What Creators/Innovators Can Learn from The Top Five Regrets of the Dying
Simone was cleaning out a storage unit before a move when she found a box of paintings from her twenties, before she pivoted to the commercial illustration work that now paid her bills reliably. She sat on the concrete floor going through them, surprised by how much she liked the strange, unsellable ones. She had told herself for years that she would return to that kind of work once client projects allowed for it, and there had always been another client. That evening she scrolled through her portfolio site, full of polished, on-brand pieces, and could not find a single thing in it that had surprised her to make. She was not ashamed of the work. She just noticed, clearly for the first time, how long it had been since she made something purely because she wanted to see what would happen.
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
Making the work you actually mean
It is easy for a creator to follow whatever sells or gets attention until the body of work no longer resembles what first made them want to create. A creator who periodically checks whether current projects still reflect their own intentions tends to avoid years of quietly polished but hollow output.
Paying work rewards consistency, and consistency can slowly crowd out the riskier ideas worth pursuing.
Once a season, make one small piece purely for yourself, with no client or audience in mind.
The collaborator who fades from view
Creative partnerships often burn bright during a project and then go quiet once it ships, with both people assuming they will reconnect once the next thing starts. The next thing usually starts before that reconnection happens, and years pass.
Project-based work gives relationships a natural end point that is easy to mistake for a real one.
Message one past collaborator this week just to see how their work is going.
Working hard versus creating honestly
Long hours can look like dedication to the craft, and they can also be a way to avoid the harder, more honest work of admitting a project is not working or that your real interests have shifted. Both patterns build slowly, without ever feeling like a choice.
Busyness is easy to mistake for progress, especially when a body of work is genuinely growing.
This week, write one honest sentence about what you actually want to be making next.
The throughline beneath the portfolio
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 fulfillment as something the next project would finally deliver. For a creator, that is worth sitting with honestly, not a guaranteed forecast of your own future regrets.
Making work that reflects your real intentions can mean turning down paying projects that would otherwise fund your life. Protecting collaborator friendships takes time a deadline will always claim first. Being honest about creative doubt can undercut the confidence a client or audience expects from you. These pulls tend to sharpen precisely when a project is most demanding.
Name one thing, honestly
- Does your current body of work still reflect what first made you want to create? - Which past collaborator or creative friend have you let drift since the last project ended? - Where have you performed confidence recently instead of admitting real uncertainty about the work?
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, write one honest sentence about what you actually want to be making next.