Tax Time Epiphany

I don't know who this wonderful woman is, but I do know that she is now my spirit animal. 

I don't know who this wonderful woman is, but I do know that she is now my spirit animal. 

Tax time is particularly stressful for freelance writers like myself, since traditionally none of our income is taken out for taxes when we’re paid, so we end up having to pay all of our taxes either in quarterly installments or in one, giant, soul-crushing chunk at the end of the year. 

As a freelancer you want to hit a sweet spot where you’re making enough money to feel like you’re on the right track and doing what you’re supposed to do to support yourself and your family, but not so much that you need to start selling your belongings to pay for a massive tax bill. 

I’m happy to say that when I visited my ace accountant Roei this year I hit that sweet spot. For the first time since I unwillingly left the world of salaried employment and staff positions when I was laid off from The Dissolve in April of 2015, I made substantially more money as a freelancer last year than I did as a staff writer for either The Dissolve or The A.V. Club. Of course, considering the very modest salaries I received from both places, that’s not saying a great deal but I did find it enormously reassuring. 

My accountants. What they lack in experience, they make up for in youthful enthusiasm

My accountants. What they lack in experience, they make up for in youthful enthusiasm

After all, when you’re freelancing, living paycheck to paycheck and providing for a growing family, it’s easy to feel like you’re on a treadmill where you keep having to work harder and harder to stay in the same place. Alternately, it’s easy to feel like you’re running in quicksand, and every attempt to extricate yourself from your precarious financial predicament just ends up making things worse. 

Trying to make a living can feel exhausting and overwhelming and at times even impossible. So perhaps I should not be surprised that when I’ve written about my struggles and frustrations as a freelancer, particularly those involved with getting paid (a process made much easier and less angry-making by most of my income coming from Patreon like clockwork the 6th or 7th of each month now) some commenters and even writer colleagues encouraged me to get a straight job to pay the bills and feed my family so I could concentrate on writing about things near and dear to my soul. 


This advice was offered with the best of intentions, but the only jobs I’ve had since I was twenty years old involved writing about pop culture, or talking about pop culture on TV. I don’t even know what getting a straight job would entail, or how I would go about doing so. I haven’t made a resume or done more than a “getting acquainted phone interview” in twenty-one years. And I’m not sure how not doing what I love and what I’m good at, and have been doing forever for the sake of starting out as a complete newcomer in another field I have no affinity for or experience with would solve any of my problems. 

So it was reassuring being told by my accountant that following my own path and focussing most of my energies on Nathan Rabin’s Happy Place makes sense from a financial and business perspective as well as a creative and emotional viewpoint. At this point, Nathan Rabin’s Happy Place is still a labor of love and a crazy dream but it’s also a reasonably dependable, growing small business. 


It’s reassuring to know that aggressively pursuing Nathan Rabin’s Happy Place is a responsible fiscal decision for my financial future and my growing family, and not just something that I need to do on an emotional and creative level. Of course, in this business, things can always take a quick, dramatic slide for the worse, to the point where I'm worried I'm jinxing myself just by writing this, but it feels good to feel like I'm on relatively sound footing financially. At the moment. Within reason. All things considered. In a market like this. Okay, those are maybe enough modifiers. 


Of course my wife and I are having a second child and moving into a new home imminently so it’s safe to say that whatever increased income I have will go towards those vastly increased expenses but that’s okay. For the last 11 months, it’s felt like the universe has continually been telling me I was on the right track, and the right path, with Nathan Rabin’s Happy Place and its various components like Nathan Rabin's Happy Cast. But when you’ve got a family to provide for it’s nice to get that reassurance from the dude who handles your taxes as well. 

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