Around this time every year, my social media feeds start blowing up with people talking about tax returns. And for a lot of my friends, it’s like second Christmas. They make big purchases. One of my friends bought a car this year. Last year, a couple used their return on a down payment for a house.

But tax season is completely different for people without a regular job. Freelancers and entrepreneurs don’t have the same luxury. And seeing that I work freelance and my wife owns her own business, filing our taxes doesn’t fill us with the thrill of hundreds (or thousand!) of extra dollars coming our way.


Unlike regular workers, we don’t have a payroll department automatically withholding our taxes from our paychecks. We’re on the hook for that ourselves. And generally, that means we end up owing.

We’re basically the exact people that the IRS makes payment plans for.

Since we started working for ourselves, we’ve owed almost every year. The one year we got a return, I backed into our neighbor, so every cent of our return was spent sending them to a body shop.

But, it’s not as frustrating as you might expect.

When you work for yourself long enough, you come to expect that you’ll end up owing taxes. You make a plan through the year to set aside a portion of your earnings, so that you don’t end up going broke paying off your tax debt.


Instead of a huge obstacle, it becomes a minor inconvenience.

Because at the end of the day, it’s all about managing expectations. If you expect to have to pay a few hundred (again, or thousand) dollars every April, it’s much more manageable than getting blindsided it every year.


And then, on the off chance that you actually do get a tax refund—like we are this year, hey—you get a nice surprise no longer how little your refund is.

So now, we just have to figure out what to do with this extra $130 we’re getting from the Federal Government.


We’ll probably just use it to pay off another credit card

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