What Career Professionals Can Learn from The Top Five Regrets of the Dying
Renee hit her fifteen year work anniversary the same week a networking app surfaced a message from a college roommate she had not spoken to in years, congratulating her on a promotion. She stared at the message for a while before replying, then noticed she could not remember the last time she had reached out to anyone from that part of her life first. That night she pulled out an old planner from a drawer, flipping through years of meetings and deadlines, looking for evidence of the person she used to be outside of work. She found some, but less than she expected. She was not unhappy exactly. She was just quietly aware that fifteen years had gone by according to someone else's calendar, and she had rarely checked whether it was also going by according to hers.
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 career on your own terms
It is easy to follow a career path built from a series of individually reasonable decisions that never add up to a life you actually chose, because each step looked sensible at the time. A professional who periodically checks whether the current role still reflects their own priorities tends to catch drift early, while it is still easy to correct.
Momentum and sunk cost make it genuinely hard to change direction once a path is underway.
Once a year, write one paragraph on whether this job still fits the life you actually want.
The friend who becomes a contact
Professional life is full of relationships that feel close at work and then quietly stop the moment a project ends or someone changes companies, replaced by an occasional online reaction instead of an actual conversation. The friendship does not end in conflict, it simply stops being tended.
Professional contact can feel enough like real connection to excuse never following up on it.
Message one former colleague this week and ask how they are actually doing.
Working hard versus being honest at work
Staying late can be a genuine investment in your career, and it can also become a habit that avoids a harder conversation, about a role that no longer fits or a disagreement you have been avoiding. Both patterns tend to grow slowly rather than by any single choice.
Overwork is visible and praised, while honesty about doubt rarely earns the same credit.
This week, say one true thing in a meeting that you would normally soften.
The throughline beneath the resume
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, treating satisfaction as something to earn once the career finally settled. For a professional, that is worth sitting with honestly, not a fixed prediction of your own future regrets.
Choosing work that fits your values can mean turning down a promotion others would take without hesitation. Protecting friendships outside the office takes time a demanding role will always claim first. Being fully honest at work can slow decisions that a fast-moving team needs made quickly. These trade-offs rarely resolve cleanly, and most careers ask you to feel all three at once.
Name one thing, honestly
- Does your current role still reflect what you actually want, or momentum from years ago? - Which colleague turned friend have you let fade into an occasional online reaction? - Where have you chosen to keep the peace at work instead of saying something true?
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
This week, say one true thing in a meeting that you would normally soften.