Self-Employment, Taxes, and Shame: An Anonymous Author and Tax Preparer Answers Our Questions

We regret to inform you, Scratch readers, that it is tax season. Is there any topic more stressful for writers than taxes — the mysterious bills we all have to pay annually without any real training or schooling? Well, we have one bit of good news on this front. In the Scratch rolodex, we happen to have a double agent of sorts: a freelance writer, novelist, and professional tax preparer. We’re going to let this enigma keep their identity secret during this interview because they’re sharing some delicate info, such as their salary for a W-2 job, how much ghostwriting a YA series pays, and their clients’ most common hang-ups. Be sure to stick around to the end for the real tax-nerd talk, like whether married freelancers should file separately, or just how screwed Maggie will be if she didn’t (hypothetically) pay her quarterly self-employment taxes last year.

We’re grateful to our Anonymous Writer & Tax Preparer for sharing their experience and knowledge, and we hope this conversation helps demystify some of the tax process and encourages a lot more self-compassion — or at least an easing of the self-employment tax stress — before that looming April 15 deadline.

Legal disclaimer: None of the following is to be considered financial or legal advice!

This interview has been lightly edited and condensed. 

Maggie: How did you end up becoming an author who also does taxes? 

Anonymous Writer & Tax Preparer: I've always had a lot of jobs, which I think is true for many writers. A lot of freelance stuff, a lot of weird W-2 admin jobs. And I've never made a living writing books as myself (I’ve done some ghostwriting). In 2020, I was full-time freelancing, not doing any W-2 work, and then we all know what happened. I had actually been getting my taxes done by the company that I work for now for a few years, and every year they would send out this “We're hiring” email. Every year I would think about it, and it was just too much of a commitment, but then in 2020, I had lost probably 80% of my freelance work, and my financial picture had gotten really dire. And so I was like, “OK, I guess this is my time to learn how to do taxes.” I didn’t sign up right away, but I started the work in 2022 and I’m going into my fourth season as a tax preparer.

Is it mostly during tax time that you're getting work as a tax preparer? Or all year? 

It’s a year-round job. It's a salary W-2 job. But don't get too excited, because we haven't talked about how much I make yet. But yeah, during tax season — from January to mid-April — it's anywhere from 40 to 70 hours a week. The rest of the year, the expectation is about 20 hours a week.

During 2020, what kind of freelance work was drying up for you? Was it writing or other work?  

I was doing the weird stuff that you do when you've been around for a long time. I was copywriting for a couple of different FinTech startups. They disappeared. I was doing some ghostwriting projects for people, writing memoirs or business guides or whatever. I had been doing a fair amount of that kind of ghostwriting, and that too disappeared.

Who do you work with as clients when you're preparing taxes? Do you cater to other freelancers? What kind of tax situations are you mostly seeing?

I work primarily with a company that bills itself as being geared toward artists and freelancers. My clients are mostly artists, film people, writers, a lot of people with just 17 different day jobs who are trying to keep the dream alive. My sweet spot, the folks that I most like working with, are people in the $30k to $250k range. I work with a lot of families, lots of queer folks, lots of younger people, lots of people with really serious generational trauma around money. That’s sort of my specialty: people who have a lot of fear and don't know what they're doing, and have just really stressful financial lives, and [are] trying to make art and probably would rather never think about taxes.

What was the training process like to become a tax preparer?

I did 400–500 hours of training starting in October, then started doing tax appointments in January. Most of my colleagues are also people who are from creative backgrounds who don't necessarily have a finance background, I think the idea being that it's easier to teach artists to do taxes than it is to teach tax people to work with artists. Because creative people do have specific financial lives and concerns that are not necessarily going to be common for somebody who's used to working with people with conventional W-2 jobs that they stick with for a long period of time, who are just thinking about money in different ways.

That makes a lot of sense, actually, because it is really hard to explain to non-creative industry folks what our finances even look like. What are some of the big mistakes you see your clients making? Maybe in terms of keeping books or leaving money on the table, or not getting their taxes done at all?

I really try to avoid language like “mistakes,” or you're “doing something wrong,” or “you don't know what you're doing,” because I feel like there's so much shame already that so many of us have around money in general. Financial planning or budgeting, in particular. We don't learn this stuff in school. Most of us don't learn this stuff in our families of origin, and yet, at the same time, we have this whole culture telling us if we're not making money, we're not doing real work. And if you don’t have some intuitive knowledge of how to do this, it’s because you’re stupid and you don’t understand money and you’re not good at anything, so I really try to help people set that framework aside and just look at what is really important. 

