At What Price, Success?

Among my circle of friends are many who share my disgust of the traditional working environment. And in recent weeks, among this same circle, there are many giving up the fight altogether. Starting their own business, taking a sabbatical, cashing in their mutual funds for a few months traveling the Far East.

It’s a shaky time for me to think of so extreme an exit strategy. I like stability, as well as paying my rent. Considering a leave of absence from the working world makes me uneasy, and, to be honest, a little nauseous.

What these escapees had in common was their initial drive to succeed. A lawyer friend who graduated top of his class grew to hate the legal grind. A senior editor despised the rigidity of style guides and her perfectionist-of-a-boss and took the summer off to start a freelance career. A loan consultant who worked nights and weekends in the hopes of making manager sold her million-dollar home to teach English to monks in Thailand.

I had my own ambitions but found that on my sluggish climb up the corporate ladder that I was met with overly aggressive colleagues and a more grueling workload with each and every rung.

It’s a point of considerable contemplation for me – understanding the balance between doing what you love and finding good people to do it with. That’s a magical combination, but is it even possible? A couple of recent conversations are making me think otherwise.

Last week I met up with a former colleague whom I worked with for a number of years. The job was anything but glamorous, but we had a blast. In fact, it was one of the best jobs I’ve had in my life. Extenuating circumstances (best left to another blog post) forced us out of that place, but he quickly landed on his feet. His new job isn’t anything to write home about, but he adores his new boss who gives him leave off of work to go back to school and finish a bachelor’s degree in computer science. Not a bad move.

A later conversation with a friend of a friend fueled my internal debate. He was an ambitious and highly paid lawyer to the stars. But his bosses were unbalanced and his clients unhinged. So he saved up enough cash to take a year off traveling through Southeast Asia.

He’s back in the states and wondering about his next career move. But during our conversation, he shared with me his interesting conclusion. You can be an overachiever and take a grueling, rough rode to financial and professional success; or you can settle for a little less prestige and a little less glory. But you’ll be in the company of sane co-workers and enjoy a life outside of the office. Unfortunately, you can’t have both.

My job searches typically focus on the work itself: Will this look good on my resume? Where do I move up from here? Rarely do I wonder if I’ll like the people, or if I can share a laugh or even a friendship with my coworkers. It was important that I liked my new boss, but I focused on the tasks of the job hoping the friendships would develop. Funny, they never seemed to.

So there’s my conundrum. Finding more value in what I do or who I spend my time doing it with. It seems like pure luck to me, but maybe there’s a strategy to it. If you were able to have found both, I’d love to hear about it.