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 to take, some to the end of their days: avoidance of embracing one’s true nature. 

The strongest of the latter group reassure themselves that they’re “doing the right thing” by attaining middle management so their kids can have the opportunities they didn’t (I personally believe that foregoing your own fulfillment sets a terrible example for your progeny). Others spend their lives bouncing from job to job, looking for that one, magical situation in which they can finally be happy.

For those freedom lovers 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 buy three beers. 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 happily 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 sweetie or be tired of being broke all the time. 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 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, 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 and accept the shackles of accountability to others.

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 who only gets an hour for lunch, 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 she 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 rest of the team, 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 her 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, she 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 she reaches this point on the map, she already spends little time doing the things she enjoyed in the first place – she teaches others to do them so she can bring in business and “be the face.” It doesn’t happen all at once, so frequently the Boss still thinks she’s one of the guys long after the rest of the team is secretly relieved when she’s out of the office on calls.

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

It’s not easy, 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 business, to government and everything in between. Free-spirits-turned-leaders are our best hope for a future built on hard work and a unified vision, and that's one hope we can't afford to let go.

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

What is this?

When I was a little girl growing up in rural Iowa, I wanted to be a radio star. It's important to dream big.

I made it all the way to the airwaves of Minneapolis, which isn't bad, but eventually life (and ownership deregulation) overtook my aspirations and I started working straight jobs. I'd been writing for publication since the age of 11, when Highlights Magazine published a poem I'd submitted, so I kept freelancing all along: music features, celebrity interviews, trends and the occasional thought piece. I loved to tell stories but I wasn't a great journalist; by the standards of real journalists, I'm sure I'm still not.

Now straight work is steady income, and I've always enjoyed making money. At my peak I was earning over six figures, and I won't lie, I loved it a lot. I got pretty used to it, in fact, and thought I could be happy for the rest of my life traveling, paying my bills on time and spending $300 at Target without batting an eye (after all, is there anything you can buy at Target that you don't need?). But at 34 I was confronted with a few hard truths about myself:

• I didn't like corporate America
• Corporate America didn't like me
• I wasn't getting any younger, so...
• If I was going to try something big, starting sooner would be better than later.

So I did. In late 2002 I cashed in my tanking 401k and went halvesies on an an existing tiny tabloid monthly and a disadvantaged coffee shop with a crazy Persian genius named Mehrdad. In hindsight, it was absolutely the dumbest thing I've ever done. But it turned out to be a great decision and today we employ a handful of people, pay an unfair amount of taxes and otherwise positively contribute to society on our own terms - as the owners and publishers of VITAL Source Magazine in Milwaukee.

We recently sold the cafe for a fair price; the magazine and its revenue tributaries are thriving. I've learned an unbelievable amount about running what can still only be classified as a micro-business and I think some of my experiences might be interesting (or maybe even helpful at times) to other people who either are or think they would like to be in my position.

This blog is called Five Indians because that's the size of my staff. Together, we create, edit, design, sell ads for, print and distribute a city-wide magazine that just celebrated its sixth anniversary. We started in the back of the coffee shop, surrounded by crates of produce and sharing computers. Now we own a couple of fleet vans and have real offices with warehouse space and a loading dock. Significantly, I've held on to my house and am raising a great kid.

That's a little about me. Next time it's all about business.