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Ask people who've lived it
Ask a quick question
I open my laptop to work and thirty seconds later I'm somewhere else entirely
Why do I feel guilty every time I sleep in on a weekend?
How do we pay down technical debt when every sprint is full of urgent features?
I moved to a new city at 34 and don't know how to make friends anymore
I say yes to everything, then resent everyone who asked
I want to build a personal brand but I don't know what I'd even be known for
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.”
Kirsten on understanding what consumers want“Before you ask whether the market is big enough, ask what’s changing in people’s lives. The best opportunities start there...”
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.”
Lin on scaling computeRaised $300M+, incl. $250M Series C and led PyTorch team at Meta.
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.”
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.”
Kit on cutting a huge to-do list to three big things“I used to write forty-item lists and call it ambition, but it was just avoidance dressed as hard work.”
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.”
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.”
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.”
Stanley on finding initial traction“Your first customers don’t need a scalable solution. They need their problem solved. Do it manually until you understand what’s worth building...”
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.”
Peter on which AI tools are worth paying forLed product teams at Meta, Amazon, Roblox and reddit product 0 to 1M+ users.
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.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
Jim on learning faster and remembering more“Before you decide you’re bad at learning, look at how you’re learning. Give yourself a method, remove distractions, and practice recalling what matters.”
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.”
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.”
Grant on growing an AI startup“When growth stalls, doing more of the same won’t save you. Sometimes your small team needs to make one bigger bet.”
Ask about real life
Our company has reached $1 million in annual revenue, but I still handle the biggest sales calls, product decisions, and customer escalations myself
I’m interviewing a candidate for our first engineering leadership role, and they sound impressive, but I can’t tell whether they’ll enjoy writing code with a team of four
A client of six years just called demanding a full refund for work we finished months ago. She's threatening a bad review if I don't comply. I want to stand my ground but I'm scared of what it'll do to my rating
I've been quoting hourly rates for freelance logo work, usually around $35 an hour, but a client just told me a competitor charged them $2,000 flat for the same scope. Now I don't know if I've been undercharging for years or if flat rates are just a different game entirely
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Top perspectivesPsychology professor, Arizona State · Author of Influence
“Networking freeze usually comes from self-focus, not social failure. Prepare one genuine question and one small piece of value you can offer. That shifts your script from “Will they like me?” to “How can I be useful to this person?””
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Their Delphi, answering in their voice
I freeze up and go blank when I meet new people at networking events.
Freezing is usually a planning problem, not a personality problem. Before the event, write down three openers and three bridge questions, then lower the stakes by practicing on baristas and neighbors first.
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