My heart is pounding, my mouth is dry, my gut is churning. I’m staring at a huge tax bill — thousands of dollars. Like, more than $5,000. It’s all the more astonishing because this is not what I’d been expecting.

My husband and I are both freelancers who work at home for clients all over the world. We love our work, and it’s a great lifestyle — except for a few little details. For one, all our income is 1099 income, which means that we are taxed differently here in the U.S. than salaried employees.

This has been true at least as long as we’ve been freelancing, which is the last 10 years for me and nearly all his working life for my husband. We understand 1099 taxation; we know it’s part of the payoff for the flexibility and freedom of our work, of being our own bosses. We make quarterly payments to the IRS with the amount estimated based on our prior year’s taxes so the hit isn’t as bad on tax day itself. We always owe something then, but it’s never a big deal.

This year, however, things turned out very differently.


At the end of 2017, new tax legislation passed that took effect for the 2018 tax year. I’ve read several articles about people who are surprised that their refunds are smaller. (Refunds — ha! What an idea.) I understood the shell game our wretched government was playing, giving salaried workers more in their take-home paychecks (paychecks — ha!) while changing the tax code so their actual tax liability is at least as much, if not more, than before.

Fools, I remember thinking. Pay attention! This isn’t real! I marched along, smug in my knowledge that as a freelancer household, none of that applied to us.

I was entirely oblivious to what was coming.

Here’s how it breaks down for us: Our income is not a lot — we made rather less than $50,000 last year between both of us; it was not a super great year for a lot of reasons. Because all of that income is 1099 income, it’s subject to self-employment taxes. Those taxes are applied to our net income, not our gross income, which means we can deduct legitimate business expenses and are taxed on what’s left.

We had some business expenses last year, though fewer than in a typical year. My husband, a commercial illustrator, bought a large-format printer that was several thousand dollars and one initial batch of ink that was another cool thousand. I, an editor and writer, bought lots of paper, toner, and red pens.

We didn’t go to any conventions in 2018, so we had no travel expenses. (I traveled plenty to be with my mother while she was in hospice before she died, but that, of course, was not business related.) I didn’t buy a new computer though I sorely need one. Mine crashes on the regular, but I’ve worked out ways to keep it limping along — for now.

What I’m seeing all over — from so many other freelancers I know or follow on social media — is that this problem is much more widespread than just my husband and me.

We both have home offices, so we can claim a percentage of the mortgage and utility costs proportional to the square footage of those spaces. That’s nice. But speaking of that mortgage, we moved in the summer of 2017 and bought a house that cost more than the house we sold — a house that had been fully paid for. So, for the first time, we have a mortgage. We paid over $9,500 in mortgage interest in 2018, and I was so looking forward to being able to deduct that. In fact, the only reason I felt we could afford to take on such debt with this house in the first place was because I knew the mortgage interest would be deductible.

But, hey, guess what? Our mortgage interest is not deductible. It’s not a business expense; it’s just an expense, along with groceries and health care and utilities and firewood and insurance and gas and car repairs and all the umpty-billion things a family spends money on. What the new law cleverly did was raise the standard deduction so a lot of things that used to reduce your tax burden simply no longer do.

What it boils down to is that after self-employment tax is figured on our total income, that very same income is totted up again, the standard deduction is applied, and we’re taxed on the remainder.

Last year, our total tax liability amounted to not quite 11% of our total gross income, the money that came in the door. This year? Nearly 20%.


I am appalled, shocked, and freaking out about how to pay this bill. I’ve already investigated the IRS’s payment-plan program, and we’re going to do that. We’ll have to pay interest and penalties, but they don’t seem to be too onerous. I know the changes to what we owe now aren’t entirely due to the new tax bill; we deducted some moving expenses in 2017, and we did have more business expenses that year as well. But what I’m seeing all over — from so many other freelancers I know or follow on social media — is that this problem is much more widespread than just my husband and me. Not a day goes by when I don’t see a new, unhappy post about taxes.

