Long time no post. But you’re used to that. I guess I’m making up for it in length. The biggest thing going on with me in the past year is my employment status.
Last time I updated, I was working for a company called CipherTrace. The time before that, in between jobs (I always like to take a year or so off between jobs if I can afford it), and the time before that, still at SugarCRM.
Now? Well, now I’m retired. At least for the time being.

CipherTrace (best place I ever worked in a number of ways) was a scrappy little crypto analytics startup that got swallowed up by finance giant Mastercard, in the bowels of which giant it only lasted a couple of years before being digested into something wholly unrecognizable and eventually meeting the same fate as everything else that one swallows. That was a painful process, but a surprisingly lucrative one, and when I recovered from the elimination experience enough to get my bearings, I assessed my finances to a level that I never had before and realized… maybe I can take more than a year off. In fact, after taking everything into account, downloading a budgeting app (since Mint died and its replacement Credit Karma is total ass, I switched to Rocket Money, which is excellent) and cutting back from the irrationally exuberant spending of a well-employed Silicon Valley techie to something more practical, I realized… do I ever have to work again?

And that’s my current status, retired punctuated with a question mark, not a period or an exclamation point. My investments are not tuned for early retirement. My personal investment style is aggressive and risk-tolerant, but I tempered this by listening to the experts about the merits of tax-advantaged retirement accounts. Consequently, I mostly hold very volatile investments which could tank dramatically but also hold great upside potential, and year 2045 target date funds locked up in retirement accounts where I can’t touch them without penalties for another decade and a half. (Stupid retirement accounts… I shoulda known, just like most parts of life, what works for most people most of the time is not right for me.) I don’t think I ever actually believed I could escape the capitalist meat grinder early, so I never considered focusing on building a bridge account (the investment account early retirees depend on to bridge the gap from actual retirement to legal retirement age). I have one, but it was never the focus and represents a relatively small percentage of my portfolio. So there are two significant risks to my retired status: my bridge account could run out before the retirement accounts come online, or my volatile investments (or the broader market) could tank. I’m retired… unless it turns out I’m not. The money will last unless it doesn’t. I can live a frugal life without working for an unspecified number of years. (It’s also possible I could be lured back to work rather than forced, but it would require exceptional circumstances.)
I’ve been trying to find the right terminology for this situation.
- Semi-retired is not correct, that implies working less, but still working some. I am working not at all.
- “I have no responsibilities here whatsoever.” – a quote from A Few Good Men, accurate, but not enlightening.
- Freelance Bum – basically my current job title (I stole it from the web comic Sluggy Freelance). Also accurate but not enlightening.
- I toyed with Schrödinger’s Retirement for a bit, because I both am and am not retired simultaneously until I observe how the next couple of decades go. Accurate, but I have to explain it every time, and not everyone will get the reference.
- I’m not “retired”, I’m “retired?”–the question mark is part of the word. Needs even more explaining.
- Sometimes I say I backed into a LeanFIRE retirement (FIRE stands for Financial Independence, Retire Early, and the LeanFIRE folks are a subset who focus on getting there sooner by aiming for a more modest standard of post-retirement living compared to other FIRE enthusiasts). I wasn’t aiming to do the FIRE thing (maybe I should have been, given my relationship with work), but I found myself in a similar situation to what the LeanFIRE folks aim for. They would get it, but again, not everyone has heard of the FIRE movement, let alone LeanFIRE.
- So I’ve pretty much settled on “indefinitely retired”, because it conveys the right tone of “maybe permanent, maybe not”.
So, that’s what’s going on with me work-wise. I was notified of my termination in March 2024, was officially off the payroll that May after a couple of months of garden leave, and realized I was possibly not just taking a break but actually retired around the beginning of this year (2025). I’m loving it. I still work on my podcast, I’m catching up on media I missed over the years because work ate my time and my motivation to do things, I’m learning about things I never had time for before, I’m working on code projects (of my own choosing, at my own pace, on my own terms), I’m picking up activities I haven’t done for years (like posting on my web site), I’m getting my house clean and getting rid of some of the too much stuff I have, I’m seeing my friends more often, etc, etc, etc. Without a job, it’s possible to have time for a life.
Schrödinger’s Retirement: 8/10, I highly recommend it. The only drawback is being uncertain whether it’s forever.