What Coaches/Mentors Can Learn from The Top Five Regrets of the Dying
Darnell had spent the morning helping a client map out a five year plan when his phone buzzed with a message from someone he had mentored a decade earlier, now thanking him for advice he barely remembered giving. He felt genuinely glad, and then, oddly, a little hollow. He spent his days helping other people get honest about what they wanted, yet he could not remember the last time he had done that exercise for himself. That evening, instead of prepping tomorrow's sessions, he sat with a blank page and tried to answer his own standard first question, what do you actually want your life to look like in five years. It took him longer to answer than he expected, and the answer surprised him more than he would have guessed.
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
Coaching from your own values
It is easy for a coach to help everyone else reflect on their life direction while quietly avoiding the same exercise, because the role itself can feel like enough self-examination by proxy. A coach who periodically applies their own questions to their own life tends to coach with more honesty, not less.
The emotional labor of a full client schedule leaves little energy left over for your own reflection.
Once a season, sit with your own signature question and write down a real answer.
The peer who stays a professional contact
Coaches and mentors often build wide networks of respectful professional relationships while letting the ones that could have become real friendships stay surface level, assuming there will be time to deepen them later. That time rarely gets scheduled on its own.
Professional respect can feel like enough connection, which quietly excuses never going deeper.
Invite one peer or former mentee to an actual conversation with no professional purpose.
Working hard versus being honest about your own limits
Taking on more clients can be a genuine expression of care, and it can also become a way to avoid admitting you are stretched thin or unsure about your own direction. Both patterns build gradually, without ever feeling like a deliberate decision.
A full calendar is often mistaken for proof that everything is fine.
This week, tell one trusted peer something true about your own current uncertainty.
The throughline beneath the sessions
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 arrange later once the work was done. For a coach, that is worth sitting with honestly, not a fixed prediction of anyone's future regrets.
Applying your own values to your own life can mean turning down billable hours to protect the time it takes, which is a hard trade to make when income depends on saying yes. Deepening a peer friendship competes with a schedule already full of client sessions. Being honest about your own limits can unsettle the confident image clients expect from you. These pulls tend to be strongest during exactly the seasons when your practice is busiest.
Name one thing, honestly
- When did you last answer your own signature coaching question honestly, for yourself? - Which peer relationship have you let stay purely professional when it could be a real friendship? - Where have you hidden your own uncertainty behind a confident professional role this month?
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, tell one trusted peer something true about your own current uncertainty.