Finding Purpose as a Jack of All Trades

I was listening to the Tim Ferris Show podcast one morning on a run. It was the “Tools of Titans” episode, which featured quotes from interviews with writer and entrepreneur, Derek Sivers. I listened and nodded at Sivers’s words of wisdom but stopped mid stride when he mentioned the Buridan’s Ass Paradox.

As the story goes, a desperately hungry donkey faces a major dilemma. The donkey stands exactly midway between two identical piles of hay—lost in indecision. He never chooses, and eventually dies of starvation.

The story caught my attention because my old boss—the editor-in-chief of a magazine I worked for—told me a different version of the same tale several years earlier. Her purpose for telling it and my subsequent reaction say a lot about the journey I’m on today.

After my first year at the magazine, I didn’t grow in any particular role and lost interest in proving my worth. I started as a junior writer and editor. Eventually I managed writers and print deliverables. Later I jumped into digital marketing. The editor-in-chief saw me as a generalist with no real value.

She called me into her office one day and said, “do you know the fable of the salty penis darling?” “No,” I said. She replied—and I am paraphrasing—“a naked man straddles the ocean with one foot touching land on either side. He can’t choose a side and eventually falls into the saltwater. Hence the salty penis. That’s you darling. You’re like the man with the salty dick.”

I stood there stunned trying to hide the horror I felt, but it was written all over my face. I was embarrassed, offended and full of disdain for a woman I blamed for making me feel miserable.  She concluded by telling me that I was a jack-of-all-trades and a master of none. Ouch.

I still think of her with less than fuzzy feelings, but I look back on that experience differently now. She was right. I was a generalist. I worked hard, but I lacked purpose, so I adapted to changing needs to prove my worth. I took on new roles and exceled without passion, eventually plateauing. Ultimately, I failed to become an SME (subject matter expert) as they like to say in the corporate world.

After I left the magazine, I got a job at a beauty manufacturer. I started there as a content writer, later became a project manager, and eventually a sales manager. I continued to take on different roles and justified it by saying that I liked randomness, adventure and change. That was all true, but it wasn’t not the whole story.

I also have a deep desire for passion and purpose. Change makes life interesting and I’m committed to it, but I’ve also used it to distract myself from what I really want.

I’ve always loved to write but didn’t feel I had anything to say. I didn’t’ think I lived a life worth scribing so I focused on climbing the corporate ladder instead. I thought to myself, if I don’t have a grand plan, purpose, or thesis, I should probably keep my pen to myself. I’m just a person with an occasional knack for words.

I internalized the generalist message for so long and allowed it to dictate my professional career—until recently. 5 weeks ago I quit my job to start freelance writing and teaching yoga. I don’t have every milestone mapped, but I’m doing it anyway.

So, to all the donkeys, dicks, and jacks out there, there’s nothing wrong with you. Life is not about finding one singular focus at the expense of all curiosity. Want to know what life is about? I have no idea, but I am on a mission to peel back the layers until I get to the essence of who I truly am. In the process, I hope to inspire you to do the same.