At age 22, I started stripping. For the next fifteen years I worked off and on as a dominatrix, porn actress, and escort.

Now I’m 49.

Here are 23 things I know now that I wished I’d known then:

#16: Pay Your Taxes

Okay—I know this isn’t sexy, but it’s important. One of the most seductive mistakes in the sex industry is not filing state and federal income tax returns because we get paid under the table or are independent contractors. If we’re responsible for our taxes because they’re not automatically withdrawn from a paycheck, we can just… forget to pay.

Money can be so, so very emotional in sex work—making it easy to get swept away and act against our own self-interests. After all, why should we give our hard-earned cash to a government that doesn’t even recognize what we do for a living?

I get all that, I really do. It seems so much better—and fairer!—to keep all that money for ourselves. That, however, is short-term thinking. By not filing, you create a hole in your employment history. Every year that goes by that you don’t amend that hole, it grows bigger. It’s not that it can’t be repaired, but it gets harder to explain away. That question will always be hanging out there: When and how are you going to get right with the IRS again? Because until you do, your grownup financial life can never really get started.

Additionally, you might think that there’s no cost to holding onto that money, but it’s not free—you just pay in anxiety and uncertainty. After all, paying taxes is a finite amount, and then it’s done—you can forget it. But when you don’t pay, you have no idea what you might owe. Even if you have a rough guess, penalties and interest add up. The number is unknowable, and therefore, unbounded. It’s like a time bomb ticking in your bank account, and you never know when it might go off. I had one friend who used to have recurring nightmares that she’d come home and her house would be cleared out, even the prized Turkish rugs she’d inherited from her grandmother. She started sleeping better only after she hired an accountant and filed for the six years she had missed.

The IRS is serious business. One unlucky working girl I knew got audited, and they raided her house and place of business. They extrapolated her annual earnings from her posted hourly rate—think about that for a minute—and hit her with a five-figure tax bill.

I was fortunate to have a good accountant when I was working. Every year I’d go in expecting to pay some huge sum, and be amazed to find out I was getting a refund, so it doesn’t always have to be horrible. I used to call sending in my quarterly installments “IRS insurance”—the vig I paid to the feds so that I could live the rest of my life how I pleased.

I’m in no position to offer tax advice, but I can say this much: If you’re having a hard time financially, and aren’t sure if you even need to pay anything, you may still need to file a form declaring that. The IRS has a quick online quiz you can take to determine whether you earn enough to need to file. It is far, far better to do something now than to put it off indefinitely or skip it altogether.

If you’re looking for professional tax advice, here are some sex-word friendly resources to help you square up this year and plan for next year. Check out the terrific book The Tax Domme’s Guide for Sex Workers and All Other Business People, by Mistress Lori St. Kitts. Well-written, easy to understand, and filled with terrific information, this is the sex worker bible. Lori helps break down what it means to be self-employed: you are a small business owner, and you should act accordingly! Also, Lori herself is available for tax preparation. You can find her at taxdomme.com.

However, if you prefer working with someone local, I recommend checking out the Kink Aware Professionals directory. Folks who are comfortable with and value alternative sexual lifestyles are listed there. Kink Aware does not vet or screen, so they are not making any endorsements. I can't either, but I can say I’ve had good results finding professional help there over the years.

Finally, here are a few helpful articles I’ve found online:

For the independent contractor who will be getting a 1099

For the independent sex worker

I offer my very best advice on money and taxes my new book, Thriving in Sex Work: Heartfelt Advice for Staying Sane in the Sex Industry, now available in paperback and as an ebook.

Until next time, be sweet to yourself—

xoxoxoLolaD

Don’t miss out on any new Lola goodness – sign up for my occasional newsletter.