A pirate looks at 60

Mother, mother ocean

I have heard your call

Wanted to sail upon your waters since I was 3 feet tall

You’ve seen it all

You’ve seen it all

If you’re not familiar, this verse begins A Pirate Looks at 40, my favorite Jimmy Buffett song. I listen to it once a decade on my birthday. Including today.

For me, 40 was 20 years ago. Twenty years. At some point, time seems virtually impossible to conceptualize. This is one of those times.

Here are my thoughts. Pardon the rambling.

So, all those years ago, I had this bucket list of goals, one of which was to write three original songs and perform them at an open mic, acoustic guitar strapped around my shoulder, a harmonica around my neck. One of those songs contained the following lyric:

Time don’t mean that much to me

I’ve got all the time I need

I have felt this way my entire life. I’ve always been all but certain that my time on this earth would stretch well past the visible horizon. I’ve made plans and set goals, always thinking I’ve got all the time I need, and then some, to complete it all.

When this pirate looked at 50, I didn’t feel any different. It felt like halftime. I was thinking big and making plans and dreaming and moving, always moving.

I don’t know what it is about 60, but it hits different, that’s for sure. Perhaps it’s the certainty that I’m closer to the finish line that I am to the start. Maybe it’s in part due to the fact that I’ve seen others pass before their time, before this time, making each moment of mine feel like it’s on loan.

There’s also the possibility that the joke’s on me. Maybe time should mean more to me, and I may not have all the time I need to do everything I want to do. So these days, I often find myself picking and choosing. What books do I still need to read? What music do I need to see live? What do I want to achieve physically before my body starts rejecting the efforts? What words am I leaving unwritten?

I guess it’s just hitting me, at the ripe young age of 60, that I may in fact be mortal. This beautiful life may not linger forever.

About a year back, in the throes of Covid, I envisioned for the first time ever a world without me. It was trippy af. Having slept for days, I found myself wide awake at sunrise as Chicago slept all around me, wondering why I would ever miss this.

Wondering why I always miss it.

As day broke through my dense, not altogether unpleasant brain fog, I could sense the whir of industry awakening beneath me, a city coming to life for another day.

And it struck me that, in the not-too-distant future, this will all be happening without me. My mind took me to an old cemetery that I walked through not long ago. There was one area dense with the newly-deceased, the dates of death recent, familiar. The grass was trimmed, and flowers and flags adorned a lot of those gravesites. The etchings in the stone were deep and clean. These are people that are still remembered and honored, perhaps only for milestones: birthdays, Memorial Day, Veterans Day, an anniversary.

But remembered nonetheless. For now.

All of the rest of that acreage seemed ancient. The ground unkempt and all but forgotten around the dilapidated, neglected broken marble. Weather and time had worn those headstones all but shapeless, eroding names and dates.

Erasing entire lives without sentiment.

It struck me that once you’ve drawn your last breath, it doesn’t take very long to be forgotten. In my mind, that makes it all the more important to do what we can while we’re here. I’m hoping my legacy lives on in the lives I touch, and the lives they touch.

Everything else returns to dust.

Growin’ up

I don’t think I was particularly adept at being young. Most people found their wild side then. They took chances. They experimented. They learned and they grew and they effed up and they survived.

Me, not so much. I was no pirate back then. I was an altar boy.

Literally.

I followed every rule. I think anxiety drew me away from what could’ve been great joys and self-serving thrills in my life. I find myself envious at times of my wildly experimental teenage clients. Their fierceness and their intensity, their freedom and their angst. I had to borrow all of that from my buddies versed in Faulkner, Kerouac, O’Connor and Dylan.

Way back then, I crafted my persona through vicarious experience.

I stayed in the lanes entirely when I was a kid and into my young adulthood. It wasn’t until I met Julie that I thought, “Oh, I’m gonna leapfrog the gutter to get to her.”

Now that I’m here

I never pictured being 60-years-old. I’m surprised to be so surprised. My father died at 68. And when I look in a mirror, I see his son, not him. Perhaps that’s just self-protective dysmorphia. Maybe I’m in full denial of my reality.

