Breaking Free from Perfectionism: 5 Lessons I Learned After Prison

Craig Stanland
3 min readSep 23, 2024

The “perfect” trap.

I’ve fallen head first and been trapped in it more times than I can count.

It sucks.

Ever since prison, I’ve had a much better handle on the perfectionism trap; the chaos of prison shatters the illusion of perfection very quickly.

Through this new perspective, I see how perfectionism showed up in my life, how it limited me, and how, at the end of the day, it’s nothing more than a foot soldier of fear.

My desire for perfectionism (and I believe so many of us are the same) was a desire for safety.

If I make something perfect, no one can judge me; they can’t criticize me, and I’ll be safe.

A few things I’ve learned about striving to be “perfect” as a former prisoner of perfectionism:

1. Perfect doesn’t exist.

Perfect isn’t objective; it’s subjective.

What’s “perfect” for one person is shit for another.

Not to mention, the part of me that strived for perfection would never let me reach it. I’d meet the initial “requirements, only to find that I could still do “better.”

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Craig Stanland

From corporate success to federal prison, I share my journey to rediscover joy, meaning, and purpose. Join me in reinventing your extraordinary second act!