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This is the first year that I’ve had to file quarterly taxes. To deal with that headache, I decided to just subscribe to Quick Books self-employed and I now have a fun little game I like to play.

I enter in expenses and watch the amount of taxes I owe drop down.

Of course, buying something just to buy it isn’t a wise spending strategy, but this does seem like a logical year to buy some of the things I’ve been procrastinating over for work, like…. drumroll… an iPad.

I think it was the Apple pencil that finally did it because for years I had no interest in an iPad. An old friend used to have one and the full extent of my interest was in playing Bubble Witch on it once in a while.

However, in the last few years, there are quite a few cool apps that you can use your iPad like Stage Write – which my current production uses – and Production Pro, which is just insane the way it integrates videos into the script and blocking.

The best thing about buying an iPad this year though was putting the receipt into my QuickBooks tracking and watching my taxes drop $65. Then the same magic happened with the case.

I realized that it’s a good year to use some of that financial stability to update or replace anything that does need it, since who knows what the future holds and if I’ll still be a self-employed contractor in future years as well.

Some other things that I’ve bought that have pushed my amount owed down include:

• Black Clothes
• CPR & First Aid Certifications
• Pyrotechnics Training
• Printer
• SMA & Bobnet Dues
• Business Cards

And another fun little tax perk, I get to claim my healthcare premiums too.

Additionally, I was able to list about 4 different shows as expenses because they are “research in my field” – but, really, they are of course research in my field.

Sometimes it feels a little confusing, because we all know the arts don’t love to fit neatly into any box, but fortunately there are categories we can look at to see what is deductible. Anything that could look “fishy,” I make sure I have full documentation on and I put a little note in the Notes box when I enter the receipt.

For instance, if I go see a Cirque show and enter the ticket cost, I will note it as Research – I am currently employed as a circus stage manager. If I ever get audited, I won’t have to think back on why I thought that expense was fine.

It’s also important to be honest about this. You know what I don’t really do? Musicals. I don’t like them. I don’t care if I ever have another musical credit on my resume. And so, if I go to Broadway to see a musical, it’s probably not going on my taxes as a deduction.

Funny story though, I did go see a musical a few years ago with another co-worker as research because the director was under consideration to direct our next show and we were in the group of people who had input on that decision. In a situation like that, 100% deductible. But also a great thing to add to the Notes section if you use QuickBooks too.

Of course, in an ideal world, your job pays for the ticket in that situation. It’s just meant to illustrate there are any number of reasons why you might really need to go see a show – but why an average IRS agent might need some help to see it that way.

Anything you use to educate yourself further is a deductible expense as long as it directly relates to what you’re doing (get some professional tax help if you’re not sure). My ability to read music was getting rusty and is directly related to my job, so I’ve been taking some music lessons this year. Deductible. I use accounting in my job and am taking accounting classes at the local community college – sadly, not deductible. If some class called business basics for people in the arts existed, it would likely be deductible.

If you drive a lot for work, you can deduct expenses at a flat mileage rate or track the actual expenses of tolls, gas, repairs, etc.

Are you a self-employed contractor? How do you do your taxes?