Failing to Fail? You’re Not Aiming High Enough

If you don’t play, you’ll never win

Herbert Lui
Published in
5 min readDec 15, 2015


“The “sweet spot” for an OKR grade is .6 — .7; if someone consistently gets 1.0, their OKRs aren’t ambitious enough. Low grades shouldn’t be punished; see them as data to help refine the next quarter’s OKRs.”

— Rick Klau, How Google sets goals: OKR’s


Reflecting on 2015, my biggest failure was actually not failing enough.

I’m certainly not suggesting that it makes sense to celebrate failure. Rather, it makes sense to celebrate boldness, opportunity, and change — but failure is a natural byproduct of them.

For me, it meant not getting enough rejections (because I didn’t go after enough high-risk, high-reward, deals). Not enough flops (I didn’t write enough). I certainly experienced my fair share of failure, but I let my reluctance, fear, inertia, ego, and indecision get the best of me. I let this prevent me from executing to the fullest.

Truthfully I’m not sure what amount of failure is good for you. It really depends on your situation. For me, I feel it intuitively. I didn’t aim high enough. I end my year knowing I had more to give, and it’s not a great feeling.

“One practical suggestion I’d give anyone: You should be hearing you’re too expensive about 30% of the time. If you’re not hearing that, you’re not charging enough… It means 70% of people think you’re well-priced, or perceive your value.”

— Jon Lax, 24:30, Businessology Episode 005

I’m running a marketing company called Wonder Shuttle, and Jon Lax’s words ring in my ears. Some people have told me I was expensive, but rarely too expensive — and not by anywhere near 30% of people. Did I leave money on the table?

Obviously this percentage is situational. If you’re in a corporate environment where your reputation is fragile, that absolutely does not mean failing in 30% of your meetings at work, or at 30% of your projects. Or do something that pisses off 30% of your managers (unless you’re certain that the other 70% will become your champions).

Rather, perhaps it means failing at 30% of job interviews you apply to outside of work, in order to negotiate a higher salary or to seek a new opportunity. Or failing at 30% of outbound emails to network and meet new people (it’ll probably be greater than this).

A certain proportion of failure indicates we are being bold enough. All too often we perform way under our limits. If you’re failing 0–10% of the time, perhaps you can aim higher. If you’re failing 50–70% of the time, perhaps you’re aiming too high.

A failure percentage of around 30% shows that you are getting one thing right: you are aiming high enough.

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How can you decide what’s worth failing at?

So obviously, one thing to consider: the best possible outcome compared to the worst possible outcome, and how likely each of those are to happen. Tim Ferriss has a great exercise on preparing for fearful situations.

If you can design or plan for a situation, the best risks and failures answer: Even if you fail, what do you gain?

  • Will you learn something that’s important to your future? Or something you’ve always wanted to learn?
  • Will you get the chance to meet interesting people?
  • Will it expose you to more potential opportunities that you’re interested in?
  • Even if you fail, what can you do to get back to your starting point (both mentally and financially and physically)? Will it have any long-term consequences?

It might sound counterintuitive, but here are some failures that come as a byproduct of being bold:

1. Failure by Ambition

You aimed high and tried going for it. You did it anyway. But you didn’t succeed. So what? 90% of people are too afraid to even admit they want to do it, let alone execute on it, so you’re already ahead of the pack.

What did you learn from this failure — Why didn’t it work? Where did it go wrong? What will you change next time, so you have a better shot at achieving it? Or do you have some work to do on yourself before aiming that high again?

2. Failure by Circumstance (or Luck)

You know you don’t control everything, right? You’re a speck of dust on a speck of dust in the universe. Maybe you were too myopic. Maybe the timing was off. Were you too far ahead of your time? Or too slow? So how can you prevent this next time?

Did you have enough stamina and persistence — might you have been able to succeed if you hung in just a bit longer?

3. Failure by Curiosity

I’m not even sure this counts as failure. But in experimentation, there is always success (desired outcome achieved) and failure (anything but desired outcome). Failure is a byproduct of being creative.

What variable caused you to fail? Or was it because you’re just technically not skilled enough?

These failures indicate that you’re challenging yourself enough. You’re also more bound to come across “good luck”. If you don’t play, you’ll never win. (In nerd jargon: You expose yourself to enough risk and potential reward to yield positive outcomes.)

These types of failure aren’t desirable, but are still better than not failing at all. A lot of people are too afraid to make the decision and risk failure. When you try, you’ll have a better idea of why you failed than if you didn’t. Even if you fail, you’ll know which decision is the wrong one, which might be the right one, and you’d be able to course correct. You’re not paralyzed by indecision.

Be Bold

There are tons of incredibly stupid ways to fail. You could follow someone’s advice blindly and fail (if you’re going to fail, do it on your own terms!). You could have knowingly overestimated your own abilities and failed. You could have made an impulsive decision, not planned accordingly, and failed. You could have sabotaged yourself. That’s also the second meaning of the headline — don’t fail for the sake of failing.

But the ultimate failure is the one where you let your fear, inertia, or ego keep you from trying in the first place.

Herbert Lui is the Creative Director at Wonder Shuttle, a marketing agency that crafts stories through content. Their most recent product is the content canvas. It’s a framework that marketers and strategists use to create useful, contagious, content.

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Herbert Lui

Covering the psychology of creative work for content creators, professionals, hobbyists, and independents. Author of Creative Doing: