The Parable of the Two Lawyers

On being a bestseller

I got married in St. Augustine. We weren’t wealthy and still aren’t, but for our honeymoon we took our combined cart-girl and adjunct instructor money and went out on a charter sailboat. It’s the only time I’ve ever been sailing and I miss it; I understand why WASPs and those aping them are drawn to the sea and the aesthetic of it all. For a certain class of person it must be unimaginable not to tack periodically into the wind while using the word “summer” as a verb.

You know the type.

The captain of the charter boat took us past a number or other, smaller vessels anchored in the Intercostal Waterway, and indicated one in particular. That one, he said, belonged to a friend of his- Mr. M.- a constitutional lawyer by profession. He wasn’t much of a professional, though. While still young (in his late 30s if I recall) he’d left full-time law behind to sail up and down the coast, from Maine to Florida and back, and that was all he wanted to do. Whenever he needed money, Mr. M. would contact his old firm- which was very in-demand and always had consulting work for him to do remotely- and once he’d billed up $10,000 or so, he’d go back to sailing until he felt like typing a few briefs again. He could have been a millionaire many times over, but he preferred to do merely what he had to do to live the life he wanted. He worked to live.

A few years later I was back in school (I’d been a bit unrealistic about what an adjunct could expect or earn) working on my teaching certificate needed for employment in the public system, which fortunately never happened. But while doing so I worked a third shift security job in a big office building in a major city. I mostly read books and kept the building from escaping from under me; there were hardly any people there from 11:00 pm until 7:00 the next morning. But that just meant that the people I did meet were the most interesting, none more so that another lawyer, Mr. W.

Mr. W. was a Jewish defense attorney out of central casting- brash, mouthy, aggressive, but with the talent to back it up in the courtroom. He charged $2,000 an hour for his services; by the time he’d said hello on the phone you owed him $20. I recall once that my boss had to go to his office during the day to escort out an insane vagrant who’d come into to building to give Mr. W. a resume he’d written with a marker on notebook paper. Mr. W. took the trouble to ride down on the elevator with my boss and the unhinged homeless man, berating the latter for his writing and organizational skills while the man screamed death threats at him and my very nervous manager. Mr. W. fully knew the risks he courted with such behavior; I learned (much later) that he was in our building because his former law partner had been killed in his old office by a disgruntled client. Evidently I was meant to protect him from unhappy drug lords.

Typical payment plan

The thing was, there was no reason for any of it. Mr. W. was a very, very wealthy man, leasing space in a building for what must have been several hundred-thousand dollars a month and employing a large team of fellow attorneys and their respective staffs. He was in his 60s and could have retired years earlier, or at least moved into a less engaged role to spend time doing other things. But like clockwork, he was there every single day. I always knew I had exactly an hour of work left when I saw him come out of the parking lot elevator at 6:00 am, in a suit and tie, briefcase in hand, waving ever so cursorily to me as he speedwalked to the main elevators. He came in before everyone else, before his secretary, before the cleaning ladies were done. He could do anything he wanted and what he wanted to do was argue with people for money. He’s probably still doing it. He lived to work.

One can think of Mr. M. and Mr. W. As opposites, two poles at either end of a continuum that all men must place themselves upon. There are noble and pathological versions of each. Some men are driven to labor at some purpose that holds inner meaning to them beyond the mere material significance of the work. Others view labor as a burdensome intrusion on contemplative leisure, best to be minimized or done away with if possible. In the great middle ground between such views lie most of us, and of that number few pause to reflect on what they gain in trade for the years of their life.

You might think of the “work to live” camp as ‘Classical- OrthoCath’ and “live to work” as ‘Judeo-Protestant;’ it would be a bit overly simplistic, but most schemas are. The first looks at labor as basically a curse, the second sees it as an opportunity. I don’t want to judge one as necessarily better than the other, only point out the dichotomy. Both are in some measure necessary to keep society running. Rightly considered, work is the physical manifestation of will, leisure the instantiation of intellect. Unwilling work and unthinking leisure are the hobgoblins of our age, unfortunately.

