Won't you be bored not working?

I left Asana in May 2025, feeling burnt out and no longer inspired by the company and security team’s direction. My plan was to take some time off to spend on hobbies, recover the joy in programming and building things, and figure out what I wanted to do next.^[1]

When talking to people as an adult, the question of employment is sure to come up. When I told people I’m “funemployed”, they’d often respond with “that’s awesome” or “won’t you get bored?”. I didn’t notice myself getting bored, and figured I’d write about what I spent my time doing.

Outdoors

I wanted to spend more time outdoors, which turns out to be much easier when you aren’t working. One of the things I like about San Francisco is that there’s fantastic nature within a four hour drive, but one of the things I don’t like about San Francisco is that there’s very little within a 45 minute drive. This means you can’t really get out after work^[2] for most of the year to do anything nontrivial. Being free during the weekday meant I could schedule some longer trips, as well as drive around the Bay Area to go trail running.

Running

Spending more time running was one of bigger goals for the year. I’d finished my first marathon and 50M earlier in the year, and wanted to keep ramping up towards a 100M race. I unfortunately ran into a few hurdles and didn’t progress as much as I’d hoped to. I did hit well over 1000 miles for the year, but this wasn’t helped by the amount of backpacking I did or a hamstring injury in August that took months to rehab.

I also learned that consistent trail running takes more effort than I was demonstrably willing to spend. The trails that are a shortest drive away (East Bay) get hot in the summer, and the alternatives (Marin or the Peninsula) left me stuck in frustrating traffic on the return leg.

In the end, I spent hundreds of hours running and did improve^[3], but not nearly as much as I’d hoped.

Backpacking

I didn’t initially plan to do much backpacking, but trips started happening and I ended up spending more time backpacking than I have since high school. I did 6 multi-day trips across the Western U.S., as well as some day hikes to prep and dial in gear.

Sophia and I hiked the Lost Coast Trail with some friends who were newer to backpacking. Logistics were annoying and involved an extremely expensive shuttle, but it was a beautiful hike along the coast of California.

A friend who was similarly unemployed invited me to go backpacking, so we drove to Wyoming to hike the Teton Crest Trail. It was cool to be back and see the rest of the range after climbing the Grand Teton a few years ago, and the trail was gorgeous. I’m hoping to return one day and run it in a day. After that warm-up, we drove to the Wind River Range and prepared to do the Wind River High Route, a 95-mile off-trail route through the remote high alpine range. My friend unfortunately got sick, and we decided that attempting a hike where we could be days from help if something went wrong was a bad idea, so we pivoted to spend a couple days in the Cirque of Towers instead.

Upon returning home, I was inspired to push myself and go for a bigger hike that I’d been looking at for a while. Off of my trail running fitness and recent altitude acclimation, I planned to do the Big SEKI Loop over five or six days. The tone for the trip was set in the first couple of miles, when I started getting blisters and had to return to the car to swap out my shoes to a pair I don’t like. I made the call to switch shoes too late and the rest of the trip turned into blister management that limited my enjoyment of the incredible scenery. On the third day, I decided to bail and cut the trip short at around 90 miles. It was a great trail other than the hot slog up the initial Granite Pass, and I’d like to return to at least the portion I didn’t get to.

I injured myself shortly after^[4] that trip, but was recovering decently so joined a group of friends on a backpacking trip to loop around and summit Matterhorn Peak. Standing on a peak always makes me see why people enjoy mountaineering so much, but I don’t like the amount of inherent risk the hobby seems to entail.

I wish backpacking and climbing were more compatible, and I can see a path to making them go together as I improve. The Cirque and the Sierras both have big climbing objectives at a moderate grade that require multi-day trips, and I’d like to return to both for some of the incredible alpine climbs. Until then, it’s hard to justify backpacking while not unemployed, since time off is so precious and outdoor time can better be used on climbing and big trail runs. As a result, I suspect this year will be an anomaly in my backpacking career.