I don’t know. I’m not sure I care.

More often than not, I find myself defiant. I still keep my career running at a pretty breakneck pace. I run through nearly a dozen client sessions a day with all the energy I can muster. I run this Substack with as much clarity and care as time will afford. I run a 5K nearly every morning.

I guess I’m always running. I may be under the delusion that I can win this race, outrun the inevitable. I know I can’t, but I’ll take the delusion. I like it better than the alternative.

I can’t say I dislike being 60. This is actually a really good time in my life when I take stock of it, and I’ve done a lot of that lately.

I don’t like the idea of being old. But I don’t mind aging.

Full disclosure, I do fight my age to some extent. I spend way, way more of my time with people in their teens and 20s that I do people in their 50s and 60s. I listen to their music. I try to pick up on their lingo. They keep me feeling young. I recommend this.

I think back on these 60 years with such gratitude. So far, I’ve enjoyed the great luxury of experiencing the entire kaleidoscope of emotions. I’ve been blissfully happy, and in deep despair. I have loved, and I have grieved and I have created. I have hurt, and I hope I have healed as well. Most days, I remind myself that my greatest dreams have come true, and there’s plenty of runway for many, many more.

What’s next

So, my plan is to be good at being 60. I want to keep working for as long as I can. I want to hold onto my precious health. But I also want more joy in my life. I want to spend more time with the people I love. I want to dance to good music. I want to laugh my ass off.

I want to surprise myself with what I can do.

I know an awful lot of people, probably many of you, don’t want people to know their age when they hit a number like 60. They don’t want to be seen as old.

And listen, I’m not immune to that kind of vanity. When someone tells me that I don’t look or seem my age, I’m into it, for sure.

But these days, I find it way more important to live my truth. I dig this time in my life. I feel like I’ve learned some things, but I’ve got a hell of a lot to learn. I feel like I’ve seen some things, but there’s so much more to see. I feel like I’ve shown love, but I’ve got a lot of love left to give.

I like the story I’m writing now. I like not knowing how it ends. I think that’s what keeps me alive and feeling young and vigorous and curious.

But I also like the perspective I’ve grown to have. I don’t take much for granted anymore. My life is filled with way more gratitude and appreciation and wonder these days. That hasn’t always been true. I like to think that age allows me more of an outward focus. For so much of my life, I’ve looked inward. I’ve learned a lot about myself but suffered far too much undue goddamn anxiety.

Now, I’m going to make an attempt to focus more outward. I want to know you. I want to help you through your struggles and celebrate your victories.

So if you’re like me, a pirate looking at 50, 60, 70 or 80, let’s look forward. Let’s do what we can do while we can still do it. It’s a big world to take in.

My moments matter now. They do not stretch to the horizon. Perhaps they just meet it. But I’ll take it. I’m big on abundance, but something about scarcity makes time more precious. I’m far less likely to squander it, I think.

The thing I’ve learned most, and it’s taken virtually every second of my 60 years to recognize it, is that it’s OK to be happy. I’ve learned that from my wife Julie, from time with my son George and his fiancé Lauren, and my friends and family. I’ve heard it from young people that I’ve worked with. There is no reward for misery and suffering. And even if you’ve been through an awful lot, and I have, misery and suffering are not requisite. You are allowed joy in your life. I am allowed joy in mine.

And I missed some before. I’m going to do my level best not to miss any going forward.

Going forward

So I declare today a beginning, a new dawn. My next day.

I’m going to worry less about screwing up. I’m going to create more of my own content, in a way I organically know how to do. And I’m going to read and listen and learn from yours.

I still have a whole bunch of pins to put on the map.

I’m going to touch as many lives as I can in as positive a way as I can. I’m going to do my best to lead with love and curiosity.

I’m going to leave it all on the field.

And every 10 years on my birthday, I will listen to that Buffett song. I like that verse up top the most. To me, it’s an invitation to see and do more. It’s a mandate that I’m not finished with my work and my experiences here. But one day, that ocean is going to be calling me home.

But not today. Today, we sail.