Recently, I noticed that having scheduled obligations causes me a lot of stress. I sort of noticed it while I was working at Dropbox. When I wasn't very excited about the tasks at hand, my mood would deteriorate over the course of the weekend. I always chalked that up to enjoying my weekend activities more than work (if I didn't, why wouldn't I just work on weekends?). But recently I realized that it doesn't matter what the schedule is for, and actually just the fact that it exists at all. I've experienced almost an identical feeling the day before a vacation, for example.
So what is it about having obligations that's so stressful? Well, for me, focus happens in bursts. For example, at MIT I had one representation theory problem set where I got stuck on a problem. I didn't want to do anything other than crack it. The result was that I spent about 14 consecutive hours holed up in my room working on that one problem set, and I think at least 8 were on that single problem. Another great example is Battlecode in 2014, where I coded the first version of my program in a stretch of about 11 hours, and then the next week did 3 consecutive 10 hour days working on improvements.
These focus bursts sometimes happen at times that cause me to sleep at a different time from usual. Recently, we realized that RNG manipulation in Pokemon Red and Blue was possible with significantly more consistency than we thought previously. That kicked off a search for setups for the most important sections of the run, and as a result I didn't sleep until 10:30 in the morning.
The problem with having a schedule is that these focus bursts are mostly unpredictable, and an obligation the next day imposes a limit to how late I can stay awake. So obligations either mean that I have to cut it short or not start in the first place. In both cases, I end up feeling unhappy because I wasn't able to do the things that I wanted to be able to do. By keeping my schedule as open as possible, when I'm going on something, I don't need to have any reservations about continuing to go full throttle on it.
In college I had a simple method for dealing with my schedule. Classes were soft obligations; sleep always took priority. There were a select few classes where I would make an effort to wake up on time, and if I were awake I would generally go to class, but overall I think that the attitude that I had led to me enjoying college significantly more, and learning is much easier when you enjoy the process.
It's no coincidence that I chose my stream schedule to be rather minimal. I chose three days per week because based on my experience with a full time job, having five days of commitments was too much. Additionally, I deliberately chose a start time that was in the afternoon, so that I would have a good amount of flexibility with when I go to sleep the night before. With my 2pm start time, I generally try to wake up by 1:15, so even if I'm up until 5 I can get 8 hours.
Interestingly, there's a big difference between deadlines and obligations. With deadlines at school, I was able to move that work time around and adjust it if needed. Even with significant amounts of procrastinating, the deadlines never really turned into obligations, with the exception of Algebraic Geometry where I would wake up roughly 10 hours before the problem set was due in order to work on it.
I don't know exactly how I will want to deal with this sort of thing in the future. At some point, I will need to have a steady source of income, and a full time job creates a huge 8+ hour obligation 5 days a week. Depending on the exact work, it might still be workable, but otherwise I might end up looking at alternative working arrangements. I'm hoping that there's some cultural shift that turns the 40 hour work week into something else, but who knows how likely that is. One of the temptations of working for myself is that I would be able to do this kind of experimentation.