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Ask a quick question
What do you wish you knew before having your first child?
I replay the same conversation in my head for hours after it's over
My instagram following has been stuck at 800 for two years and I don't know what moves the needle
My best performer has been missing deadlines for two months straight
I sell used phones on facebook marketplace and my listing photos look like everyone else's
My ex wants to stay friends and part of me wonders if that's just a slower breakup
Ask the experts
Lorraine on getting noticed for your work“Doing great work doesn’t guarantee recognition. Make your impact easy to explain so people can advocate for you when you’re not in the room.”
Guillermo on building Vercel and Next.js“The best things we've done for our brand is the things that we did without thinking we're working on our brand.”
Nick on metabolic health, nutrition, and brain healthHarvard MD, Oxford PhD, Dartmouth valedictorian and #2 Science Bestseller on Substack.
Omar on what to figure out before quitting for a side project“I went all in only after my side hustle matched my salary on half the hours, because once it had legs, the real unknown became whether I could build systems instead of just doing the work myself.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
Lin on scaling computeRaised $300M+, incl. $250M Series C and led PyTorch team at Meta.
Pedro on where machine learning is headed“The same basic paradigms have been used since the 1950s. At the end of the day, we’re going to need some new ideas.”
Lenny on breaking into product management“A few paths actually work. The safest is transitioning internally, partnering closely with a PM until you can make the case. The second is joining an early-stage startup where everyone does everything. Regardless of path, become the person who deeply understands the customer and can translate that into product insight.”
Moses on making it to the top when you started with nothing“I had love for the game, parents who kept me grounded, and a city that taught me how to compete. What kept me going was consistency and curiosity. You control what you can control, stack good days, and let the game reward you when it's time.”
Tim on picking investors for a first raise“Start with angels and seed funds who actually write checks at the idea stage, because most VCs won't touch you until you have traction or a warm intro.”
Jessi on deciding what comes first when everything is urgent“I learned in hospice that when everything feels urgent, the first thing is to steady my own nervous system so I can see what is actually life-or-death and what only feels that way.”
Céline on protecting your health in a noisy information world“I protect my health the same way I protect my patients: by curating my information diet the way I curate my food. I go to the source, I follow people who've been right before and correct themselves when the evidence changes, and I stay open to changing my mind. Certainty that cannot bend is not strength; it is a vulnerability.”
Codie on buying businesses and building wealth“You don’t need a revolutionary idea to build wealth. You need a business people already pay for, and the skills to run it better.”
Vanessa on sexual expectations couples never say out loud“I don't believe in a universal normal for any stage, but I do think it's completely natural for that early honeymoon frequency to taper off after about a year.”
Andrej on how far we are from AGILed Tesla Autopilot computer vision team and founding member of OpenAI.
Alastair on handling a teammate who undermines you in meetings“I would name the pattern in private first: I noticed you agreed in the room, then raised concerns afterwards. If you disagree, raise it in the meeting so we can deal with it straight away.”
Spencer on life inside an NBA organization“I used to think pushing past your body meant toughness, but the league taught me that the hardest skill is staying on the floor.”
Julie on becoming a better manager“Your job as a manager is to help other people do great work. Start by understanding what’s getting in their way.”
Nyree on why you crash at 2 p.m. after a full night's sleep“Eight hours in bed means nothing if your brain never entered deep restorative sleep, and by 2 p.m. your adenosine tank is still full from incomplete overnight clearance.”
Jeffrey on why treating symptoms is the wrong place to start“Symptoms are late signals, not first causes. In chronic illness the biology starts drifting years before a diagnosis. If you start at the symptom, you are downstream. You may mute the alarm without finding the fire. The body is a network, so ask what shifted in the person's story and physiology that made the symptom possible, then address that.”
Ask about real life
My 15 year old son used to tell me everything. Since he started dating his girlfriend six months ago, he barely looks up from his phone when I talk to him. I don't know if this is normal or if I'm losing him
We always said we'd get married. Then he doubled his income and suddenly wants to wait a little. When I out-earned him early on, I never once hesitated
I have $22,000 left on my mortgage at 3.2% interest and $22,000 in a savings account earning almost nothing. My advisor says the market averages 8% a year but I hate carrying debt into retirement in five years. Do I wipe out the loan or put it to work in the market?
I've played soccer for eight years, all through school. Practice is three nights a week now and I dread every one of them. My parents keep saying I'll regret quitting senior year. Do I owe this sport anything at this point?
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Top perspectives
Top perspectivesHappiness scientist · Professor at Vanderbilt & Harvard Business School
“What you're describing is the arrival fallacy: the belief that hitting a goal will finally deliver fulfillment, and the letdown when it doesn't. The emptiness is actually useful information.”
Director, Harvard Study of Adult Development · Author of The Good Life
“You've reached the top of the ladder and found it was leaning against the wrong wall. The Harvard Study shows people who chase wealth, fame, and image often feel worse after reaching those goals, while those who pursue relationships and meaning feel better. The emptiness is information.”
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I've hit all my career goals but I feel strangely empty and unfulfilled.
That's the arrival fallacy: the goal was a proxy for something deeper. Audit your goals against three tests. Are they non-zero-sum, approach-oriented, and non-positional? If they were mostly about status or winning, that explains the hollow feeling.
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