I was talking to a couple of other Quantified Self Toronto members about the management of unstructured time, since one of them was taking a gap year from school and the other one had just wrapped up regular employment. “How do I make sure I don’t waste my time?” they asked.

Here’s what I’ve been learning from semi-retirement: it can be easy to make good use of your discretionary time. (And to feel like you’re making good use of it!)

When I was planning for this experiment, I worried that I would end up frittering away the time on frivolities that people frown on: vegetating on the couch, playing games, getting sucked into the blackholes of social media and random Internet browsing.

It turns out that when you fill your life with so many more interesting possibilities, it’s easy to choose those instead. It reminds me of something I’ve learned about finances, too. Many activities make me just as happy as other activities do, so I might as well pick activities that are free or inexpensive and that align with my values. Likewise, I might as well pick activities that give me multiple benefits or that align with how I want to spend my time. A movie is diverting and it’s also good for learning about emotions and storytelling, but watching a movie while folding laundry is more useful than watching a movie in the theatre. I enjoy cooking more than I enjoy eating out. I enjoy writing, drawing, or spending time with W- more than I enjoy playing games.

So I don’t fill my days with plans or box myself in with calendared intentions. I look at the week ahead and list tasks that I need to remember, promises and appointments I’ve made, and maybe make space for one or two personal projects or ideas that I don’t want to forget about. I have a regular client engagement on Tuesdays and Thursdays, which I do because I like the client and what I get to help them with. Sometimes I take a week or an entire month off, to re-set my sense of time. Even during my regular weeks, I try to leave plenty of space.

It’s important to have space to follow where your interests and energy take you. I try to minimize the number of things I’ve promised to other people so that I have the flexibility to follow opportunities when they come up. That way, if I don’t feel like writing, I don’t. Maybe I’ll draw. Maybe I’ll code. Maybe I’ll work in the garden. Maybe I’ll tidy the house. Maybe I’ll read. Maybe I’ll plan.

I make exceptions for conversations. It’s hard to not schedule those if I want to make sure they happen at some point. Left to my own devices, I might never get around to talking to people. So I pay someone to handle my scheduling, and I ask her to space some of the optional ones apart (maybe one a week?) so that I have room for focusing on my things. It’s a little weird scheduling three or more weeks in advance, but space is important.

The rest of the time goes to whatever I feel like doing the most at that moment. It helps that I feel good about the things that I want to do, like writing, coding, and drawing, and that many of the things I do are also valued by others. I remember coming across in some book (was it Early Retirement Extreme? I should dig that up again) the idea that you can raise your skill in some activities or hobbies to the point that people are willing to pay you for it (now or in the future). Other things like exercise or cleaning the kitchen have their own rewards.

Did I luck into wanting these things by nature, or did I shape my wants to fit what I wanted to do? It’s hard to say. Most of it feels natural, but I do consciously tweak my motivations. Here’s an example of where I’m deliberately working on hacking my wants: exercise. W-‘s been helping me build a strength training habit through lots of encouragement and positive reinforcement. I also remind myself that the time I spend exercising will pay off both short-term and long-term, and that helps me get better at picking it over other alternatives (ex: bike to work and get some exercise versus work from home). It’s like what Mel wrote about digging out a path of least resistance so that it goes where you want to go. The other day, I was on my bike for almost 4 hours: 6 short trips, back and forth, covering mostly the same ground. I might not add as much to my “Done” list, but it’s good for me.

One of the benefits of choosing to spend my time this way is that it’s easy to say no to the common time-wasters that people often beat themselves up about. You don’t feel that need to escape because you haven’t been trying to keep yourself disciplined all day long. This also means that you aren’t wasting the emotional energy you’d otherwise use to beat yourself up about bad decisions. =) There are tasks that I postpone or don’t get around to, but it’s not because I suck. it’s just that I wanted to do other things instead, and I may get around to those tasks someday.

Even leisurely activities become experiments. I spent one Monday watching animé practically the whole day. I’m studying Japanese, so I watched the episodes with the original soundtrack and English subtitles. It was fun hearing the sounds start resolving themselves into intelligible words… and it was interesting feeling that barrier of “Oh, I should be doing productive things because it’s a weekday morning!” start to erode as I learned more about giving myself permission to follow my interests. (It turned out that watching those animé episodes was great for helping me follow along with the audio and the script. I often listen to just the audio as a way to immerse myself in the language and enjoy commuting or working… Bonus!)

Maybe the trick to managing an unstructured schedule isn’t to get better at discipline, but to get better at wanting good things, to get better at seeing the value in different activities. Then you can trust in yourself, with a little review and feedback so that you can tweak your course and make better decisions. At least that’s what seems to be working for me, and it might be something that would work for you too. =)