It’s a Young Man’s Game…Or Is It?

A bunch of different threads in this post today, the result of a bunch of different threads “runnin’ around the ol’ Duder’s head”  the past few weeks. So bear with me while I talk through things out loud. Hey, it’s cheaper than therapy, although a lot less effective, I’ll grant you (and probably not very interesting to you).

So, a month ago I wrote about how I’d thought about spending the summer when I was 26 at the surf break known as the Mexican Pipeline. I finally made it there this year, in March, when I turned 51, and I wasn’t ashamed to say that, upon my arrival, the waves were intimidating.

Puerto Escondido definitely intrigues me as a potential long-term destination. (I have every expectation that if I wind up dying of old age it will be in a foreign country. After seeing the way my father, a World War II veteran, was mistreated by this country’s health system, what can a selfish deadbeat like me expect as his body starts to wind down? But that’s a topic for a separate post.) But when I thought about spending significant time in a surf-focused life, I wondered if that really made any sense to an aging (as are we all) middle-aged man.

Puerto Escondido is a destination for young surfers from all over the world, and there’s a reason that particular demographic overruns the town during peak season. It takes strength and fitness just to step into the ring at a serious wave. And while I still go to the gym and play hockey and lead a generally fitness-focused lifestyle, well, there’s a reason I play in the over-50 hockey tournaments now. Can I still handle a wave like Puerto? Yes. But it’s exhausting. And potentially dangerous. And my recharge capabilities aren’t what they once were. Those are just facts.

So when I look at potential paths I might take — and I do that a lot as this year in which the generations of my family changed hands winds down — I question whether such a pursuit is an appropriate core focus of my life. In fact, I question WHAT should be the focus of my life to come.

And that’s an important question because in just a few months my father will have been gone for a year, at which point (or shortly thereafter) my role as executor, trustee and caretaker of the family’s assets and physical legacy will come to a close. And I have some decisions to make.

Do my brother and I keep our family’s house (our sister has no interest in keeping her share)? Does that mean I remain living there? If so, what do I do for a living around here? If not, do we rent out the house? Or do we sell? If we rent or sell, where should I go and what should I do? And if we keep the house, how do my brother and I come to terms about what we should do about various aspects of the house’s management and upkeep (and who should pay for them)?

Questions of career, location, home, legacy — questions that have built up over the close-to-a-hundred years of my parents’ lives and the lives of the children they produced, including me — are about to require an answer. And as those of you who know me well can attest, I have a wide range of interests and dreams pulling me in an even wider range of directions.

The security of a “straight” job back in Corporate America has its appeals but in my field those options are largely out west. And even if they’re in around here, among the reasons I didn’t opt for a commuting-into-Boston career when I got out of college is the fact it’s a hellacious, dangerous, expensive and exhausting commute from Plum Island. And it still is. But shouldn’t I be maximizing my income (and savings) at this point in my life in an attempt to set up my so-called “golden years”?

Or: What about carving out some sort of niche, working-for-myself career? Can I parlay my skills (cough, cough) and experience into something that lets me work from, say, the office on the third floor of the house at Plum Island? Travel — to Boston, New York and beyond — is easy enough. My mother always implored me to be my own boss (as she was), but I’ve yet to make that happen. Maybe I can create enough of a career yet stay at home — and keep that home in the family. But can I even create that career now, at this age?

Speaking of which: underlying all of these internal (now external) debates is the aforementioned fact that I recently turned 51. I’ve already experienced light doses of ageism and I can only expect them to increase, right? Is Corporate America or building one’s own career every bit a young man’s game as living for surf in a grubby apartment in Mexico?

Then there’s the age-old dream — and those of you who’ve known me for any length of time have heard me talk about this since I was a teenager — of buying a sailboat and taking off. I came close back in the ‘90s (Mom, in her infinite wisdom, refused to help me out financially then, for which I remain thankful). I came close in 2011 (which, given what happened to Mom and Dad in 2012 and 2013, I’m glad fell through). And when I returned to New England last spring I planned on two things: one, helping Dad; and two, buying a crappy, old boat and fixing it up to head south in November. That plan went with Dad in July, but there’s no reason the plan can’t be resurrected this year.

I follow the journals of friends who are living a life of early retirement. I follow those who continue to work but live on the road. I monitor the experiences of those courageous souls who never bought into the system in the first place. Hell, I even adore the fictional character Travis McGee and his plan for “taking retirement in installments.” So the pull of that dream I’ve had since I was a boy remains strong. And this might be the time to make it happen. Selling the house would certainly generate enough cash to go. Keeping the house and renting it out would generate at least some income on which to live. Hell, there might even still be enough money left in my savings to go as I’d planned to last year (though I’ve been burning through a lot of it this year as I’ve been living at the island and chipping away at what’s needed doing), but would managing that be more trouble than it’s worth?

No matter what I wind up doing, I still need some sort of purpose in life though, don’t I? Elon Musk raised the question of a universal basic income as a response to the rise in workplace automation, but questioned what, if anything, such “free” income could do for people in terms of a reason to live. As I’ve been mostly idle for the past year, I’ve come to realize that a focus, a calling, a purpose is a good thing. It’s a requirement, actually. Elon’s right.

Which brings me back around to today’s original question: What to do when those things that might function as a focus in my life are largely geared toward those (much) younger than me? Do I rage against the dying of the light? Or take up a serious golf habit?

These are the things I ponder of late. A lot.

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