Failure and regret

How one can save you from the other

One of the biggest and most insidious creative blocks on this planet is the fear of failure.

Not only does the fear of failure keep people from starting at all, it’s also a major fuel for procrastination, and it’s what perfectionism is all about. And they’re all really powerful forms of self-rejection. The Venn diagram is pretty damn close to a perfect circle.

It’s always amazing to me—and I say this having experienced it myself—how easy it is to be thrown off by this particular fear. Its twin sister, fear of success, often factors in here, too, but fear of failure is the star of the show. It takes the things we feel called to do—called to where we can literally taste that dream—and turns them into the engines of our own defeat, embarrassment, and ruin.

It makes no sense, right? If we want it that badly, how can we let that fear get in our way?

At the risk of sounding like a broken record, I’m going to point back to our culture, which venerates success as the pinnacle and only acceptable goal for life, and has a million words for people who’ve failed, delightful terms like “loser,” “wanna-be,” “flop,” “also-ran,” “tried-and-couldn’t,” “dud,” “flunkie,” “bomb,” “inadequate,” “washout,” “wreck”… need I go on?

Latin has a lot of words for war because the Romans were obsessed with it. We have all these words in English because we’re obsessed with failure—and with having many ways to remind people who’ve failed that they haven’t measured up.

At the same time, we’ve all heard that failure is where you learn. That can sound counterintuitive—doesn’t success teach us, too? Sure, it teaches us that we knew how to do something. Or it teaches us that we were really, really lucky. But as much of a cliché as it is, it’s got nothing on learning from your mistakes.

I’m gonna give the floor to George Clooney for a second here:

I realized that George Clooney was an incredibly wise man many moons ago (I’d guess at least 20) when I happened to see an interview on TV with his father, Nick. Nick mentioned how, when George decided to be an actor, his response, like that of most parents, was that George needed to have “something to fall back on.” George, at a rather young age, replied, “Dad, if I have something to fall back on, I’ll fall back.”

(I have, unfortunately, never been able to find that interview on video, and believe me, I have tried.)

It’s no surprise to me, then, that he’s spot on here. While there are a lot of things that go into fear of failure, and ways to deal with it, the one we don’t think about enough is how fear of failure directly leads to regret.

If you’re like most people, regret might be the one thing that scares you more than failure and isn’t either death or public speaking.

Regret is not something most people want to think about, because it’s scary and because it can really bring you down and reinforce that sense of failure that we’re trying to get away from. I get that.

That said, I find it incredibly useful in my life, especially when I’m making decisions (of any size, but particularly big ones), to ask myself how much potential regret I’m facing if I make one choice over another.

Here’s an example: A few years ago, the universe basically dumped, right into my lap, the opportunity to ask Paul McGann, who played the Eighth Doctor on Doctor Who (among many other substantial roles), to be on my podcast. I’m not exaggerating—the setup was right there, tailor-made, and all I had to do was walk up and ask the question. There was a part of me that was absolutely terrified to go put myself out there and potentially be rejected…but I also realized in that same moment that the only thing worse than that rejection would be to fail to ask at all.

Why? Because then I would wonder for the rest of my life what would have happened, and would probably kick myself every time I thought about it. I would regret not having taken the chance. All things being equal, I’d rather be definitively rejected and know it than live with that sort of mental torture for the rest of my days. Seen that way, the decision was easy—I had no choice but to ask.

The same is, of course, true for the creative things we want to do. Some of them may be idle curiosities, but others call to us. One great way to feel the difference is that the true call tends to cause pangs of envy when we see someone else doing the thing we want to do, little fleeting moments of “That should be me!” that we may tuck away from embarrassment at the audacity of that notion before we even realize they’re sending us a really valuable message.

That creative call is the one that’ll set us up for regret if we spend our whole lives ignoring it, even (especially!) if that’s because someone else once told us we weren’t good enough or couldn’t do it. Idle curiosities may or may not lead us anywhere, but the ones that turn us as green as a bunch of kale are vital messengers in the preemptive war against regret.

I’m not saying that considering regret is all it takes to get past fear of failure. Fear’s a complicated beast, and it’s not always comparatively easy to thwart. But it can certainly help us get past it in the moment, especially the important moments, even if we don’t do it perfectly.

I also want to point out that, despite the fact that our pal George mentions regret at age 65, there’s no upper limit on when you can finally answer that call, assuming you’re physically and mentally able at whatever advanced age (and even that may not really be an issue, depending on your mindset and how clever you can be about it). How you see yourself is more important than any idea about having to do things when you’re “younger.” Sharon Jones didn’t record her first album until she was 40, Estelle Getty was 62 when she landed her role on The Golden Girls, and Grandma Moses finally answered her call and began her painting career at 78 (now that’s a lapsed creative!).

So… what are your regrets-in-waiting, and how can you keep them from becoming reality?

PS: As I plan my new course, I’m still looking to talk to some folks who are stuck creatively—who want to be making something but aren’t, for whatever reason. If that’s you or someone you know, get in touch!