What Leaders/Managers Can Learn from The Top Five Regrets of the Dying
Walter's assistant of nine years gave notice on an ordinary Tuesday, and the two of them ended up talking for an hour after the announcement instead of the planned ten minutes. She told him honestly that she had loved the work but had watched her own creative ambitions sit untouched year after year while she supported his. Walter drove home stunned, not because she was leaving, but because he realized how many of his own directs might be quietly making the same trade without ever saying so, and how long it had been since he had actually asked anyone what they wanted from their career rather than from this quarter.
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
Leading in a way that is actually yours
It is easy to lead the way your own first manager led you, or the way the org expects, without asking whether it reflects what you actually value. A leader who periodically checks whether their style still fits them, not just the role's expectations, tends to avoid a slow drift into a version of leadership they no longer recognize.
Some expectations of the role are simply non-negotiable, regardless of personal preference.
Name one leadership habit this week that reflects the org's expectations more than your own values, and adjust it slightly.
The colleagues and mentors who quietly fade
Professional relationships that once felt close, an old mentor, a peer from an earlier job, often dissolve through nothing but time and distance, not conflict. The loss tends to go unnoticed until you need that relationship again and realize how much has lapsed.
A genuinely demanding stretch of leading a team can leave little room for anything beyond it.
Reach out to one former mentor or colleague this week with no professional ask attached.
Working hard versus staying honest with your team
Constant availability can look like dedication, and it can also be a way of avoiding a harder conversation, about your own burnout or a decision you privately doubt. Both patterns grow slowly, without ever feeling like a deliberate choice.
Some weeks genuinely demand full availability, and that is not the same as avoidance.
Tell one direct report an honest limit this week instead of quietly absorbing it yourself.
The throughline beneath the role
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 contentment as something to earn later. For a leader, that is worth sitting with honestly, not a guarantee of what you personally will regret.
Leading on your own terms can mean pushing back on norms the organization expects you to uphold. Maintaining outside relationships takes time a demanding team will always compete for. Being honest about your own limits can unsettle a team that relies on your steadiness. These pulls tend to be strongest in the exact seasons when leading well matters most.
Name one thing, honestly
- Does your current leadership style reflect your own values, or mostly what the role expects? - Which mentor or colleague relationship have you let quietly lapse? - Where have you stayed available instead of naming a real limit to 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
Tell one direct report an honest limit this week instead of quietly absorbing it yourself.