Going where the opportunity is

How I ended up here

When I left private practice, I had burnt out.

I had hit 30, looked up for the first time in a while, and realized I didn’t like the train I was on. There was nothing necessarily wrong with being a working professional, per se. But it just turned out not to be the life that I wanted for the next 30 years.

Not long ago, I remember hearing a way of putting something that has really stuck with me, which goes something like:

Did you make great decisions as a teenager? Then why would you let that young person dictate what the rest of your life would look like?

I’m not doing it justice, but the idea is basically that by making teenagers make early, influential decisions about their education and career paths, we are imbuing them with a level of responsibility over a huge decision in a way we simply don’t with most other big decisions. And we ourselves often feel much more allegiance to career path-type decisions we made at a young age just because it was us, instead of thinking of our teenage selves as the silly children that we were.

All of that is to say, it is very difficult to know at 18 (or 23, or 30 for that matter) exactly what it is you will be content doing for the rest of your life. And it made me feel better to realize that my path had been chosen by a snot-nosed teenage punk (me) who didn’t necessarily know what they were doing.

While I didn’t have that level of clarity when I left private practice, I (and others around me) knew I wasn’t happy, so I did something about it.

The difference between knowing something academically and really knowing it

I had a lot of explanations for people when I left. I had to - I got a lot of questions.

I seemed to be succeeding in a well-trodden and reliable path, and people could not understand why I would be getting off the gravy train.

Among the many, many explanations I gave, one still holds true today:

I think I’m probably going to equally dislike everything I do, so I might as well do the thing that will have the greatest rewards.

In other words, if in the end a job is always going to be just a job, then all other things being equal, you might as well optimize for the rewards that job will lead to. Money, freedom, status - whatever floats your boat.

This harkens back to something I realized over and over every October in school - I used to pick courses in August based on what sounded good and might fit in well with some grand career plan - but by mid-October, I would always realize that school is school, whether I liked courses or not rarely had to do with the subject matter, and all else being equal, I should have just picked a good schedule. Jobs are similar - it’s more important who you’re working with, what the schedule is like, and what the ultimate rewards are, than what it is you’re actually doing every day.

In any event, I had some sense that I probably would come to equally dislike any job I did, and so I decided all else being equal, I’d like to at least optimize for wealth and autonomy. So that meant entrepreneurship.

Academically, it’s easy to understand why entrepreneurship (if you have the stomach for it) is the safest bet. Starting a business is an asymmetric bet in the sense that it generally has fixed risk (the business failing) versus an incredibly large reward (even small, shitty businesses you’ve never heard of can grow to be worth millions and millions of dollars). So, like in financial trading, you’re better off in the long term taking a series of asymmetric bets (starting businesses) until one hits big, than slowly grinding it out at a safer career that may have a higher floor (you’re simply not going to starve as, say, a lawyer) but also an infinitely lower ceiling (the vast majority of lawyers come nowhere near being wealthy, and those that do usually do it through means other than actually practicing law). Great - simple - let’s do it.

But of course, it’s not really that easy. Starting businesses and having them fail is incredibly emotionally difficult. And worse? Toiling in them for years while they are small and not particularly attractive. I don’t watch many of those talks anymore where famous entrepreneurs get on stage and tell you all about their stories because I’ve seen enough and frankly don’t trust much of what they’re saying.

That said, the one part I do trust - and that makes me feel better - is that almost all of them have stories about toiling in obscurity for years before becoming what others described as ‘overnight successes’. And - at least to me - they do seem to lower the mask a little bit during those points of the conversation, and there does seem to be some leftover pain there. I’ve been feeling that for a few years now, and it is no joke.

I knew in theory, having watched/read up on this whole entrepreneurship thing a lot, that early struggles were a thing. But actually going through it, experiencing it, and finding the motivation to keep going when I know I could just hang a shingle and be a successful lawyer? That’s one of those things that you just don’t understand until you’re really in it.

Breaking down the ego

When you’re a working professional - particularly in law - a healthy ego is a job requirement. Because success in law is relatively easy owing to the fundamental supply-demand imbalance of professionally regulated services like law, there’s just never a shortage of people who need you and will pay you to help them, even if you’re absolutely terrible at your job. Not to mention the way society tends to treat lawyers with a level of respect that isn’t necessarily deserved.

Business is very much not like that. Semi-publicly not becoming an overnight millionaire over the past 2 years in front of all of the friends, family, and acquaintances who knew and respected me as a lawyer, and who have been quietly murmuring about what a shame it is that I seem to have lost it and am wasting my license while tilting at entrepreneurial windmills, has slowly but surely killed off that healthy ego I had.

I was a pretty successful lawyer and on a path to becoming either a prominent counsel or potentially a judge at some point. That pedigree of success led me to believe I’d quickly achieve a similar level of success in tech. Particularly legal tech. A successful lawyer who taught himself to code? I was obviously going to make ‘Uber for law’ inside of 2 years.

Oopsie woopsie.

I might still make something big at some point. But at this stage, I’ve accepted that when it comes to business, I am a full-blown rookie and have to act as such. Thus - the short-term plan.

Accepting what’s right in front of me

I came to legal tech to save the justice system with my brilliance. I keep building very cool legal tech apps that make lawyering easier, simpler, and would necessarily improve the quality of legal service delivery. I show them to my colleagues. 5 times out of 10, they look excited/confused and rattle off 25 new features that might convince them to try it and maybe pay me $30 a month to use it.

The other 5 times? They ask if they can just pay me to do the work for them instead.

By accident, I’ve been building up a legal outsourcing business that is about as unsexy as a business could be. But - that’s where the money keeps coming from. And of course, the tech I’m building makes it easier to service the contracts and doesn’t have to be super polished because I (and the occasional person I contract with to help me) am/are the only people using them. And, because it’s not a subscription tool they’re paying for but for a real person to deliver a finalized product, the price per engagement is exponentially higher.

So? Do that, my wife says. You can go pretty far servicing lawyers’ needs as an outsourcing company built on top of the connections, legal expertise, and home-built tech that you have, she says. And as always, she is right.

It’s not ‘Uber for law’, but there’s clearly a large market for servicing a variety of my colleagues’ needs, and a scalable business to be built.

Do I love the idea? No. Am I saving the world? No. Am I capable of doing it, and does it have a good shot at becoming a successful company? Absolutely.

So, that’s what I’m doing now. I get to keep building and using my cool tech, while actually seeing money come in the door and happy customers (my colleagues) go out.

It’s not the dream that I thought/wanted it to be. But it’s a viable business and a good schedule.

TIL - www is a subdomain

I don’t know why this never occurred to me before, but the ‘www’ prefix we all grew up using for websites is a subdomain. And now understanding what a subdomain is, it seems really weird to me that basically all websites operated on that one subdomain for years. It seems very arbitrary. Wonder if I can find any interesting articles about that and why it started dying off.