Mavericks and Leaders

There are only three paths in life for a free spirit: lazy dreamer, maverick and leader. Of course there’s a fourth option, and one that many attempt – some to the end of their days – avoidance of embracing one’s true nature. The strongest of these reassure themselves that they’re “doing the right thing” by attaining middle management status so their kids can have the opportunities they didn’t (though I believe this is a myth, and that foregoing your own fulfillment sets a terrible example). Others spend their lives bouncing from job to job, looking for that magical situation in which they can finally be happy.

But for those who recognize their own nature and acknowledge its calling, none of the choices are easy (assuming the absence of a trust fund). Lazy dreamer is the most attractive option for the young. Life is simple: when you have ten bucks, you get three beers at your corner bar. You might have a guitar, or a cat, or a collection of first edition Raymond Carver hardbacks – things you cherish not for their material value, but because they’re special to you. You’re probably satisfactorily under-employed somewhere that offers a flexible schedule. Your friends are artists and activists, and collectively you reinforce each others’ belief in simple pleasures and the evils of material enslavement. It’s a good life for awhile, and some folks keep with it all of their days.

For others, there comes a time – typically in one’s late 20s or early 30s – when la vie bohème loses its charm. You may want to set up house with your baby, you might be tired of being broke all the time or perhaps you’re simply sick of hearing that you’re a chronic fuck-up. At this disheartening fork in the road, there are two paths: the aforementioned denial of your nature (at least temporarily) or the reinvention of yourself as a maverick.

Mavericks are the mythic darlings of American culture. They work tirelessly in pursuit of their personal goals while bowing to no man; they are the innovators, the self-made millionaires, the rock stars. They don’t punch a time clock. For hard-working free spirits, this is probably the best life imaginable. It’s helpful to have an in-demand business skill you can hone into a personal empire, but even if you don’t you can dedicate yourself to becoming a skilled artisan and make a nice living while maintaining your independence.

One thing not taught in maverick school, though, is the catch: the successful ones will find themselves at another fork in the road, and they’ll have to make a choice: to stay free and accept the limits of the one-man band, or to build something larger than one person can achieve.

It’s the very definition of irony. While mavericks enjoy (immensely, really) widespread fraternity with other mavericks, with the people for whom they provide services and with any envious joe they find on a barstool at 5:30 on a Friday night with their shirtsleeves rolled up and their Blackberry still on, leaders enjoy no such thing.

The transition is sneaky. The typical maverick starts small, building a core group of talented, like-minded people all focused on “the mission,” just like he is. Everyone is in a key role, so everyone is equal. The crew works hard and often plays hard together. It’s kind of intoxicating.

For awhile. The nasty surprise for many mavericks is that, at the end of the day, it’s ultimately a “real” job for the others and at some point each of them will critically assess whether this is their best personal opportunity and how much they can invest in it for the return. They also look to him to be told what to do, which means that the once-free spirit now has to constantly assess processes, performance and short and long-term goals. In other words, he has to be the boss.

And this is when the maverick has to grow up or go home, to figure out whether fulfillment lies in the initial dream or the cultivated goal. By the time he reaches this point on the map, he already spends little time doing the things he enjoyed in the first place – he teaches others to do them so he can bring in business and “be the face” of the organization. It doesn’t happen all at once, so frequently the boss still thinks he’s one of the guys long after the rest of the team is secretly relieved when he’s out of the office on calls.

I think a little part of every maverick dies inside when he realizes he’s arrived at that fork. One path leads to continued independence, possibly at the expense of opportunity, the other to the greater responsibilities and concomitant rewards of leadership.

It’s not as easy as it looks, and it’s understandable why so many sane people avoid it at all costs. But true leadership is needed at every level of our existence, from family to government and everything in between, and free-spirits-turned-leaders are our best hope for a future built on hard work and a unified vision. This July, as we head into the presidential election with not one, but two nominees who built their initial reputations on personal credibility, it seems many of us may be feeling the same way. And it’s about time. Let’s keep it in mind between now and November. VS

“Just do what must be done. This may not be happiness, but it is greatness.”
—George Bernard Shaw

This article/blog/column also appears as “Editors Desk” in the print and online editions of VITAL.