Have you failed enough?

Failing sucks. It makes people feel unfit, unacomplished or unlucky. It always comes with value destruction: money, confidence and the worst of all, time. I too hate to fail, much like the next fellow. Some of my failures still linger and pop up in my memory, even 20 years down the track. For the most part, I have completely forgotten what I should have learnt or why I should treasure them. So when startup gurus praise failure, I can’t help but cringe. When you fail you are only closer to success so you’d best fail fast or fail big, as the saying goes. However you frame it, failing sucks.

And yet, it is undeniable that embracing failure is an important part of a healthy entrepreneurial and venture capital ecosystem. Silicon Valley’s road to riches is paved just as much by its world-changing endeavors as it is by its hundreds of thousands of stories of failure. If nothing else, emerging ecosystems around the world need to embrace flops like the Valley, even if it means faking it and sometimes forgeting about embracing success.

As I was writing this post about setbacks, I stumbled upon Johannes Haushofer’ CV of failures. Currently a Princeton Professor of Psychology and Public Affairs, Johannes created his now popular CV to provide students with perspective about how professional life is a string of hits and misses both equally as important to leading a successful professional career. “As a result, they are more likely to attribute their own failures to themselves, rather than the fact that the world is stochastic, applications are crapshoots, and selection committees and referees have bad days.”

So I paused my writing this post to craft my own CV of misses. As it turns out, I am quite good at failing. I am sure you can appreciate this by glancing at my flipside CV. It is much denser and richer than my CV of achievements. While curating my setbacks , I realized I am prouder of some of the failures presented in this one-pager or ‘sheet of life’ (as the literal translation from Spanish). Thinking about my experience, I am never proud for quiting fast and almost never remember what I learnt. I would argue setbacks are not important because of what you learn but rather because of how it defines you. It is more than just how an experience allows you to avoid certain career paths or business models,or scaling strategies or choosing the right partners. It is important because it means you tried, you persevered and you learned about yourself even if you end up making the same mistake twice.

Try and fail and try again

We should all seek to have lean careers. No questionnaires, self help book can replace the value of trying. You may know your personality type, you may know your strenghts and weaknesses, the value of your credentials and your education ROI. No preparation or career coaches can truly anticipate where you will lose yourself in a task for hours or become so focused on your job that you can’t stop thinking about it or feel the unique statisfaction of solving a problem for one person.

People that try big things usually try small things too. There are places you can only get to by betting on the small. It seems the yellow wood has many many diverging roads and not only two. Taking the road less traveled is a mindset rather than a single courageous action. Courage, not craziness. As such, messing up is a first derivative of the philosophy of trying. I believe that no plans and trying gets you from Caligrafy studies to the Hyperloop, from killing startups to curing polio, from South Africa to space. The challenge is that it is hard to measure the value created by failures. Success is the only input that can be plugged into the cost–benefit analysis.

My own path is as non-linear as they come. After failing to acquire a retail competitor, as VP of BizDev at a retail company, I was so disappointed I wanted to quit. When the opportunity knocked, I joined a hot Brazilian startup founded by brilliant HBS grads, hopping onto an Internet bubble about to burst. When the lame Mexican Internet party was over, our division was absorbed by a media giant which in turn fired all the management team after one year. Thankfully, I had just applied for an MBA at Stanford which may or may not had failed admission process and invited me to be a member of the class of 2004. Twelve years laters, I am writing this medium post like your stereotypical VC.

Failing big challenges

One of the most, if not the most, sought after qualities in a founder is the capacity to persevere. Yes, perserverance is to failures what luck is to success. Facing years of challenging times in the pursuit of success for a single endeavor builds more character and yields more experience than a serial entrepreneur flipping a few startups a couple of years at a time.

Failing fast is for quitters. If we all seek to fail fast then most of the best startups would not be here including AirBnB, Fondeadora and BlablaCar. Perseverance needs patience, vision and heart. Quitting only needs Melox.

Failure is a point and challenge is a continuum. Facing challenges does not always ends with failure but often does and facing challenges is paramount to becoming a better leader. Nothing signals challenges more than large undeniable failures. My failure to turn around a retail company after 6 years of trying allows me to help founders go through challenges and face the terrible odds of succeeding.

Your failures reveal you

How you recognize failure; how you hold yourself in face of insurmountable challenges; how you treat your partners, your allies, your creditors, your employees reveals your character and the people you care about. I am proud that in the face of financial dire straits, while I was the CEO of a failing retail company, my father, President of the Group, never allowed the 1,000 strong employee headcount to miss one payday. Partners and founders we are associated with have shown their true colors in times of doubt and failure.

As professionals, failure is an essential part of finding ourselves: testing our limits, growing, building strong relationships. Your failures define you more than your successes ever will. It is almost impossible to understand a path without seeing the most interesting half of the story. Any career should be about trying, overcoming challenges and knowing oneself better. Tolerance to failure is a consequence of great character.

Succeeding is awesome. You get recognition and redemption. The bigger you succeed, the more pleasure you get out of it. Indeed success creates value: money, reputation and new opportunities. However, all that awesomeness can be as empty as your number of twitter followers, your unicorn status or your crayon portrait in the news. Landing rocket ships or financing the next digital revolution are highly overrated achievements. You may be divorcing, insulting nations or worse supporting Strumpf for President while you enjoy your awesomeness. So instead of obsessing about success you should seek to becoming a better you, you should try more, take unconventional paths and embrace challenge. You should go live a life full of bad outcomes. Go fail.