Riding an Escalator into an Avalanche

So, you want to own your own business. You think it would be “cool” to “be your own boss.” Here’s a thought experiment for those of you on the verge:

For this experiment, you will need an ordinary laundromat coin operation mechanism and the real-life heart inside your chest. Imagine cutting your still-beating heart out of yourself. Don’t worry. The blade is hot, it’s not painful so much as it is terrifying and exhausting. It actually feels kind of nice. Maybe a little bit freeing. Now, take that small, miraculous piece and roughly bolt the coin op machine to the ventricle wall. Then, for the rest of your life, wander the market in a mad, desperate attempt to find someone, anyone, to feed that meter and keep you alive. Sometimes you have too many quarters and you can’t carry them and your heart at the same time. Sometimes you have no quarters at all, and you know you have to keep looking even as your vision blurs from lack of blood pressure. This is who you are now. Anything you had before fades away. Maybe your friends and family help you in the search at first, but there’s only so much a single person can handle. Besides, you made this choice. You launched this glorious venture. You made your coin-op heart, you keep that fucker beating.

Now, imagine if the government wanted half of all your quarters.

Doesn’t that sound fun?

I made more money in the first quarter of 2015 than I have ever made in my entire life. I made 15% more money this quarter than the last time I made more money than I’d ever made (Q2 2014). I would have made nearly 50% more if everybody that owed me had actually paid me.

And I owe the IRS all of it for 2014 taxes. I nearly broke myself trying to keep up with taxes last year, and it still wasn’t enough.

I’ve been trying to pay off what I owe before the April 15th deadline by paying 2014 taxes instead of my 2015 estimated. This means that, come 2016, I’ll owe even more than I do right now.

On the bright side, a lot can happen in 9 months. Theoretically, after I finish paying 2014 taxes, I’ll simply roll the unpaid balance from my 2015 estimated taxes into the rest of the payments. Which means that I’m increasing my payments by 25% across the board. Except that I can’t pay 2014 without wiping all my accounts. So now I’m adding 2014 to my 2015 estimated, and my tax burden goes from being 50% of my income to a cool 75% or more.

If this is supposed to get easier, I’m not seeing it. Every time I do something wrong, I work to figure out what, then how to fix it, then I implement the change. Then something else goes wrong, and no matter what I do in terms of money, or service, or clients, it seems like I’m always back here. Exhausted, broke, and frantically trying to figure out how to get my ass out of this one.

In May it will be two years since I went freelance full-time. They say it takes at least two years to get your feet under you. If something magical is going to happen by May, I’d really like to know about it.

Editor’s Note: As usual, I wrote this before the money came in. And as usual, we have just enough to limp along for another 30 days. As usual, I wonder how much longer I can keep this up.

Second Editor’s Note: I wrote that other editor’s note while extremely exhausted from 2+ days of not much sleep. We’re actually doing much better than we were this time last year, or at any point ever. I am stressed out about taxes, and it’s true that I can’t afford to pay them all, also that we’ve had some unexpected financial losses, but we’re on solid footing for the first time in a long time, and it’s going to work out. In fact, one of the reasons I’m exhausted enough to have this kind of break down is because, unlike previous similar breakdowns, I’m actually working instead of just burning myself out looking for work.