As I was going through my morning information routine, I noticed a number of articles that I’d put in the “how to not fail” bucket. I read a few of these and noticed a consistent tone of “failure is bad — here’s how to avoid it.”

Throughout my life and career I’ve failed at many things, large and small. I view failure as a fundamental part of every entrepreneurial endeavor, whether it’s a failed project, hire, partnership, relationship, lead, customer, or even the entire business. One of the great things about entrepreneurship in America is that failure is an accepted part of the cycle.

I used to say something like “one of the great things about America is that failure is acceptable.” When great people fail, they acknowledge it, learn from it, get up, dust themselves off, and get back at it. If you accept reality, you can fail gracefully and hopefully learn something from it. It’s never fun — and it can be really stressful / painful / emotionally hard — but it’s a part of learning, evolving, and growing stronger and better.


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As I was going through my morning information routine, I noticed a number of articles that I’d put in the “how to not fail” bucket. I read a few of these and noticed a consistent tone of “failure is bad — here’s how to avoid it.”

Throughout my life and career I’ve failed at many things, large and small. I view failure as a fundamental part of every entrepreneurial endeavor, whether it’s a failed project, hire, partnership, relationship, lead, customer, or even the entire business. One of the great things about entrepreneurship in America is that failure is an accepted part of the cycle.

I used to say something like “one of the great things about America is that failure is acceptable.” When great people fail, they acknowledge it, learn from it, get up, dust themselves off, and get back at it. If you accept reality, you can fail gracefully and hopefully learn something from it. It’s never fun — and it can be really stressful / painful / emotionally hard — but it’s a part of learning, evolving, and growing stronger and better.

While I fail at stuff regularly, I’ll never forget the deepest cycle of failure I’ve been in to date. As the Internet bubble popped exploded, company after company that I was an investor in failed. As I grappled with this, I felt like I had been run over by a truck. After I got up, a steamroller came and flattened me. As I was peeling myself off the ground, the steamroller backed up and smushed me again. Then, I realized I was lying on top of a hole and the top fell in and I tumbled down to the bottom. As I was looking up at the sky, some jerk came into view, poured gasoline onto me, and then dropped a flaming stick on top of me.

By the summer of 2001, I realized that every day had been worse than the previous day. I no longer got up in the morning and said “ok, today will be better than yesterday”; instead I resolved myself that every day would be worse, until it eventually got better. Then 9/11 happened.

I hung in there, kept getting up every day and doing my best, working hard to make informed and intelligent decisions, and helping all of the companies I was an investor in however I could. A few more failed, but a nice number survived and ultimately thrived. Things eventually got better. And I learned a lot.

In my worldview, the best leaders understand that failure is an integral part of things. The cliché “fail fast” is one of my favorites. When things aren’t working, deal with it. Another is the famous line from Atlas Shrugged: “Nobody stays here by faking reality in any manner whatever.” Denying that failure is part of our existence is akin to faking reality.

While I accept “the experience of failure” feels “negative / crappy / depressing / hard / sucky,” I don’t believe that “failure is bad.” Deal with it, learn from it, pick yourself up, and try again.

Comment by Michael Gates
I left a lucrative career in investment banking to pursue a lifelong dream of opening up a restaurant lounge in Manhattan. Suffice to say, the business eventually failed and it completely wiped me out personally - and I mean completely. Though my failure has been an extraordinarily painful and embarrassing process, I've learned a hell of a lot. I'm very thankful as it has made me a stronger, wiser, more humble person. Going forward, in my future business endeavors, I'd much rather go into business with a partner who has experienced their own failure at some point and learned from it, rather than team up with someone who is green on the failure front. You gotta have that notch on the belt.
March 2009
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