Whimsy isn’t something you have to earn- it’s something you possess and cultivate, and if you are drawn in a direction out of whimsy and authenticity you are too lucky to ignore it. That’s the kind of thing that shows you who you are meant to be.

At the bottom of the hill where my winery is located, there’s a little bar in a shopping plaza. They have decent beers and a few hard liquors to choose from, but they’re really more of a taproom than a full bar. All the same, they are the semi-official post-shift watering hole for cooks, servers, and occasionally office people in the winery. We’re all regulars by face if not by name.

When the beer offerings aren’t tempting me after a long day, I tend to go with whiskey. They have a few pricier bottles to pick from and their cheapest bottles I’d call “middle shelf-” whiskey’s that would be in the $30-$50 range if I got one for myself. Better than rotgut and bottom-shelf well whiskey, but not as speedy as ultra-premium brands. If I’m not feeling like Jameson’s “Black Barrel” expression or one of the slightly spendy local whiskeys, the Old Forester “Bottled-in-Bond” is a reliable choice with a couple small rocks in it.

It was an evening after a rough day. I got my little glass, sat down at a table outside facing in to the parking lot and up the hill, and decided to update the family that it was in fact That Kind Of Day.

My father sent back his approval. “Old Forester was your grandfather’s favorite. There was always a bottle in your grandmothers den.”

I stared at the little glass and thought to myself, “Finally, after 40 years, I’m turning into an Old Man.”

I like telling people I’ve been a little old man since the age of 12, and my body is finally catching up with me.

While drinking at that same bar, I once eavesdropped on a conversation between another patron and the bartender about the idea for men to “earn their rocking chair”- living their life in such a way while young that they can enjoy relaxing and doing nothing when they get old. Besides the fact that barring a lot of luck I will likely never be able to retire, I tend to ascribe to Tim Ferriss’ philosophy of “don’t put off everything you love until you are too old to actually enjoy it.”

Ferriss believed in treating a retirement fund as a final emergency fund . “What should I do if I find myself never able to work or make money again?” He postulated instead saving up to do multiple micro-retirements throughout your life, saving up enough each time that you can essentially take occasional month-long sabbaticals from earning in order to do whatever you want.

As the men talked, I mentioned a story I learned from a personal inventory exercise I do were a man attends a business seminar and the guy giving the talk asks him “What do you want to get out of this?” The man answers off the top of his head, “I want to make a million dollars.” The presenter pauses and says “Okay, if I were to give you that money right now, then what would you do?” The man thinks for a minute and then says “Well, I guess I’d go fishing.” The presenter smiles and says “It doesn’t cost a million dollars to go fishing.”

Money is good for what it gets you. It can buy you freedom and it can offer you choices. If you are fortunate enough to have the choices you want, you are fortunate enough.

It doesn’t cost a retirement fund to sit in a rocking chair on a sunny afternoon.

I don’t have any real memories of my grandfather. I was barely two years old when he died. During my time in medicine, I worked with a number of nurses and others who had known him as well was my father and uncle. There was a joke that if all three living Strengers were in the building, something was bound to happen.

Instead of my grandpa, there were several people in my life who exemplified what I wanted for myself as a senior citizen. One was an elder Scout leader who never spoke down to anyone, not even the snot-nosed mouthy teens in their care. One of them active in the Order of the Arrow- Scouting’s Honor Society, and probably the only reason I stayed with Scouting long enough to me a leader and camp councilor myself. He’s the man who would ask questions, tell stories, and is the reason I wanted to learn to smoke a pipe.

There was my Great-Uncle Butch, who always had a kind word, a fast wit, and a laugh that warmed your soul. My aunt’s father carved as a hobby and always chipped the elves, trolls, and dryads he saw in logs and stumps to the surface. Being old didn’t mean you had to be ornery and lose your sense of whimsy. They taught me that if you do it right, you get too old to care who thinks otherwise.

That all said, let’s set the vibe for the afternoon.

I smoke a pipe and cigars occasionally. I love the rocking chairs that I’ve lucked into getting my hands on. I spend time writing at an antique desk I lucked into finding, and wear an anachronistic beard that takes more maintenance, but fits me better than more modern styles.

I also wear wool sweaters and shawls in season, walk with a carved copper-shod stick frequently, and wear a gray wool wizard hat and cloak when I feel like it. It’s all a vibe, it’s all whimsical, and it is all absolutely unapologetically me.

My grandfather used to have a pipe that my dad keeps safe, but doesn’t use. It’s carved like a sea captain and might be a Meerschaum if I remember right- the bowl was yellowed, but clearly not used enough to get the golden-amber patina of continuous use. When I sit at my desk, I look at my long red churchwarden-style pipe in its holder and wonder if I won’t someday get to try out Grandpa’s.

Until then, I’ll recall the Old Man That Was and the Old Man That Will Be in one of the rocking chairs that I earned just by wanting it and having worked a long day. I bought a bottle of Old Forester to keep in my bar- arguably a pricier, better expression than the one my grandpa had access to- and I’ll pour a bit tonight. Grandpa died long before I was old enough to drink with him, but at least he knows I’ve got his favorite- and if I’m lucky, I’ll wind up a little like him in the end.

Stay Classy,