Career-Man vs. Entrepreneur-Man, a personal dilemma

Image via Wikipedia Today is the first day of the rest of my life.

Okay, that's a bit dramatic. But, really, it is the first day of the next phase on my path, which I see as more of a bend in the boardwalk than a fork in the trail.

My path began in publishing. I worked as a scout for an international agency and as an editor at Viking/Penguin, but prior to that I founded Rockstop! Magazine, back in the early 80s.

I have always started things. As a media entrepreneur, I was one of the founders of the web-based literary journal Ducky Magazine and founded this web log in 2004.

But for the past 16 years I have been basically a company man, most of that time with The Nature Conservancy, where I held various management positions and, most recently, with Ashoka, the global association of leading social entrepreneurs.

Part of what attracted me to Ashoka was the opportunity to meet social entrepreneurs around the world who were developing business models -- some non-profit and some for-profit -- with the goal of changing the world, flipping a system, or addressing a market failure.

What interested Ashoka in me was my combination of expertise and entrepreneurship. Well, the entrepreneurial itch overtook me recently and I've now left Ashoka to scratch it.

I'm developing a green energy investing platform to reduce the barriers to entry for small retail investors who want to catch the wave of the new green economy. It's in the very nascent stages and probably too premature to talk about, which is both exciting and daunting.

Daunting because the "Career-Man" in me is struggling mightily with this new phase, with his alter ego "Entrepreneur-Man."

You see, I've always created things on the side. Now I'm starting from scratch and spending more time on it than just nights and weekends.

Career-Man excels at crafting a vision, building teams, and management, and he's a pretty good at marketing and raising money. Entrepreneur-Man loves starting things.

But this start-up stuff has got Career-Man all tied up in knots. He's used to having the framework in which to operate, while Entrepreneur-Man likes to build an entirely new framework. Therein lays the struggle.

I tweeted about this earlier today, which generated a few comments from followers and friends.

One wrote, "As a note of encouragement, a job is one thing, your work is another. Now you simply have more ability to focus your energies without navigating so many distractions."

Another wrote, "When you figure out how to keep Career-Man at bay, let me know!"

And finally, another friend was reminded of one excellent line in an otherwise forgettable Tommy Lee Jones-Cate Blanchett film, "The Missing."

In the film, Blanchett plays a young woman alone in the wilderness, who must reunite with her estranged father (Jones) to track the mystical, psychopathic killer known as Chidin (Eric Schweig). Chidin and his brutal pack of army deserters have kidnapped a collection of teenage girls, and have taken Maggie's daughter (Evan Rachel Wood) as their most recent prize.

My friend wrote, Jones' "nemesis says something like, 'The wolf and the good dog within you fight. I wonder which one will win.'"

To which Jones replies, "Whichever one I feed the most."

I must keep feeding the Entrepreneur-Man, because a job is one thing, and my work is something completely different. No doubt the path will be bumpy, but the rewards will be the journey.