Rule #2019: A Pirate Looks at 59
In the final days of the year, I find myself doing less reflection on the year that’s ending and more preparation for the year ahead. This will be my last year in my 50s—the decade my father always promised would be my best. He told me not to fear my fifties but to embrace them as years of success. That advice helped me face the challenges of the decade with optimism, always looking for clear skies ahead. It was simple “Don Hill” wisdom, but it turned out to be absolutely right.
This blog was designed as a map for my children, a chart they can follow when they need advice and I’m no longer around to dispense it (in 40 or 50 years, of course). Like all good cartographers, my job is to take what I’ve learned from the past and use it to sketch a more accurate map of the seas ahead—building on what my dad once gave to me.
And yes, the fifties have been the best years so far. Not because everything is easy, but because it’s the decade you finally realize you’re a Pirate.
Jimmy Buffett wrote A Pirate Looks at Forty as a sad reflection, with the line, “The cannons don’t thunder, there’s nothing to plunder.” He was wrong. He wrote it at 40 and had no idea what the fifties would hold. (Sorry, Jimmy—no one bats a thousand.)
To me, being a Pirate means realizing that rules are made to be bent, that life is a gift to be seized. As Pirates, we become captains of our own fate: every ship that approaches is an opportunity, every island a place to bury treasure, sip rum, and breathe in the view. Pirates understand life is fleeting; the rope could be waiting any day. That knowledge can either paralyze you with dread or inspire you to wring the most out of life. I highly recommend the latter.
And being a Pirate means you get to swagger a little. Not the drunken Captain Jack Sparrow stagger, but the steady walk of a man who has fought battles, survived storms, and lived to tell the tales. It’s the confidence that comes from knowing obstacles will appear daily, but most of them vanish with a stern stare and a loud “Arrrgh!” The few that don’t—like bad hips—become the limp of character, a scar that proves you’ve truly lived.
The joys of pirating have surprised me. Yes, there’s been financial success, but more importantly, there have been great adventures: moving to Florida, selling businesses, starting new ones, getting a new knee, and deepening my love for family. Who knew the simple joy of talking to your two-year-old (gifted) granddaughter could melt your heart in ways you never imagined?
A good Pirate also learns that sailing alone is neither fun nor safe. You depend on your shipmates, and the best ones are rare treasures. You can’t be a good Pirate without a crew.
So as I set sail into this last year of my fifties, I do it with full sails, clear skies, and the most beautiful pirate wench by my side. 2019 is going to be one hell of a year. Arrrgh!
Love, Dad