Edition #27: When Enough Is Never Enough

On gratitude, ambition, and what AI is quietly doing to our sense of meaning

By Mykel Salomon · 2026-06-27

<h3>On gratitude, ambition, and what AI is quietly doing to our sense of meaning</h3><hr><h3>🔓 Opening Reflection</h3>What happens when you get everything you wanted, and it still doesn't feel like enough?My guest this week, Jack Wagoner, can tell you the exact moment he learned the answer. He was sixteen, living in France. He'd moved there alone, barely speaking the language. On his first day of school, a teacher called on him in front of the class, and the only sentence he could produce was je ne comprends pas. I don't understand.For a while, he was failing at everything. No friends. No income. Bad grades. And, strangely, he felt alive — because everything was new.Then he did what high performers do. He fought his way back. Within a year he was nearly fluent, had a tight group of friends, and was running a business with four employees from his bedroom. By every measure, he was winning.And he told me that standing in front of the mirror, at the best he'd ever been doing, he felt the emptiest he had ever felt.That was the moment it clicked for him:It was never about how much he did. It was about how he was feeling before he did any of it.Here's the part that should stop you. Jack is nineteen years old.He's already mapped a trap that takes most of us decades to even notice — the quiet machinery of more. We optimize for achievement, not for feeling alive. We tell ourselves the next win is the one that finally lands.And now we've handed that machinery an accelerant.Because AI is very good at helping us get more, faster. The question this week isn't whether it can.It's what happens to us when it does.<hr><h3>🔦 Signal of the Week</h3>We were sold a simple story: AI would take the busywork, and give us our time back.The early data tells a different one.A 2025 study out of the University of California, Berkeley found that AI, on the whole, does not reduce people's workloads. Instead, workers take on more — more tasks, more variety, more responsibility — partly because the tools make "more" feel possible. One analysis of over 10,000 workers found time spent on core job tasks rose anywhere from 27% to as much as 346% after AI adoption. And here's the detail Jack named in our conversation, now confirmed in the research: people are spending the time they used to take as breaks on more prompting — squeezing AI into lunch breaks and bathroom breaks instead of resting.Then there's what it does to our heads.A widely cited 2025 study in the journal Societies surveyed 666 people and found a clear negative correlation between heavy AI use and critical-thinking ability — with the effect strongest among the youngest users. A separate MIT experiment found that people who wrote essays with AI struggled to recall what they had written minutes earlier. Better output. Worse memory.Jack has a name for the mechanism. Before Google, your brain stored the information. After Google, it stored the search you'd use to find it. AI takes that one step further — now we offload not just facts, but the thinking itself.The promise was that the machine would free us.The early signal is that, without intention, it quietly expands the work and thins the thinking.<hr><h3>🌍 In the Wild</h3>Here is what that quiet trade-off actually looks like.<h3>1. The duality of gratitude and ambition</h3>Jack's core idea is deceptively simple: you can be fully grateful for where you are and fully ambitious about where you're going — at the same time.Most people pick one, and both failure modes are real. Pure gratitude with no ambition slides into complacency. Pure ambition with no gratitude — the protocol Jack was running in France — burns you out, because every achievement is a down payment on a feeling that never arrives.The fix isn't to want less. It's to stop making the feeling conditional on the next win.He told me about interviewing a billionaire who said the founders we all look up to don't actually want more money anymore. They want peace. And they can't get it — because they've spent their whole lives telling themselves peace is something you earn after the next achievement. So the finish line keeps moving, by design.Ambition pulls you forward. Gratitude lets you arrive.You need both, or the running never stops.<hr><h3>2. Why "more" keeps lying to you — and AI makes the lie faster</h3>There's a reason the feeling fades. It's called hedonic adaptation: we all have a happiness baseline, and we drift back to it after the highs and the lows. As happiness researcher Sonja Lyubomirsky has shown, this reset is evolutionary — if our ancestors had stayed satisfied after one good hunt, they'd never have hunted again.The problem is that the survival mechanism is still running in a world where most of us aren't fighting to survive. We're fighting to feel fulfilled. And the baseline keeps pulling us back to neutral, often faster after good things than bad ones.Jack put it in terms anyone who's played a video game understands. Put the game on easy mode and hit a home run every at-bat, and it's fun for about ten minutes — because anyone could do that. Turn the difficulty up, strike out a few times, and the home run finally means something. You feel responsible for it.Now connect that to AI. When the output gets effortless, the win stops landing. So we chase a bigger one. AI closes the gap to "achieved" faster than ever — which means we hit the reset, and reach for more, faster than ever.The machine isn't just speeding up our work.It's speeding up the emptiness.