The basics that are really important when you're freelancing are how much money is coming in and how much money is coming out. So whatever systems you can put in place that help you stay on top of that, whether that's using accounting software, whether you have a spreadsheet, or a little notebook that you're writing stuff down in. I tell people to set up a separate bank account with a debit card that you're just using for work stuff. And so that way, if you're only doing one thing, you can look at the credit card statement at the end of the year and there's your business expenses itemized for you. And that can also help people get a little bit more control over those transactions.

How much money are you making from being a tax preparer, and how much from your writing jobs? 

I'm making $43,000 through this job preparing taxes, and I made $29,000 gross last year freelancing. Again, that’s gross, meaning ahead of my expenses, so that's not profit. That's my total. And about half of that was a D&A (Delivery and Acceptance) payment for a novel that I sold a couple years ago. And then the rest of it was primarily copy editing, proofreading, that kind of thing.

How do you feel about that balance — in terms of happiness, but also what your time is worth? In other words, how do those numbers impact how you feel about your work? 

I think that we are staggeringly underpaid at my day job, and the freelance piece feels pretty precarious. Like, I have no idea if I'm going to be able to sell another book. I don't know if I'll be able to sell another book for $30,000, which is what I sold the last one for. I don't know if I'll have to sell another book for $5,000. I don't know if I'll ever sell another book again. 

The freelance work is really inconsistent from year to year, so the only money that I really count on seeing is the salary. I'm in my forties. I don't have kids. So my overhead is really low, but $40,000 . . . people certainly do get by on that amount, but I would prefer not to.

That freelance income from last year, $29,000 with the book payment, is that typical for the past several years? 

That's pretty much the higher end. The year before was similar, and then the year before that was pretty disastrous on the freelance side. From 2020 to 2023 was really pretty dire, so some of it has picked back up. I wrote books under a pen name for the last couple of years. So each of those years had either a D&A payment or a signing payment. And I don't know if that's gonna continue. I’d like it to, but I also have to write another book first.

That's the other thing that’s so hard about finances in this business, right? You can have a really good year when you actually sell or finish a project, but it takes so much time, and you have to do so much work up front that you don’t necessarily get paid for, and that can be years! 

Yes, and that’s very hard to explain to a CPA who works with people who have traditional W-2 jobs. That you do all of this work for no money for a long time, but it's a real job. I think it's very easy for us to devalue our own work, and the meaning of our own work, and the value of our own work, because many of us are not getting paid well for it, and that's how our culture shows value — with money. 

So that's another conversation that I really try to have with people, which is to say, “This is work. It is meaningful work. You are doing labor. The fact that it's not being compensated right now doesn't mean it's not labor, and it doesn't mean you're not business-like.” Which I know is what you all talk about a lot with Scratch. Because writing is work, but it's also joy and pleasure and creativity and all of these other things that we want to have in our lives. 

Even in the eyes of the IRS, you are performing work in the attempt to earn money, which means that you are a business. This is why a lot of my tax appointments sometimes feel like therapy appointments, because there's also a lot of emotional labor, which is often my favorite part of the job, is getting to have those conversations with people.

Is that because people will come to you ashamed about how little they made, or not seeing their expenses as real expenses? How does that come up?

A really significant percentage of people, especially first-time clients, will come into the appointment and they'll be like, “I'm the most disorganized person you'll ever talk to. I'm really bad at math. I hate taxes. I'm a failure as a human being.” And I get to be like, “Actually, you're the fourth person [who] said that to me today.”

Taxes are very overwhelming. I do 400 hours of training before I can talk to somebody about a tax return with just a W-2, so it's not a transparent system. It's not supportive. There's no real explainer for how to do it. There's nothing intuitive about it. So there is a lot of justified confusion. And then when you put on top of that all of this shame and anxiety, there's lots to unpack, typically. 

Did you enjoy doing your taxes before this became a job for you? 

