Tales From Taxes

We finished our taxes this weekend. This was a Sisyphean task that we had been dreading for the better part of the year. By the end of the ordeal the wife and I, filing jointly, also shared the same headache. The sort of all-encompassing headache created from a combination of hunching over laptop screens, sorting paper, and trying to not grit ones’ teeth as the refund calculator bounces up and down the charts. 

Taxes were strange this year because I was first laid off in January. Then I was collecting unemployment after my severance ran it’s course in the eyes of the state. After that, I received some sort of payment from no fewer than 15 different people/organizations. The whole time, looking for that nice, stable full-time employment that would put us back into a better tax bracket.

Or something.

Filing this year’s taxes was a fantastic exercise in reflection. Looking back over everything, I had become something of a sole proprietorship. A freelance business. I had gone from working in advertising technology – my last paid profession – full time to just some-of-the-time. In exchange, I wrote more. A lot more. Paid gigs from people I knew. Paid gigs from people I had never known.

The kicker? For our 2016 taxes – when we both had exceptional full time employment – we owed a lot back to the Fed. This year? Just about broke even.


2017, as weird as it was for me, ended up reconciled.

So, an observation of 2017, via our finances, because that seems to be the American way.

Everyone will feel bad for you when they hear about a lost job. No one gives a damn when clients drop off or find ways to not pay you. Now when I hear about someone losing their job or getting laid off, show them the bright side. It is a chance to think creatively, do what they want for a moment, and open themselves up to all the opportunities they turned down because they were to busy with their last job.

I never wanted to run a business. I never cared about invoices and tracking expenses. I just wanted to take photos and write things down. I never wanted to pay for an accountant or for a subscription to Office Excel. Although, I do love lead generation and talking to people about projects. It is inspiring to talk to other people about all the great shit they want to do.

About 37.8% of my budget goes to coffee. Being a sole proprietor of a weird little company-thing requires extra juice.

I officially spent enough on printing to justify just buying a damn printer. The printer is now smarter than I am, which means I think I have to claim it as an employee next year.

If I take enough photos of my dog with my pro gear, at what point do they become an employee so I can start writing off their vet bills as an expense.

Seeing the invoices and expenses laid out in black and white is a massive motivator. It is easy to lose sight of what is being accomplished when the work is piecemeal and right under your nose. This can be like trying to find your way when the map is zoomed in all the way. Sometimes, direction comes from pulling back and seeing the whole lay of the land.

Maybe I continue going all out on the freelance market. Maybe I build up into an actual company with responsibilities. Maybe I find the allure of a team and a full time job and a computer loaded with software IT departments use to track my every action.

Maybe 2017’s numbers will tell a bigger story.

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