“Fail Better” -- But How, Exactly?, by Laura Braunstein

“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

                                          -- Samuel Beckett, “Worstward Ho” (1983)

“Try not. Do. Or do not. There is no try.”

                                          -- Yoda, The Empire Strikes Back (1980)

I’m learning something new this year. (Never mind what it is.) I’ve been struck by how this process has an emotional dimension that throws me right back to my early 20s, when so much in my adult life was new, professionally and personally. Now that I’m apparently middle aged, I thought that I wouldn’t get discouraged anymore, or so quickly fall into self-doubt. But I was wrong: every frustration brings back the same emotional experience of those earlier frustrations, half my life ago.

And yet -- I am finding it easier to move past the setbacks, and more satisfying to persist. What’s the difference between then and now? I believe it’s because I now know a few ways to get through it, to have the discipline to work at the constant slog of improving, to keep going. I’m better at what Beckett called “failing better.” And I finally believe that failure – both the small, incremental failures along the way and the potential failure of a great investment of time, focus, and energy -- is not a referendum on my worth as a human being.

This may be sacrilege for someone of my generation to say, but I think Yoda was wrong. Sure, in a literal sense there is only doing, or not doing; but sometimes trying and doing badly – very badly -- is a way of getting better at simply doing.

Maybe you have already heard that. [Editor’s Note: I have quoted Jake the Dog on this website.] What you might be missing are the actual concrete strategies to help you keep doing badly in the face of warnings, explanations, the damnation of faint praise, and other discouragements. How, exactly, does one “fail better”? Here are a few suggestions:

• Commit to failing for a given amount of time, or a given amount of tries. For instance, spend 10-15 minutes, every day, failing. Have no goals other than spending that time. The objective is not, “I’m going to knit a sweater by the end of the month” but “Every day I’m going to spend 15 minutes with this yarn and these needles, and knit some crap.” If you’re trying a Couch-to-5K, understand that the program is predicated on your failing, for weeks, to actually run a 5K. You may be miserable at times, and you’ll just want to quit. Don’t.
• Save or record your failures. Write down how many minutes you spend each day squawking on the clarinet or writing crappy code. Have a folder called “Shitty First Drafts” and put a shitty first draft in it every day. Even if you never ever look at them again, your early failures may contain ideas to expand upon once you feel more confident. Documentation of the specific places or processes where you tend to screw up or get frustrated is also valuable information.
• Ask for help from mentors, but be very realistic about your expectations of their time and energy, particularly if they are volunteering (as opposed to someone from whom you are taking paid lessons). Getting a quick email that says, “This works, do more of it; this doesn’t work, try something different” is valid and useful feedback, and more likely to foster your eventual independence. Beware of mentors who seem to have ulterior motives, or who seem to be overly invested in your success -- or, sad to say, who interpret your request for help as having ulterior motives. (A whole ‘nother guest column could be written about effective ways to be a mentee.)
• Share the fact that you are trying, even if you don’t share your failures. Make sure -- and this may be counterintuitive advice -- to share with people who are not experts in the thing you are trying to do, but rather are experts in supporting you. Ask your partner, not a published poet, to read your first few pathetic poems. Eventually you’ll want an expert opinion, but the point of sharing early failures is not to get feedback but to get the support to keep trying in the face of the drudgery of failure. These are the people in your life to whom you can say, merely, “I did this and I failed” and they will say “yay, go fail at it again.”
• Or, don’t share. Fail privately if that’s what works best for you. There’s no reason that you have to broadcast your attempts. Failure does not have to be a social process, or be out there on every social media account. It is okay to take some time alone and apart to work on something that only you know about. Failure can be very humbling and it can demand a lot of humility. You may feel more comfortable keeping those feelings to yourself.
• Find something to inspire you to keep failing -- a song, a quotation, a book, or an activity like running or meditating or wandering in the woods or singing loudly and off-key while alone in your car. Every time I know I’m going to fail at something new, I play a song that was recorded the month that I was born: “The first days are the hardest days, don’t you worry anymore.”

There is no last word on failure (until, of course, you die -- which in itself is not a failure: think of how long you got to live!), but eventually you’ll feel like you’ve failed enough that one of your efforts might represent something approaching a qualified success. By all means, share it. Let it go out into the world. Be proud of what you’ve accomplished. But remember to honor the failure that got you there, the missteps and the shitty first drafts crumpled in the wastebasket and the stupid ideas that finally led to the ones that might not have succeeded, exactly, but at least failed better than all of the other ones.


Laura Braunstein is the Digital Humanities Librarian at Dartmouth College in Hanover, NH. She has two children, two cats, one husband, and a hell of a lot of stuff to get done. She would like either Rachel Bloom or Julia Louis-Dreyfus to play her in a movie. Follow her on Twitter at @laurabrarian.