Jumping Out of a Perfectly Good Plane

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Why would anyone jump out of a perfectly good plane?

That has always been my view on skydiving. And it has also been my view on changing careers. I mean, why would I want to jump out of a perfectly good legal career? However, as I’ve been thinking about it (and I’ve been thinking about it a lot!), I have begun to question if this really is a perfectly good career for me, if this really is a perfectly good plane.

I have practiced law, in various capacities, for (gasp) nearly twenty-five years. I started as a law clerk for a judge, then moved on as an associate in a large regional law firm (the dreaded “Big Law”), and after about ten years there, and a brief stopover with a small boutique firm, I went in-house for a corporation before ending up as an attorney in higher ed. It’s funny to me how this appears so seamless and well-considered written down when, in actuality, my career trajectory has been anything but. In fact, I never intended on going to law school in the first place — it just sort of happened.

I was an English major, creative writing to be exact. I was going to write the Great American Novel. I was also young and impatient, and maybe a little (or a lot) naive, so when those early writing gigs after college didn’t quite pan out the way I had envisioned, I panicked and, in a fit of desperation, I fled … to law school. My sister was already studying for the LSAT, so one weekend I borrowed her prep books, holed up in a room in my parents’ house (yes, I had moved back home), and the next week took the LSAT, earning a score high enough to get into any of the in-state law schools. I enrolled in one later that September, thinking to myself (reassuring myself?) that I didn’t actually have to be an attorney, that I could do anything with a law degree, that having a law degree would simply expand my options.

Fast forward to the present, to a legal career that has had more ups and downs (and more downs than ups) than the gnarliest of roller coasters, with extended periods of unemployment (due to a RIF and a health issue and getting unceremoniously knocked off the partnership track at Big Law), decreasing job satisfaction and increasing anxiety. My best days at work were the ones that were routine and mundane, when I didn’t have any contentious encounters (with my colleagues as much as with opposing counsel), when I wasn’t trying to manage the unrealistic expectations of my clients, when the buzzing of my cell phone late at night didn’t set off some nerve-rattling Pavlovian flight or fight response. I found myself fully wedged into this rut and feeling like I had even less options with a law degree. And yet there was so much else I could (and wanted!) to do with my life, which brings me back to this so-called perfectly good plane.

Who says this plane is perfectly good anyway? Not me. I might’ve thought that at one point, or expected as much (reassuring myself?), but not anymore. Sure, it’s relatively safe, and stable (though there has been an unduly amount of turbulence), but am I really going anywhere in it, anywhere I want to be going? Plus, I’ve been on this plane for a while, sooner or later it’s bound to run out of fuel. And then what? How much longer can I stay up in the air like this? I’m not sure how much time I have left. I feel fine, but who knows? I’ve already had one health scare, which my mother has blamed on job stress and there could be something to that (yet I wouldn’t admit it to her). I need to get off this plane while I still can!

I have never skydived, but from everything I’ve heard or read or seen about skydiving, it seems to all come down to taking that first step, to jumping out of the plane, that perfectly good plane. That’s what has kept me from skydiving (along with my fear of heights) — taking that first step, out into nothing, free-falling, hurdling at lightning speed towards the rapidly-approaching earth. The idea of that makes my heart race, my stomach flutter and my palms sweat — the same reaction when I considered leaving my legal career. And that’s where I was, and where I’d been for far too long, trying to take that first step, because if my training as a lawyer has taught me anything, it’s to be risk adverse.

But then I thought about it (and I’ve been thinking about it a lot!), and being an analytical attorney I asked myself: why do I have to jump? Seriously, why can’t this plane just land safely and let me off? That’s what planes are supposed to do after all. And it also occurred to me that I’m not on this plane alone. I have my “flight crew” — my wife, my family, my friends — and I’ve connected with former lawyers who’ve made similar moves and have lived to tell about it. Together they can help me land this plane. It might not be at my precise destination, and the landing could be a bit bumpy, but at least I’m not jumping haphazardly into nothing — jumping haphazardly into nothing was what got me into this situation. With a plan (and for once I have a plan) to continue doing some legal work on a freelance basis while I pursue my passion for writing, I can finally get off this damned plane!

Yeah, it’s still kind of scary, and I don’t know what the future holds, but I never did anyway (who does?), and it sure as hell beats staying on this plane that has turned out to be not nearly as perfectly good as it seemed.

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