How are we supposed to make this work? How are we supposed to survive on 80% of the small amount we earn — especially when this was so unexpected?

Everyone I know is feeling squeezed and pinched and facing burnout, financial uncertainty, and distressing politics.

We could try to raise our rates, but that’s always risky. I also feel like I’m adequately, even comfortably, paid for what I do. I know what other freelance editors charge. My rates are probably on the lowish end of the scale, but they feel fair to me.

Working more is not the answer. I can barely keep up with the work I’ve got; my desk is piled high with manuscripts I’m eager to get my red pen on. My husband and I routinely mention to each other how nice it would be to actually have — you know — weekends. Even one-day ones. Maybe even once a month. Maybe?

My husband is actually working to get out of the freelance-illustration-for-hire business. He’s hard at work on a new art and writing project that we hope to take directly to an audience. I hope we can afford to give him the time to finish creating and launching that this summer. But this, too, isn’t an answer for everyone facing this 1099 tax conundrum.


It’s hard to pin down the exact percentage of the U.S. workforce that is self-employed, though everyone agrees the number is rising. Companies love to hire contract workers: It gives them flexibility to grow or shrink their payrolls at a moment’s notice — not to mention saving on benefits, which cost more all the time. Gone are the days when a worker would be hired in an entry-level position right out of school and spend his (and it was usually “his”) entire career at that same company, rising through the ranks with experience, receiving periodic salary increases, and retiring with a good pension and health benefits.

Many workers enjoy the freedom and flexibility of self-employment. I definitely chose this path, quitting one of those increasingly rare career jobs that I’d held since college to go out on my own. I earn a lot more per hour than I ever did at the university — depending on how you count the hours, that is. I only manage to spend four or five hours of my day doing actual proofreading, copy editing, or writing. Those are the hours I keep track of on my spreadsheet.

The rest of my far-more-than-eight-hour workday is spent doing all the business of running one’s own business: communicating with clients, billing, reconciling, chasing down late payments, taking checks to the bank and packages to the post office. Also, ordering those red pens and boxes of toner and paper. And, of course, keeping up with social media; since my entire business has grown through word of mouth, it’s important to stay present and connected.

I’ve worked so hard to get where we are. It starts to feel… personal, somehow.

I would hate to give up what I’ve built and the life I enjoy. But I have to confess, when I look at what it costs — particularly as I gaze upon this horrific tax bill — I remember that secure, salaried university job and think, Should at least one of us try to get a job? That’s assuming we could even get jobs at our age, with our resumes, in our tiny community.

I honestly don’t know the answer. Our world is changing, and we’re all scurrying about trying to adapt. Everyone I know is feeling squeezed and pinched and facing burnout, financial uncertainty, and distressing politics. It’s a big reason why my husband and I moved to a remote, serene island and into a house I sure hope we can continue to afford.


Don’t get me wrong: I believe in paying taxes. I am, in fact, happy to do so. I want to live in a society of people who support each other in this way; I like roads and schools and safety regulations. Heck, I would like single-payer health care, too, if that’s not too much to ask.

It’s just, when I read articles like this one about how Amazon is going to pay zero taxes on its $11.2 billion profit this year, it’s hard to feel like the system is working at all, much less working fairly. (Wow, this may be the first time I’ve even kinda-sorta agreed with Donald Trump on something!)

I never thought I’d reach middle age and feel so on the edge. I began supporting myself at age 18 and paid my own way through college. After my trophy-wife years, I’ve been not only supporting myself, but often my husband as well. Yet, seeing our tax return made me feel like an irresponsible child. Like I’d had my head in the sand. Like I can’t take care of us.

I hate this. I’ve worked so hard to get where we are. It starts to feel… personal, somehow.

Are you hit harder by taxes this year — and are you salaried or freelance?

Can we talk about it?