this can take months and still may end with no takers.

4. If your agent finds a publisher willing to do a deal, you get to sign the rights and control of your book away in exchange for an advance that’s likely far less than Britney Spears’s. Your chances of earning out your pittance of an advance (making additional income beyond the advance) is very low. Your mileage may vary.

To be fair, traditional publishers by and large do an excellent job with the blocking and tackling of editing, layout, cover design, and printing. Plus, there’s the benefit of filtering out non-celebrity shlock, though perhaps at the cost of missing some diamonds in the rough.

Marketing

While good at editing, layout and printing, traditional publishers are famous for being terrible marketers. This possibly relates to them not caring much about missing diamonds in the rough. That is, publishers are unlikely to do a great job marketing that diamond in the rough so it could gain traction.

In a fascinating recap of publicly available testimony from the Penguin/Simon & Schuster antitrust case, traditional publisher executives admitted that their primary marketing expense consists of advances to celebrities that range from $250K to millions. Whereas the rest of their marketing expenditures on these same books are an order of magnitude less. In one case, a publisher spent $1.2M on an advance to an author but only invested $62K to market that book. In another, a publisher paid a $450K advance but spent only $36K on marketing.

Why this lopsided ratio? Because traditional publishers focus on either people like Britney, Michelle, and Matthew, who can market their own books by, say, posing topless on the book cover, or franchise authors like James Patterson, Tom Clancy, or Colleen Hoover, who bring their own audience.

Self-Publishing

With the introduction of Amazon’s Kindle Direct Publishing (KDP) in 2007, self-publishing quickly overtook traditional publishing in terms of new books produced per year.

Using self-publishing services like KDP, anyone with an idea and an ability to operate a word-processor can publish a book. And they do…at a rate of over 2M new books every year! As an added incentive, the author has full control and gets to keep 60 - 70% of the net revenue versus the traditional publisher earn-out royalties of just 10 - 15%.

Without the agent/publisher filter, however, the quality of self-published books varies greatly, and it’s not just the writing. All the specialized work of editing, layout, cover design, and printing must be handled either DIY or via freelancers. The DIY folks often end up with typo-ridden books that aren’t very readable and have ineffective covers.

And the cost of hiring professional freelancers in each of these disciplines adds up. My estimated cost to self-publish using middle-of-the-road estimates for vendor pricing came out to nearly $26K, approximately the cost of a new Honda Civic.

Vanity Publishing

Hiring freelancers to edit and design critical aspects of a book has several disadvantages as compared to the traditional publisher route. First, just finding and vetting individuals for each task is a big job. Second, the quality of these freelancers may differ significantly, and new authors are not in the best position to determine freelancer skill levels. Last, coordinating it all so that the timing works and last minute changes flow through the entire cascade of activities takes serious project management chops.

The heaviness of this self-publishing activity gave rise to “vanity publishers” who do the work of the publisher but do not filter for writing quality. Vanity publishers (who generally don’t like to be called vanity publishers) handle everything from editing to putting the final manuscript on the various self-publishing platforms. They make money from authors who pay for these services, but generally don’t make anything on book sales. So they don’t care much if the book sells.

These mismatched objectives between author and vanity publisher have led to a pretty scammy business that swindles money from unsuspecting authors and often produces low quality books.

Hybrid Publishing

Hybrid publishing emerged as a response to the limitations of the traditional publishing model and the challenges of the DIY/vanity self-publishing model. A few of the key hybrid publisher criteria as described by their own organization, the Independent Book Publishers Association (IBPA), include to:

• Vet submissions—I’ve heard of hybrid publishers accepting as few as 10% of submitted transcripts and as many as 40%.

• Ensure editorial, design, and production quality.

• Pay authors a higher-than-standard royalty. Author royalties range from 50% to 85% net of printing and distribution costs (remember Amazon gets their 30% - 40% off the list price).

So unlike vanity publishers, hybrid publishers have “skin in the game” given that part of their compensation is a royalty on every book sold. Many in the r/selfpublish Reddit community see paying anyone calling themselves a “publisher” as a non-starter. I see it as a positive—hybrid publishers want to do everything in their power to make sure the book sells.

My Journey

As you might have guessed, I didn’t even try to get an agent and go the traditional route. Instead, I submitted the Outsmart the Learning Curve manuscript to nine publishers and was lucky enough to receive six hybrid publishing offers! Yay me!

Perhaps more interesting, with these offers came contracts, pricing sheets, and more. So I suddenly had an inside scoop on the world of hybrid publisher services, costs, and royalties.

In Part II, I’ll break down all the numbers. You’ll learn how widely these offers varied, how there’s some level of vanity publisher scamminess even with IBPA approved publishers, and why they all essentially said, “If you’re writing this book to make money, you’ll likely be disappointed.”

Read Part II here.

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