Dare to Suck!

Steve Upstill
8 min readJun 2, 2022

I don’t know about your world, but success counts for a lot in mine. Especially in America, defining goals and running your life in their direction loom large if you expect to feel like a complete human being. From the platoons of self-help books on the shelf to the whole of startup culture, if you’re not on the road to somewhere then there must be something wrong with you.

Coming behind, at a distant second, is a competing ideal: the notion that the journey is the reward, that getting across the finish line may be less important than having a goal and working on it, opening to whatever adventures happen along the way. Even in startup culture, failure is much prized as a learning cycle — toward ultimately prevailing. Either way, success is still the dominant frame.

Let’s not minimize achievement, but what about the complementary space? You know, a space where drive doesn’t suck all the oxygen out of the room? To be maximally provocative about it: What if it’s okay to suck, and maybe even a good thing to suck? If you can’t imagine such a space, or recoil in horror at the very idea, we should talk.

How hard would you work to avoid failing in public? About something you care about? Among people whose esteem you prize? Personally, I would walk barefoot over broken glass to escape such a situation. But any time I feel so averse, it’s a hint to check if something interesting is going on, and this is no exception — as I learned long ago from an article in Keyboard Magazine entitled (I think; it seems to be beyond the reach of even the Internet Archive) Dare to Suck.

A sad tale

It was a rueful piece. The writer — let’s call him Floyd — recounted a night out in a jazz club in New York. In the wee hours, after the scheduled sets were finished, it was time for the musicians in the audience to take the stage. Some pretty notable musicians headed hence; one of them looked at Floyd and gestured for him to join in. Floyd resists in all politeness and humility (justified humility, from the sound of it), but the dude persists: “Come on man, we’re just messing around. Come have some fun!” But Floyd just wouldn’t have it; paralyzed with fear of embarrassing himself, he stayed rooted at his table, looking on.

Floyd spent most of the piece musing sadly about what a mistake that was. He had been invited not to play, but to play. Without being paralyzed by fear of failure, he might have surprised himself. Even if not, he might have found that the others responded with the support and grace of the community they gave every indication of being. But worst case, at least he’d have tried. He would have become part of a group experience from the inside, whatever it turned out to be, participating. Joining the dance.

Instead, none of that happened. None of it could happen, because he was so wrapped up with succeeding that he had foreclosed all such potentialities.

It’s easy to read this fable as a carpe deim message to knuckle down and be better/braver than you are. Just get more character, dammit! But we have plenty of Hallmark™ cards and affirmations to that effect. There’s another, less obvious, lesson in there: that sucking — I’m talking about flailing failure and hilarious misperformance — is key to any number of endeavors, and you’re going to lock yourself out of a wide range of achievement if you can’t, that’s right, Dare To Suck.

Learn without Sucking? Not happening

First, consider the stark fact that sucking is how we learn.

Remember the “10,000 hour rule” that a person needs to put in that much time to master a non-trivial skill? It’s questionable in the details, but there’s no doubt that you have to spend a LOT of time sucking at something before you’re any good. I’ve been told to plan on making 1,000 bad drawings before you produce something you’d ever show. If all you care about is getting to the point of mastery — unless you’re comfortable with sucking for a really, really long time — you’ve set yourself up for misery and failure.

You have to find some other way to get you through all those hours. Maybe this week you get a little better at this one fingering technique. Perhaps you make a faulty woodworking joint fifty times before it fits right. Or you keep your ass in the chair writing for endless hours of miserable frustration, but then this one turn of phrase comes from nowhere, and that keeps you going. The point is: getting to be good isn’t a good enough reason to stick with it. If you can’t Dare To Suck at it, you’re done before you start.

Creating without Sucking? Not happening

How many creative endeavors die in infancy (or conception!) because the creator couldn’t face an extended period of floundering frustration? It’s the focus on the end result, and unwillingness to engage with the prerequisite period of sucking, that bears a lot of the blame.

There’s a great thought that might be helpful with this quandary. (Unfortunately I can’t track down the source, but I’ve seen it attributed to Picasso.) It goes like this:

Those of you who are making something new need to forget about making it beautiful, or right, or perfect. You are making something that didn’t exist before, and you should be satisfied with that. Those who follow in your footsteps can worry about perfecting it. Giving birth to it in the first place is such an achievement that simply bringing it into existence should be enough.

Samuel Beckett, one of the more despairing writers of the 20th Century, was a bit more pithy:

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

To make this uncomfortable reality a bit less abstract, let me opine about the only creative endeavor I know anything about: writing.

