What Entrepreneurs Can Learn from The Top Five Regrets of the Dying
Priti ran into an old college roommate at a conference, someone she had once talked to every day and now had not spoken to in six years. They caught up over coffee for twenty minutes before Priti had to run to a pitch, and the whole flight home she kept thinking not about the deal but about how easily an entire friendship had quietly disappeared under back-to-back launches and fundraising cycles. Nothing had gone wrong between them. She had just stopped making the call. That night she found herself listing the other things she had let slide the same way, promising herself she would fix them once the company stabilized, a promise she realized she had been making for years.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
Building a company that is actually yours
It is easy to shape a company around what investors, mentors, or a competitive market expect success to look like, rather than around what you actually want to build. A founder who occasionally checks whether the venture still reflects their own values, not just an investor's growth targets, tends to avoid years of quiet resentment even inside a successful company.
Some investor and market expectations are simply the price of raising capital, not something you can opt out of.
Write one sentence this week on whether your current roadmap reflects your own priorities or someone else's.
The friendships that fundraising crowds out
Old friendships rarely end in a single moment during a busy founder season, they fade through a hundred skipped calls and postponed catch-ups that each felt reasonable at the time. The loss usually only becomes visible much later, once the gap feels too wide to easily close.
A genuinely demanding raise or launch really does leave little bandwidth for anything else for a stretch.
Text one old friend today, no agenda, just to reconnect.
Working hard versus staying honest with your team
Founders often treat constant availability as leadership, and it can also become a way to avoid harder conversations, about burnout, a cofounder conflict, or doubts about the direction. Both patterns build up gradually, never announced as a decision.
Real crunch periods exist, and treating every hard week as avoidance would be unfair to yourself.
Name one honest thing to a cofounder or trusted advisor this week instead of working around it silently.
The throughline beneath the hustle
This book is not a research study, it is one caregiver's synthesis of what she heard repeatedly while sitting with people near the end of their lives. The regret beneath the others was that people had not let themselves be happy along the way, assuming satisfaction would arrive once they hit some future milestone. For a founder, that is worth sitting with now, not a fixed prediction about what your own exit will feel like.
Building a company on your own terms can mean turning down capital or advice that would otherwise accelerate growth. Protecting old friendships takes hours a demanding raise will always claim first. Being honest with your team about doubt can unsettle the confidence investors expect a founder to project. These tensions sharpen exactly during the seasons when the company most needs you.
Name one thing, honestly
- Does your current roadmap reflect your own priorities, or mostly what others expect from a founder? - Which old friendship have you let go quiet without meaning to? - Where are you staying busy partly to avoid a harder conversation with your team?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Name one honest thing to a cofounder or trusted advisor this week instead of working around it silently.