Will (paper)work for food

I was a mid-high-flying lawyer who lost his mojo and couldn’t get a job that paid a living wage. Now I’m just grateful I can do paperwork again to feed my family—at least until the Trump administration selects me as the tribute from District 8.

I don’t think I could hang as a millionaire. If anything, I’d probably hang myself out of guilt if I had to do it for long. That said, while I’m not nearly as fancy as my babymama, I’m still pretty fancy. So don’t get it twisted—I’m down like James Brown to make a million dollars. 

I just know I’d feel guilty spending my money on all the fancy stuff I like to do—like globe-trotting adventures, arts and culture, and pro sporting events—and would feel called to give much, if not most, of the rest away. Not even to “worthy causes” either. Just folks I cross paths with who are down on their luck and need a helping hand.

I used to be way more about my paper. Back when I was a human rights trial lawyer, I was on a trajectory to be that millionaire. I wasn’t quite a high-flying attorney, but I wasn’t low-flying either. More like a mid-high flyer. If Michael Jordan is the quintessential high-flyer, my law game was comparable to Dennis Rodman—a dirt-dawg warrior who gets the job done by doing the grimy, unpretty, often rough things that lead to winning.

I was never the best lawyer in town, but at one point I do believe I was the baddest. Sometimes you need a badd man for the job, and I was that dude.

But I don’t get down like that anymore.

When I was on the cusp of blowing up—right when my big boy bag was finally about to come through—the Universe delivered me a mega-size slice of humble pie. Out of nowhere, I suddenly couldn’t do lawyer stuff like paperwork without suffering nausea and migraines. Reading emails from opposing counsel literally made me want to puke. Court? Out of the question.

At first I thought it was temporary, like a paperwork pulled hammy. But after a month, I accepted that this wasn’t merely a case of the yips. I was done. I had lost my fastball. This wasn’t just philosophical--I simply couldn’t do the work.

Back when I was chasing paper, the plan was to get to $2 million so I could hang up my briefcase and quit lawyering for good. I didn’t know what I’d do next, but I assumed the plan would magically materialize once I hit my number.

Now I see what would’ve actually happened: by the time I hit $2 million I would’ve either been too burnt out to learn new tricks, or I would’ve moved the goalposts on myself. Every dude I’ve ever known who was mega-motivated to make a million and did so wasn’t motivated to do much else except make two million.

That’s how it goes with paper chasers. It’s just never enough.

That insatiable mindset seems to be a prerequisite for getting ahead in this thing we call life. Which is why running my own law practice always felt like a Sisyphean struggle. At bottom, while I saw the benefits of balling out of control, I just wasn’t motivated enough by money to be a top notch entrepreneur.

I did well enough at lawyering that I’ve lived comfortably but modestly the past two and a half years off my savings and a series of working-class part-time jobs—canvassing, substitute teaching, and staffing a neighborhood rec center. To be clear, none of these were living-wage jobs, but I had enough cushion that I lived like a pharaoh compared to my coworkers, most of whom lived paycheck to paycheck. One reason it was hard to connect is because they were always short on paper—and either didn’t have money to hang, or I felt called to pay for everything if we did, which wasn’t sustainable.

To be even clearer, I wanted a job that paid a living wage. But these were the jobs I was qualified for. While I might know some big words and can talk fancy, I lack marketable skills. I spent most of my adult life learning and practicing the law, and I’m not qualified to do much else. Which is why I know I wouldn’t have magically found a second calling when I hit $2 million. I’ve been searching for two years now and I’m still looking.

I believe in my writing and that I’ll eventually blow up like you knew I would. But my first book dropped and the world shrugged, and so far publishers aren’t clamoring to publish book two. So last summer I accepted that I would need to pivot off the Will Write For Food plan for the foreseeable future and find a better-paying job to make ends meet. 

The problem? I was trained to be a professional paperworker… but I couldn’t do paperwork.

Some days I cried out of frustration because I couldn’t do the one thing I’d ever truly excelled at. Nearly two decades in the law, and all I had to show for it were student loans and a wounded spirit.

Then my former unofficial mentee—now a good friend and peer—suggested I’d make a good public defender and invited me to job shadow him. I always thought PD work was rough and that I was too good for it. Turns out I was only right about the rough part. I loved everything about the experience, including the rough stuff. More importantly, I knew I could do the work and hang.

Back when I was clout-chasing, I fooled myself into thinking I was meant to be a fancy lawyer. But the reality is, I saw way more of myself in those indigent clients than in the suits in any boardroom. I once thought criminal defense was “slumming it,” but, bless my heart, I’m a dirt dawg warrior. These are my people.

While many folks caught up in the criminal justice aren’t guilty of the crimes they’re accused of, most are guilty of dubious decision-making that led to the allegations. They need help navigating a super-duper confusing justice system, and they deserve someone who speaks both their language and legalese. It would be my honor to be that dude.

What struck me most was the high level of discourse the lawyers enjoyed. Watching my friend negotiate with the prosecutor—a guy around my age who came across more like a victim advocate than a true blue cop—was refreshing.  When I remarked on it, he casually said, “We’re just dealing with people’s liberty, so we can be civil and work things out. Now, if you mess with my money? Then we’re taking the gloves off.”

Bars.

And while there’s still paperwork involved, it’s way less fussy compared to civil court. In criminal court, they still let you handwrite on forms and file stuff at the desk like it’s the nineties. As a meathead with a heart of gold, that’s the kind of paperwork I can hang with.

Criminal law is rough, but it’s also way more civil than civil law—superficially rougher, but in many ways spiritually gentler. And while I’m grateful I finally found my calling—at least for now—I’m just as grateful I found a job I can do that pays good paper.

The irony? That same salary would’ve felt paltry a few years back when I was flying mid. But now, I’m just grateful I can paperwork for food again.