Even the most accomplished writers will never get anywhere without a willingness to suck. Notoriously, the first draft of anything is terrible. Anne Lamott is a renowned novelist and memoirist, but what will make her name shine down the ages is naming and teaching the principle of the “shitty first draft”.

For anyone who cares about their writing, the temptation is always there to perfect each sentence, each paragraph before moving on to the next. But that temptation is a trap, because it becomes an endless process of tweaking at ever finer levels. If any progress actually accrues, the result pales compared to the enormous amount of effort/time/frustration invested. Demotivation, thy name is tweaking.

By contrast, the shitty first draft points in the opposite direction: getting anything down, no matter how bad. The operative idea is “getting it down” and out of your head. See what she’s doing there? She takes a prospect full of fear and loathing (failure, and the dread thereof), and just sets it aside, specifically embracing suckage in the interest of getting somewhere, anywhere. And make no mistake: having a shitty first draft that expresses all your ideas badly, replete with unreadable spelling, mystifying usage and second-grade grammar, is a wonderful achievement — especially compared to all the perfect manuscripts that don’t exist.

What happens then? Well, let’s hear from Chris Abani:

People think that writing is writing, but actually writing is editing.

A shitty first draft is just a compost pile for editing. And that ain’t nothin’.

I’m not a painter, or a composer, or an architect, or a filmmaker, but I have to believe there’s an analogy to be made with such other endeavors: even if there isn’t an analogue to the shitty first draft, having the Devil Of Public Regard whispering in your ear at every stage of the game — especially when your work is at its most tentative and tender — can only gum up the works.

Growing without Sucking? Not happening

However you define your own personal growth, the prescription is the same: work your edges. There will always be a territory that you’ve mastered, that you feel comfortable navigating, your home base. Venture much beyond that and you enter the wilderness of insuperable challenge, beyond the pale. But in between, there’s land that you may visit, tentatively, before ducking back to safety, until you next venture forth, again and again, until it too becomes comfortable and you realize that your comfort zone has grown.

How would you expect to expand your territory without ever failing? Just as the definition of safe is “risk-free”, the less-safe — the growth zone — must come with an element of risk and/or discomfort — by definition. Unless you Dare To Suck by moving into those areas of risk as boldly as possible, they never will become part of your home. And the “success” of staying safe will haunt you.

It’s simple, really. If you’re going to grow, you have to work your edges, and if you work your edges, you’re going to fail, at least part of the time. To put it the other way round: if you’re not failing at least part of the time — because you don’t Dare To Suck — you’re not getting anywhere interesting, and/or repeating yourself.

The Inescapable Necessity of Failure

Success is the ability to go from one failure to another without any loss of enthusiasm. — Winston Churchill

Failure and ongoing suckage are not just a way-station to success. Sometimes failure is the only item on the menu — and yet it’s still necessary to proceed.

Changing the world is like that. No matter how impeccable the goal, no action by an individual will ever move the earth. Even those with their hands fully on the levers of power — the effectiveness of which is always more apparent than real — find themselves thwarted routinely. For the rest of us, it is only collectively that we make any difference at all, but even if there is a mass movement, one person more or less doesn’t make the slightest difference. As individuals we are utterly powerless, yet only if we move forward together — only if we all proceed as if we have the power — can anything happen. And success is not guaranteed even then. But without the attempt — without proceeding in the face of near-certain failure — failure is guaranteed.

Once again, Gandhi:

It’s the action, not the fruit of the action, that’s important. You have to do the right thing. It may not be in your power, may not be in your time, that there’ll be any fruit. But that doesn’t mean you stop doing the right thing. You may never know what results come from your actions. But if you do nothing, there will be no result.

George Clooney and his wife Amal, the international human-rights attorney, have a certain history of activism, both individually and together. Clooney, who is in a better position than most to make a difference, summarizes his experience nicely: “You fail and you fail and you fail and you fail, until you don’t.”

It’s not Disneyland

The relationship between success and sucking is like a world with a shiny surface, under which is a churning mass of chaos where the real work gets done. Kind of like Disneyland: step through the bushes and you’re in a nondescript warehouse district. It takes a lot of hidden activity — messy and not much fun — to maintain that gleaming surface. It’s fun to focus on the surface and convince yourself that this is the way things are. But we know better, don’t we?

Even as a kid, I never found Disneyland to be all that alluring, much less The Happiest Place On Earth. I’m much more interested in the underneath. That’s where the real stuff happens — but only if you Dare To Suck.

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