Find people who've been there
Describe your situation. Get their perspective.
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Ask people who've done it.
Ask a quick question
I mess up once at work and suddenly I feel completely worthless
My shoulder's been aching for a week but I don't want to lose my lifting streak
Should I leave engineering for something that uses the rest of my brain?
I moved to a new city at 34 and don't know how to make friends anymore
I have no idea what to charge for a logo design and I'm afraid of pricing myself out
My instagram following has been stuck at 800 for two years and I don't know what moves the needle
People worth learning from
Nir on why we reach for our phones without deciding to“Your brain has learned that opening social media relieves a quick pang of boredom, loneliness, or uncertainty, so it now cues the habit before you consciously decide.”
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.”
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.”
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.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
Peter on taking back your evenings from your phone“I stopped checking messages after 6 pm and told my team to call twice if it was truly urgent; nothing broke, and I got ten hours back every week.”
Kyle on what revenue leaders look for when they hireHead of Revenue, Shopify Canada and grew Owner.com $3M to $21M ARR.
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.”
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.”
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.”
Peter on which AI tools are worth paying forLed product teams at Meta, Amazon, Roblox and publishes Behind the Craft episodes.
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.”
Kathryn on negotiating higher pay and getting it“I watched my own mom retire dramatically underpaid after 30 years, so I teach women to frame the ask around what they’ve already delivered and what they’ll deliver next, not just what they need.”
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.”
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.”
Guy on keeping customers from churningSold Brightback to Chargebee and CMO at Chargebee.
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.”
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.”
Real Life Situations
We spent $30,000 on a booth at a big SaaS conference. We came home with 400 badge scans, and most of them were students, vendors and people outside our market
Last week my director asked if I'd lead the team. That means less code and more meetings, and I've written code for nine years. How do I know if management is for me?
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?
My two senior analysts have been sniping at each other in meetings for a month, and now junior staff are picking sides. One filed a complaint against the other last week. I have to sit them down together and I don't know where to start
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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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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