How to fail and keep going – Written by Alex Hugo

This is best described as a letter I wrote to myself during a specific time in my life it has been rewritten over and again when I revisit it during times of defeat.  It serves much better as inspiration than instruction.  Please read it as such. 


Once again I find myself in this position, embracing the shame of defeat.  Feeling the guilt for inadequately preparing myself and standing in the wake of my own rout.  Do I cowboy up and try again?  Or do I move on to the next thing because this is clearly a sign I should I do something different?  That begs the question I have been wrestling with for months, “What do I really want to do with my life?”  What an ambiguous question.  Taken at face value, it should be simple to answer.  If only I knew the solution.

It is difficult to dream toward the future while standing in the face of failure.  But especially challenging when you have failed the same thing time and again.  It takes courage to dream again.  To look your failures in the eye and understand the words of Alexandre Dumas “Life is a storm, my young friend.  You will bask in the sunlight one moment, be shattered on the rocks the next.  What makes you a man is what you do when that storm comes.  You must look into that storm and shout as you did in Rome.  Do your worst, for I will do mine!  Then the fates will know you as we have known you.”

I’ve been defeated, so now what?  Will this be my breaking point?  I’ve come too far and fought too hard to end it now.  There is only one question left to ask myself, ‘Am I worth it?’ Do I value myself enough to embrace the shame that comes from the failure and walk with strength through the fear I starting anew?

How do I do that? How do I  reassess and re-evaluate myself with accuracy during a setback?  There is no secret formula, no personality test, and no career advisor that can give me the answers I seek.  The only viable method is self-reflection.  ‘What went wrong?’ ‘What went right?’ ‘What can I learn from this?’ ‘What can I still do?’  ‘What can I do again?’  ‘What should I not do again?’ ‘ Why do I want to do it?’  It’s not easy, but it really is that simple.

What separates those who try again from those who don’t? I believe it is a proper view of their shame.  One that leads to honest humility.  Here I invoke the words of Napoleon Hill “Failure is the habit of quitting during temporary defeat.”  This defeat is not my failure, my response is where I decide whether or not I really failed.  To fail or not, that is my decision.


 “I never fail, I learn or succeed.” – Nelson Mandela 


From bad grades to being stood up on dates, and losing money I have “learned” a lot.

I’ve learned how to squander an opportunity through procrastination and poor execution then watch my friends walk across the stage while I sit in the stands full of suppressed regret.  I’ve learned how to get rejected and conceal my sadness and shame with sarcasm and self-destructing lies of ‘I don’t care.’  I’ve learned to sit across the table from a superior and walk away limping because I got ripped a new one.  I’ve learned how to eat crow when I trusted someone without verifying the legitimacy of their ability to come through on an agreement.  I’ve learned what kind of man I don’t want to be by watching others around me and seeing the effects that has on everyone around them.  I’ve learned how to look in the mirror and convince myself to try again.  I’ve learned where to put my hope in and when to withhold my pearls from the pigs.  I’ve learned to take great pleasure in the simplicity of little joys.  I’ve learned to get off of the ladder and out of the box and see this life as a grand adventure where I get the chance to live and intentional story.  I’ve learned that the heartbeat of humanity is not to collect federal reserve notes, but to do things you like with people you love for a reason you care about.

One of the greatest things about experiencing defeat is that it shows you just how resilient you can be.  I resonate deeply with the words of Elijah Woods character from Green Street Hooligans.

“I’ve never lived closer to danger, but I’ve never felt safer.  I’ve never felt more confident, and people could spot it from a mile away.  And as for this, the violence? I gotta be honest, it grew on me.  Once you’ve taken a few punches and realize you’re not made of glass, you don’t feel alive unless you’re pushing yourself as far as you can go.”

Ever wonder why many of the most successful people throughout history also had great failures?  It’s because of that very idea tucked in the words of a rather obscure movie.  Once you know you won’t break when you get hit, the fear shrinks and a world of confidence opens up like never before.  It’s those who live scared of failure that truly lose.

So where you right now? Did you screw up? Not make the team? Flunk the test? Lose the job? Get turned down? Been told you’re inadequate?  Did you fail?.  Are you going to let the weight of negative responsibility keep you down? Or are you going ask yourself “now what?” Don’t be so stoic that you block out the emotions that come with the loss.  Embrace them, work through them, and remember they are not your master.   Defeat sucks and some things are harder than others.  But failure. That’s a decision.

Put in the effort to rebuild what you lost or chase what you’ve never had. Take the chance to reclaim your hunger for why you want it.  Redesign it, change course, or do it all again. “An inconvenience is only an adventure wrongly considered” (Chesterton)   The journey is yours and if your drive is to please those around you, collapse is imminent.  Vision hustle, and perseverance, that’s what it takes to succeed.  The metric is your own, but the method holds no secrets.


Written by: Alex Hugo

Photo by Trevor Brown on Unsplash