Make Failing a Daily Habit

If you’re looking for a rah-rah success read, you’re on the wrong page. However, if you stay, I promise you won’t be sorry.

I love failure. And I am an expert at it.

I fail every single day. Sometimes I do it more than once, which makes me even happier.

So now you may be asking yourself, has DrJ slipped a gear or what?

Nope. You’re getting, as they say on Twitter, #TRUTH.

Because if you are not failing, you are not trying hard enough.

Or, as the poet Robert Browning, suitor of the elusive Elizabeth Barrett, wrote: “Ah, but a man’s reach should exceed his grasp, or what’s a heaven for?” (Spoiler alert: He did marry her despite robust parental interference, and apparently the result was quite heavenly.)

So, what’s your excuse for not failing?

In an informal survey I just completed, I found that the reasons for not failing fall into three bins.

Some people just don’t see their failures. Or shortcomings. Or, for that matter, reality, in its many shapes and forms. Now actually, this is failing, but in such a way that it does no one any good. You can’t learn from something you never noticed, so it doesn’t count in my book. Also, in the long run, it makes for a lonely life. Sharing our frailties is a great way to make friends. How cool is it to have the freedom to share who you are, warts and all, with someone, and to know that they’ll still want to hang out with you?

Then there is the Bizarro World strategy, where everything is opposite. Instead of ‘You can’t win if you don’t try’, they recite ‘You can’t fail if you avoid participating.’ At work, these are the folks who clock in; drink a lot of coffee; grouse about office politics or the weather or any of the million other things that add no value, and over which they have no control. By the end of the day they might have managed to fit in some modestly productive activities. But maybe if they attempted something big, or at least new, and failed at it, and repeated the cycle a few times, eventually they’d discover what really living is about.

The third group is made up of those who do participate, but never bite off more than they can chew. And swallow. And digest. (How is this possible? Maybe it’s genetics, like curly hair or funny shaped toes.) Pristine resumes that show ‘progressive levels of responsibility’ and other things that HR managers love, are carefully cultivated by these folks. They would never, ever get involved in anything so messy as multiple career changes, startup ventures, or traveling to the steppes of Central Asia to study the history and culture of yurt-dwelling Mongolian nomads.

Becoming an entrepreneur is how I discovered that failing isn’t nearly as bad as people think. You can fail and do better next time. You can fail in one area while making huge progress in another. You can fail, and in the process, discover that your true meaning in life is totally not what you’ve been doing for the past X number of years, and be utterly grateful for that life-changing fail. And I’m pretty lucky, because that’s what happened to me, and now I get to work every day with a bunch of awesome people who have no fear of failure.

We accept failure willingly because the heaven we’re reaching for is really, really far from our grasp. And we’re not going to be satisfied by lowering the goalpost. In fact, we’d like to raise it even higher.

The fact is, getting there may only be 10% of the fun. The other 90% is in the striving, the sharing, and the everyday satisfaction of beautiful teamwork.

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Three Ways to Fail at Managing Teams

I grew up in a home where both mom and dad were active union members, and it gave me a clear message about working life: there is labor, and there is management. Labor’s job is to make stuff happen. Management’s job is to oppress labor.

I was fine with that worldview for a long time. But eventually, I grew up and, somewhere along the line, I became management. I even got to like being management. The funny thing is that my parents, the union loyalists, are the ones I have to thank for that. Here’s why: they didn’t just teach me that oppression was a bad thing. They also made me realize that it can be just as bad for the oppressor as it is for the oppressed.

Oppression is the hallmark of bad management. It’s the butt of Dilbertesque jokes about pointy haired bosses and evil functionaries, and it’s the bane of workers at all levels of organizations. Typically, oppressors are actively engaged in doing what they do, so it’s easy to vilify them for committing crimes against the workplace.

Sins of commission by management are many. Sins of omission are few, but they can be every bit as demoralizing. Here are three that I will address ad seriatum. (That’s Latin for, ‘I’m going to do this one at a time, because hitting you with all three, and no breaks in between, would be seriously uncool.’)

First, there is failure to observe. You might remember something like this happening early in your working life. It happened to Stacy on the very first job.

The team had a serious problem. Stacy was new, and bright, and identified a solution. It was simple, and it would have worked, but the manager couldn’t see it. Boss only saw Stacy, barely 21 years old, too new to know the score, and without a resume to provide credibility. Being laughed at and chided for offering such a naïve opinion was deeply humiliating, and to this day Stacy is reluctant to make suggestions.

Second: failure to nurture. Ari works as an analyst in the innovation department of a huge maker of scientific products. Ari applied three times for the company’s ‘high potential’ program, but the manager never followed through, and Ari was passed over each time. Ari is creative, smart, and well liked. The manager is not. Did the manager feel threatened, or was it just laziness? No matter. Ari has given up.

And third: failure to acknowledge. And herein lies a particularly sad story. Morgan has been in a supervisory position in a critical function of an organization for over two years. If you ask the team members, you’ll get nothing but glowing reports. But the manager gives no recognition, or support, or praise of any kind. Morgan feels unliked, weak, and fearful of job loss. Despite having opportunities to leave, and to move up, Morgan stays. Why? Because Morgan is there to serve the team and does not give up easily. And also because, in leaving, the team would no longer have a shield from the icy chill of the boss’ indifference.

Many failures are just learning experiences, but the failure of management to team well – as exemplified here – causes real damage.

So, if your work experience resonates strongly with that of Stacy, or Ari, or Morgan… or their managers! – then beware. When leaders fail to team, they eventually lead a business to fail.