how your mistakes + failures point the way to your success



I was in an apartment in downtown Manhattan talking to a friend about a chunk of my life I felt I’d lost to an unhealthy relationship. I could have done so much more, I said, if I hadn’t allowed myself to get so sidetracked, my self-esteem yanked inside out until I didn’t think I could do much of anything.

She mentioned that regret is nothing but an energy drain.

Duly noted.

She pointed out how much deeper my relationships are now because of everything I’ve been forced to learn about myself and my fear of intimacy and my attraction to difficult situations. If anything, she said, I am likely to become an expert on authentic, loving, nurturing relationships, not in spite of but because of my spotty history with them.

This is the flip side, the gift side, of our vulnerability.

I have a close relative who dealt with his traumatic childhood by becoming a psychologist.

In my years of working out, I couldn’t help but notice how many personal trainers were recovering from body image issues and eating disorders.

And I’ve always been kind of fascinated by novelist Dennis Lehane’s admission that he decided to write mysteries in order to learn about plot. At the time, he was a talented MFA student who wrote literary short stories…and couldn’t plot to save his life. Now he writes some of the most gripping fiction out there: critically acclaimed, on bestselling lists, turned into movies by Martin Scorsese and Clint Eastwood.

Odd, how the things that make us vulnerable are the things that can make us so strong. Our mistakes and failures point the way to our success. They expose — if we’re willing to look — the blind spots in our understanding. They show us where we need to go, and what we need to learn, and who we need to partner with or mentor under in order to become what we need to be.

And if you know anything about deliberate practice, you know that the fastest way to learn is through making mistakes. Mistakes force the brain to slow down, to evaluate things, to pay sharp attention and truly think its way forward (instead of shifting into automatic pilot). When you’re pushing the edges of your abilities, you lay down new neural pathways that pave the way to greater learning and deeper accomplishment. It’s not easy….but it’s damn effective, and ten thousand hours (minimum) of deliberate practice seems to be what separates the good from the great.

So if we learn this much from our mistakes, why do we get so afraid to make them? Or admit them?

What is the price that we pay?

Fail. Forward. Fast. (“Reward Excellent Failures, Punish
Mediocre Successes.”)

–Tom Peters

“Fail often to succeed sooner.”

— IDEO company slogan

Jun 3, 2011

15 comments · Add Yours

Once again…the queen strikes again. Thanks for spurring such intriguing thoughts in us. :) Your abilities are uncanny. I guess that is why you can call yourself a badass. Thanks for this post!


I like your friend’s thinking.
And, you have reaffirmed many thoughts I’ve recently had on deliberate practice as well. Much to think about – thanks for the questions.


Your readers may enjoy this article as well:
Although it specifically refers to music practice, I think it can be extrapolated out to many other areas.


You are one of the most insightful people that I have never met.


One of my favorite quotes:

“Ever tried. Ever failed. No matter. Try Again. Fail again. Fail better.”
Samuel Beckett


whoa this site looks different from the last time i checked (rss feed reader here).

this reminds me of two seneca the younger quotes:

“per aspera ad astra” (through hardships to the stars)


“It is not because things are difficult that we do not dare do them. It is because we do not dare do them that they are difficult.”


I’ll admit it. I’m a mystic romantic. I didn’t get this way because I wanted to be. I got this way because I wanted to know… No! I NEEDED to know, the meaning of life and how it all worked. I needed to know the three essential questions all religions must tackle: Is there a God? Is there an existing identity with a memory of self, after physical death? Is there such a thing as an immortal soul?

In my early twenties I fell into a journey which led to those answers. It was an insecure and somewhat frightening time of my life which I did not want or ask for. Yet, it was enlightening. It was sad and happy, lucid and insane. I was ripped to shreds and then delivered to the doors of perception. And by walking the walk, I came to answer the questions with yes, yes, yes.

I mention this now because I don’t believe there are coincidences for me, or for you, Justine. And I don’t believe that experiences affect only the brain. It nurtures your soul. And I don’t mean that literally. That intimacy you reel reluctant to embrace, it’s a connection to your innermost self, that part of your which lives forever.

Okay, I know I’m coming off preachy. I’m not into organized, let’s-get-together-and-pray religion. None of that is for me. Even praying is not for me. And yet, I sense a deep connection to ALL There Is. And I know, even though I don’t believe in a personal God, that when I need help and reassurance, it’s there for me…when I believe it. Contradiction? Yep. I go in and our of faith. And when I’m in it, the lessons you talk about all make sense, usually in hind sight.



Awesome post. It took me a while to figure out that an excellent failure is a good thing. I thought I’d share this quote (since it fits so well into the topic of this post):

“If you’re not making mistakes, you’re not taking risks, and that means you’re not going anywhere. The key is to make mistakes faster than the competition, so you have more chances to learn and win.” ~John W. Holt, Jr.


At a workshop I participated in recently, we agreed to one ground rule: to try our hardest to succeed, but if we were to fail, to fail magnificently. The workshop was in devised theatre – telling stories using untested ways and words we had yet to discover. Having the mandate to fail magnificently gave us the freedom to succeed.


I watched “Under the Tuscan Sun” last night and one line stood out to me. The “crazy blond” (Katherine) said “Regrets are a waste of time – they’re just the past crippling you in the present.”

And you’re so right about so called weaknesses being turned into strengths. I was a stubborn kid – drove my parents crazy. Well, that stubbornness is why I’m still writing and nearing those 10,000 hours. I refuse to give up. (Although I’ve been tempted!)

Thanks for another great post Justine,


This is a great post. I definitely connect with your thoughts on relationships and regret- it’s a waste. I’ve learned a lot from my past mistakes. Sometimes, I don’t think it’s the mistake I’m afraid of making, is that I’m fearful of how long it’s going to take me to learn from it!


The biggest question life seems to ask me is Will you give up? And my happiness seems to depend upon how close I am to giving up or how full-forward throttle-down I am willing to eff up in whatever I am pursuing. The irony is that I often feel like I have the wisdom necessary for success despite the terrible depression and sadness I often feel. Though I often feel life is a bitch, I’m still standing–at least for now.


Considering the number of mistakes I’ve made in my life why am I not a genius? Mistakes can be rebranded as ‘learning opportunities’ but the problem is that so often we learn the wrong thing: we get caught lying and punished – we’re supposed to learn that lying is wrong and we shouldn’t do it but most of us simply learn to become better liars.


Good point Justine. There are those who have drawn the Boogey Man from under the bed and choose to keep him in the daylight. Two purposes can be served — to observe and see him for what he isn’t, and to display his lack of bite to others similarly situated.

As for fear of failure … isn’t that his specialty? The truth is, the only real failure is having failed to try. I’d rather fail magnificently than stop trying.


I really like that idea of aiming for magnificent mistakes, beautiful heroic failures. It’s only writing, after all. If you crash the plane, you can still walk away.

@Jim — good point. Learning from your mistakes requires self-awareness, critical thinking, a good coach, the ability to be honest with yourself.


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