Modern backpacking gear is significantly better than the gear I grew up with. I had days where I carried food, water, and all the other gear necessary for a long trip and still had less than 20 pounds on my back. It’s so much easier to put in big days and enjoy them when I’m only carrying an additional 10% of my body weight.

Climbing

I spent the summer working towards a goal of climbing a big wall with some friends. We learned to aid climb, practiced hauling, and worked to become less slow. We spent some enjoyable trips in Tahoe and Yosemite, and aimed to do the South Face of Washington Column in the fall.

The government shutdown was underway when we’d planned our trip, and we decided not to go due to staffing shortages on the Yosemite Search and Rescue team. We still learned a lot, and are planning to return to the Valley in the spring to accomplish this goal.

Travel

I didn’t travel very much, but was able to be a bit more spontaneous. Sophia and I took the Amtrak to Colorado to spend some time exploring Boulder, and we took another Amtrak to Portland to visit a friend I hadn’t seen in a few years. I went back to Santa Barbara with a friend and visited the Channel Islands for the first time. I even finally visited my sister in Delaware just in time for her to move away.

Fitness

I obviously spent some time running, but I also had a lot more time to dedicate to being a bit more physically well-rounded in general. When I left Asana, I was unable to do even a single body-weight pullup. I worked on this every day and became able to do five in a row within a few months. I feel like I can be a lot more dynamic when climbing now — when there’s a big move I don’t always need to think about technique first and can sometimes just quickly move through. While I can tell more pullup strength would still help, I eventually stopped actively training them because our bar at home was causing me elbow pain.

I also spent a fair amount of time in PT, both rehabbing an injury and trying to reduce my likelihood of injuries. It appears that sitting at a desk for twelve hours a day for at least decade has not been conducive to balanced muscular growth. Along with strengthening some of my weaker muscles, I also spent some time stretching and trying to become more flexible. Hopefully this is a practice I can keep up even as I return to work, since it seems important for long-term health.

Computers

I did a bit of programming. Perhaps less than I’d hoped for, but also more than I expected. I even contributed a few minor fixes to open source projects I use — this is much easier when it doesn’t feel like it’s wasting precious evening time.

FunctionTrace

I picked up FunctionTrace again and completed a few eternally-postponed tasks.

I built a new website, along with infrastructure for collecting payments and issuing licenses. Every now and then someone emails about using FunctionTrace commercially and I have to figure out what to do. Now that I have a website, people can clearly use it non-commercially and easily purchase a license for commercial use^[5].

I rewrote the main FunctionTrace implementation from C to Rust. This allowed me to simplify some things, more easily support newer versions of Python, and makes it easier to add some features that I’ve been putting off for a while. It was also just a good excuse to revisit some of the earlier assumptions for the project and figure out better approaches.

I’m not really sure where to go with FunctionTrace from here. I don’t find myself using Python much anymore — my new company isn’t a Python shop, and I would no longer write non-trivial projects in it. I’m still interested in the problem space, but it’s hard to justify working on a tool that isn’t particularly popular and that I don’t use myself.

NixOS

I’ve been dabbling with Nix for a couple of years, and finally decided to fully commit. I moved my desktop off of OpenSUSE^[6] and onto NixOS. OpenSUSE is a perfectly good operating system, but the idea of having a deterministic machine that’s fully defined in code is very compelling. Nix is one of those ideas that feels like it’s obviously the right way to do things and solves a bunch of problems, but it’s unfortunately hobbled by a fairly steep learning curve and a community that doesn’t seem to agree on much.

To migrate, I came up with a scheme where I dual-booted with my /home mounted on a separate drive. I’ve used separate drives for / and /home for a while, and this made it easy to maintain working copies of both OpenSUSE and NixOS that I could switch between without really noticing. Once I’d gone long enough without exiting NixOS, I wiped the OpenSUSE drive and committed.

I also switched a lot of my other configuration. Part of what was compelling about NixOS was seeing how few processes were required for a modern Linux system to run, and it felt like a good time to do a bit more pruning of my other software. I used KDE for many years, but it always felt like it provided more features than I needed, so I switched to Niri and manually configured some of the other features I wanted to. This was painful at times^[7], but means my machines now do essentially what I want them to and nothing else.

