I filed my taxes this weekend. Well, rather I sent all my financial info off to my accountant and he compiled it and let me know how much I owe. A very pleasant number by the way. The whole process took me less than an hour. It was not always this easy.
The first time I freelanced full time, well half a year to be honest, was 2005, the year after I finished gradschool. Half a year at SF Opera and half a year freelancing. I did my taxes myself. Mixed income sources from two states. It was a mess. Having never had most of my income from 1099 sources before I was not prepared for how much I needed to have saved in order to pay the taxes. W2s are easy. Money is withheld at each paycheck and at tax time you settle up the balance. For me I had the whole bill all at once. Yikes!
I spent the next few months stashing everything away until I had enough to pay my, what felt to me, rather large tax bill. There must be an easier way.
The next year I got myself an accountant. Nice guy. Treats his clients on a sliding scale based on income and takes on a lot of artists. “Don’t worry,” he said when I first met with him, “I make my money with investment bankers so I can help guys like you out.” Awesome.
It took me a couple of years to really get my system down in terms of breaking up expenses into categories that make sense, how to notate per diem and travel days for him and so forth. By 2008 I had my system in place.
Now it’s easy. I just email him a text file with all my numbers and he sends me back a dollar amount to be made out to state and/or federal tax boards.
While I said it takes me less than an hour there, in truth, there is a bit more work than that. Sure the final compiling of numbers takes almost no time at all, but I enter data regularly, all year long.
I maintain a spreadsheet to track all my expenses, personal and business. Yes I know I could use quicken or quickbooks or any number of software programs. I like my spreadsheet. I set it up to do various totals and calculations that I find useful or interesting. And the layout works really well for me. Sure it is missing a few bells and whistles and may not be the prettiest of things, but it gets the job done. And done well.
By entering the information regularly, I try to do end of each day, but on busy tech schedules it often gets relegated to Mondays, I only ever have five or ten minutes of work at a time. Usually less.
Spreading the work out over the course of the year was one of the best choices I ever made with managing money. No one likes a huge pile of work. Certainly not me. Yet that was what I faced that first year, and a not-insignificant pile the year or two after as I smoothed out my system. It is no fun. It leads me to waiting until the last minute, because really, sifting through a huge pile of receipts is a fucking pain in the ass. Ten minutes, five minutes, two minutes, no problem.
Learning what is an expense and what is not has been a huge lesson. I am very conservative with my numbers. If there is a grey area I tend to err on the side of not counting it. But one of the best tricks I learned was to organize my life in such a way that I could maximize my expenses.
When I lived in New York nearly all of my friends were business colleagues, designers, directors, choreographers, producers, and a few actors, etc. As such my social life revolved around work and nearly every dinner party, round of drinks, and so on was in the context of talking about one project or another. Nailing down design details or finishing up a few last bits of production meeting at the restaurant or bar was a typical evening. After all, this is New York where most business of this kind happens in public.
California has been quite a bit different. A smaller percentage of my social life is inherently work related. There are fewer late night, post-tech, restaurant excursions. The relative percentage of the categories of expenses has shifted dramatically. A lot are quite a bit less. But then, when I work in New York, I get the highest daily travel allowance the IRS allows. It all balances out.
Navigating taxes is certainly not fun but I have learned quite a bit through trial and error. The most important thing I learned was to get an accountant. In matters of great importance there is no suitable replacement for a professional.

