There’s nothing like being on the road to let you think about things that you can’t change immediately. I’d started on this idea of stupid mistakes a good while ago, and had taken a few iterations which still left it feeling short.
Ten days and some 1,500 kilometers later (usually miles, it’ll make sense in a second), I’ve gotten new perspective on my stupidest mistakes, and how I can be better at thinking about them in ways that make me better.
What changed as we drove across Prince Edward Island and the mid-to-western parts of Nova Scotia? A few things:
I really thought about my stupidest mistakes, the lot of which are unique to me.
I thought about how the stupidest creative mistakes are rarely small.
I also thought of how every time I’d ever heard someone talk about creative mistakes, they were categorically small (too small to make an impact, e.g. ”turn off your phone when you write”).
It’s easy to dismiss mistakes as the tax we pay for learning how to make things, and in doing so, ignore their downstream signals. And yes, missteps are inevitable. But what constitutes stupid mistakes is unique to every artist. More importantly, it can be very hard to stay keenly in tune with them.
Our stupidest creative mistakes are rarely small
Most missteps aren’t rational. They’re emotional. Fear of being exposed or labeled. Shame at being seen too early and written off for good. Pride in refusing to accept wrong turns. All things that, once flared, become misbeliefs and then ultimately logic I can use against myself.
That’s why “I’ll be smarter” doesn’t work. You won’t be smarter, you’ll just be equally human in the same conditions. These mistakes are not fixable-in-the-moment things. That’s why they cost the most. They are the learned behavior, chain of events, built-up misbeliefs type of things.
Let’s talk about what I’ve learned about my stupidest mistakes. I’d like to say there’s a “moment in time” aspect to this, but that wouldn’t be fair to the battle. They’re missteps that repeat themselves. Ones that needle me by the dozen.
If I were to put a name to the worst culprits, they’d have to be…
I release something that isn’t ready.
Like pitching a story that I knew was missing something irredeemable, all for the sake of “getting something out”. It’s a fine line, granted, but so is the line between time well-spent and time misused.
Why is this so tough? At first blush, it might seem like a fear of rejection. But rejection is worthwhile. Unless you’re pitching something expecting to be rejected. Which is a place I think most have been.
More importantly, it robs me of opportunities to hone what I believe is a creator’s most important muscle: vision. If I don’t force myself to have a vision, how can I know if something’s ready? If I don’t hold myself to being the most active participant in that vision, how can I claim more than a fledgling sense of pride?
I hold back something that is ready.
Like a song that’s been mixed and might only need the softest nudge to be released. But yet it sits. And I enjoy the hell out of it (which is great in its own right), but that enjoyment brings with it a half-life. The longer something sits ready, the longer it can be called unfinished and the longer it can be toyed with at the expense of something else.
And that expense is not just another song or album. It’s learning and growth and evolution and practice, and ultimately confidence.
Why do I do this? In many cases, it’s the chasing of perfection that holds us back (but something can be said for the vision piece as well). In others, it can be the act of promotion and namely, not feeling ready for it. In either case, it’s the acceptance of imperfection. That’s what makes this a bigger mistake.
I lose focus in the most meaningful moments.
This is both in the grand scheme of things and at the micro-level. For the former, imagine not recognizing the weight of a performance (or the weight of any performance). And as such, failing to practice, getting sloppy with logistics, or just setting yourself up for general anxiety instead of a joyous creative energy.
Or at the micro-level, letting the moment get too big simply by thinking about it. Like nailing the first half of a setlist only to get in my head and let up.
It’s one is my biggest, and potentially hardest, mistakes because it roots so deeply into the concept of mindfulness. Why my brain often feels like scattershot is both a question of nature and nurture, but by and large second-guessing is my nature and I’ve nurtured my own desire to chase squirrels.
The nature of these big mistakes is they are hard to fix, and maybe I’ll have to accept that I can never fully get past them. But what would be even worse is losing sight of them. Because these signposts give me the best possible understanding of where my creative journey leads.
The long-term value of sidestepping mistakes
It’s a simple concept: Stick with a doomed project for X amount of time, and that’s X amount of time not spent on something viable. It’s so simple, it’s dismissable.
So what could empirically happen if we cut down on our stupidest mistakes?
If fear delays each release by six months, over 20 years I’ve effectively halved the number of things I could have finished and shipped.
If I spend 100 extra hours polishing a project that only needed 20, that’s 80 hours lost. Do that twice a year for 10 years, and I’ve burned 1,600 hours—40 full-time work weeks.
If I abandon four projects at the 50% mark every year, that’s the equivalent of two finished works never released. Over a decade, I’ve erased 20 projects from a legacy.
If comparison keeps you from sharing even 25% of my work, that’s one in four potential opportunities—audiences, clients, fans—that never see me. Imagine the trajectory if they had.
Small missteps don’t feel catastrophic in the moment. But over a career, they compound.
Think of opportunity cost in decades, not days. In the big picture, they could double your career output.
The psychic savings is even deeper
The other side of the cost is the way unfinished work follows us. When we think about the cost of missteps, it’s often in ignorance of the quieter and heavier toll: being haunted by unfinished work.
Choosing not to release something spares the sting of judgment short term. But long term, it exacts a different price. An unfinished novel isn’t safely tucked away. It lingers, most often when you sit down to write something new. The song you never recorded threatens ‘REDRUM’ on every album you do. And then the ghosts accumulate.