No. I didn't know what a 1040 was before I started this job. I didn't know anything. I was the person going in being like, “What’s happening here?” In fact, I didn’t know what self-employment tax was before I started doing taxes. In 2016, I ghostwrote this young adult franchise, and I got an enormous amount of money for me at the time — but I also basically had to write four books in 365 days. Still, to this day, it was the most I’ve ever made, and I thought, “This is great. I’m set for life. I’m gonna buy a house. I’m gonna have savings. Everything is gonna be so fantastic. I finally made it.” And then I did the taxes and the [tax] payment was more than I made the first year I lived in New York, and now I’m the person who has to tell people about their huge tax bills.

Oh my god. That’s so sad. Self-employment taxes are so rude!

Yeah, and I actually never caught up. Maybe that’s a consolation for your audience. I do taxes for a living, and I owe the IRS around $20,000 still. 

Actually, here is a tip: As long as you are interacting with the IRS, and you are making some effort to pay it off, you’re OK. It's really a pretty chill entity to owe debt to. The interest rates are not that high, and it doesn't go on your credit score. 

State tax debt is different, though. The states are typically quite aggressive. New York will take away your driver's license eventually if you don't pay them. Things like that. But the IRS is a slow-moving machine. 

That’s very good to hear about the IRS, actually. So, a question about freelancers, who may or may not be me, who use TurboTax or something like it: I'm always worried whether, by using software instead of a human tax preparer, I am leaving money on the table? Am I answering a question wrong and I'm gonna get audited? Is tax preparation software a bad idea? I actually do enjoy doing my own taxes, generally.

Again, I want to stay away from “good” and “bad” as a framework. I think one thing that is good to know is that Intuit (the company behind TurboTax, Quickbooks, etc.) is a massive corporate lobby and is directly the reason why you cannot file taxes for free in the United States, Like they just killed that Federal Free File program, which was very popular and very successful. They also deliberately have [an] opaque pricing structure. I think it's really confusing to figure out what you are supposed to be paying for your tax return. I see a lot of people who come in with returns that they did in previous years through TurboTax, who are paying $200-300 for a really straightforward tax return. 

So if you have maybe a W-2, or a couple of W-2s and some freelance jobs, and you feel like you know what constitutes a business expense for your field, and you feel good about that and you enjoy the process of going through the website, that’s totally fine. There’s nothing wrong with that. For some folks, it's not a financial option for them to pay somebody to do their taxes. My firm is on the low end and it would cost maybe $300-400 to do a tax return through us. And a CPA is going to charge you $800 or $900, so some folks can't afford that. That is real. 

There's no moral advantage to doing [taxes] yourself. Like, if you enjoy it and it makes you feel in control of your finances, great. But if you hate it and you're miserable and you feel like you might be doing things wrong and you want to talk to a human being, you’re allowed to do that.

What are some instances where it makes more sense to pay a tax preparer than do it yourself? 

There are definitely things that I can do that TurboTax cannot do. We can talk through business expenses. If you took a trip and you don't know if this is a research trip, or what parts of it count as a business expense? That's something we can talk about. If you're somebody who has any complexity to your financial situation, like if you're not living in the United States, if you have W-2s with multiple states, if you worked in multiple states, if you have a kid and are not married to the other parent and want to know who gets a better deal filing as head of household and claiming the kid, that's something I can do. 

I'm also a person you can talk to. We can talk about the future. We can talk about plans that you might make for writers. You know, if you’re gonna get an advance payment next year, and it's gonna be this really large sum of money, and then you might get nothing for two years after that, we can talk about maybe you want to stack all your expenses in that year, and we can talk through all of these different situations.

Maybe that ties into the advantages of getting taxes prepared by someone who has special experience with freelancers and creatives instead of just a random tax accountant. Is that something you talk to potential clients about? 

Oh, for sure. I would say look for somebody who advertises themselves as working with creative people, because it's just a very different financial life in many ways. There’s bad therapists. There’s bad doctors. There are also bad tax preparers. So you do want to find the right fit. 

If you go to someone to get your taxes done and they make you feel bad, or if you get a bad vibe, or your refund is suspiciously enormous and the person seems really sketchy, you don’t have to go back to them! 

OK, this has actually been a hot topic in the Scratch group chat of late: Do you think freelancers who are married should ever file separately, or is there an argument that freelancers shouldn’t even get married, for tax purposes?

