Winners and Windmills

Written by Alora

Topics: Entrepreneurship, Leadership, Lessons & Epiphanies

No Tilting at Windmills Accomplishment-oriented people often share a very common character trait: we hate to quit.

More often than not, this is a combination of our own need to conquer whatever mountain we have set our sights on, and our belief that others are counting on us to succeed. In both cases, those assumptions are frequently over-estimated.

Our Inner Don Quixote
One of my single favorite things in the world is to fix something that no one else has been able to resolve. This is something that plays well to both my intellect and my ego. Some of the most clever bosses I’ve ever had have seen this and known precisely how to play it to their advantage. Conversely, the best bosses I’ve ever had have also recognized this, and helped me manage this tendency so that it did not run me into the ground (which it is often likely to do).

One of the reasons I love working in startup environments is that they are precisely the type of place where a hundred different problems can crop up on a weekly basis, and someone with initiative and ingenuity can dive in and fix them before they ever get out of control. The sense of accomplishment is greater than anywhere else, and it is in stark contrast to large organizations where rallying support can take weeks, and then actual execution can take months.

I absolutely love this.

The downside, though, is managing this inclination. The adrenaline high is great, and it can carry you through boring meetings and bad days, but what happens when – like any other addict – the highs get lower and lower, and the downtimes in between get longer and longer?

In my experience, what happens most often in this type of situation is that we regroup, psych our selves out, buckle down and try again. Sometimes this works. But usually only for a while.

The problem is that things change. Whether it is our passion and energy, or whether it is the environment we are working in, the normal course of organizational and personal development means that the things that used to fire us up will change over time. And the types of environments in which we are most successful will also change over time. One of the hardest things for accomplishment driven people to recognize is that the circumstances that made an environment invigorating and exciting to work in have changed and they are not going to change back.

When this happens, the best solution for everyone is to find somewhere new and walk away.

Most of us do not give up easily. If we have felt successful in an environment – especially if it is one in which we have also felt personally connected to the people – letting go can be painfully hard. Culturally we are trained to “never quit.” But that’s crap.

“Winners” (however you define it) don’t win because they endlessly beat their heads against a brick wall. Winners win because they suit up for a match, and when it’s over they evaluate their performance, get some rest and prepare to do better next time.

People Are Counting on Me
This is the biggest ego stroke of all: “I can’t quit. They NEED me.” Nothing fosters self-paralysis when you are miserable more than the belief that the environment will fall apart if you are not there to hold it together. I spent years under this deluded and egotistical belief. And then when circumstances entirely outside of my control (health) took me out of the game for a little while, do you know what happened? Nothing. The world didn’t come to an end. The work still got done. Things progressed the way they should.

That was in part because I had done such a good job at setting things up so that they were more sustainable than they had been when I arrived. But it was an invaluable lesson to me, because it reminded me that (especially someone else’s) business would go on just fine without me if it needed to. The difference is that my life, my emotional well-being and my family obligations couldn’t.

My personal life and family obligations are another topic for another time, but it wasn’t long after that discovery that I had a realization: my emotional well-being required that my work leave me with a sense of accomplishment – or at the very least, a sense of a potential for accomplishment. (And, incidentally, my ability to live up to my obligations to my life and my family require that I am feeling good enough about work that it does not poison my attitude and infect the rest of my life.) And the moment it became clear to me that a working environment was not conducive to that, it was time for me to move on.

That is such an important lesson to learn, because if you stick around out of habit, or nostalgia, or a hope that things are somehow going to return to the way they were, then you are running the risk of burning yourself out beyond repair. You are also running the risk of losing touch with the things you loved about your job and your co-workers. And if that happens, all your left with is bitterness and anger. Unfortunately, it’s hard to see that until it’s too late.

“Winners never quit, and quitters never win,” may be a great soundbite, but it’s really a dangerous fallacy – like size 0 supermodels, or wrinkle-free aging.

Winners recognize that being a winner is a convergence of passion and skill with opportunity and circumstance. It’s a balance, and all of those things have to be in place to truly be a winner. Once that balance is off, getting it back in the same environment is rare, because the change is usually based on new needs of either the individual or the organization.

When that happens, winners move on. They say, “Thank you for the opportunity.” They say, “Good luck!” They keep their friendships. They take a break. And then they find someplace else where their passion and skill can match up with opportunity and circumstance to help a new team on a new endeavor also be winners.

And if they catch it early enough, they do it all without getting bitter and resentful that the environment they used to love has changed and can’t give them what they need anymore.

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