Freedom to Fail, Freedom to Fly

Freedom to Fail Freedom to Fly


What was the biggest life lesson you learned from your parents?

Is there any line or refrain that echoes in your head even now?

While the lessons from my parents were many, the statement that I’ve been thinking about this year is this:

“Nobody can make you feel embarrassed without your consent.”

“Embarrassed,” as in “embarrassment.”

Embarrassment (n) — a feeling of self-consciousness, shame, or awkwardness

That’s a powerful statement – that embarrassment is entirely an internal emotion – thus, one that you can conquer.



My favorite 1960s superhero growing up was Daredevil.

While Peter Parker / Spider-Man both shared my first name and was relatable as an insecure high schooler, Daredevil took this a step further – he was a superhero despite an actual handicap – he was blind.

Sure, Batman could swing from ropes off of skyscraper rooftops, but Daredevil did the same thing as a blind man.

To me, this calls to mind the Fred Astaire – Ginger Rogers analogy. While both were superb dancers, Astaire (properly) pointed out that Rogers did what he did, but “backwards, and in heels.”

While Daredevil’s ostensible superpower was his heightened reflexes and “radar sense” that enabled him to more than compensate for his lack of sight, his actual superpower was listed on the comic with the tagline:

“The Man Without Fear.”

Daredevil’s true superpower was a lack of fear.


Don't let your fear of what could happen make nothing happen

One of the classic career counseling questions is “What would you do if you knew you could not fail?”

Put another way, what are you so passionate about that you would do for free, if you were so wealthy you did not need to work – did not need the money?

This, of course, isn’t the only relevant question when planning and shaping a career – some jobs inherently pay more than others, regardless of the level of skill exhibited or passion applied.

But fear (especially fear of embarrassment or fear of failure) often stops us from reaching our full potential. Put another way,

“We have nothing to fear but fear itself.” — President Franklin Delano Roosevelt


I wrote earlier about several of my career failures.

For me, the one that stands out, even a dozen years later, is my lack of success on Capitol Hill.

I failed as a Congressional staffer purely out of shame: I lacked the emotional fortitude to knock on another hundred doors – to walk in, introduce myself, and give my resume confidently to the Staff Assistant, Legislative Assistant or Chief of Staff of 100 more Congressional offices.

In short, I was simply too embarrassed as a 22-year-old to face the additional dozens of rejections required to achieve ultimate success.

In giving up after 40-some approaches and applications rather than 100 or more, I essentially talked myself out of a longer career on Capitol Hill than I ultimately had – mostly through shame and embarrassment.

I can’t help but wonder how my Congressional career (capped at a too-short 11 months) would have been different had I been, like Daredevil, entirely devoid of fear.

The Power of Persistence

Persistence - Freedom to Fail

There’s a saying in sales that’s “Every no is one step closer to a yes.”

That’s true in most aspects of life.

Were we each gifted with a crystal ball that could tell us definitively how many attempts success would take – exactly how many

  • calls it would make to land the sale,
  • first dates it would take to find our soul mate, or
  • auditions it would take to land that first (or seventh!) “big break,”

the attrition rate would be far smaller than it is.

And yes – this works both ways.

The flip side is if said crystal ball were to reveal it would take 230 auditions to finally break through and land a speaking role in that hit Hollywood movie, would you still pursue that acting dream?

If you knew it would take not, 10, not 50, but 300 first dates before you and a handsome stranger fell irrevocably for each other, building a decades-long romance and life together – would you still go through the painful process of self-discovery and rejection required of those first 299 first dates?

The Takeaway

For me, the moral is that most people give up far too soon.

Most people allow potential (but unrealized) emotions like fear or embarrassment to prevent them from taking the risks required for the best pay-offs.

We’re now in the thick of October, of Q4 of 2016. My hope is that you seize these next few weeks and months to take those risks, to act unburdened by fear or embarrassment.

Give yourself permission, and freedom, to fail.

Because it’s only once you’ve done so that you also truly open yourself to the possibility to succeed beyond your wildest dreams.

And in so doing, granted yourself the freedom to fly higher than you’d ever thought.

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