<hr><h3>3. The struggle was where the meaning lived</h3>AI's flagship feature is removing friction. But for a lot of people, the friction was the point.Growth is where we find fulfillment. And growth requires struggle — the strikeouts before the home run. When you sand that away, the work can deliver the same result while feeling like it meant nothing.So people compensate the only way they know how: by doing more. Which is exactly what the burnout research is now showing. The tool that was supposed to give us margin instead becomes a reason to expand the job.And you cannot win that race. Jack said it plainly: we're comparing ourselves to a literal machine — one that doesn't sleep, doesn't take vacations, doesn't need a weekend. A 24/7 system you try to out-grind will simply break you.The way out isn't to work like the machine.It's to get clear on the things the machine was never the point of. Jack uses AI constantly — for the CRM, the speaker sheet, the parts of his work he gets no fulfillment from. But he won't let it generate his ideas, write his questions, or choose his guests. Those stay human on purpose.Use it for the friction you don't want.Guard the friction that makes you you.<hr><h3>4. Gratitude as a competitive advantage, not a consolation prize</h3>Here's the reframe that I think will land hardest.We tend to picture the most driven people as the ones running away from something — the David Goggins model, motivation as escape from a life you hate. Jack's argument is that gratitude isn't the soft alternative to that drive. It's the stronger engine.Think about risk. The person who hates their life has a safe option: stay put, and at least avoid sliding backward. But the person who genuinely loves where they are can take the bigger swing — because the worst-case outcome is a life they already love. They're not afraid to fail.Gratitude doesn't make you complacent. It makes you brave.And it's a skill, not a mood. Jack's progression, for anyone who finds gratitude "fluffy":<ul><li>Don't start by forcing it. Start with "I'm not unhappy that happened." Then, over time, "I'm grateful that happened."</li><li>Move past being grateful for things — the house, the car, the podcast — because those can be taken away, and your gratitude leaves with them.</li><li>Land on being grateful for who you are: the traits and choices that built those things. That, no one can repossess.</li></ul>And one he insists on: gratitude shared is gratitude amplified. Text one person today — thinking of you, grateful for you. It sounds cheesy. It also builds a bond that's hard to break, which matters more, not less, in a world optimized to keep you prompting alone.(Note he was deliberate about this: he is against turning gratitude into another journaling chore. People are already burnt out. This is a reframe, not a new task on the list.)<hr><h3>5. What a meaningful life looks like when everything is possible</h3>AI keeps lowering the barrier to entry — to building, creating, starting. That sounds like pure freedom. It has a shadow.When you can try anything, it gets easier to commit to nothing. To quit each thing right before it would have paid off, because something else looks shinier. We watched a smaller version of this with the internet — the endless drop-shipping, side-hustle, get-rich-quick churn, abandoned the moment it got hard. Lower barriers also make it effortless to compare yourself to everyone succeeding at the thing you just put down.So in a world of infinite options, Jack's definition of a meaningful life isn't more options. It's clarity:What actually lights me up? Who actually adds value to my life? If I spent my time with these people for the rest of my life, would I regret it?That last question isn't a coincidence. It points at the most durable finding we have. The Harvard Study of Adult Development has tracked people for over 85 years, and its clearest result is that the single strongest predictor of a happy, healthy life isn't achievement, money, or fame — it's the quality of our relationships. Loneliness, the researchers found, is as damaging to health as smoking.If AI really does take more of the doing off our plates, the most human thing we could do with that time is obvious.Spend it with each other.<hr><h3>💬 The Big Question</h3>If a machine can produce everything you achieve — what's left that's actually yours?If everything you're chasing arrived tomorrow, would it finally be enough? Or would you just move the line?Because if we don't decide what enough means for ourselves, the world will happily decide it for us. And it will always, always pick more.<hr><h3>🧠 A Small Exercise</h3>No journaling. No new habit to feel guilty about. Just five questions to sit with this week.<ol><li>What am I actually chasing — and why? What have I quietly attached to "success"? What do I believe I'll feel once I get there?</li><li>Where did I outsource the struggle this week? Did removing it make me feel free — or just make me reach for more to fill the space?</li><li>What's one thing today I'm "not unhappy" happened? Start there. Don't force gratitude. Just notice it.</li><li>What trait of mine — not possession — am I grateful for? The thing that builds the things. The part no one can take.</li><li>Who would I text right now if I told them I was grateful for them? Then actually send it.</li></ol>This isn't about doing less or wanting less.It's about making sure the life you're sprinting toward is one you'd actually want to arrive at.