There are three major shifts that I'm struggling with:

• becoming a person who can tolerate more pain in order to achieve certain goals, such as fitness
• becoming a person who can easily enjoy people's company and appreciate what's interesting about them
• becoming a person who can make longer-term commitments, trusting that things will work out

Sometimes I wonder if it's worth making these changes. Maybe I should just go with how I bend, building on strengths instead of fiddling with weaknesses. If I follow that principle, I might instead:

• look for ways to make the most of the things that come easily to me
• explore the shifting connections around ideas and conversations instead of focusing on specific people
• maximize freedom, flexibility, and agility

The first set of paths seems harder than the second, but will it work out for me better? Taking the easy way still leads to lots of interesting possibilities and less wasted energy. On the other hand, trying difficult things can expand my confidence and help me challenge artificial limits. Also, I tend to over-estimate how difficult things are, and I tend to be more adaptable than I expect. So if the first set of changes is better for me (based on the reasons given by philosophers and learned from other people's lives), it might make sense to give those a good try–at least for a number of years.

Let me take a closer look at each of those shifts to see if I can puzzle out what I'm struggling with and how to transform that.

Becoming a person who can tolerate more pain in order to achieve certain goals, such as fitness

I still feel anxious at the prospect of combined pain and stress, like the way I seized up after spraining my ankle in a krav maga class. On the other hand, I feel okay with the slight discomfort of the gentle running program that W- is helping me with and the Hacker's Diet exercise ladder I'm doing. I've dealt with some pain along the way to working on other things. Most things are not supposed to hurt a lot (otherwise you're doing it wrong), but a little wobbliness is understandable.

Taking the long view helps. I remind myself that pain has so far been temporary and that memory is thankfully fuzzy about stuff like that. Gradually, as my strength and tolerance improves, I should be able to take on more and more.

Becoming a person who can easily enjoy people's company and appreciate what's interesting about them

I'm okay with people. I like them as an abstract idea, and I get along with people online and in real life. I probably just have to get out more, ask more questions, share a little more of myself in conversation, and become more comfortable with having people over.

Becoming a person who can make longer-term commitments, trusting that things will work out

Seeing the difficulty that people have in transferring leadership roles and knowing my own inconstancy of interests, I hesitate to take on longer-term commitments or bigger roles. Maybe this is something I can learn, though. I'm surrounded by opportunities and role models, so it's as good a time as any to pick this up. For some of the bigger decisions, I find it helpful to learn from other people who have dealt with similar things before.

What would be some triggers for switching strategy and following what's more natural for me? If I'm not making any progress or if I notice myself being consistently unhappy, that might be a good sign that I need to reconsider my plans. In the meantime, I'm making very slow progress, but it does seem to get easier and less scary each time I try this.