Between Generations and Happy to Steal from Both

By Don Hall

"When I ask older people,* they say it's the smart thing to get a stable job with benefits and a secure salary even if I don't like the job. When I ask younger people,** they tell me to take time off, that it's completely fine to jump from job to job until I find something that, I don't know, fulfills me."

* Older than 33.
** Younger than 33.

My friend is leaving her job. It seems things are getting fairly dismal over at my former place of employ and that, perhaps, I got out while the getting was good. Unlike me, she's leaving without any kind of severance package and is a bit lost in her Next Step on the Journey sort of deal. She wanted to grab lunch and see how I'm doing as a gauge for what comes next for her.

"You don't seem to fit either category. What's that all about?"

A couple of years ago, the brilliant Lauren Chooljian embarked in interviewing those of a certain age about where they were, career-wise, at age 25. Her experience was that many 25 year olds (she being one at the time) were so anxious about establishing a secure career path at a time of technological revolution that some couldn't sleep or eat. Connecting that to the increase in the What Anti-Depression Cocktail Are You Taking? Club of Millennials, she wanted to know why we on the further side of 25 weren't sucking down Zoloft like Skittles just to get out of the house.

One of the things she uncovered was that, for the most part, those on the other side of 50 weren't that focused on career and mostly lucked their way into the gigs they had today. Not quite the random discovery in a malt shop mythology of 1940s Hollywood but in the same camp. Now in solid careers, these folks were loathe to change it up as they did in their youth but getting where they are today was more a matter of chance and being open to opportunities than an intentional focus on career.

My dad is a pretty clear example. He started by flying planes, then flying stunt bi-planes in films. He moved on to being a rock 'n' roll deejay in Kansas City in the '50s. He then migrated to real estate, where he made both his bones and most of his money until he retired a few years ago. The path was anything but straight and narrow let alone made any pragmatic sense but he did just fine.

My career path is equally as chaotic and without any sense of direction. Graduated college with a degree in Music Education, came to Chicago to be a professional jazz musician. Taught public school music for nine years. In the meantime, I started a theatre company. Ran that for a long time. Worked random jobs throughout (voiceover work, telemarketing, construction, a facilities manager for a local massage school, paid comedic improviser, improv teacher, minimum wage at a local tobacconist, House Manager for NPR, Director of Events for WBEZ, host of The Moth. If there was a plan, it was that of a stumbling drunk or of some asshole who simply wasn't paying attention.

Her question caught me off guard. Upon reflection, I realized that, because I am of the X Generation, I am caught between the Boomers and the Millennials and get to steal a bit from both. I have the hardcore work ethic of the Boomers and the curiosity and joy of the newest technology of the Kids. I remember the world before the Internet and have successfully transitioned in the fully realized digital world. I respect the stable gig but am not satisfied with staying in one place for much longer than a decade before I jump to another rail.

Gen Xers like to piss and moan a lot but I'll admit that I really dig my generational place in the world. I like being 51 and in-between my dad and my nephew.

My advice to her? Take a few months and think about a thing she can do every day—that makes her some money—that she really likes doing. My perspective is that life is simply too short to settle for a bullshit day-to-day but that you don't want to follow a dream that leaves you homeless or living in your parents' basement.