No Precedent Required
Five questions every lawyer should be asking right now
Lawyers are trained to be risk-averse. It’s the job. You spot the downside, flag the exposure, protect the client. It’s what makes us valuable. It might also cost us our careers. The biggest risk isn’t moving too fast. It’s standing still and calling it diligence.
You already feel it. Maybe you’re an associate thinking there has to be a better way to practice law, a GC who just got asked about AI strategy and didn’t have an answer, or a law student sensing the traditional paths you’re being shown are too narrow for a world changing this fast.
We’re all wondering: is what I’m building here going to compound, or is it going to flatten? The K-shaped economy isn’t a new idea. One arm goes up, the other plateaus, and the distance between them gets harder to close as time goes on. @amytam01‘s recent article applied it to the career divergence happening in tech. It got me thinking about what’s happening in law.
I’ve been on enough sides of this to see the pattern. My career has been a journey across government, Big Law, legal tech, and now venture capital. Every role gave me something I couldn’t have gotten anywhere else. Each move felt like a risk at the time. Looking back, I’m glad I didn’t wait.
The valuable skill in law used to be production. Can you do the work? Can you do a lot of it under pressure and bill accordingly? That skill still matters, but it’s no longer scarce. The scarce thing now is judgment: can you tell which work still needs a human, can you evaluate AI-generated outputs and know when the machine got it right and when it’s confidently wrong?
Two stories from friends at law firms brought this home. At one firm, an associate was suspected of using AI. The work was coming back too fast, too clean. Instead of asking how, the firm imposed a blanket ban. At another, a junior used AI to draft a memo without checking citations, and a partner caught hallucinated cases. The junior received a warning to not use the AI tool again. Both are understandable responses.
But both missed the same thing: an associate had shown up curious about a better way to work, and the firm didn’t have a framework to channel that curiosity into something productive. The skill that matters most now, judgment about when to trust the machine and when not to, is a skill you can build. It just needs a culture that treats curiosity as something to develop, not something to manage.
These are the questions I ask myself. I think they’re worth asking whether you’re staying, leaving, or somewhere in between.
Is the work you’re doing teaching you something that will be more valuable in next 1, 3, or 5 years? If you’re getting better at tasks that AI handles competently today, you’re running out of runway. If you’re developing judgment about clients, strategy, or when technology helps and when it doesn’t, that compounds.
When was the last time you were genuinely uncomfortable at work? Not stressed, uncomfortable. Learning something you didn’t know how to do. Operating outside the frame you were trained in. Discomfort is the signal that you’re on the steep part of the learning curve.
If your role disappeared tomorrow, what would you be known for? Not your title. Not your firm’s name. The skill, the judgment, the thing people come to you for. If the answer is something a large language model can approximate, figure out how to build a unique set of skills. If the answer is taste, context, relationships, or the ability to navigate ambiguity no system can handle, you’re building something durable.
Are you the person in the room who understands how AI is changing your practice area, or are you waiting for someone else to figure that out? This isn’t about becoming technical. It’s about being the lawyer who has used the tools, who knows what they’re good at and where they break. That person is becoming extraordinarily valuable.
Can you explain what you do to someone outside of law in a way they actually understand? Not the practice area. Explain the problem you solve and the value you bring. It’s what opens doors to roles that didn’t exist five years ago.
If you’re answering these honestly, you’re already ahead of most of the profession.
When I graduated law school, there were three paths: private practice, government, or in-house. Today you can build AI products, join a venture fund, or work at an AI lab where your legal judgment makes the product work. The path isn’t three lanes anymore. It’s being built in real time.
And you don’t have to leave law to be on the upper arm of this curve. Some of the lawyers compounding fastest stayed at firms and became the person who understands how AI changes the practice. Others raised their hand in-house, or turned regulatory expertise into the most sought-after skill in legal tech, or built systems to productize what they know. The upper arm isn’t about leaving. It’s about refusing to stand still.
You don’t need permission, a budget, or an institution behind you. Start with free tools, a trial, a YouTube breakdown on your lunch break. It matters whether you have judgment and curiosity. And if you’ve read this far, you probably have both.
You already know the answer. You’re just not used to acting without a precedent.