“Style,” opined the Earl of Chesterfield, “is the dress of thoughts.” And like our thoughts, style can be a messy, ever-evolving kind of thing. We get stuck in ruts. We try to be something we’re not. We’re suddenly thrust into new circumstances that force us to be honest with ourselves—a total reevaluation of who we are and how we think.

That’s where I find myself now, as a newly minted owner of a 996 series Porsche 911 Carrera 2.

Which is a ridiculous thing to say given the nature of this publication. But the past year has seen some fairly profound changes. Without going into detail, I’ve lost a loved one, I’ve concluded a longtime relationship, and I’ve left a city I was part of for one where I’m a stranger. I had always intended to get a 911, but this 996 came at a time where I find myself wondering what my path forward is.

The question of personal style is a direct outgrowth from these metaphysical matters. The P-car is not my daily; that’s the job of a Jeep Wrangler, my fourth. Which in turn is the result of having grown up partly on Cape Cod, where the Wrangler and its forebears are essentially the official vehicle. The Cape is full of happy memories for me—especially the childhood kind—and every Wrangler I’ve ever had has been an attempt to hang onto them.

That was the realization that hit me as I took the keys to the Porsche. When I lost the afore mentioned loved one, it changed my interpretation of my favorite book, Moby Dick: it wasn’t about perseverance, it was about letting go. When I heard that 3.4-liter flat-six rumble to life for the first time, I realized the carefree, tanned, ready for the next no-shower-happy-hour image I tried to project with my Jeep wasn’t me anymore. If it ever was.

So what’s my style now? Well, that’s a messy, ever-evolving kind of thing. What I know is that the Wrangler doesn’t feel quite right anymore. It’s part of my past. And when you live like that, you can’t grow. In that sense, my 996 may prove to be a good life decision. It’s as much an evolution of style as it is an overdue reckoning with my own sense of self.

For that matter, it might even be the most honest thing I’ve done in a long, long time.