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Describe your situation. Get their perspective.
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Ask people who've lived it
Ask a quick question
My cofounder and I are about to split equity and neither of us wants to bring up the numbers first
My son ignores me the second I ask him to do anything
What do you wish you knew before having your first child?
I'm burned out but I can't afford to quit my job
My shoulder's been aching for a week but I don't want to lose my lifting streak
My portfolio has ten projects but recruiters still skip past it in ten seconds
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.”
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.”
Stanley on turning a scrappy experiment into a public company“We saw a macaroon shop in Palo Alto with orders they couldn't fulfill, so we built a static HTML site with a phone number and took orders by hand. The scrappy part isn't a phase you graduate from; it's a discipline. You automate after you understand the problem deeply, not before. Change everything except the mission if the data says so.”
John on Building a differentiated business“When you can’t outspend your competitor, give people a reason to choose you that money alone can’t buy.”
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.”
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.”
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.”
Kirsten on how AI changes what consumers buyTime 100 Most Influential People and dollar Shave Club sold for $1B.
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.”
Guillermo on building Vercel and Next.js“I want people to write these verification loops because it's gonna give me conviction in the product that it'll deliver to my customer.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
Alisa on growing from founder to CEO“The habits that made you a successful founder can become your biggest obstacles as CEO. Growth starts with seeing how others experience you.”
Kevin on two months of runway and what to do next“I spent 14 months in the desert with Circles and almost every time I thought a breakthrough was coming, it wasn't, but staying in the game turned out to be the whole game.”
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.”
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.”
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.”
Vinod on which jobs AI will replaceLed KV's first OpenAI investment and juniper Networks: 2,500x return.
Nick on metabolic health, nutrition, and brain healthHarvard MD, Oxford PhD, Dartmouth valedictorian and #2 Science Bestseller on Substack.
Ask about real life
Every time I rebuild my morning routine, one bad night's sleep knocks it out and I don't restart for weeks. The last one ran 11 days. I keep planning bigger ones. What would make a routine survive a bad day?
We laid off part of the team last month, and now the remaining employees agree with everything I say in meetings but raise concerns only after I leave
Our board wants an AI strategy by next quarter. I've watched three hype cycles, and this one has real revenue behind it, but so did the last bubble. How much of our budget do we put into AI?
We launched a new feature yesterday, traffic tripled, and checkout now times out for some customers even though all our staging tests passed
More on Delphi
The experience of one life should help another.
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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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Go beyond reading or watching. Ask their Delphi a question, bring your own context, and follow the ideas that matter to you.
Explore a different angle, ask why, or dig into how something applies to your situation.
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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