The overarching answer to this question is that it is very uncommon for there to be a benefit to filing separately. The vast majority of the time, across the board, it is a better tax outcome to file jointly. Sometimes that will change if one person makes dramatically more money than the other, and by dramatically, I mean like hundreds of thousands of dollars more than the other person. But in most cases, it's the same or better outcome. 

Where this gets complicated for freelancers, especially, is with student loans. So if your student loan repayment is being calculated based on your income, if you file jointly with your spouse, it's going to be your combined income. So that is the most common reason that I see for people filing separately. 

The most important thing to know, though, if you are a freelancer who is married, filing separately, you are not eligible to receive the health care subsidy tax credit. Which means if you got the healthcare subsidy throughout the year, when you go to file taxes, you will have to pay it back, which is horrible, and a really, really big financial consequence for some people, depending on how much they already got for that credit.

Yeah. I am one of those spouses who makes dramatically less, and I have student loans, and I used to get the healthcare subsidy, so it really did feel like I ended up paying much more after I got married. Trade-offs, of course! But yeah. I hate it! I thought this country wanted people to get married!!

That's the hardest part of this job is that so much of this is so unfair. The United States is a garbage empire. I'm just watching people's lives get destroyed in real time, and there's nothing I can do about it except try to be compassionate when I give them this terrible news that actually they have $6,000 tax bills because they have to pay back their entire health care subsidy because they didn't know. It really sucks. 

So those are kind of the components to that question for most people. That’s another thing that I can do that TurboTax cannot. If you make an appointment with me with your spouse, I can literally click a button and tell you whether it’s better to file separately or not.

Speaking of garbage empires . . . I got so mad paying my taxes last year, because I just hated that I owed money to this government. I don’t mind paying taxes that help my community, but this was so painful. Does everyone have to file taxes? Are there options to morally opt out?

What you’re talking about is tax resistance, which has a long and marvelous history in this country, and if folks are interested in not paying their taxes for moral reasons, I would direct them to the National War Tax Resistance Coordinating Committee. They started being really active around the Vietnam War and have a ton of incredible resources on their website. One thing they talk about is that this choice is a lifelong commitment.

I will also say, if you have freelance income and you want to get involved in tax resistance, it is still to your benefit to file a tax return, even if you are not going to pay your taxes, because all of your 1099 income gets reported to the IRS, but the tax return is the only way you can report your business expenses to the IRS. So if the IRS does come after you, if you don't file a tax return, they're going to come after you for what you would owe on the full amount of your 1099 income. But if you do file a tax return, they're going to come after you for what you owe on your profit, which is probably going to be a lot less. 

In an ideal world, would you still have this kind of day job and write, or would you rather just write full-time?

I'm ready for my leisure era. I would rather be sitting with the cat right now on the sofa, reading books, and going to protests. The odds of me earning a living as a writer of the kind of books I want to write are very small, and that could change, but the industry is not sending a lot of hopeful signs right now. 

Sidenote: I just want to say, it's really bad out there. If people are having a feeling that it's really bad and somehow it’s because of them — it’s not you. Last year was just really hard across every industry that I work with. Everybody. So many of my clients had dramatically reduced financial years. This administration . . . So many people lost government funding, postdoc funding, arts funding. It is really bad across the board. I don’t know if that’s comforting to people, but it’s definitely not just you. Lots of people are having a hard time. 

Back to me: There are a lot of things about this job that I really like. There's an increasingly big network of leftist finance people who are really invested (no pun intended) in changing this system that we live in. We don't like it. We want it to change, but money is a very useful tool to have in the system that we live in. It allows us to take care of ourselves and the communities we care about, families and chosen families. So looking at ways to, as ethically as possible, manage what we have, increase what we have, and build resources, that's really interesting to me. So I do see continuing on this path.

It sounds like it feeds something that you care about deeply, and that can have an impact on you. Do you feel like it feeds your writing work, too, or is it very separate?

It's pretty separate for me, but I really love the feeling of going into an appointment with somebody who is very stressed out and terrified, and at the end of the hour having them say, “I feel like I understand this better. I feel more empowered. I feel ready to go make a budget or track my expenses.” To see that arc from terror to some kind of empowerment is really beautiful for me. That’s kind of all you can ask for in a day job.

And that's something you don’t always get directly as a writer. Do you think there's something in particular about being in a creative field that makes people more likely to either think they don't understand money or taxes, or really not understand money or taxes? I feel like I hear that a lot from friends who are creatives. 

