The company that I’ve been employed by for the last ten years went public last September, and the lockup of my shares expired in March. So that meant that one large source of leverage my employer had over me has disappeared, and the amount of money we had saved changed significantly; that change in leverage and savings, combined with the fact that 10 years is a long time, made me think that my default assumption should be that I should change something about my employment. Basically, if your context changes, then how you react to that context should also change.

Exactly what I should change, though, isn’t clear. Do I want to look for another job; if so, what would I want to get out of that other job? Do I want to retire; if so, do we have enough money saved up now to be able to retire? Is my default assumption wrong, and in fact my current job is the best place for me right now, even though the incentives have changed significantly? Or is there some significant change that I can make to my current job while sticking with my current employer?


Starting from the second option: I don’t think we have enough money saved up yet to be able to retire without a fair amount of worries while continuing to live in our current location and with our current lifestyle and obligations? I could be wrong, but it’s certainly not a slam dunk.

That alone doesn’t mean that we can’t retire right now: almost everywhere else in the country is cheaper to live in than the San Francisco Bay Area. And our lifestyle isn’t immutable: cutting down on extra spending in order to get more free time sounds like a plausibly good choice. (Though the flip side is that, if we were to retire, we might reasonably want to travel a bit more than we had been doing recently, so you can make a case that our expenses could go up!) I’m pretty sure there are places in the country where we could retire right now, so certainly retiring is in the solution space.

Also, I just turned 50 this year, and my body has reminded me periodically over the five years or so that it is past its warranty. Still, all things considered, I’m reasonably healthy now, as is Liesl; there’s definitely something to be said for making more space to enjoy that relative health while we still have it?

But I also don’t want to take it as given that I would enjoy not working more than I would enjoy working. Some people who retire and end up stagnating, going into physical and mental decline; also, I like thinking about stuff, and work is a good source of challenges in that regard. So, if I were to retire, I would want to think hard about what my days would look like, and how likely it is that I would enjoy that more than what I’m doing now.


Going down the other branch: let’s assume I stay employed. Do I want to stay with my current employer, or to go somewhere else? I like my current job and it continues to provide me with interesting challenges; I certainly don’t want to leave it just from a “grass is greener” point of view. Also, I like my coworkers, and I’ve been pleased at how many of them seem to be sticking around post-IPO; I don’t take that lightly.

The flip side is that, while there are aspects of developing software that my current job is unusually good at exploring, there are also aspects of developing software that I’m interested in that my current job isn’t as good at exploring. So I can imagine a job that let me explore either certain interpersonal aspects of software development or certain detailed technical aspects of programming in ways that my current job doesn’t give me as much scope for. Having said that, the areas that I might be interested in exploring also the sort of thing that, in my (admittedly limited) experience searching for jobs, can be hard to figure out from the outside, so I’d want to be a bit careful in changing jobs to try to explore those dimensions.

Also, it’s the case that the reward structures for significant numbers of jobs around here aren’t as interesting to me now as they would have been 10 or 20 years ago. In particular, the idea of joining a startup in hopes of getting a payoff a decade later is a lot less interesting to me at 50 than it was at 30 or 40. Which is fine, there are lots of public companies out there with more straightforward compensation plans; that would be a change, but this whole line of exploration is about what I want to change, so I shouldn’t assume that’s a downside.


Also, there’s the morality of the issue: when I get into the amount of money that I need to be able to even think of retiring at our current standard of living, I have to wonder, is keeping that money for ourselves at all a moral thing to do? I think you can make a pretty strong case that the answer there is no; but then, if you follow that reasoning, I guess the best behavior is to keep on working as long as possible for as high a salary as possible with as low living expenses as possible, giving the rest away?

And that’s definitely a coherent position. But the flip side is that a different part of me also thinks that it’s good for people to be able to retire! And, when people do retire, I think they should be able to do so without either taking a vow of poverty or constantly worrying that a bad stock market turn will wipe them out. And I also don’t think that there’s anything sacred about retiring at 65? Work has a lot to recommend it, but American culture spends too much time defining people’s value in terms of their work; I don’t like that.

I don’t know how to reconcile those two positions, though. So, for now, I’m saying that the second position is okay.


So: I don’t really know for sure if I would want to retire right now even if I could, and retiring would be a potentially risky experiment to run. But, if I don’t retire, it’s not at all clear to me that I would want to change jobs. Changing jobs is worth thinking about, and quite possibly actively exploring, but still, after going through the above thought processing, staying at my current job sounded more plausible than I expected.

Given that uncertainty, is there an experiment that I could run that would help me shed some light on the situation? The biggest question right now is whether I find not working to be an attractive enough idea that I’d be willing to significantly shrink expenses, whether through moving or other economizing. (Also, side note here that, while I’m writing this post as if it’s just about me, it’s really the needs of the whole family that are most important here: in particular, I would not make tradeoffs that Liesl wasn’t completely happy with.) And the obvious way to get information about that is to work less: maybe take several months off, maybe work part time.

I’ve thought about both of those options; maybe it’s risk aversion, but I decided I wanted to go down the “work part time” route. I don’t want to explore starting a different kind of career or anything, and I don’t think I’m burned out to an extent that I need a prolonged break: I just want to be able to relax a little more and spend a little more time on non-work interests. If I can switch to working three days a week instead of five days a week, I think that it’ll free up a meaningful amount of time, but it’ll also still leave me collecting enough salary that we won’t have to dip into savings, and it’ll leave connections in place at work that I value.


Of course, it’s one thing to say that you’d like to work three days a week, but it’s another thing to convince somebody to pay you to do that. This, though, is where having worked for the same company for 10 years comes in: it’s given me ample time to build up trust with them, and it means that I’ve got knowledge of their systems that are very different from what a new hire with similar technical abilities would have. So hopefully I should be able to work something out that leaves both my employer and myself happy enough with the situation?

Which is the way things have turned out: after talking it over with my boss and with HR, we’ve managed to work out a plan that meets my goals quite nicely. So, starting next week, I’m going to switch to working Monday / Tuesday / Thursday.

We’ll see how this goes, but I’m actually not seeing this as a particularly short-term experiment? Since coming to that decision, I feel like my worry level has reduced: it’s nice to feel that a break is coming up, but it’s also nice to feel that my finances are going to remain predictable. So I think it’s entirely plausible that I’ll actually remain in this state for several years; hopefully it will work out well for both my employer and myself, and we’ll be able to keep on going with this setup for a while.

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