Have you ever caught yourself avoiding opening your bookkeeping software? Waiting until the last possible second to deal with taxes because the whole thing just feels… overwhelming and a little shameful? Like, somewhere along the way, you internalized this story that you're just not good with money, and that's just how it is?
Here's what I need you to hear: you're not broken. And there is so much financial magic available to you as a self-employed web designer that most people in your world have never even been told about.
That's exactly what came up in my conversation with Hannah Cole, artist-turned-tax expert, founder of Sunlight Tax, and author of Taxes for Humans, in this episode of the Profitable Web Designer podcast.
Hannah specializes in educating creative entrepreneurs about taxes and financial empowerment, and the way she talks about money will genuinely change how you see your business finances.
This isn't a dry tax episode. It's about worthiness, rebellion, and what it really means to take up financial space as a woman running a business.
Hannah's origin story is one a lot of us will recognize, even if the details look different.
When she got out of art school, she was doing well. She had a grant, residencies, a gallery interested in her work. She sat down with her dad's accountant, excited to start her professional life, and the first thing out of his mouth was: “When are you going to get a real job?”
That experience compounded over time. More accountants. More subtle (and not-so-subtle) messaging that creative work wasn't legitimate, wasn't a “real business,” didn't warrant real financial guidance.
And then she lost a job at a New York City branding agency she loved because her boss, despite running a big, successful creative firm, was allergic to his own numbers. He didn't know if he was profitable. He managed his anxiety about money by going out to get more contracts, but a lot of that money would just walk back out the door again. When he finally got bookkeeping set up, he realized he was hemorrhaging money and had to let everyone go.
Hannah saw, in a very earth-shaking way, how much power you can lose overnight when you don't have a handle on your numbers.
So she went back to school for accounting, specifically to bring accessible, empathetic financial education to creative people. People like you.
The Story You've Been Told About Money
Here's the thing that we talk about a lot inside the Web Designer Academy, and Hannah names it so perfectly in this episode: so many of the women in our world have internalized this belief that their businesses are not legitimate. That's because they're freelancers, or sole proprietors, or running a small creative business, they're not “real” businesses. And that belief holds them back from charging profitably, from stepping into leadership in their own businesses, from looking at their numbers without shame.
Hannah takes it even deeper. There's research showing that we talk to girls and boys differently about money from the time they're small. We tell boys to take risks and grow their wealth. We tell girls to save, be careful, and stay safe. Those messages seep in over decades, and by the time you're sitting down to figure out your business finances, you're carrying a ton of cultural weight that has nothing to do with your actual capabilities.
And on top of that? Nobody teaches us this stuff. There's no tax education in our schools. Nobody knows the tax code. You are not behind everyone else. You are not broken. The information just hasn't been made accessible to you in a way that felt safe.
If you've ever avoided looking at your numbers because you were afraid of what you'd find (or afraid of being judged for what you didn't know), Hannah's free visual guide to designer's tax deductions is a fantastic place to start. It translates creative-speak into tax language, so you can finally see exactly where all your business expenses fit on your tax return.
What You're Actually Missing When You Only Hire for Tax Prep
Hannah makes a distinction that completely reframes how most web designers think about accounting, and it's one of the most valuable things in this episode.
When you hire an accountant just to do your taxes once a year, you're getting a cattle-call service. Tax prep firms say yes to everyone, put them on extension, and ram them through as quickly as possible. To run a profitable tax prep business, you basically cannot answer questions. You have to go fast. So you're not being educated. You're just getting a form filed.
The real value of accounting happens outside of tax season. Tax planning. Investment strategy. Bookkeeping systems that actually work. Quarterly tax guidance. That's where the growth protection is.
And for a lot of web designers, especially those in early stages of business, the only touch point with an accountant is that one tax return moment a year. No wonder it feels like taxes are just this scary thing that happens to you once a year, rather than a system you can actually work with and benefit from.
The Tax Magic That Most Creative Entrepreneurs Never Hear About
What Business Expenses Can I Deduct As A Freelance Web Designer?
