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Failure: when your best just isn’t good enough, and other cheery thoughts

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Motivational quotes don't work, and these demotivational quotes don't work even better.

A lifelong pessimist and cynic, I often seek solace in the wisdom of Despair Incorporated’s “demotivational” poster series. Their pessimistic yet amusing musings are made whole by the images that perfectly illustrate each proverb (see examples below). As inappropriate as these demotivational posters may seem for self-confident entrepreneurs, the nuggets of truths that seed each of them is worth considering. I’ve taken some of my favorites and (perhaps aptly) applied their wisdoms to successfully failing as an entrepreneur.
DEFEAT: For every winner there are a dozens of losers, odds are you’re one of them.defeat-770136  
As founders, we must be totally committed to the success of our companies. If we aren’t, we’re dead on arrival. That being said, we must keep in mind that 9 out of 10 startups fail for reasons both within and outside our control. The odds are never in our favor and yet we persevere (see below). If failure is never considered a possibility, we are bound to pour more resources – financial, emotional, and temporal – into fruitless endeavors where they could better be used elsewhere. While Despair Inc. is correct in its assertion that there are dozens of losers for every winner, there are also dozens of winners for every winner. Just because you’re a “loser” this time doesn’t mean you won’t be a winner the next. The more time and money spent on lost causes, the less for other promising opportunities. This brings us to our next demotivator.

PERSEVERANCE: The courage to ignore the obvious wisdom of turning backaec74b73e8793914f5efca6d2270fa2e
Entrepreneurs need incredible perseverance to navigate the incredible swings in fortune that go hand-in-hand with every venture. Putting so much on the line again and again to achieve success takes heart and courage; but sometimes it takes more courage to admit you’ve failed than to keep trying. In many ways, we’d rather go down with the ship than lick our wounds and live to fight another day. Deep down, our perseverance may stem from an unwillingness to admit to others and especially ourselves that we’ve fallen short of expectations, especially when you have rarely failed at anything substantial up until that point. We owe it to our investors, our families, and ourselves to know when we’ve moved beyond perseverance and into reckless abandon. Don’t go down with the ship, especially if doing so drags others down with you.


BLAME: The secret to success is knowing who to blame for your failuresblamedemotivator
…including yourself. Entrepreneurs often fall into the trap of blaming external events for their business’s failure. A wise man I know once said, “most businesses aren’t murdered, they commit suicide.” We must be able to look dispassionately at whether market conditions or our own missteps caused our venture’s demise. Without properly identifying what went wrong, we can’t address those pitfalls during our next project. We can and should take responsibility for what went wrong, even if it was mostly out of your control. Perhaps the market wasn’t ready or early trials were misleading. In either case, at least some of the blame falls on you, and you should accept and be okay with that. Everyone makes mistakes, but not everyone admits to them. If you are forthright in your post-mortem assessment and accept blame where it’s due, your investors will respect your honesty, self-reflection, and integrity. This is crucial as you’ll likely need them around when you start your next company.

AMBITION: The journey of a thousand miles sometimes ends very, very badlyambitiondemotivator
“The journey of a thousand miles begins with one step,” said Lao Tzu in his “Daodejing” over two and a half thousand years ago. It’s true. Many entrepreneurs don’t anticipate starting their own company and only find themselves at that point after taking a series of small steps. At the same time, entrepreneurs often see the final exit dollar signs as the ultimate end goal and metric of “success”. The ending is not everything. In fact, the journey there is more important. It is tremendously educational and should, as Kant would say, be treated as an “end in itself”. The war stories and lessons you accrued while building your startup are what make up your life, not the money you earned. And though Despair Inc. in right in saying some long journeys end badly, sometimes the journey itself is the real prize.


We as entrepreneurs must understand that nothing ever goes smoothly and that ultimately things may not turn out as we’d hoped. But that doesn’t mean things didn’t turn out for the best. If you are currently a failed entrepreneur or looking to start your first company, take solace in the fact that everyone fails many, many times during their lives and that the definition of a successful person is someone who gets up one more time than they get knocked down. Dare, don’t despair.

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