Wojak meditating at the midnight hour

All this is to say that I sense what might be a change in my circumstances on the horizon. I’ve evolved a good bit from that young man on the boat, the one who could log an overnight shift, a morning of reading, an afternoon of classes, and a long drive home, in a truck that burned as much oil as his body burned Red Bull. I have more responsibilities than ever now, but also more resources. I like to think I’ve disciplined myself to make good use of work and leisure both.

Thus, I’m happy to announce that as of today, I’ve become a Substack bestseller. What began for me as an after-hours leisure activity has grown into a significant part of my life and identity. I never thought I’d get as far as I have and even less did I imagine I’d make money at this. I took the chance that rather than charge for content that I would put my best efforts out there and let people decide to patronize my mission if they thought my general output worthwhile. That theory has paid off in ways I didn’t anticipate. But it also leaves me at a bit of a crossroads- how far do I want to go.

For example, having thought about it, I’ve decided that I will consider appearing on podcasts, which I’ve previously declined out of hand. When I was smaller I could justifiably avoid conversations about my work, but as I now have a paying public I feel obligated to engage in dialogue on some level beyond writing and commenting. If I’m going to opine about things I should talk to others doing the same. Don’t mistake me; I’m not holding myself out there as some sort of public intellectual offering a desperate public my assorted wisdomings. But I don’t think it would kill me to be a bit more accessible to those who share my views, and to those who don’t for that matter.

I don’t plan to do this full time as my only job, ever. My writing is and will remain ancillary to my teaching. That said, my role as an instructor may soon evolve. I like where I work well enough, but my girls are aging out of their current program and cannot attend the all-boys academy that employs me. As such, I plan to seek out something Christian and Classical, or at least amenable to my overall ethos. This could be something that already exists, or something that comes into being with likeminded fellows. I’m very open.

For the most part

I need to come up with something for my paid subscribers as an offering of gratitude for their patronage. I’ve had a lot of ideas but none that seemed great upon reflection. Perhaps something new will occur to me soon. One thing I’ve considered is custom reading lists built around specific learning goals. I get asked all the time for book recommendations; perhaps people might find a whole curriculum geared toward some specific end edifying. If that appeals to you, or you have some other idea, let me know in the comments.

I wish to thank all of my subscribers, paid or not, for all of your kindness and support over this last year and a half. I meant for this to be a leisure activity balancing all the work I did. But as this project has grown, at the same time as my real-world responsibilities, I’ve had to discipline myself to perform both without taking from either. I learned I had inner resources beyond what I’d imagined. I could drive myself to do things I hadn’t thought I could. Whatever I’ve taught any of you, know that you’ve all taught me about myself. I knew I could do this, and I knew I could work like I do, but I had no idea I could pull off both at the same time. That was the lesson your readership taught me. When I come home exhausted at the end of a day spent wrangling teenage boys and use what’s left of myself to care for my own family, I can atill find it in me to type out my thoughts, often on my phone, as I am now (my girls are watching Bluey while I hide for a moment). And of course the useful part for all of my readers is that if I can do it, so can you.

Do you work to live, or live to work? There’s a paradox in the parable. You can do one or the other, but I’d say you’re only really free, and only really successful, when you can choose to do either and both when called upon. Can you grind yourself like axe blade on a stone, indifferent to comfort or ease? Can you endure hunger and poverty and embarrassment for your ideals? More importantly, can you tell when it’s time to do one and not the other? Can you balance temperance and justice, and wisdom and fortitude? And most important of all, have you set your eyes on faith, hope, and charity, having worked out your salvation in fear and trembling, that you might enjoy the peace that passes understanding? Our earthly approximations of these things are a child’s notion, yet though that’s the best I can hope for, I’m still a long way off.

By the way, if you’re wondering what I’m buying with my Substack riches, I have gotten a few books, but the vast majority of the money just gets mixed into the general family fund. You the subscribers have gotten my daughters trips to fun places, school clothes, their own books, and much else besides. But my personal favorite thing to spend my writing money on is this:

That’s the good stuff, old-school non-homogenized whole milk from a small dairy operation in a rural area not far from where I used to live. I get it for my girls. I feel every bit the aristocrat when I turn my nose up at the store brand stuff and get them the best milk I can find. The rich guys can have their sailboats, and more power to them. I’m happy to give my girls a healthy start. Thank you all for making that possible.