Pretirement Motivation: The Bosses I’ve Had

The longer I work, the more the quality of my relationship with my supervisor seems to count toward my job satisfaction.  I’ve had several managers in my life with whom I worked for significant stretches of time.  I was really fortunate with most of them but, two of them, well, hoo-wee!  They did more to plant me on the long path to pretirement freedom than anything else.  More later about what I learned from working for them, and getting away from them.  If it’s true that we learn the most from the challenging people in our lives, then I am grudgingly grateful for this pair’s abundant gifts to me.  Or something.

The longer I work, the more the quality of my relationship with my supervisor seems to count toward my job satisfaction.  I’ve had several managers in my life with whom I worked for significant stretches of time.  I was really fortunate with most of them but, two of them, well, hoo-wee!  They did more to plant me on the long path to pretirement freedom than anything else.  More later about what I learned from working for them, and getting away from them.  If it’s true that we learn the most from the challenging people in our lives, then I am grudgingly grateful for this pair’s abundant gifts to me.  Or something.

When I started out in my career, trying to get my first foothold on the rock face of the mountain climb ahead, I didn’t care to whom I reported.  “Just gimme the job and I’ll figure it out.”  In my twenties my attitude and best plan was that I wanted some kind of a coherent non-profit career.

What a strange thing the manager/report relationship is, when you step back.  You’ve had maybe one or two interactions with the person in an unnatural competitive interview process.  The next day, that near-stranger holds a huge amount of power over your every day existence and entire professional future.

Managers matter, too.  In college, one of my very best friends and I held part time jobs working at a golf club with a team of other students.  We took golf bags off carts, cleaned the clubs and kept the driving range stocked with balls.  Clearly, the job was not complicated or demanding, which was a perfect counterbalance to working so hard for good grades.

One day, the assistant golf pro who managed us, an easy-going fellow, was suddenly gone. I never learned why.  In his place was a new guy, Wade, who was memorable to me only because he was wound so tight that it was comical to other people.  It was a golf course, not a hospital emergency room, but Wade was prickly, ambitious and clearly insecure in his new assistant golf pro role.  I don’t actually remember any words he ever uttered but, as with nearly everyone we humans encounter in life, I recall perfectly my inner reaction to him:  Poor Wade’s vibe was, “Saguaro Cactus.”

In fairness, the assistant pro job was probably an important promotion for Wade, because this private club was selective, expensive and had an influential membership.  Wade sometimes manifested his innate stress by snapping at us about this or that inconsequential thing.  He caused the fun tone we had previously enjoyed to evaporate from our little team of eager college kids, who were mostly there to earn a few simple bucks without a lot hassle.

I never had words with Wade but my friend did.  I don’t remember when Wade left my life or vice versa, but I happily and instantly erased him from my mind.  Years later, his name came up when I was talking with my good friend.  Right out of college this talented friend had started his own software company at the dawn of the dot.com era.  His company followed the classic tech startup script: Identify a niche, write some code, create a product, secure some sales, attract  venture capital, grow the staff to hundreds and, in a few years, sell the company.

He still works full time for himself, though he probably doesn’t have to anymore.  I once asked my friend his motivation for starting his own companies, which always awed me as a person who gravitated to what I felt was the comfort and safety of large organizations.  He didn’t hesitate:

“You remember that guy Wade?”

It took me a beat before I did. “Oh, that guy.  Ha!  I wonder where he is now?”

My friend said, “I don’t know, but I couldn’t see myself working for jerks like him the rest of my life.  That guy made me determined to never have a boss.”

I, on the other hand, proceeded to have several bosses, and I take responsibility for my choices.  I always assumed I had no business having a business, and I think I was 100% right about that.   I also never saw myself as an S&P 500 corporate type, because corporations seemed to me dog-eat-dog environments, where the profit motive caused people to step on someone’s head while competing to climb the ladder.  Now that I have some career experience, I’m sure that’s mostly an incorrect Darwinian stereotype about major corporations.  Nor did I see myself in the military, though I really admire people I know who did go that route. I think I might have liked the Navy or Coast Guard, but that’s just my current self speaking to my earlier self, which is pointless.

Rather, I distinctly decided during my senior year in college that I wanted to pursue my passion for trying to make a difference through some kind of public service, and that I’d probably do so working for a larger non-profit organization or government agency.  I assumed non-profit organizations filled with passionate people who worked to make a difference in the world were also places where I stood the best chance of being treated as a human being myself, rather than an expendable corporate cog, which seemed kind of important, too.

I’m not qualified to judge corporate life with any accuracy but I think I was basically correct about non-profits.  I’ve generally been treated well and I feel that, frequently, I’ve enjoyed the satisfaction of having helped make a difference.  For the most part, I’ve reported to humane leaders who appreciated my contributions and who coached and rewarded me fairly.  I’ve tried to model my own behavior as a manager on what I learned from those fine leaders, some of whom remain mentors and even friends.

I also learned a lot from surviving the more toxic leaders I reported to.  A couple of my many educational takeaways from them were:

  1. “Don’t wish for my boss to change.  I’m the one who needs to change something.”  When I have realized in the past that I’ve lost respect for my manager, I have learned that I am one who needs to act.  People above them have different relationships with them, so no one is likely going to act because I’m unhappy.  It was easy to remain stuck by fooling myself that “This is just how work and bosses are”.  That is simply not true.  I need to analyze the situation and calculate my happiness level in it then, if necessary, start sharpening my resume and cultivating my network.
  2. Life is too short to be unhappy at work.  Some of the most miserable people I have ever met address their unhappiness with work by trying to cement themselves in place more firmly.  Their hate for their jobs and unwillingness to solve it through taking action puts them in a posture of constant pain, which manifests in all kinds of toxic behaviors.  They seem to me like a child who thinks that if he holds his breath long enough, the person he’s angry at will pass out.  Not me.  I believe in monitoring my work happiness and remaining prepared to leave when the organization I once worked for has changed around me unsatisfactorily in some way.  I try hard to stay entirely positive and grateful about being employed but also committed to freeing myself to do something else, if needed.  We work in this modern world of few pensions, few protected unions, no contracts and “At-Will Employment.”  If there is to be any fairness at all in such a lopsided world, we have to approach the agreement to hold a job as a two-way street.

Though my current situation is a good one, a big point of this blog is to help me plan for how to spend my time after I eventually retire the sword and want to do something else, as nearly everyone my age seems to be contemplating.  What I want is still a work in progress.  I hope through this blog that I can explore myself but also learn from others’ experiences in creatively tackling this common question stemming from a growing desire for more work freedom.  In other words, I want to start defining my pretirement.

That exploration is still ahead of me but I realize after nearly three decades of working for organizations, during which I’ve had several significant supervisors, some of whom were wonderful to know and others whom I was relieved to flee, I think I am evolving to the place that my good friend started out with:  At some point, I want to be done with bosses.

What about the bosses you’ve had?

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Author: See: Pretirement Political Consumption: Setting and Forgetting It @ Pretirement Freedom

Like a lot of people working through the later innings of a 9-5 career, I'm thinking about what's next. What most excites me is exploring the endless variety of paid and unpaid possibilities offered by "pretirement," the best word I've found for this unique phase.

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