The Cloud

Ever since I bought programsareproofs.com, I’d been self-hosting everything off of my desktop. This gave me a ton of control and made some things easy (updating my website only took a single file write), but had a few downsides. I was mildly worried about security of exposing my desktop with important credentials/etc to the internet via nginx, but the biggest problem was that my website went down whenever my desktop turned off. As our electricity bill continued to climb, it felt silly to keep a beefy desktop running just to serve a mostly static site.

I migrated some of my services to static hosting provided for free by Cloudflare, and moved some of the dynamic services to a small NAS^[8] that idles at around 5W instead. Now my desktop is able to hibernate without taking anything I need offline. While I feel a bit bad about reinforcing the Cloudflare hegemony, the only traffic I send over their network is publicly visible and I can easily migrate back if they start behaving questionably.

Music Player

Since college I’d been using an unmaintained command line music player that was mostly configured the way I wanted it. That software finally stopped building on NixOS, and since I had some free time I figured if I wrote my own it would work exactly the way I wanted it. I’d been meaning to try Ratatui, so I picked it up and wrote a very custom music player that I now use every day.

Self-Enrichment

I read significantly more this past year than I have in a while. I enjoy reading, but it’s hard to fit in with all the other things I’m trying to when working so I mostly read when I’m on planes or vacation. With my schedule unfurled, I found I had time to read in the mornings or evenings and went through some of the books I’ve been wanting to read. According to my iPad, I read 39 books in a mix of genres.

I took a beginner Chinese language class at CCSF, which provides free tuition for city residents. I’m still rather bad at it, but I’m still learning and might be able to communicate a little bit the next time we visit China.

Interviewing

In late August, I was asked to interview for an interesting security role at OpenAI. As one may expect, my first interview loop in years did not go particularly well. Embarrassingly, I bombed at least the coding round and did not receive an offer^[9]. I’ve never been good at interviewing, and I realized that I’d need to practice a bit before I could count on getting a new job.

I started doing some Leetcode practice and went through most of the Grind 75 list. After a few weeks I was used to the format of the problems and felt like I had at least a 50% chance of finishing Hards within 10 minutes^[10]. I also thought a lot about how I wanted to convey myself and what I wanted to present in behavioural rounds. I procrastinated, but started setting up practice rounds with companies in November. By Thanksgiving week I mentally moved a few companies from “practice round” to “seems interesting” and started actively interviewing.

Interviewing was exhausting. I talked to ~20 companies, about half of which weren’t a good fit and one of us dropped out of the process early. I did 8 onsite rounds and received 7 offers. According to my calendar, the whole process took ~90 separate calls and over 80 hours, not including any time it took me to travel, take notes, and prep.

This was the first time I’ve really interviewed since 2018 when I left Green Hills, and I took it a lot more seriously this time. While I’ve done a few one-off interviews in the years since then, this was the first round of interviews I’ve done where I’ve talked to enough companies to have a good sense of the job market and to get over my nervousness during them. I don’t see how I could’ve managed this process while still being employed, and I think I got significantly better results this way.

I ended up with several compelling offers from companies that I’d enjoy working at, and after much internal debate I chose Airtable^[11].

Why Go Back to Work?

In a way, I feel like I was tricked by the OpenAI interview to switch into interview mode. Combined with troubles some friends were having on their job search, messing it up shook my self-confidence and made me worry that I might not easily be able to find a job if I wanted one. Now that I’ve gone through the full process and it’s too late, I’m no longer worried about that.

I left Asana because I felt burnt out and was tired of the company. By the end of the year, I felt recovered from that, and the intangibles^[12] of having a job started to look compelling. I learned more about how I want to spend my time, both now and after I’m retired, and felt like Airtable could mesh with that for the next spell.

Besides, I’ll have plenty of time to not work in a few years, once LLMs have discarded us. The time of programmers, those futile, neolithic understanders of code, appears to be coming to an end.