<hr><h3>🎙️ This Week's Episode</h3>The Emptiness Behind Achievement — Gratitude, Ambition, and Staying Human in the Age of AIGuest: <a target="_blank" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80 ember-view" href="https://www.linkedin.com/in/jack-wagoner-speaker/">Jack Wagoner</a> — host of The Grateful Podcast, TEDx speaker, and coach on performance through gratitudeA conversation that isn't really about AI tools. It's about us — and what happens inside a person when everything outside starts accelerating.We get into:<ul><li>The mirror moment in France where "the best I'd ever done" felt like the emptiest he'd ever been</li><li>Why high performers chase a feeling that bigger achievements can't actually deliver</li><li>Hedonic adaptation — and how AI speeds up the cycle of more</li><li>Why removing the struggle can quietly remove the meaning</li><li>Gratitude not as complacency, but as the engine that lets you take bigger risks</li><li>A practical, no-journaling way to actually build the habit</li><li>What a meaningful life looks like when the barrier to everything keeps dropping</li></ul>🎧 Available on <a target="_self" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80 rbJlXBzRbySbuPCWQzjoswVAGlGBFmEhY " href="https://open.spotify.com/episode/4DlGpxj0ZReAeyuhGGv8GT?si=NzB9a3c-TOORuIyx8gugsQ">Spotify</a>, <a target="_self" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80 rbJlXBzRbySbuPCWQzjoswVAGlGBFmEhY " href="https://podcasts.apple.com/us/podcast/s2e25-gratitude-ambition-a-secret-to-success/id1843402023?i=1000774025505">Apple Podcasts</a>, and <a target="_self" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80 rbJlXBzRbySbuPCWQzjoswVAGlGBFmEhY " href="https://youtu.be/81Q8za1NI00?si=eB6pOixeyv6rjP4q">YouTube</a>.<hr><h3>🧭 Thought to End the Week</h3>We have built tools that can do almost anything for us.The danger was never that they'd take our work.It's that we'd hand over the parts that were never about the work at all — the struggle that grows us, the patience that earns the win, the presence that lets us feel it, the people who make any of it worth doing.Gratitude and ambition were never opposites. One is the engine. The other is the reason you ever wanted to drive somewhere in the first place.So chase the big thing. Build it. Want more — there's nothing wrong with more.Just don't let the chase convince you that you're not already, right now, standing in a life worth being grateful for.The code may change. And it will. But our humanity is the constant.See you next week.— Mykel<hr><h3>📚 Sources</h3><ol><li>University of California, Berkeley (2025), reported via Fortune — AI does not reduce workloads; workers take on more and spend break time on additional prompting, raising burnout risk; ActivTrak analysis of 10,584 users found task time rose 27%–346% post-AI adoption. <a target="_blank" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80" href="https://fortune.com/2026/03/13/ai-isnt-reducing-workloads-its-straining-employees-time-spent-emailing-doubled-deep-focus-work-fell/">https://fortune.com/2026/03/13/ai-isnt-reducing-workloads-its-straining-employees-time-spent-emailing-doubled-deep-focus-work-fell/</a></li><li>Gerlich, M. (2025), AI Tools in Society: Impacts on Cognitive Offloading and the Future of Critical Thinking, Societies 15(1):6 — negative correlation between AI use and critical thinking via cognitive offloading; effect strongest in younger users (n=666). <a target="_blank" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80" href="https://www.mdpi.com/2075-4698/15/1/6">https://www.mdpi.com/2075-4698/15/1/6</a></li><li>MIT Media Lab, Your Brain on ChatGPT (Lee et al., 2025), summarized by EDUCAUSE — AI-assisted writers showed reduced memory retention and struggled to recall what they'd just written. <a target="_blank" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80" href="https://er.educause.edu/articles/2025/12/the-paradox-of-ai-assistance-better-results-worse-thinking">https://er.educause.edu/articles/2025/12/the-paradox-of-ai-assistance-better-results-worse-thinking</a></li><li>Harvard Business Review, AI-Generated "Workslop" Is Destroying Productivity (BetterUp Labs / Stanford, Sept. 2025) — 41% of workers encountered low-quality AI output, ~2 hours of rework per instance. <a target="_blank" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80" href="https://hbr.org/2025/09/ai-generated-workslop-is-destroying-productivity">https://hbr.org/2025/09/ai-generated-workslop-is-destroying-productivity</a></li><li>Harvard Study of Adult Development (Robert Waldinger, ongoing since 1938) — quality of relationships is the single strongest predictor of long-term happiness and health; loneliness as harmful as smoking. <a target="_blank" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80" href="https://news.harvard.edu/gazette/story/2017/04/over-nearly-80-years-harvard-study-has-been-showing-how-to-live-a-healthy-and-happy-life/">https://news.harvard.edu/gazette/story/2017/04/over-nearly-80-years-harvard-study-has-been-showing-how-to-live-a-healthy-and-happy-life/</a></li><li>Sonja Lyubomirsky, The How of Happiness / Harvard T.H. Chan talk — hedonic adaptation and the happiness baseline (~50% temperament, ~10% circumstances, ~40% intentional activity). <a target="_blank" rel="noopener noreferrer nofollow" class="text-[#4FD1C5] underline hover:opacity-80" href="https://hsph.harvard.edu/health-happiness/news/the-good-life-a-discussion-with-dr-robert-waldinger/">https://hsph.harvard.edu/health-happiness/news/the-good-life-a-discussion-with-dr-robert-waldinger/</a></li></ol>