When I try to make long-term plans, my attention generally slides most easily towards plans that involve things that I have already done, or that I know how to do. It makes sense to focus on the things known to be easy first, but what doesn't make sense is the degree to which I am averse to obstacles.

Right now, I see obstacles at three levels:

Wall

At a distance, every obstacle or new challenge looks like an impassable wall. I can get around it, maybe under or over it, but it just doesn't make sense to go through it. When I think about going from my bedroom to my bathroom, punching me-sized holes in the walls between them and walking through just doesn't seem like a viable plan, so I don't think about it.

This makes sense for literal walls (usually), but not for obstacles like a task that requires a skill I don't have yet. When I make plans at this high level with any attention at all paid to feasibility, I end up excluding every possible plan that would involve learning a skill or otherwise doing or figuring out something new.

This is a problem.

Staircase

Sometimes, if I focus in on one particular obstacle, it turns out to have a bunch of different parts, many of which are soluble, and only a few of which are actually hard, by which I mean they require attention or willpower. Then instead of a wall, it looks like a long, steep staircase. I know I can get up to the top, but it's work.

Hallway

Finally, if I focus on the staircase, sometimes it's just a series of tasks, none of which requires much willpower in the moment, it's just sticking to it that requires willpower. If I can set up the series in a manageable way, then the staircase flattens to a hallway and doesn't feel like it's work at all, just another path I can take.

Obstacles are Scary

I don't seem to gradually see my obstacles with greater resolution as I think about them more. Instead, it feels like a discontinuous, sudden shift in perspective. Moreover, my brain seems to think that there really are three different kinds of things that can appear to be obstacles. If I look more closely at a wall and it turns out to be a staircase or a hallway, it doesn't feel like I just have a higher-resolution picture - it feels like I was objectively mistaken about what kind of obstacle this was.

I think this is because obstacles are scary. More precisely, plans that involve a route through an obstacle are scary. Making a commitment I don't know how to execute yet feels like making a promise I know I can't keep (because it would involve walking through a wall). I really, really don't like doing that. 

Making a commitment I know will be a lot of work feels like, well, a lot of work.

So if I realize that a wall is just a staircase, it feels like all the routes through that staircase have switched from lies into promises I can keep.

I'd like to be able to think about this differently. I'd like to be able to imagine obstacles probabilistically, with a certain chance I'll be able to figure it out - and to automatically think of "think about how to get past this obstacle" as a step in the plan, instead of either making "impossible" plans or avoiding opportunities for growth altogether. I suppose the next step is to find out whether anyone else has had success making this change.

Have you?