The Importance of Failure: 3 Lessons

I learned a lot about failure during my time on Wall Street. Over the fifteen years, I felt like a failure every month. Failure did not feel good. Sometimes the feelings would get too much and I would almost quit. I had to learn to deal with failure otherwise it would destroy me. This is the story of my failures, what it taught me, and how I learnt to deal with it.

Lesson One: Failure starts early. My first memory of failing is when I was nine or ten year’s old on sports day at my school (I was a fat kid), but let’s skip past that, and focus on the more recent times. I applied to MIT, Stanford, Berkeley, Wharton when I was 17. My dream schools. Didn’t get into a single one. I still have the rejection letters from each one of them in a file at home to remind me of that. I still managed to get into a good university, managed to graduate on schedule, even get a job I liked. But that sense of being a failure has always stuck with me.

Lesson Two: I will fail regularly. You won’t believe the number of things I have failed at. Let me give you the bigger ones that come to mind. I got a D in a Math class in my first quarter in college; I only got one banking job offer when I graduated in 1999;in my mid twenties I tried to move laterally to other banks and was rejected by every bank I applied to; I was divorced before I was 30 and during the years I was married, I lost touch with all my real friends. Hope that gives you an idea of just how big a failure I am.

Lesson Three: We can learn from our failures. Nothing has motivated me more to succeed than failing and nothing has taught me more. The best bank that rejected me in my mid twenties was the one that gave me the biggest guarantee to hire me in 2006. Why ? because I had gone back and figured out why I failed and fixed my weaknesses. I re-married at age 31 and am still happily married after seven years and two kids. Why? Because I went back after my divorce and tried to understand systematically all the reasons my marriage had failed.

So here’s what I learned about failure: 

What failure isn’t: Failure is not about making mistakes. Allow yourself to make mistakes. Mistakes are inevitable and part of the journey. If you don’t make mistakes you will not achieve anything. Everytime I feel like I have failed, I have to remind myself of a Michael Jordan quote, which goes like this: ‘I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed’. I have to remind myself of that because, some days, I feel like such a failure I don’t want to get out of bed. But I do.

What failure is: Failure is when you walk away from the opportunity that scares you. Failure is giving up on your dreams to do something more ‘practical’. Failure is when you settle for a life that doesn’t fit your dreams.

Here’s how you avoid failure:

Take responsibility: This is your life, your only life. You alone are responsible for it, you alone can control it. Learn to think for yourself early. Know what drives you and makes you happy. Do only those things that you have chosen for yourself.

Take action: Once you know what you want to do, take action, move towards your goals. You will fall, you will fail. That’s ok. Get up, take more steps. Don’t be as Thoreau said in Walden: ‘The mass of men lead lives of quiet desperation’. Keep taking action until you reach your goal. It is never too late, and nothing in your life is permanent.

Think Big: Don’t limit your beliefs and what you think you can achieve. Just because something hasn’t been done before, doesn’t matter. Why can’t you be the first person to do it? So go out there and attempt the impossible, do the thing that others aren’t doing, that others think you are crazy for doing. Remember the bigger the goal, the less the competition.

What to do when you feel like a failure:
There will be times when you will fall, it will hurt and you will doubt yourself and whether its worth it. Here are the techniques I use then:

Say thank you: Though failing is never fun, remind yourself of what you have already achieved, how far you have already come. Nothing makes me feel better about my life than having gratitude for what I have already achieved.

Help others: The best way I have found to feel better about myself is to help others. Something as simple as when I have lost a deal or a trade, I will take my analysts for lunch, figure out what they are going through and how I can help them on their journey.

Give yourself a hug and take a nap: We are too hard on ourselves and treat ourselves with a lot of violence. One thing I learnt from Tara Brach is this technique: look at yourself in the mirror, put your hands on your heart and say ‘I am sorry for what you are going through, and I love you’. If that’s too hard for you then just go to bed, sometimes your mind and body just need time & rest to heal.

Call your grandmother: Some people will love you no matter who you are and what you have done. In their eyes you were a success the day you were born. Let those people know how important they are in your life.

Good luck on your journey. I hope that your failures lead to all the successes you deserve.

I would love to hear about your failures and where they led you. If you like what you read and want to hear from me again please sign up at the top of the site to follow.

For more about me, check out my blog here!


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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