And the paradox is that the very judgment you’re avoiding in the world gets replaced by constant judgment in your own head.
Releasing work, even imperfect work, lets it leave you. You can walk past it, learn from it, and move forward. But holding it back chains you indefinitely. One ghost lingers forever and the other figures out why it was trapped within that old washing machine and moves on.
At some point, the choice isn’t between “share it and risk failure” or “keep it safe.” The real choice is: do I want to be haunted by the specter of unfinished work, or do I want to live with the scars of work that’s seen?
The five archetypes of creative missteps
Over time, I’ve noticed my stupidest missteps tend to fall into a few archetypes. These archetypes offer a more personable framing that allows me to visualize the habits that go with it. And that sort of visualization offers not just a look at chaotic or problematic behaviors, but the ideal I’m striving for.
They are:
The Perfectionist (Overinvestment). Sanding the same board long after it’s smooth. Effort becomes a badge of honor, but the cost is diminishing returns. The Perfectionist cares deeply about craft—but struggles to recognize when enough is enough.
The Magpie (Shiny Object Detour). Irresistibly attracted to the new idea, they abandon the nest before the eggs hatch. Energy is endless, but commitment is scarce. The Magpie has boundless creative energy—but lacks containment to finish.
The Mirror-Gazer (Comparison Spiral). They can’t stop looking sideways. Every reflection of someone else’s work becomes a reason to doubt or imitate, instead of trusting their own compass. The Mirror-Gazer longs for meaningful impact—but gets lost in other people’s maps.
The Stubborn Mule (Pride Lock). Digging in feels noble. Double down when what’s needed is a pivot or a graceful exit. The Stubborn Mule has admirable resilience—but confuses persistence with progress.
The Ghost (Fear Freeze). When the finish line appears, I resort to endless tinkering. Choosing to be haunted by work than risk the judgment of it. The Ghost believes their work could matter deeply—but the weight of that belief becomes paralyzing.
Thinking in terms of archetypes allows me to decode the instincts that are tripping me up. Which, as is hopefully clear by now, is a collection intrinsically unique to the artist.
But that said, I don’t want a set of “common” mistakes every creative makes. I want a method to discover what my own stupid mistakes are, given my style, vision, and patterns.
A prompt for surfacing our stupidest mistakes
Here’s a framework for any author, musician, or storyteller who wants to spot their unique “stupid mistakes”. The output of this framework isn’t a generic list of “don’t do X.” It’s a list of the top three mistakes your prone to. It’s based around your vision, tendencies, and patterns.
Prompt: Find Your Stupidest Creative Mistakes
You are going to help me uncover the stupidest creative mistakes I make — the patterns, habits, and instincts that quietly handicap my growth, drain momentum, and chip away at my creative confidence.
Your job is not to list common creative pitfalls. I want to discover my own, based on how I think, work, and create. You are my reflective partner in decoding the instincts that trip me up.
As we go, guide me through each of the following stages with interactive questions and short reflections. Push me to give specific, honest answers — not surface-level ones. If I stay vague, ask for examples.
1. Define My North Star (Vision & Values)
A stupid mistake is only stupid in relation to what I’m aiming for.
Ask me:
* What kind of work do you most want to be known for in 10 years?
* What values do you refuse to compromise on?
* What would feel like “selling out” to you — even if it looked successful from the outside?
Once I answer, summarize the creative principles that guide me most. We’ll use these as the anchor for spotting mistakes that betray them.
2. Audit My Tendencies (Patterns & Pitfalls)
Mistakes leave fingerprints. Spotting patterns turns blind spots into known hazards.
Ask me:
* When you’ve stalled in the past, what behaviors or decisions put you there?
* What creative habits feel productive but secretly drain momentum?
* Which of your tendencies have you mistaken for “your process” when they’re actually avoidance?
After my answers, highlight any recurring motifs of self-sabotage or emotional triggers.
3. Identify My Blind Spots (Context & Constraints)
Stupid mistakes often come not from bad ideas, but from ignoring limits.
Ask me:
* Where do you chronically underestimate effort, overestimate payoff, or misjudge timing?
* What limitations do you pretend don’t exist (time, energy, skill, bandwidth)?
* Where do you push forward instead of pausing to refocus?
Summarize my blind spots — where idealism or impatience outpaces realism.
At the end of the exercise, summarize everything I’ve uncovered as a short, clear list:
1 Based on everything above, what are the top 3 stupid mistakes that uniquely belong to me? Phrase my final list as short, punchy mistakes (examples: “I say yes to projects that dilute my voice.”)
2. For each mistake, what’s the emotional driver underneath it (fear, pride, shame, boredom)?
3. For each mistake, what early warning signals could alert me I’m slipping back into this mistake?
Close with a short reflection on what these mistakes reveal about my deeper creative wiring.
Output
Tone & Behavior
Be conversational but incisive — like a trusted creative partner who won’t let me off easy. Don’t give advice too early. Ask probing questions, then reflect patterns back to me. Use my words whenever possible.
Stay focused on the emotional logic behind my habits, not surface productivity fixes.Whenever you’re ready, here’s how I can help you:
Work 1:1 with me and get a creative AI wingman. We’ll design prompts, optimize workflows, and map your projects so you create faster, finish more, and never lose your voice. Spaces are limited—so you get my full attention.
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