“What type of job are you looking for?”
It’s the question every Supreme Career Generalist dreads. If you’re a mid-career adult who can’t seem to fit into the corporate world, have a “colorful” career history, or have too many interests to choose just one, you’re not alone!

[tc_animate type=”slideInRight” duration=”2″ delay=”2.5″]“Most men lead lives of quiet desperation and go to the grave with the song still in them.”
Henry David Thoreau


I’m a Renaissance Man. A Jack of all Trades. A “Supreme Career Generalist.” That may sound like I’m a secular angel who simultaneously apotheosizes humanity while underscoring lesser beings’ sad limitability. Or that the problems I encounter on a daily basis have everything to do with repression by political and religious factions fearful of losing power in an intellectually evolving world.

I’m not that glamorous. Or important.

In fact, I’m destined to forever be several rungs lower on Jacob’s employment ladder. Always reaching. Occasionally finding. More often flailing. Rarely attaining. Never achieving permanent career satisfaction.

What’s a Very General Background Worth?

My employment history has, to the casual eye, no threads tying it together. That’s because I have a lot of interests, and for a long time, I thought there was something wrong with me because of this.

I graduated from college many years ago with an English degree (but only because I was forced to choose something), and then figured I’d become a writer. I did freelance work for a while. I got bored. But I had to pay the bills. Thus, my illustrious Generalist Career began. Highlights include:

  • Dog walker
  • Gardener
  • Professional housepainter
  • Patio installer
  • College financial aid and academic counselor
  • Software trainer
  • Summer camp manager
  • Middle school English tutor

I’ve also

  • Installed more air conditioning units than God
  • Snaked CAT6 cabling through unsurpassable ceilings
  • Commercially plowed snow
  • Worked in sales
  • Found myself adrift (for a time) in a boat insurance call center
  • Directed a state maintenance facility for an incompetent facilities director
  • Developed county mental health education programs for an incompetent manager
  • Managed absentee owner condo properties
  • Dealt junk (real junk, not heroin)
  • Operated several small businesses

Currently, I am a carpenter’s apprentice. Don’t ask. I’m just a generalist here.

The good news is that I can do a lot of stuff. The problem is I can’t define what I really want to do.

[tc_note note_color=”#B3D8DF”]A psychiatrist would probably say I have a deep seated aversion, even fear, to commitment.

I’d counter by saying my engagement maintains my mental acuity, plasticity, well-being and happiness.


Generalists’ Fear of Commitment

Try as I might, once I achieve threshold competence in a position, it’s time for me to leave. The rose in the job fades and it’s only a matter of time before I prune my dying growth to renew again, somewhere else doing something else.

Indeed, despite my colorful career background, I actually pride myself with considerate hobo standards. I always honor two weeks’ notice after tendering casual employment.

But, to the outsider, jumping track from a good, solid paying and secure gig seems reckless, maddening, even horrifying. Especially after a certain age. And to be sure, it is. Believe me.

But it’s not quite horrifying enough for me to stop doing it.

Dodging the Dog-and-Pony Show

What’s maddening to me is submitting to the corporate machine. Someone else’s exacting timeframe. Pretending to care about the bottom line drumbeat or falsified progress report. Or winning a disposable award. Decades flipping the hourglass, wondering at the end what was really accomplished other than a stable paycheck, a puny 401K, and some trapping sense of pride in the midst of a dust-gathering portrait at headquarters’ entrance.

Enough is Enough!

If you’re a Supreme Career Generalist, fear not! The generalists’ curse is worth it! Leaving a stale occupation is liberating and reinvigorating. Losing is the start of finding fulfillment. Moving on is what beats back that perpetual empty feeling of a deadened and dead end position.

Limp through life – you’ll get lost. “Woulda….coulda….shoulda.” Yes, society is drunk on the juice of the specialist, but you don’t have to drink from their pot!

Job Searching for Generalists

Job hopping may sound romantic. It isn’t. Working to find new work is work. If it wasn’t, work would be called fun. This is where things get really hard:

“What type of job are you looking for?”

It’s the question that I and every other Supreme Career Generalists dreads. It’s our curse. We’re interested in everything. We’re highly intelligent. We’re flexible. And we learn quickly. Surely there’s a place for us, where we can deflate the despair of long-term routine and make work fun.

The first step is to realize that whatever path you choose, it’ll eventually become boring. Once you’ve come to terms with that, tune in next month for my strategies on keeping your sanity.