"So, how does it feel to fail?"

This lovely question was once asked of me when I was most vulnerable as a leader.

In this issue of Leadership Advantage, we will talk a little about the underbelly of all success → failure.

– Andrea

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Leadership Story: So, how does it feel to fail?

It was January 2001. The first Monday after the holiday break.

I had just told my team at EchoFactor that the startup we had been working at, the startup I founded, was no more.

• Some of the team understood.
• Some were angry.

I was shaken, but felt I had navigated the situation the best I could.

Timing-wise, this was in the midst of the dot-com crash.

We had a term sheet from a VC in hand, a solid business model, and hockey stick growth… and none of that mattered.

The public company that we were spinning our startup out of, was in trouble, and the board no longer supported us becoming a separate company.

I had just finished delivering the news to my team, and I was in the kitchen of the shared office building, pouring myself a cup of coffee.

A former colleague walked up to me. He is someone who had reported to me (but was not a part of my startup.)

He looked at me smugly and asked, “So Andrea, how does it feel to fail?”

This was someone who I had helped out many times when he was on my team, someone I had supported when others criticized his work, and most importantly, someone I considered a friend.

His words echoed in my head, “How does it feel to fail?”

I wish I could say I had a witty response, that I whipped out one of the many phrases about how failure is just learning, or “you miss 100% of the shots you do not take,” or about taking a risk.

But I just blinked a few times then looked down as I stirred my coffee. I stood frozen to the spot until he chuckled and walked away.

I was reeling from how someone I mentored could take joy in my team’s failure.

Then, for the first time in my work life, I started to cry at work.

Not tiny tears, but big, loud, ugly crying.

Luckily a friend happened to come into the kitchen and saw me right at that moment.

She quickly ushered me into one of the little windowless conference rooms and I proceeded to completely melt down in her arms.

I’d like to say I learned how to fail better over time.

Or, maybe I just learned how to frame failures as experiments that did not have the results I hoped for.

But either way, in everyone’s story, failure is intertwined with success.

We only get to eventual success by building up and learning from our failures.

When you accept learning from failure as a necessary step, success will show up at your door.