How do you know that what you’re doing in your business will work?
You don’t. We don’t.

We lay some bets and see what pans out. (With a whole lot of elbow-grease in the meantime.)

It’s one thing to acknowledge that “failure” is part of how our businesses grow, but honestly, most of us are 🙄 if things don’t work out.

My own attitude towards business failure was minted in my 20’s at my first “real” job.

During the dot-com boom (the late 1990’s) I worked at Intuit on the Small Biz team (QuickBooks, et al).

The internet was just becoming a thing, and companies were trying on new business models faster than a bus full of tourists hitting a dressing room at an outlet mall. Can we make money doing THIS? How about if we did THAT?

We didn’t have the slightest idea what would pan out in the brave new digital world that lay before us — but we DID know that if we hesitated, some other company would get there first.

So we didn’t hesitate.

We formed new products lines, tested markets, put our “betas” up for sale — and watched what happened.

What happened was — a lot of them flopped. The market wasn’t there after all, or the profitability wasn’t right to move forward. And if things weren’t right, we closed it down.

And we celebrated each of the shut-downs with a party. (One huge fringe benefit of the dot-com boom: lots of company parties.)

At one of them, our Founder/CEO Scott Cook showed up and — beer in hand — spoke to our small crowd. He wanted to make sure we understood that there was zero shame in a failed attempt.

I remember one thing he said quite clearly: “If we’re not failing, we’re not placing enough bets.”

He made sure we knew it was company culture.

It’s influenced how I’ve approached uncertainty and risk ever since. I’m not saying I’m 💯 free of angst when things don’t pan out. But I had a great teacher.

So, next time you’re anxious about failing, maybe it’s time to ask yourself:

Are you placing enough bets?