Job Hopping Is the Best Life Choice I Have Ever Made

Changing jobs beats drinking, doing drugs, or having sex to get out of a lifeless rut

Source: Author

I have more than 75 plants in my apartment. I love them all. However, I like these best. When I least expect it, my bunny ear cacti sprout crazy extensions seemingly overnight.

It’s as if the cactus got bored and decided to completely alter the course of its professional life. This way of living resonates with me.

I have had a total of five careers in my life. Somewhat ironically, this makes me feel young. Because chances are it’s more likely that people who are younger than me will follow a similar trajectory than people my age or older.

In this article, I illustrate and reflect on the consequences of repeated career flips. I hope the color I add to my experience can help inform yours, if only in some small way.

It’s easy to regret life decisions. It’s also, most often, nonsensical.

Here’s a rough sketch of my career timeline:

  • 1988 to 2000 (age 13 to 25): Radio producer and personality
  • 2000 to 2002 (age 25 to 27): Inside sales representative
  • 2002 to 2008 (age 25 to 33): Student, entrenched in academia
  • 2008 to present (age 33 onward): (Mostly freelance) writer and editor
  • 2016 to 2020 (age 41 to 44): Craft cocktail bartender/general manager

For too long, I regretted most of these career changes. This is until I placed them in the proper context. It’s easy to look back on something you didn’t finish and wonder what could have been.

My career changes used to make me feel like a loser. Then I discovered I was only a “loser” to the extent that I spent valuable time ruminating. It’s one thing to be critically introspective; it’s entirely another to get stuck in unproductive thoughts.

Ruminating can lead to an idealized version of what could have been. It ignores the reality that a series of decisions and events — big and small — shape your life. You can’t cherry pick the ones you want to do over and expect to maintain what you love about your present life and what you aim to accomplish in the future.

Concrete example — had I stayed in radio way back in the year 2000, I might have never attended college, gotten married, had a child, and moved to California, my home for the last twenty years. You can’t have it both ways, right? If I opted to continue my radio career I likely would have ended up in Columbus, Ohio rather than San Francisco, California. Big diff.

California shaped me. It (with a big heartfelt assist to my ex-wife) turned me into the person I am today, sociopolitically and personally. My most recent three career changes led to various forms of personal triumph and tumult, which helped morph me even more. I continue to grow and evolve, to explore my (productive) introspective and spiritual sides.

I credit the career — and inextricably linked life changes — I foisted on myself over the years for my ability to constantly develop as a human being.

I didn’t have to leave radio, go to college, decide on writing as a career, and take a four-year hiatus from writing to tend bar and learn something completely new. I could have made a lifelong career as a radio personality or professor. I could have opted for stability, as opposed to the type of professional fluidity that creates opportunity stasis never could.

It’s constant change — even uncertainty — that creates opportunity. It ends ruts. I have tried everything in the book to remove myself from past lifeless ruts. Alcohol. Drugs. Sex. This doesn’t mean drinking, doing drugs, or having sex doesn’t help. These things can and — to a reasonable extent —do help during a rut, be it acute or ongoing. They’re just not the solution.

As I look back, the solution — for me — has been trying something new. I’m convinced it has kept me young, relevant, and fresh. It also — possibly — made me a bit less wealthy than I am today.

I have written about panic selling stock because I felt cash insecure. This was often the case. However, I sometimes sold because I truly needed the cash. I often needed the cash at these career-related crossroads.

I spent roughly six years entrenched in academia. Taking classes. Reading everything. Doing research. Writing and publishing papers. As an undergraduate or graduate student, they don’t pay you much to do these things. So, from a purely bean-counting, numbers perspective, you could say my career changes cost me money and delayed the wealth building process.

But this tells an incomplete story.

I’m a better writer because of my varied life experience. If I spent my early 40s in my original radio career or academia instead of in a barroom, I would not have been able to seamlessly slip back into the world of writing the way I have.

My work-related fits and starts color most everything I write about and how I write about it. As far as I know I’m one of a small number of people to hit earnings of nearly $2,000 a month in my second and third full months on the Medium platform (article detailing the process forthcoming). There’s no way I could have done this as a one-career guy. It’s my agglomeration and accumulation of experiences — job experience and job experience leading to social and life experience — that make me interesting enough to produce content that pays on this type of platform.

Had I kept one job forever, I would have chosen stability over creativity. I could not have succeeded as the person who works the same job all day, every day and, then, if I’m not too sleepy, works on my passions at night. I work my passion all day, every day. And I can do this because I traded stability and security for the excitement and growth only living different lives within one lifetime can bring.

This is merely my way of viewing my world. It’s what moves, motivates, and makes a difference for me. I would have capped my earnings potential by staying in one career for too long. I would not have been able to jump into the flexible world of freelance writing, where limits on how much you can make exist in ways decidedly different from traditional employment.

I often look at people — successful people — who have carved out prosperous lifelong careers with a mix of admiration and envy. But then I realize that’s simply not how I roll. One person’s seemingly calm stability is another person’s rut and cue for change.

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I write about doing life and personal finance, focusing on the psychology of our relationships with other people and money. I’m anti-guru, pro-empowerment.

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