How far should one go toward self-reliance? I suppose that’s a question everyone must answer for themselves, but I’ve got a few ideas. For starters, I am not and never will advocate dropping everything and moving into the woods to live off the land. As tempting as that may sound sometimes, I believe you would lose more than you would gain.

But anywhere in between it really becomes a matter of risk management. How much risk can you tolerate? For me, one limit is “where a mistake could cost me life, liberty, or more money than I can afford to lose”. For example, a friend and I have been starting a business. While I’m more than happy to cut corners and do things ourselves whenever we can, when it comes to handling out taxes I don’t feel we know enough yet to tackle that one on our own. The cost of failure is too high.

We did, however, look over all the forms we would need to file and see how much of it we felt comfortable with. Research and practice runs cost you nothing except time. In this case we still didn’t feel comfortable enough to take the risk of doing it ourselves. We’re hiring a professional, at least this time.

On the other hand, we are still looking to do the bookkeeping ourselves. Even though we are a bit befuddled by the software we bought, we believe we can figure it out. The risk of failure there is lower because we are still keeping manual records in the mean time. Yes, it could end up costing us more next tax season if we still haven’t gotten a handle on the software, but it could also save us a fair bit of money as well. It’s a risk worth taking, at least for now. We will revisit this decision in a few months before the pile of records gets to be too high.

So while I will never be able to be 100% self-reliant, technically, I don’t believe that is really the goal. It’s certainly not a realistic goal, in my mind. As long as the tax code and legal code to which I am subject remains inscrutable to me there are risks I just will not take just to be able to say “I can do it ALL myself.” I’d be even less self-reliant in prison.