Failure

Never Take Failure Lightly

I’ve made some pretty big mistakes in my personal life. If you buy my wife a few beers, she’ll have you rolling on the floor, I’m sure. Don’t worry about me; I’ll just be in the corner quietly crying into my scotch.

I’ve had a few professional failings, as well. OK, maybe more than a few.

But there’s one simple and yet enormously critical reason why those mistakes and failures didn’t drag my life down into a deep, dark pit of despair and red ink. While I understood that failure was a fact of life – particularly that of a risk-taker – I also knew it was by no means a good thing. I took it hard and I took it to heart. 

Truth is, failure is to be avoided and its negative impact minimized. It’s not to be taken lightly. And if you brush it off like it’s no big deal instead of learning what went wrong and making changes so it doesn’t happen again, it will happen again … and again and again. And it will ultimately drag you down with it.  

I bring this up because I hear a lot of casual references to failure these days. The entrepreneurial crowd in particular seems to have a cavalier attitude toward it. You might even say that popular literature has romanticized the notion of failure.

Here’s the thing. There is nothing romantic about failure. It is certainly a nuanced subject, I grant you that, but let me tell you a story that makes some hard-hitting points.

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The biggest mistake I ever made in my career was walking out on a late-stage startup where I was the number two guy to become the top guy at an early-stage startup. I rolled the dice and lost big-time. How big? I kept some of my stock but, trust me, you don’t want to know how much I left on the table.

It still makes my skin crawl just thinking about it.

Funny thing is, I never regretted the decision. I know exactly why I made it at the time. But the financial and emotional impact was so great that I spent a great deal of time understanding what it all meant. As a result, I came away from the experience with two big insights.

The first was that 20+ years in the corporate world had burned me out. Granted, I was a senior executive, but as long as there was still one guy above me, well, that was starting to grate on my nerves because I didn’t always respect that guy’s ability. The writing was on the wall, but it’s a good thing I took the time to see it.

The second was that, once you set your sights on something big – I mean really big – it takes a very long time to achieve that goal. Perhaps a decade or more. Making it happen in a couple of years is simply unrealistic. It rarely happens. Again, I understood why I left that former job, but if I ever had an opportunity that big and that solid again, I knew I had to stick with it.

A couple of years later during the nuclear winter that fell on Silicon Valley in the wake of the dot-com bust, I started my own company. I knew what I wanted to achieve and, while it’s been a bumpy road with lots of twists and turns, I never lost faith. I stuck with it even when things looked grim and some questioned my sanity.

And while I can’t call it a success yet, by most measures, it has been. I’ve just got some pretty lofty goals and some tough metrics in my head. But that’s just me.

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The point I want to make is this: Never take failure lightly. Never just write it off as a rite of passage, something everyone goes through, c’est la vie and better luck next time. Don’t say, “I’m an entrepreneur, a risk-taker, failure is part of the game; no worries,” and then do the same thing all over again.

Sorry to be blunt, but that sort of thinking is foolish. This is not Utopia. This is the real world. And in the real world if you do the same thing over and over and expect a different result, you’re a fool. Simple as that.

After decades growing up in the business world – the real business world – I had a pretty good idea of what success and failure looked like. I knew them when I saw them, and I took neither for granted. So when I failed big, it hit me hard. I learned a lot from it, made changes and stuck by them. So far, so good.

Don’t get me wrong. I’m not saying you should let it take you down, wipe out your drive and destroy your confidence. I’m simply saying you shouldn’t take it lightly. There’s so much to learn from it you would not believe. Success may give you confidence but failure brings wisdom … but only if you take it seriously. 

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