Sometimes it's hard to plan ahead because there are just too many factors to consider, too many things I don't know, too many divergent paths. I can come up with different scenarios, but I can't figure out a lot of things that would make sense in all the likely scenarios. Some of the scenarios are exciting, but some of them are also scary. They're hard to hold in my mind. They fight my imagination. I can't plan straight for these. I can't come up with step 1, step 2, step 3. At best, I can come up with if-then-elses, but I still have to wait and see how things turn out.

Sometimes it's easier to take life one day at a time, because if I think about too large a chunk, I start getting lost. Sometimes it's better to not focus on everything that's needed, just what's needed right now.

It rattles me a little bit because I'm more used to seeing clearer paths. Or do I only think that I'm used to that?

Let me try to remember when I felt that sense of clarity and certainty. I was certain about taking computer science; I loved programming even as a kid. I was certain about teaching after graduation; I loved helping people learn. I was certain about taking a technical internship in Japan; it was an interesting thing to do. I was certain about taking my master's degree; it was a logical next step, necessary for teaching, and the research was interesting.

I was not certain about being in Canada, and I was often homesick during my studies. But I was certain about W-, and now this place also feels like home. I was certain about IBM and about the people and ideas I wanted to work with. I was certain about saving up an opportunity fund so that I could explore other things someday. I was certain about starting this 5-year experiment with semi-retirement.

So I'm familiar with what it's like to plan for a chunk of certainty – half a year, four years, decades. It feels good when a plan comes together, when I can see how each step leads to a future I've already lived in my head.

I am certain, now, that I'm going in roughly the right direction. I don't know exactly how it will work out, but I know that it will be interesting.

Ah! There it is, I think, the thing I'm trying to grasp. The future Sacha of this five-year experiment is fuzzy in my head. That evaluation point is only two years away now, and I should be able to imagine her more clearly. But aside from a few abstract characteristics (future Sacha is a better developer and writer, future Sacha continues to be happy, future Sacha gets to work on what she wants), I don't have a good sense of her yet – not with the same solidity of past futures. I'm not sure what to put on that Conveyor Belt of Time (as Mr. Money Mustache puts it) aside from generically-useful gifts to my future self: decent finances, relationships, skills.

Circling back to the metaphor that emerged while I was drawing and writing my way through this question, I suppose this is like the difference between hiking along a trail with a view – or even unmarked ground, but with landmarks for orienting yourself – versus exploring the woods. Not that I know much of the latter; I've never been lost in the woods before, never strayed from the safety of a trail or the sight of a road. (Well, except maybe that one time we were hiking along the Bruce Trail and got turned around a little bit, and we ended up scrambling up a slope to find the trail we really wanted to be on.)

I can learn to enjoy exploring, knowing that in the worst-case scenario, I've got the figurative equivalent of supplies, a GPS, emergency contacts, backup batteries and so on. I can learn to enjoy observing the world, turning questions and ideas over, noticing what's interesting about them, perhaps cracking things open in order to learn more. I can learn to take notes, make maps, tidy up trails, and leave other gifts for people who happen to wander by that way.

Ah. That might be it. Let's give that a try.