On a regular basis I receive an email telling me the enrollment window for the employee stock purchase plan is open. I always enroll. Buying company stock at a discount is one of the better deals a regular employee gets offered, and I’ve worked plenty of places that had nothing like it, so I know what it’s worth.

Then there’s the part the money people keep saying.

Ask most financial advisors about loading up on your employer’s stock and they’ll tell you to be careful. I’m not an advisor, but the reasoning is easy to follow. Your salary comes from that company. Your health coverage comes from that company. If a big chunk of your savings sits in its stock too, a bad quarter doesn’t just dent your balance. It shows up the same month as a hiring freeze and a thinner bonus pool. Everything you depend on moves with one ticker symbol, which is the opposite of diversification.

Lately I keep seeing that same shape somewhere else.

Like retirement accounts, most of us get access to AI through our employers. The company picked the vendor, signed the contract, and handed out seats. It’s convenient, it’s paid for, and it’s probably the model you use all day.

So, what happens when the seat changes?

I don’t mean that as a doomsday question. Companies adjust this kind of thing constantly, for boring reasons. Usage costs more than anyone forecast, so everybody gets a token budget. A model gets swapped for a cheaper one that’s almost as good. A security review decides which tools can touch the codebase and which can’t. Any of that can land on a Tuesday, and none of it requires a villain. It’s budget.

Then there’s the bigger version. If you leave, or your role gets cut, your access ends before you return your company laptop. Everything you had learned to do with those tools, you suddenly can’t do, on exactly the day you need to prepare for presenting the best version of yourself at your new place of employment.

AI is becoming part of how work gets done whether we like it or not. If your only real access runs through your employer, you’ve stacked two things in one place: how you earn and how you work.

So, months ago, I diversified. I bought a Mac Studio and started running open weight models on it.

I want to be honest about the trade-offs, because they are significant. I love technology so I spend a lot of money in any given year on gadgers, but this was not an impulse buy. the Mac Studio was very expensive, and I had to think about the purchase for a while. Also, the open weight models I run are not as capable as the frontier models. For some tasks the gap is immediately obvious.

But, I found a sweet spot. For a lot of what I actually do (drafting, summarizing, reading unfamiliar code, thinking out loud before I write) the local models are more than good enough. Nobody throttles me at the end of the quarter. Nobody deprecates the one I had gotten used to. There’s no renewal date and no seat to lose. The capability ceiling is lower, but I can roam wherever I want to go.

Privacy turned out to matter as much as the access. Nothing leaves the machine. When I’m working through something half-formed, or something I wouldn’t paste into a tool owned by somebody else, that’s worth real money to me.

None of this means you should go buy the same hardware. That’s the expensive end of the range, and I went there because I was able to make it work within my budget. Except for the privacy benefit, you can pay a subscription you fund yourself and accomplish the same level of independence. A modestly configured laptop running a small model also counts. The exact machine you use isn’t as important as owning access to AI that isn’t tied to your employment.

Here’s a thought experiment I recommend you run. If your work AI access vanished tomorrow morning, write down what you couldn’t do anymore. Then find the cheapest way to replace the most valuable things yourself.

I still enroll in the employee stock purchase plan every time I get a chance. However, the majority of my investments are driven through other vehicles.