A long, long time ago, playing with a cassette tape player in my friend Mike's suburban basement, I figured out that I can't stand the sound of my own voice.
I think we were recording ourselves doing half-remembered Monty Python sketches (I remember the Spanish Inquisition as a particular favourite), and needless to say as we recorded we assumed we were breathtakingly funny. We were strange teenagers, after all, and we understood these strange and weird bits so well. How could it not be amazing?
Well, I won't debate the comedic worth of what we did. (Mercifully, that magnetic tape has no hope of being found in listenable condition.) What really hit me, as we played the tape back, was the fact that my voice was so unexpectedly nasal and awful. I couldn't stop thinking about it, analyzing it, trying to hear the sound in my own head the way it had come out of the tape player so I could stop it sounding that way.
That's exactly how you should feel about your past work.
Especially the work in your book.
I'm not talking about excuses – blaming various imperfections on client, account or production interference, budgetary woes, or the failure of the satellite to deploy. (Yes, my partner and I had a great idea killed because a telecommunications satellite didn't reach orbit and crashed.) Anything that's been so dreadfully affected by such things probably shouldn't be in your book anyway.
I'm talking about the work that you've put in the front of your book thinking it was the best thing you'd ever done. The work that got you jobs. The work that got you awards.
How could you have made that work better?
If you're any good at this creative thing we do, and sure as hell if you want to get better, you have to face that question.
Me? I cringe at almost everything I've done – stuff that's been at the front of my book, done really well for clients, even won awards. I can't look at it without thinking about what I'd change, what if I'd tried harder at that headline, how could I have looked at it from a different point of view. And I try like hell to apply those lessons to what I'm doing today. That's the only way I know for my work to get better.
Yes, as that great creative director Crash Davis once said, you have to play this game with fear and arrogance. That's just as true when standing in front of the client or your account team, as it is in front of a nasty fastball pitcher who likes to throw inside. That's for the show.
Inside your head, as you stand in the batting cage or hunched over your keyboard, you think about all the people who can do it better, and you analyze and try different things and make tons of mistakes and, slowly but surely, you learn.
You get better.