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How to Succeed at Failing


I used to suck at failing.

As an entrepreneur, I have come to realize that (with one colossal failed startup under my build) I suck at failing precisely and wholly because I didn’t think I could fail.

I lived a nice, comfortable life for many years working freelance for some of the biggest corporations in the world (from entertainment, to corporate law, to publishing, to investment banking).  For the most part, I worked on my own terms and made great money doing it.  The money (back in the late 90’s and 00’s) came fast, easy and with few consequences.  Failure was not an option (there was too much money floating around and, in this society, money doesn’t equal failure – lots of money equals success).  But getting easy, fast money in the era of unaccountability tainted us all (even those of us who liked to think of ourselves as being better more substantive than this ideology).  Of course, we know now (post financial markets crash of 2008) that there are serious flaws in the way our culture defines failure and success.  While money can buy comfort and certain freedoms, it turns out that it really can’t buy happiness and it might even bring on its own form of misery.  And failure isn’t the dirty word we’ve all been taught to believe it is.  Quite the contrary, failure is the diamond in the rough – a key ingredient to our success and to achieving our goals.

Good times and tons of money made heroes out of everyone (the entire country seemed invincible) and closed us off to the notion and acceptance of failure on a personal and societal level.  By rejecting the idea of failing (“failure is not an option”) we open ourselves up to failing all the more.

My first startup failed one year ago.  It devastated me financially, emotionally and psychologically.  It was, I admit, a shock to my system.  I’m still recovering.  After everything I’d been through in my life, I simply found it hard to believe that my business (my baby) could… f-f-f-FAIL!  There are three reasons for this:

  1. (1) I was very arrogant.  In the past, sitting in the comforts of a cushy job, whenever I thought about the possibility of starting my own business, I always figured that, if and when I decided to launch a startup, I would succeed – period (I knew it would be hard work but I had no doubt that I would succeed).  Why?  Because I’m fly, my ideas are great and I’ve helped make other people’s dreams come true in corporate America.
  2. (2) I’m not 20 years old – age plays a factor in ones ability to bounce back from failure (the idea of failing after 30 is a bitter, fat pill to swallow – not to mention the fact that the timeline of your goals you so meticulously laid out in your 20’s has now been derailed by a couple of years invested in a failed venture – all of a sudden, time is not your friend).
  3. (3) Most importantly, I didn’t believe I could fail so I didn’t prepare to fail.  I know, it sounds self-defeating to prepare for failure but here’s the big key to this whole failure thing that nobody tells you: the fear of failure is worse than failure itself.  In this case, avoiding the idea of failure means you can’t prepare adequately for a “Plan B” or “Plan C” in the event of failure.  This, ultimately, closes off your opportunities which, in turn, leads to more frustration and a feeling of hopelessness.  What if you fail and can’t pay back people who invested funds in your startup (family, friends, investors)?  How will you look at them?  How will they look at you?  Can you regain that trust?  Without accepting the idea of failure, you can never truly ponder these questions and arrive at the crucial answers (knowing the answers to these failure questions will help you understand more how to approach people for funds to begin with).

Now that I have my second startup, I realize that failure has less to do with what you didn’t accomplish and more to do with how you define yourself in the absence of certain accomplishments.  I now allow failure to help me reshape my goals and bring even more meaning to my successes (and there have been successes!).  Which leads me to something that is a curiosity to me:  We fail more than we succeed (the overnight success story is few and far between and, even if you do achieve success fast and early in life, repeating that success without a series of failures is nearly impossible).  If we spend our lives experiencing multiple, successive failures (at whatever we set out to accomplish) before we actually succeed, then why are we better at failing.  Why does failure hinder so many people and kill so many dreams?

A well-known, respected VC told me that he doesn’t take an entrepreneur seriously until they’ve failed.  When he learned my first startup failed he decided to meet with me when I pitched him my second startup.  Why?  Because, not only did I bounce back from my failure, I understood the importance of owning my failure.  Instead of being embarrassed by it, I wear my failure like a cape (the way Superman wears his cape).  It helps me to fly and deflect negativity!  I haven’t perfected how to handle those massive failures that can rock ones world to the core, but I’m much better at it now thanks to friends, family and determination.

There is much that can be said and debated about this topic but this much I know from my personal experiences:  Accepting the idea of failure as an entrepreneur doesn’t invite failure, it opens you up to potential solutions and opportunities that will free you from the feeling of failure when it hits.

The best way to bounce-back from failure is to expect it, accept it and, yes, embrace it.  Failure is not a dirty word.  It humbles and empowers us.  Last time I checked, those were both amazing things.

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