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The Art of Winging It
Plus: My Psychoanalysis, Waffles and Shopify
Blake Bottrill
April 14, 2025
Some weeks it’s abundantly clear what I’m going to write about. This isn’t one of those weeks.
I heard someone say on a podcast last week that inspiration is perishable. That if you’re struck with an idea, you have to act on it now, before it decays in the fridge like those $7 blueberries you swore you were going to add to oatmeal every morning. I have a 9 month old vacuum that eats mine now, so no wasted blueberries!
That’s usually how these newsletters get written. This right here? This is me winging it.
The Art of Winging It
I actually think winging it is underrated.
Not in high-stakes surgery. Not when assembling IKEA furniture with a toddler nearby. But in most creative endeavours? “Wandering”, as Bezos calls it, is the point.
You don’t schedule your best ideas. They sneak up on you while folding laundry, or peeing, or having a borderline existential moment in the frozen foods aisle.
David Ogilvy had a much classier take:
“Big ideas come from the unconscious. This is true in art, in science and in advertising. But your unconscious has to be well informed, or your idea will be irrelevant. Stuff your conscious mind with information, then unhook your rational thought process. You can help this process by going for a long walk, or taking a hot bath, or drinking half a pint of claret. Suddenly, if the telephone line from your unconscious is open, a big idea wells up within you.”
So… Winging it is not lazy. Winging it is faith. Faith that something worthwhile might emerge if you feed your subconscious enough high quality inputs.
Stillness Is Not My Strong Suit
There’s been a quiet theme trying to break through my dopamine-clogged skull this week: slow down. Snippets from books. Conversations with friends. Even ChatGPT psychoanalyzing me with unsettling accuracy:
“You crave momentum not because you’re impatient — but because stillness is existentially threatening. Stillness feels like stalling. Stalling feels like regression. And regression feels like death.”
...Cool cool cool.
And yet, it hit hard because it’s true. I’ve built a life that objectively works. My family is healthy. Work is fulfilling. My mind is much quieter than it was in my 20s.
And yet I still wake up some mornings feeling like I’m behind on an imaginary scoreboard that only I can see. My only solace is that I’ve studied enough evolutionary psychology to know that this is totally normal.
Parenting Is 113% Winging It
If there’s one domain that shatters your delusion of control, it’s parenting. I’ve learned probably about as much in 9 months of fatherhood as I did in 9 years of self-improvement.
And most of that learning has been retrospective. I didn't plan the right thing. I accidentally did it and then hopefully took notes.
The best moments of my life didn’t arrive because of meticulous planning or perfect routines. They arrived when I stopped trying to wrangle the universe, or a crawling baby, into compliance.
The Real Challenge? Enjoying It While It’s Good
The tension I wrestle with, and you probably do too, is this:
How do you stop white-knuckling your way through “the good old days” while they’re still happening?
There’s a part of me that’s always trying to “optimize” the moment instead of living it.
What’s the best use of this 45-minute nap window?
Should I be journaling this memory before it fades?
Can I speedrun meaningful family connection before the bedtime routine starts?
It’s like trying to enjoy a sunset while adjusting the aperture settings on my camera.
Sometimes… I should just watch the damn sunset.
Words I Wish I Wrote
“You have been assigned this mountain so that you can show others it can be moved.”
Links & Learnings
Now that ChatGPT has access to memories across all chats I asked it to psychoanalyze me based on everything it knew about me. It got weird. But, also kinda scary accurate.
The Wednesday Waffle.
CEO Tobi’s memo on AI at Shopify.
Psst… DSTLLD has a podcast now, too. I know — like the world needs another podcast, right? But here’s the thing: if you can tolerate my written rambles, you’ll probably find my in-person yammering… well, moderately tolerable. It’s basically me and a guest chatting about the same offbeat stuff you read here, except now you get to hear me stumble over big words in real time. I’m not saying it’s the greatest thing in the universe (trust me, I’ve listened to it), but if you like DSTLLD, there’s a good chance you won’t hate it. Win-win! Subscribe or follow on your favourite podcast platform:
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PHOTW: Create a line item in your budget strictly for raspberries.
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