Five Prolific Creators Who Struggled with Procrastination

The procrastination monster is real — and it can be defeated.

Jack Calhoun
5 min readJun 17, 2022
Photo by Brett Jordan on Unsplash

It’s good to have role models.

No matter what stage of life we’re in, there are always people out there doing things we admire and that we aspire to do ourselves. Role models give us the blueprints to do the things they’re doing, which motivates us and saves us time and frustration.

But here’s the mistake we often make when choosing which folks we want to model ourselves after: We pick out people who are nothing like us. The ones who embody the characteristics and attributes we wish we had, but don’t.

For our role models to be effective, it makes a lot more sense to model the people who are a whole lot like us. The ones who’ve struggled with the same demons we do, yet still managed to reach levels of success we’d like to attain ourselves.

So for chronic procrastinators like me (and, since you’re reading this, I assume like you), we can take inspiration from successful, accomplished people — some present, some past — who have also fought the procrastination monster and managed to defeat it, or at least keep it on a leash.

Here, then, are five such creators, all of whom have confessed (or were known) to have struggled…

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Jack Calhoun

20+ years as managing principal of a wealth advisory firm. I write about the principles of sound investing, the solopreneur life and the wisdom of experience.