Failing fast hurts

Yehoshua Zlotogorski
4 min readAug 18, 2020

The startup ecosystem is ripe with the “fail fast” mantra.

But there’s a secret founders know about “failing fast” that no one talks about.

It hurts.

There’s a good reason why it’s necessary. Get out the door. Build, measure, adapt, repeat. The more tests you run, the closer you are to the big hit. The one discovery that takes you from ‘zero to one’.

Sounds simple right?

Wrong. Like everything that sounds simple in theory, it’s missing the key ingredient that makes this loop possible: emotional resilience.

See, failing sucks. It hurts our ego, our self esteem, how people see us.

There’s a reason we try to avoid it.

That’s why founders need grit, right? 💯, but that’s only one part of the psychological puzzle.

When you get injured, your skin heals, but there’s always a scab, a scar.

A physical mark that everyone can see. A Behavioral tic that gives you away. An emotional cut, though hidden, can leave the deepest scar.

Falling down bruises you. Even though you heal, it leaves you with raw skin. A scab.

So does failing.

When I fail, it takes time to bounce back. If not time, conscious effort. You see, I don’t want to fail again. I have less energy to be vulnerable and open to mistakes. This means that talking to users, investors and employees is harder. Especially if those are people I care about — like friends and family.

Why? Talking to users, investors and employees requires real listening. It requires being open to the fact that you were wrong. Being vulnerable.

As you fail, your scabs build up. Your callouses grow. Opening up, being vulnerable, isn’t as easy as it used to be.

The in depth discussions you used to have? They become less frequent. Less in depth. Less genuine. It’s easier to skirt the real issues and make do with niceties because who wants to open up again and reveal the soft scar tissue?

I’ve felt the callouses and sensitivity around the scar tissue build. I’ve also erupted at friends over a weekend because I didn’t have the patience to explain (again) why something we’d tried didn’t work. After all, I had been confident in presenting it just a week before.

This week we’re fresh off of trying a new feature at Alpe Audio, and I experienced the pleasure of failing fast again.

Our users want to learn new things, in depth. They want to achieve mastery of topics. And they want to do this while they’re “on the go” — running errands, commuting or out on a jog.

Have you ever listened to a podcast and wished you could pause for a moment and just dive deeper into that one interesting topic that was being discussed? I thought it was just me but apparently I’m not alone!

So that’s what we built and tested.

The idea was simple — users want to learn more about topics they choose, not necessarily the teacher. But it flopped. We didn’t do a good enough job on the design, the messaging, the specific pain point.

We definitely learned all kinds of things, things we hadn’t anticipated. So it was a successful failure. Classic fail fast. And it hurt.

We had thought about this, spent hours talking to users, hyped ourselves about it, put in time and effort, felt like we were “on to something”. You know the drill.

Back to the drawing board.

Part of the drawing board is building up the emotional resilience to try again. Unfortunately, failing fast really is part of the job description. So you have to deal with it. Here are some ways that help me.

  1. Find a confidante. A friend, a colleague, a partner, whom you can talk to honestly and without boundaries. Someone who reflects a positive reflection for you. This isn’t a constructive criticism circle, it’s a support group.
  2. Mindfulness has helped me. Meditation occasionally (when I have the energy for it) or simply watching the sunset.
  3. Take a break from the tough conversations. Two week sprints help — focus on product one sprint and then interviews and the tough conversations.
  4. Take a real break if you can!! ⛵️⛰🧙‍♂️
  5. Work out and blow off steam. 🏋🏼🏊🏼‍♀️

So yes. Fail fast, you have to. It’s the only way to learn enough, try enough, change enough, to succeed. But be aware of the emotional toll.

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Yehoshua Zlotogorski

Building Alpe Audio. https://alpeaudio.com. Lifelong learner. Tokenomics design & analysis. love: web3, building, investing. Host of @EthereumAudible podcast