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Adii Pienaar

Now working on Receiptful. Co-Founder & ex-CEO of WooThemes. Author of Brandiing. New Dad. Ex-Rockstar.

Are We Failing Too Fast?

As startup entrepreneurs, we are constantly reminded that we should be failing as fast as possible.

That failing - whilst obviously secondary to succeeding - is seen as a "feather-in-your-cap"-type achievement, because we're learning and hopefully that learning leads to better execution.

Nothing wrong with that and the notion of making new mistakes (in the spirit of learning and personal improvement) is one which I advocate on my blog often.

But somewhere within this process and mindset, we've lost sight of the collateral damage that we create as a consequence: the emotions, mental challenges and fatigue suffered by the entrepreneurs that walk this walk.


I recently realized that I had completely crashed and burnt; I literally had nothing left in my tank and I was making (bad) mistakes as a result of that.

This totally stems from my decision to jump into a new startup almost a year before I had exited my previous one, which meant that I was doing two (very challenging) things at once.

The reality is that I had already started planning and working on my new startup in January (and eventually launched PublicBeta publicly in mid-2013), but I only exited WooThemes in October. In hindsight now, I can remember conversations that I had with my wife where we both agreed that it would be good to take a break from startups after Woo. Yet I not only ignored that agreement; I also started up well before I even got to the position where I could take a break.

I recently spoke to a founder-friend of mine, who said this after wrapping up his previous startup (of 9 years) and he then decided to take the last year off:

"A friend gave me an analogy after I exited my startup. She said it was a like I had been in a massive car accident, which means it takes time to heal both physically and mentally. She was right and I didn't know how badly I needed the break until I took it. For me it took traveling in foreign countries (I can't be connected to my phone all the time), sleep, meditation, and hanging out with my wife."


Somewhere within all of these startup hype words and ambition to fail as fast as possible, I had lost myself and when I realized that, I found myself in a spot where I was being toxic (to myself, those around me and even my startup).

It's fine running forward as fast as you can go. And it's fine to embrace failure as a learning event.

I don't however think it's fine to neglect the athlete, the entrepreneur and the (real) individual underneath all of the debris that this experience potentially creates.

This experience was a reminder to me that I am fallible. I might be relatively good at this entrepreneurship thing, but I will always make mistakes and there's a very personal cost attached to those mistakes. If that cost is left unattended, it becomes emotional debt that attracts compounded interest.

Ultimately, it becomes the worst kind of bad debt.

The world works in equilibrium and whilst it shift away from that often, it regularly and naturally fixes itself. This reminds me of the efficient-market hypothesis, which basically stipulates that no average person can consistently beat the stock market for an extended period of time.

Failing fast requires running forward at 200mph, which is totally possible for short periods of time. But every engine needs a tune-up every now & again; if it doesn't get that, there's no way it can sustain the 200mph speeds or survive the fender-benders that are bound to happen.

Failing still sucks, regardless of the learning or any other benefit you can extract from that.

And that suckiness has a cost that should. not be ignored even the short-term.

Take care of yourself.


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