Cavemen, Samurais and Fight Club on breaking through failure



You've heard about it, you've been told you shouldn't fear it and that 9 out of 10 startups fail.

The better arguments made a solid point that it's actually only through failure that we learn and grow. Lean Startup people, me included, have also pointed out that startups are, following Steve Blank's definition, a learning organization and therefore the only failure is failure to learn.

But it hasn't helped, right? You're still afraid of it and failing still sucks.

Let's talk about it

Still, the increasing conversation around it is good and I don't mean to diminish that effort, quite the opposite. Several of the entrepreneurs I've mentored have come to cross that bridge, heck I had one calling me on a saturday morning in tears telling me she was considering shutting down her business.

Talking about it is how we get over it. Keeping it inside is what leads to the increasingly common founder depression. People died because of it, it's not a joke.

So what's wrong with more posts, talks and the like? Nothing wrong, but it's not not enough. In today's society failure is for sure a social problem, so discussing it more openly helps changing its perception, and with it, the associated risk from a self-worth perspective.

However that's just part of the picture, and a hint of what's beyond it was in that very last statement: your self-worth. But let's take a step back.

The caveman

One thing is often not mentioned is that we're primed for false negatives, and this is purely evolutionary. Our fear of failure isn't just some modern ego-trip, it's rooted in our ancestors.

As a caveman walking in the forest, if you hear a noise coming from a bush nearby you can give two possible interpretations:

  1. it's the wind moving the leaves
  2. it's a predator about to jump out

In light of that you have two choices:

  • start running
  • ignoring it

I'm sure you see where I'm going already: if you mistake the wind for a predator and decide not to run you're dead. As such your genes will never be passed down. So from a purely evolutionary perspective we're primed for false negatives: we'd rather think there's a predator hiding in the bushes and start running, and be wrong, than just to keep walking.

At the root of our fear of failure there's a natural fear of the unknown that leads to bad outcomes, it's our survival instinct kicking in.

Do we really expect to talk ourselves our of 2000 years of evolution? I don't think so. It needs to be experiential.

Entrepreneurs least afraid of failure are those that failed and have bounced back because they know a failed startup isn't the end of the world. In part we just need more time for these genes to spread.

But I've never liked waiting games so I want to explore some options.

You are not what you own

If we examine fear of failure, while part of it has to do with our survival instinct, the other has certainly to do with social pressure.

There is some chatter going around about this, but much and to me it's largely more effective even tho still just talk.

The principle is very simple: it's only a loss if you have something to lose.

For part of my youth I was interested in Japanese history, especially the figure of the Samurai and their code of conduct, Bushido. One of the famous books on the topic is the Hagakure, the Book of the samurai, a practical and spiritual guide for a warrior. This is one of the passages that stuck with me through the years:

If by setting one's heart right every morning and evening, one is able to live as though his body were already dead, he gains freedom in the Way. His whole life will be without blame, and he will succeed in his calling

Yes it sounds crazy and you might roll your eyes, that's fine. But maybe you're familiar with the much milder, and yet equal in substance, version of it:

learn to let go

Mindfulness and even Buddhism have become increasingly popular in the business world. They are seen as a cure to stress, the key to increased productivity and so on. One of the fundamental principles, letting go, is often cited as the way to break through fear.

If you aren't holding on your reputation, on the money you could possibly lose, then you are free to give your best. Mind you, this has nothing to do with being reckless or exercising poor judgement. Non attachment is not the same as carelessness.

For a more modern take on this we need to look no further than right before the beginning of this century, although that's now 15 years ago and Fight Club seems to have completely disappeared from the new generations' movie landscape.

As Tyler Durden masterfully put it:

You are not your job. You're not how much money you have in the bank. You're not the car you drive. You're not the contents of your wallet. You're not your fucking khakis.

and now we can just add to that list:

you are not your startup

Please stop for a second. Don't just skim or read past this, it's pointless. Take a moment to breath, read it again, aloud if you can. You are not your startup. No matter how that goes it does not determine who you are.

But this is still just talking. Let's act.

Actions speak louder than words

If you think you don't have a problem with fear of failure, that you're not holding back and already giving it your best shot then you don't need to read any further. But then why are you reading this?

If on the contrary you are like most of us then you got to do something about it and here's two things that I've experimented with.

What's the worst that can happen

I still recall sitting in my room in England around 2005 thinking of resigning from my job and pursuing a lifestyle business. I was scared to death, I had been in that job for a while, money was good and I really knew nothing about being an entrepreneur.

But I wasn't happy and I wanted to do something about it. Now before you guess that I'm going to suggest you just take the plunge, as I said above about failure, this is not about acting recklessly.

One thing however that makes a lot of sense in the act of planning is not as much having a plan B, which can lower your commitment, but really take a hard look at what failure may actually look like.

