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How to make April 15 less taxing

taxesBack in my apartment-dwelling days (also known as the poor college student/law student/law clerk/early associate days), there wasn’t much money to spend, so the bulk of my activities were dictated by financial ability.

In particular, every time I had to pick up and move to a new apartment, I handled it all myself. No money for movers equals no movers. I was rather proud of the fact that I would hunker down and move myself instead of forking over hundreds of dollars to a company to do it for me. I couldn’t understand my friends who would pay for movers — isn’t it better to take a day or two, do it yourself, and save the money?

Looking back on those days, it’s easy to understand that (1) I had more “free time,” so I wasn’t losing anything by moving myself; and (2) I didn’t have the money, so it wasn’t really a choice. I finally hired movers when leaving our first house (not apartment) into our second. I rationalized it because I had no friends with trucks and because that Pottery Barn couch was a monster.

I can safely say that I will never move without professional help again. Moving was still aggravating and I was moving stuff right along with the movers, but I didn’t have to worry about the big stuff. My muscles weren’t screaming at me for days afterward and everything was done in a day, instead of the two or three that it typically took me by myself.  

So when will I learn my lesson? I spent yet another tax season preparing my taxes myself. Every year I say “I’m just going to hire someone to do it.” And every year, I believe, perhaps foolishly, that I can save money by doing it myself. The price tag for an accountant always feels too high, especially now that the solo practice is in full swing.    

Largely because of the learning curve, the tax process has taken me at least a full week of work. I’ve checked out books from the library and I’ve created better spreadsheets for my credit card and operating account check registers to keep track of expenses and expense categories.  The opportunity cost — time with family and time in the office doing office work is, of course, significant. But, as a plaintiffs’ personal injury lawyer, I don’t get paid hourly. It might be easier to justify hiring an accountant if I could identify exactly how much money I make per hour doing what I know how to do. (One more reason to keep track of time even in a non-billable firm, I suppose).

I know that most people shouldn’t represent themselves in court, so why should I act as my own accountant? The question is whether a professional accountant could save me more money on my taxes than I can do myself (you know, because they know what they are doing), even accounting for the hefty price tag. I suspect the answer is yes, but I just can’t pull the trigger. Maybe next year.

Have any of you struggled for years to do your taxes yourself, then saw the light and hired a professional? Was it worth it?