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This article was published on March 24, 2014

Why entrepreneurs are obsessed with failures

Why entrepreneurs are obsessed with failures
Aashish Gupta

Aashish Gupta (or The Fundamentalyst) is an investment banking research associate covering European Tech sector. He loves to experiment with startup ideas and write about technology, life, society and spirituality.

“The only real mistake is the one from which we learn nothing.”

While most of you must be sick of the much clichéd idea of “learning from failures” – a phrase which annoys us even more in the darkest periods of our life – I believe in the opposite. There is nothing you can learn from failure; failure only peels your character layer by layer to unleash the more enlightened version of you, which was always there.

My experience in failure is only three startups-old, but anyone who has gone through the rigors of a startup can draw a pattern of psychological changes that a fertile mind, like that of an entrepreneur, goes through.

This can be done by merely observing the lives of some of the greatest leaders, businessmen, scientists and artists. Obviously, no two people will go through same exact experiences, but in retrospect most of you should be able to map out the following three phases of your journey.

The beginning of an end

frustrated at work

Let alone starting a business, if you have lived/taken a risk even for a single day in your life, you have gone through this. The repeated cycle of idea to execution to failure is the first and the most frustrating part in any entrepreneurial journey.

 “Great success is built on failure, frustration, even catastrophe” – Sumner Redstone

The above quote reinforces our idea that this stage forms the foundation of something bigger. The list of obstacles adding to the frustration is endless. Failure to hold on to a co-founder, ineffective product, cash burn, operational difficulties, legal hassles, emotional and physical burnout, loneliness, self-pity, almost anything and everything will bring you down.

Any sane person at this point of time will break, and so will you – the best of you. Abraham Lincoln, after failing as a captain, businessman, lawyer, and several times as a politician, wrote in a letter to his friend: “I am now the most miserable man living. If what I feel were equally distributed to the whole human family, there would not be one cheerful face on the earth.”

There are other stories such as those of Harland David Sanders, the famous KFC “Colonel,” who couldn’t sell his chicken, and was rejected by more than 1000 restaurants. Stephen King, after getting rejected by 30 publishers was so frustrated with his first novel, Carrie, that he threw it in the trash.

While these are known ones, there may be other countless untold stories which never came into limelight.

 “If at first you don’t succeed, destroy all evidence that you tried.” – Steven Wright, American comedian, actor and writer

Maybe a lot of entrepreneurs follow Steven’s advice and never let out their breakdown episodes because they want to keep their “metal head, ready to take any blow” image intact.

These snippets from lives of some of the most successful people tell us that failure is inevitable, and so is breakdown in some or the other form. If you are in the same phase, do not yet think that startup is not your game.

Masochistic pleasure of failure

After being beaten down by circumstances and misfortune, there may be a brief period of inactivity because now you hate the very same idea or vision that you were once obsessed with. But even before you have fully recovered from wounds of the past you will find yourself haunted again by the same incessant urge to conquer that, without which you feel your life is meaningless.

This is because you are one species that doesn’t just adapt to the ecosystem but transform it to adapt to you as well. This urge is precisely what separates the special ones from the rest of the world, and not any talent, skill, IQ, or success itself.

Now the phoenix that you are after rising from your own ashes, there are two interesting ways in which you would be different than what you were before. When you started you knew about your strengths, which is why precisely you thought you could do it. But now your failures have introduced you to yourself and you stand naked in front of the mirror seeing every weakness you have.

Basically, you have eliminated your internal conflicts and left to fight external factors only. The second interesting part of you will be perceived by the society as nothing less than insanity, and will make them wonder what keeps the Lincolns and the Churchills of the world keep going despite repeated setbacks

The answer to this, I believe, has less to do with sheer motivation and might have to do more with an uncanny addiction to masochistic pleasure, derived from the pain inflicted by failure. The pleasure is that of rising again in the face of adversity, every time you fall down, developing a heroic perception of self, which ultimately leads one out of despair and into fearlessness.

Winter Blues Beckon As Daylight Hours Foreshorten

Call it insanity if you like, but I consider it to be a survival instinct or a mental defence mechanism that these creatures called entrepreneurs are born with.

“Our greatest glory is not in never falling but in rising every time we fall.” – Confucius

“Never give in, never give in, never, never, never, never – in nothing, great or small, large or petty – never give in except to convictions of honor and good sense. Never, Never, Never, Never give up.” – Winston Churchill

“The fastest way to succeed is double your failure rate” – Thomas Watson

The above quotes give us a sense of an obsession with failure that these great souls might have developed over a period of time. Being able to find glory in failure is the most enlightening part of this journey.

This part of my life I call ‘Madness’

This stage kicks in when one experiences a bout of success out of nowhere. It could come in the shape of an idea which makes you feel this is how it was supposed to be (that eureka moment!), or a window of some opportunity that opens up to show you just the right path.

Or perhaps it’s really not as deep

As I’ve been led to think

Am I trying much too hard?

Of course! I’ve been too close to see

The answer’s right in front of me

Right in front of me

— The Nightmare Before Christmas, “Jack’s Obsession”

There will be a moment when somehow time and space will align perfectly, and everything will happen just the way you had planned (Yes, I am talking about the law of attraction). The only point of not giving up is that you have to be there when it happens.

It is that time when all the pent up frustration and disappointment inside you will transform into enthusiasm and positive energy of equivalent magnitude. This is why failure is a slow but natural way to success, so that you give nothing less than the best when the time is right.

“You cannot force ideas. Successful ideas are the result of slow growth” ~ Alexander Graham Bell

This stage is further characterized by a frenzy of free flowing ideas and creativity, opening up an entrepreneur’s mind to newer perspectives and style of thinking which he never had access to. You become bolder, you take more risks, you experiment, and life is a ride full of madness.

Smooth seas do not make good sailors

Have you by any chance skipped the above process? Has your life been a ride on a highway so far? Then be aware that you are still at the bottom of the learning curve. Know that if you hit a plateau you will not know how to climb over.

Bobby Jones, an American amateur golfer, once said that he never learned a thing from the tournament he won. Whether it’s lady luck on your side or an extremely high IQ that got you whatever you wanted in the very first or even second attempt, do not let yourself fall into the “I am successful because I did everything right” trap.

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