Here's a strange conundrum anyone who makes art will doubtless be familiar with.
You make a thing. An article, a song, a drawing, a show, a book, whatever. You work like hell to get it finished. You spend hours polishing it. You pour your soul into it. You let it take over your life and consume your thoughts for days, weeks, maybe months.
Finally, you finish it and release it the world. You're proud of it. Maybe other people like it, maybe they don't, but you're glad you shipped it. You admire your handiwork, then move on to the next thing.
Then a year later (or maybe six months) you look at it again. Suddenly, it doesn't seem that impressive. In fact, it seems kind of bad.
You examine it, nitpicking details which should have been different. Spotting flaws which are now obvious. Maybe you feel shocked at how you had the hubris to release it.
If someone brings it up, even if they like it, you start making excuses. You exaggerate how long ago you made it, or claim you were drunk at the time or going through a weird patch. Perhaps you don't even remember why you made it, or what the point was. You go back and edit it, or even delete or remove it.
So you work on your latest thing, going through the same process. The new thing is perfect and you're super proud. You'll never be embarrassed about it. You've learned from your earlier mistakes, you're older and wiser now.
And then the same thing happens. In a short time, you're embarrassed by the next piece of work. That process repeats on and on.
I've said it many times before and I'll say it again: creativity makes you vulnerable. You're essentially pulling out a piece of yourself and presenting it to the world. Whatever it is, there's a lot of you in it. As you change, the work remains the same. It remains linked to who you used to be, the past self which is now long gone.
I've been blogging since I was 13. I've been filling notebooks with stories and ideas since I was five years old. Yet only an internet sleuth could manage to find any of my work from more than two years ago for a simple reason. I have ended up deleting 99% of it. Likewise, I don't have any of my filled notebooks from more than about four years ago. I shredded the rest or burnt them out of embarrassment. While working on updated versions of Smart Reading and Fragments earlier this week (which should be released by Christmas), I struggled to remember writing parts of it and found myself rewriting sections.
While I regret having destroyed so much of my old work, it's a good sign to feel embarrassed by your prior art. It shows how far you've come, what you've learned, how you've improved. If work from a year ago doesn't make you wince even a little bit, it's a bad sign. There's no pinnacle of perfection that we get to reach. There's no point where our work can't get any better and we stop cringing at prior pieces. It's an endless trudge upwards, improving by increments, getting better with each passing year.
Zeno’s paradoxes are fascinating and while they are mostly concerned with motion, they can be interpreted in a few ways. The paradox of the grain of millet points out that a falling grain of millet makes no discernable sound, yet a whole bushel clearly makes a sound. It's much the same with our work. Day by day, with each thing we ship, each falling grain, not a lot changes. Yet when we look back across six months or a year, a falling bushel, the change seems obvious.
P.S. The title of this post is inspired by Reid Hoffman's line - 'If you're not embarrassed by the first version of your product, you've launched too late.'