What I miss about practising law

I write a lot about why I left law, and about the habits I had to shed when I did. It would be easy to read all of that and conclude that I think of practice as something I escaped. I don’t. I liked being a solicitor, and there are parts of it I still miss, years later, in a way that sometimes surprises me. I wouldn’t go back. But it seems only honest to write the other half of the story - partly because the things I miss say a lot about what’s genuinely good in legal work, and about what anyone building for lawyers ought to protect.

The clarity of a finished thing

In practice, things ended. A deal completed. The money moved, the documents were dated, the keys changed hands and the file closed. There was a particular feeling at the end of a completion day - tired, relieved, slightly giddy - that came from knowing a piece of work was done, properly and permanently.

Building a company doesn’t offer that. Nothing is ever finished. A product launches and immediately becomes the next version. A milestone is reached and instantly becomes the baseline for the next one. I’ve learned, mostly, to like that, and I’ve written before about how the instinct to ship only finished things is one a founder has to unlearn. But unlearning a habit isn’t the same as not missing what it gave you. Every so often I’d trade a month of iteration for one afternoon of signing something off and knowing it was over.

Being taught by people who were better

The legal profession still runs on something close to an apprenticeship, and I didn’t fully appreciate it until I’d left. As a trainee, and then as a junior lawyer, my work was read carefully by people who were much better at it than I was. Drafts came back marked up line by line. Someone senior would take the time to explain why a clause I’d thought was fine would cause trouble in five years. It was occasionally bruising, but it was a form of care, and it made me good at the job far faster than I’d have managed alone.

Start-ups don’t really have that. You get feedback, plenty of it, from users and investors and the market. But nobody sits down with your work and a pen and shows you, patiently, how to make it better. I’ve had brilliant advisers and colleagues since, and I’m grateful for every one of them. It still isn’t the same as having a supervisor whose job is to make you good.

Being properly good at something

The other side of that apprenticeship was that, eventually, I became reasonably competent. I knew how a lease fitted together. I could read a title and see the problem before I’d reached the bottom of the page. There’s a quiet satisfaction in that kind of mastery, the kind you only get from doing one difficult thing for a long time.

Building companies has given me a great deal, but it rarely gives me that feeling. The job keeps changing shape, and the moment you get good at one part of it, the company needs you to do something else. I wouldn’t swap the range. I do miss the depth.

The people on the other side of the deal

This one I didn’t expect. I miss the lawyers on the other side. Real-estate work is adversarial on paper and surprisingly collegiate in practice. You’d negotiate hard with someone for weeks and then, at the end, share a weary joke about a client’s last-minute change of heart. There was a common professional language, a set of norms everyone understood, and a sense of belonging to something larger than your own firm.

I miss the late nights with colleagues too, oddly enough. Not the hours themselves, but the solidarity of a team pulling together to get something over the line.

Clients with something real at stake

Most of all, I miss how directly the work mattered. A client was taking premises their business depended on, or selling a building they’d spent years developing. The stakes were concrete and human, and you could see exactly how your work affected them. Software reaches far more people, but at one remove. I rarely meet the person whose afternoon got better because of something we built. When I do - when a lawyer mentions, almost in passing, that a tool saved them a miserable evening - it lands harder than any metric, precisely because it’s so rare. In practice, that kind of thanks came with the job.

Why missing it is useful

I’ve come to think that paying attention to what I miss is one of the more useful things I do. Each of those things - the finished work, the apprenticeship, the mastery, the colleagues, the clients - is something good about legal practice that technology could easily damage if it’s built carelessly. Automate the junior work away without thinking, and you lose the apprenticeship. Build tools that hide how an answer was reached, and you erode the craft. Design for throughput alone, and you forget that there’s a person at the end of every matter.

So I don’t miss practising law enough to go back. But I miss it enough to remember what’s worth keeping, and to build with the people who are still there in mind - the ones having the completion days, marking up the drafts and getting properly good at something hard. In the end, that’s who the work is for.