I think it is that people are more likely to think that. I can tell you, having done tax returns for people who make a lot of money, anecdotally speaking, people who make a lot of money do not necessarily know anything more about money than people who don't make very much money at all. I have had very, very, very rudimentary conversations with people about what kind of retirement vehicles are available to them when they're making $800,000 a year. 

I think that way of thinking is something that comes from the experience of having creative work subtly devalued, or not so subtly devalued, and then just not compensated. 

Do you have any advice — it doesn't have to be financial or tax advice — but advice for writers during the tax season to help them survive it?

One thing for writers to know — and writers are the only people who ask me this — is that, unfortunately, your therapy is not a business expense. The only people who get to take therapy as a business expense are therapists, because therapists are required to do therapy to maintain their license. 

I know it can feel very exhausting and maybe also embarrassing to go through all of your [financial] statements from the prior year, but remember that you are doing that work for yourself. The more you find expenses, the more you are aware of what you are spending in the course of doing your work, and the more it's going to help you on your taxes. 

Personally, I like to have a finance hour each week for myself. That's just an hour where I check in on my spending, look at my savings account, and get those habits in place on a regular basis, rather than putting all this stress and misery on yourself on April 13. It just makes it a gentler process for you.

And what if perhaps (again, I might be talking about myself here) you are a freelancer but you didn’t pay any or all of your quarterly taxes last year. Is it always necessary? What happens when you don’t?  

That is a great question. And the answer is: it depends. 

The first thing to know about is self-employment tax. Essentially, when you have a W-2 employer, they are withholding taxes from every paycheck. They're taking out state and federal income tax, Social Security, and Medicare. It's your money, but they are taking it out of your paycheck and paying those taxes on your behalf throughout the year. And when you go to file your tax return, you settle up how much you actually owed. If they took out more than you owed, then you get a refund. If they didn't take out enough, then you owe.

When you are freelancing, and by that I mean you get a 1099, it's income that somebody paid you directly. Nobody is taking out state and federal income taxes on your behalf. Nobody's taking out social security, and nobody's taking out Medicare. [Additionally], when you have a W-2 employer, they are also actually paying half of your Social Security and Medicare; when you are freelancing you are your own employer, so you pay both halves of Social Security and Medicare taxes, which is almost exactly 15% of your profit. That is on top of whatever you're paying in income tax. So those are federal taxes.

When you pay estimated [quarterly] taxes, you're essentially doing that withholding that the W-2 employer is doing, but you're doing it manually. The disadvantage to not paying estimated quarterly taxes is the IRS and the state will charge you interest on what you “should have paid throughout the year.” But if your profit is not that high, it's not going to be that much interest. [Editor’s note: This interest rate is variable! But for individual taxpayers who underpaid in 2025, the interest rate is 7% (according to the IRS).] It's not going to be a huge penalty if you want to wait until April and just pay it when you file. If you have significant profit, it's definitely going to be cheaper for you to pay your estimated taxes. 

That said, it just kind of depends on who you are as a person. What makes you feel safe and comfortable? I definitely talk to people who are like, I don't care. I will eat the interest if I don't have to think about this four times a year. If you can't afford to pay estimated taxes because you need that money to eat throughout the year, please eat and pay your rent. Just be spiritually prepared for somewhere between 25–30% of all of the freelance money that came in going back out. 

Another great strategy is that [some] people will set aside what they would pay in estimated taxes and put it in a high-yield savings account, and potentially earn more interest on that money throughout the year than they’re going to pay in penalties.

And also, there is no moral component to making a mistake or not knowing how much you owe. It doesn't mean you're a bad person. It doesn't mean you did something wrong throughout the year and now you're in trouble. It just means you owe more money. I don't think it's ever going to be fun to give the government money, but it doesn't have to make you feel like you're a bad person or a stupid person. It's just information.

I love that. Thank you so much for this. Do you have any last thoughts that you want to share with Scratch readers?

Don't forget to file an extension if you're not going to make the April 15 deadline. Again, that’s totally fine morally! And you will save a bunch of money if you file an extension. It's not an extension to pay, it's an extension to file. But it will save you the failure-to-file penalty if you file, at least!

This interview was edited by Rahawa Haile.

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