The past couple of weeks, I have been obsessing about becoming financially independent. When I was a kid, I would have thought of this as being rich. But now, all I want to do is be able to do what I want, without having to think about money. I’d like to have the option to do things for people or not, based on whether I think it’s interesting or not, taking money out of the equation entirely.

By and large, since I’ve been working, I think that I’ve been pretty responsible with money. Aside from my mortgage, I don’t owe anyone any money. I’ve refinanced my mortgage a few times, but have never taken money out. I’ve also always reduced the term of the mortgage when I’ve done this to make sure I get it paid off more quickly. Unfortunately, I just always assumed that I’d have to work until I was 65 or whatever the traditional retirement age would be. What I never told myself is “there is no speed limit”. I could have saved so much more to become financially independent so much quicker.

The question I’m asking myself now, is this what I want to do for the next 20 years? Because I’m around 20 years away from traditional retirement. I actually love my job, but there’s this voice in my head that pops up every so often asking if there’s something else I’d like to do. For most of my working career, I’d often ask myself if I could be learning something that would help me make more money and have a better career. And I have taught myself many things that have helped. But now, what about the things that I enjoy but that won’t necessarily make me money? If I didn’t have to worry about having money to pay the mortgage or other bills, would I do more things that I enjoy?

Why am I obsessing about this now? The primary reason is that my house desperately needs a new roof. This is going to cost me about $17k, which is a little more money than I have saved up. So I’m going to have to take out a loan to cover it. This bugs me for a couple of reasons. One, I hate owing people money. Two, I can’t do the job myself. My roof is very pitched and I work very slowly. So there’s really no way that I could do this. I had been feeling pretty good about myself because I had a bit of money saved and that’s going to be all gone. I’ve also been thinking about the house, which was built in 1888 and it also still needs to be tuckpointed. This is another very large expense looming. My question then is, should I fix this house up as best I can and then move? I always though that I’d die in this house, but I’m no longer sure I want to. If I did move, where should I go? This house is great because I can bike to work. But if I didn’t have to go to work, that’s something that I wouldn’t need to worry about. Anyway, it’ll take me a couple of years to pay off the roof and get the place into sellable condition. So I’m not desperate to do anything right now, but I’m starting to make a plan and these are the things I’m thinking about.