What Sales/Customer-facing Professionals Can Learn from The Top Five Regrets of the Dying
Angela closed her biggest deal of the year on a Friday afternoon and drove home expecting to feel elated. Instead she found herself thinking about a client from years ago who used to end every call asking about her weekend before getting to business, someone she genuinely liked and had lost touch with once he changed companies. She realized she now treated almost every relationship, personal and professional, with the same practiced warmth she used on a call, friendly but slightly managed, never quite off script. That weekend, having coffee with her sister, she caught herself doing it again, steering the conversation smoothly instead of just sitting in it. She put her phone away and asked her sister a real question, one with no next step attached, and noticed how unfamiliar that felt.
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
Selling in a way that fits your own values
It is easy to let a target-driven job slowly reshape how you treat people, including outside of work, until warmth becomes a technique rather than something genuine. A salesperson who periodically checks whether their approach still reflects their own values tends to build relationships, client and personal, that actually last.
The skills that make you good at the job can make it hard to tell real connection from practiced rapport.
This week, have one conversation with someone you care about with no agenda or ask attached.
The client who becomes a memory
Sales work is full of genuinely warm relationships that end the moment a deal closes or a contact moves companies, with both people assuming loosely that they will stay in touch. They rarely do, without real effort on both sides.
The relationship's structure, built around a transaction, gives it a natural end point that is easy to mistake for a real one.
Reach out to one former client or contact this week purely to see how they are doing.
Working hard versus staying honest with yourself
Chasing quota can be a real source of pride, and it can also become a way to avoid admitting that the pace is unsustainable or that a role no longer fits. Both patterns build slowly, without ever feeling like a single decision.
Results are easy to measure, while honest doubt about the pace rarely gets tracked at all.
This week, tell one trusted colleague something true about how the pace is actually affecting you.
The throughline beneath the pipeline
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 the next win would finally deliver. For someone in sales, that is worth sitting with honestly, not a guaranteed forecast of your own future regrets.
Staying true to your own values can mean pulling back from a pace your targets reward. Protecting relationships that outlast a deal takes effort a full pipeline will always compete for. Being honest about the pace can undercut the confident energy the job rewards. These pulls sharpen most exactly at quarter end, when the job asks the most of you.
Name one thing, honestly
- Where has practiced rapport quietly replaced real connection in your life, at work or outside it? - Which former client or contact have you let become just a name in your history? - Are you pushing this hard because you want to, or because stopping feels risky?
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 colleague something true about how the pace is actually affecting you.