The thing is, faced with the unknown, we imagine the worst. This goes back to the caveman argument and the predator in the bushes, we're programmed for it. So it really helped me to sit down and literally write out what failure would look like.

Ask yourself, what's the worst that can happen? And I don't mean a meteorite smashing into earth tomorrow. Be practical and realistic about potential negative outcomes of starting a startup.

In my case it looked something like this (I wish I still had the original piece of paper): if I leave my job in 3 months I'm not gonna have an income for maybe 6 months. I have this much $$ in the bank to sustain me through it, at which point I'll be out. If I fail to make it work in South East Asia (that's where I planned to head to) I can still come back to England. Friends will ask me what happened, but the likelihood, thinking about them one by one, is that they'll say it was great I tried and that they wish they had the guts themselves. As to the internet and other online communities, most don't remember what happened the day before, let alone how some guy in the UK failed at this lifestyle business. I would then have to find a job, which would probably take maybe a month or so given the experience I have and I should be able to sleep on some friend's coach for a bit while I get back on my feet.

So that's the worst that could have happened. Realistically. Not as a sort of boogie man, even tho it was still a mental exercise.

I've been through 4 different similar events in my life, and if you learn to be flexible and open minded, you can make it work for you and the experiences were always worth it, even when they were disastrous.

What's your worst startup case scenario? Please write it out, even on a piece of paper and then burn it, it's ok, but write it out.

Do it now, the rest of this article can wait.

Setup yourself for small failures

In Fight Club one of the assignments they give to members is to start a fight with a stranger. I've been collecting and will soon publish a good set of stories of failures in which you can hopefully recognize your worst fears, but in terms of taking action and doing it now, here's what you can do: find some small things you can do and fail at, and observe how little the world cares. Here's a few ideas:

  • go play a sport you're bad at in an open space where you can be seen. Chances are you'll look around thinking people are staring at you and laughing
  • are you bad at quizzes? great, go to quiz night, miss most answers
  • poorly fit? perfect, ask somebody that you know run regularly to go for a jog
  • any mistake you made lately? go tell somebody
  • take one of those hard tests online and post your low scores on twitter and social network. Watch it being swallowed by the feed into oblivion.
  • pal a game on mobile that you know you aren't going to be good at and again share your low score. Same as above, watch it disappear.

Then observe how the day after nobody even remembers. I know I know, some of us did things in high school we've been made fun of for years, but those instances are outliers if we plot them on the spectrum of all our mistakes they amount to nothing and they were harmless.

Like starting a fight you're kind of playing with fire. You might get beaten up, or in this case you might beat yourself up. And if you do this exercise mindlessly you will probably just end up doing that, but then I'm afraid no sugar coated option is going to be useful either.

On the other hand if you do it mindfully, deliberately, thinking of how that's strengthening your character and helping you realize your true potential, there lies your chance to be your fearless self.

Remember we're largely responding to primal instincts, so yes, I know that these aren't as big risks as doing a startup, but what you are trying to do is to rewire your brain to accept failure, at least certain kinds.

There's no failure badge, this is not the boy scouts

In the Lean Startup world, to further complicate the matter, there's a couple of good ideas that have been abused/misinterpreted and as result are severely damaging the ecosystem.

The one I'd like to focus on, and a very common one amongst young startups, is fail fast. The idea is a good one: recognize what doesn't work as fast as possible so that you have more runway to fix it. Plain and simple.

Unfortunately it has turned every kid on the block in a 2days startup CEO. If you live in San Francisco chances are you stood in a queue somewhere behind 2 teens boasting to each other about the latest company they started and failed.

Sorry guys, that makes no sense, you have not unlocked a failure achievement, you just missed the point.

Failing fast is about iterating as fast as possible with learning, not failure, as a goal.

As a startup your objective is to figure out a repeatable and scalable business model. If that exists it's unlikely you'll find it at your first try, so the quicker and nimble your tries are (think as simple as possible, but not simpler), the more attempts you can make and therefore the higher the chances you will succeed.

Your goal is most definitely not to fail.


Failure sucks. No matter how times we repeat the arguments about learning and so on, it's just never going to feel good and that's fine.

However, while feeling bad about it is normal, believing that it's some sort of irrecoverable mark on your life is just going to hold you back.

And letting go isn't going to be instant. It's a skill like any other. You need to train yourself just like you'd train yourself to code. Be deliberate and most important be aware of what you are primed to and fight for your better self.

Repeat with me: I am not my startup, my blog, my klout score, my pageviews, my twitter followers, my Facebook like count, my MRR.

Let's work on it together

This has been such a problem for me and a lot of the entrepreneurs I mentor that I've decided to develop a program for startup founders that, while teaching you some of the important skills like Lean, Design thinking, growth hacking, etc, looks deeply at psychology and behavior, both yours and of your customers. Because you're not the only one that is afraid. What do you think is going on in your users' head when you ask them to buy/use your stuff?

If this sounds interesting go ahead and book a call below, it's free.

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