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Ask people who've lived it
Ask a quick question
I sell used phones on facebook marketplace and my listing photos look like everyone else's
My ex undermines every rule I set and our daughter is caught in the middle
I've wanted to start a podcast for a year but I don't know if anyone would listen
Everyone on my team is more competitive than me and it's stopped being fun
My daughter quit soccer because she thinks she's the worst, and I don't know how to parent through it
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.”
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.”
Vinod on which jobs AI will replaceLed KV's first OpenAI investment and juniper Networks: 2,500x return.
Suzanne on what happens behind closed doors in a layoff“I've personally been involved in laying off well over a thousand people, and the part no one talks about is how fast the dignity gets stripped away: one minute you're trusted, the next a manager you've never met is reading you a script while someone cuts your computer access.”
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.”
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.”
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.”
Deena on raising venture money as an underestimated founder“Do your homework on who you're pitching. Most founders spray and pray, but that wastes everyone's time. And bring your full self to the conversation. The intersectional, the immigrant, the nontraditional founder, those backgrounds are not weaknesses. They're edges. The data shows diverse founding teams build better businesses. But you have to own it.”
Soleio on designing products people love“Good design starts with knowing what matters. If your team can’t agree on the problem, polishing the interface won’t fix it.”
Julian on using a system to curb phone distractions“I don't try to restart at full speed; I drop back to the mínimo viable version of each habit until the momentum returns, because a 20-minute workout and one focused block on the side project beats another day of zero.”
Andrej on how far we are from AGILed Tesla Autopilot computer vision team and founding member of OpenAI.
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.”
Jim on enjoying competition when teammates are more intense“I stopped enjoying baseball when I was chasing what everyone else valued, and I found my game again only when I started competing to raise my own level, not to beat theirs.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
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.”
Joshua on hiring an operations manager before you feel ready“Hiring my first employee scared me because it felt like a massive expense, but I learned your first hire should be operations, not another you.”
Madhavan on pricing for profitable growth“Don’t build a product and then ask what to charge. Find out what customers will pay for before you decide what to build.”
Tiago on turning knowledge into action“Saving information isn’t the goal. Organize it around what you’re trying to accomplish, so the ideas you collect become things you actually create.”
Lin on scaling computeRaised $300M+, incl. $250M Series C and led PyTorch team at Meta.
Ask about real life
My college roommate and I used to talk every day. Now it's been four months since she answered a text. I keep replaying our last conversation looking for what I said wrong
They want me to run the team. First time managing anyone. I've watched brilliant people turn into bosses everyone quietly dreads and I refuse to be that
Our CEO demoed an AI agent doing half of what my design team does in a day. Nobody has said layoffs, but I've seen the budget slides. Do I retrain now or wait to see if it's real?
One of my reps used to hit 120% of quota, every quarter. Last quarter he hit 60% of quota, and when I asked what's going on he just shrugged. I don't know if he's burned out, dealing with something at home, or just done with the job. Do I coach him or start building a case to let him go?
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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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Their Delphi, answering in their voice
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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