Fear & Failure in Dallas

A writer I follow, Yuvi Zalkow, is promoting his book this week, and he issued a challenge of sorts for other writers and creators to share their stories of fear and failure as he girds himself for the reviews and sales figures. Normally, I don't actually follow writing challenges, but I figured that the concepts of fear and failure are already talked about on this site enough that you wouldn't mind or even notice.

I thought about some of my failures. My first website that I built for a paycheck was a total failure. It never launched, so I can't point to an archive, but I will tell you that it involved the background image of a beach and small stones that were used for navigation with rollover effects in all their mid-2001 DHTML glory. It was horrible, and I honestly thought it was “groundbreaking”. When I fully realized how unusable and uninspired it was, I questioned if I had any right to build websites at all.

If I'm being completely honest, the first year or so of Vintage 56 was a year of bigger failures. The company survived, so the year itself wasn't a total failure, but I know that my part in it involved lots of medium-sized failures. I wasn't a good businessman, I got distracted by the (very minor) glory of being a creative director, and I almost permanently burned a lot of relationships along the way. I think we've all made up now, but that doesn't mean I didn't fail.

As bad as that failure was, though, talking about it didn't make a very interesting article, so I started thinking about my fears. I'm afraid that I won't deliver what I promised on every single project I take. I'm afraid that I'll fail as a business owner when I can't make a profit, I can’t make payroll, or I even have to lay people off (I don't actually have employees, yet). I'm afraid that I'll turn out to be a bad husband or father because I didn't always have the best example. Like everybody else with any ambition, I'm just afraid of failing.

Looking at that list, though, my most obvious fears are pretty boring and only worth talking about over a bottle of Scotch to my closest friends. I wanted to write something deeply honest, so I kept brainstorming until I realized one of my fears that I almost assume will happen: I'm afraid that I will never enjoy success. I'm not just afraid that I'll never be successful (though that's there), but I'm afraid that even if I have success I'll never see it because I'll be too locked into my ongoing roller coaster of feelings about what I make:

  • Every new idea I have starts with fear. I'm still thinking of the last thing I shipped, which has now become a model of execution and delivery in my head. If it was good, then it was my peak, and nothing I produce from now on will ever be any good by comparison. If nobody liked it, then I'm only proving the point that the best is far behind me. In either case I'm afraid that the next thing will fail.
  • As I dive in, I start liking it more. The more I whittle it down and tweak it, the more I can see it is actually better than what I've done before. I start to love it, and I keep working on it until I decide it's officially done. If it's an article, I do a last edit and post it. If it's a chapter, I proofread it and send it to the editor. If it's a design, I'll finalize everything and send it to my team. Whatever it is, I have to commit while I love it and before I start second-guessing all of my decisions.
  • Immediately after launching or posting, I start critiquing everything and finding things I could have done better. I decide that it wasn't that good, and I was foolish to launch. I'm afraid that my client/editor/readers won't really like it, and I become convinced that anybody who says they like it is just slow-clapping.
  • As time goes on after the launch, I start to separate myself from it, and I began liking whatever it was in retrospect. This feeling keeps rising until I’ve idealized it in my memory and the shadow of “the last big thing” is guaranteed to overshadow any future projects. I’m confident the next thing I start will fail compared to the monstrous (and unexplainable) success that this has become. I would feel successful, but by this point I've already thought about the next thing and that fear is slipping in again.

So, my fear is that, like a mouse on a treadmill, I’ll keep repeating this process forever without ever enjoying success. That’s just my irrational fear, though, and there’s no reason to believe I won't be able to one day sit back and enjoy the feeling of publishing a book without being afraid of the missing follow-up or immediately critiquing it to death.

For now, though, I'm just going to hit publish and wait ten minutes before I start either hating or idealizing this post. Ten whole minutes of feeling good starting now.