It’s been three and a half years since I left my first company, Sonar. Ever day since, I’ve worn one of the crappy yellow rubber wristbands that we handed out when we launched at TechCrunch Disrupt.

A few days ago, I noticed that my wristband had slipped off. I’m ok with it.

Good Failure = Lessons Learned

In startup land, we vocally praise failure for a number of reasons. Failure demonstrates a willingness to risk, the motivation to try, and, hopefully, a knowledge of what doesn’t work.

If I’m being realist, the last failure is the only redeeming one. Excessive risk taking is careless and effort only gets you a trophy in middle school. No, the presumption of improved judgement and unique knowledge is the only real reason that rational, profit-motivated adults still invest in and work with those of us who have failed. They are betting on past mistakes increasing our odds of future success, because, let’s face it: success is what we actually value.

Lessons learned do not come for free. There’s nothing about slipping by the pool that prevents you from running by it again. You have to consciously slow down, reflect, and change your behavior. The same goes for hiring brilliant jerks, ramping burn before product market fit, and waiting too long to cut headcount — the same temptations will be there next time; it’s up to you to avoid them next time.

Bad Failure = Scar Tissue

If learning is the upside of failure, scar tissue is the downside. Scar tissue is your body not trusting your brain to learn, coarsening itself in anticipation of making the same mistake again. Sure, a scar issued by touching a hot stove reduces your sensitivity to future burns. But that misses the point: Put on the fucking pot holders and don’t spend all your money on fancy PR next time. Success is rarely achieved by repeating what has already failed.

Scars come with a price: lost feeling, lost sensitivity, and lost flexibility. Startup success is predicated on our sensitivity to new opportunities, intrepid exploration of new angles, and willingness to try something different. Thus accumulated scar tissue poses a grave danger to entrepreneurs.

Diagnostics and treatment

The first step toward healing our wounds is to become aware of them. Unfortunately, misinformed biases can be hard to spot. We wear our physical scars, but we project our psychological wounds on the world around us. Erroneous learnings warp our perspective, leading us to act irrationally and ultimately make more mistakes. This is the insidious side of the scars of failure: they often only become apparent after they’ve already caused us more harm.

Look for the symptoms. Two that I’ve experienced include:

1) Seeing failure as inevitable. This leads to hedging, or preemptively quitting to “avoid” it.

Anything worth doing may fail. Progress is uncovering and overcoming potential risks.

2) Waiting until you acheive success before asking for help.

Similarly, any business you can do alone probably isn’t worth your time. If you don’t market your efforts, you’ll never attract the resources you need to win.

Focus on the process and enjoy the ride

These symptoms reflect an attempt to control outcomes that you can’t even fathom. Your startup is a temporary organization (the process, under your control) formed to discover a viable business model (the outcome, not under your control).

Choosing to be a serial entrepreneur is signing up for a bumpy ride. You will become bi-polar if you insist on tying your personal selfworth to your startup’s latest victory or setback. If you want to take a big swing without relinquishing your sanity, I suggest you accept that the journey is the reward.

Investor at Founder @SwitchApp, @Sonar, Fulbright, Surfer, Bad Bassist, Recovering Banker. It's been real, except for the times that were fake.

Investor at Founder @SwitchApp, @Sonar, Fulbright, Surfer, Bad Bassist, Recovering Banker. It's been real, except for the times that were fake.