When you're self-employed, you have to do your own bookkeeping. A lot of people experience this as a punishment. Hannah flips that completely.
You have to track your income and expenses because you get to deduct them. Every dollar you reinvest in your business, software, programs, coaching, community memberships, comes off your taxable income. So if you brought in $100,000 and spent $70,000 on legitimate business expenses, you're only paying taxes on $30,000.
And here's the why behind it: the US government's primary goal is to grow the economy. Businesses are what grow the economy. So the tax code is literally designed to encourage you to invest back into your business, because when your business grows, the whole system benefits.
Your business expenses are tax-subsidized on purpose. That design coaching program, that community you're part of, the tools that help you serve your clients better… these are there to be deducted. The system is rooting for you to reinvest and grow.
Inside the Web Designer Academy, we talk constantly about the value of investing in your business rather than trying to do everything yourself. And it turns out there's even a tax incentive baked into that approach.
How Do I Pay Taxes As a Freelance Web Designer?
This one trips up so many self-employed web designers, and Hannah is clear that it's not your fault.
The US runs a pay-as-you-go tax system. Employees have taxes withheld automatically from every paycheck. But when you're self-employed, there's no mechanism to do that for you, so you're required to estimate and pay your taxes every quarter.
Most people don't find this out until a year too late, when they get an enormous tax bill plus penalties because they were supposed to be paying quarterly and didn't know. Hannah's Money Bootcamp program includes quarterly accountability Q&A sessions timed right before each quarterly deadline, so you can calculate your payments in real time, without having to pay monthly accounting fees for that kind of support. It's priced at roughly one month of full-service accounting, but with lifetime access and a built-in Google Calendar that pops up the right guidance at the right time of year, every year.
What’s The Real Cost of DIY-ing Everything?
Creative people are resourceful. That's a real superpower. But trying to DIY everything, including your taxes and finances, can cost you more than the thing you're trying to avoid paying for.
Yes, you're capable. You could probably figure it out. But do you want to spend two years learning the tax code, or would it be worth investing in someone who's already done that work so you can skip ahead?
Hannah calls it Shoots and Ladders. There are some places worth jumping ahead.
How To Feel Worthy of Charging More as a Web Designer
Here’s something I constantly see with so many women web designers: they have this core, underlying belief that receiving money for their work is somehow harming their clients. That if I make more, you have less. That taking up financial space is taking something away from someone else.
And Hannah names the antidote so clearly: you are worthy of growing your business. Your business serves people. The more financially strong and stable you are, the better you can serve those people. Charging profitably so you can be rested, resourced, and fully present for your clients is not greedy. It's actually what allows you to deliver the level of service your clients deserve.
She also talks about the clients she's served who, when they paid a number that felt almost embarrassingly high to them, showed up so well, so prepared, so invested in their own results. When you're undercharging, you're not just doing yourself a disservice. You're potentially limiting the quality of the experience for the people you're working with.
And the worthiness piece isn't just emotional. It also shows up in practical ways. A lot of web designers subconsciously prevent themselves from making more money because they're afraid of the tax and financial responsibility that comes with it. They stay small so they don't have to deal with systems they don't understand. Hannah's whole mission is to remove that barrier.
When you understand how the financial ecosystem actually works, and that it's designed to support people like you, the fear starts to loosen. And that's when you can actually grow.
The messages we've all received, save your money, be careful, don't take up too much space, let other people manage the money stuff, those messages are not neutral.
They're part of a larger system that benefits from keeping creative women small and financially dependent.
Understanding your taxes, setting up your financial systems, paying yourself well, and investing strategically back into your business?
That's the quiet rebellion.
Meet Hannah Cole
Hannah Cole is an artist, tax expert, and the founder of Sunlight Tax, where she specializes in educating creative entrepreneurs about taxes and financial empowerment. She's the author of Taxes for Humans, a tax guide that approaches the subject with empathy, humor, and a deep belief that creative people belong in financial conversations. She offers a free visual guide to designer's tax deductions and her signature Money Bootcamp program, which gives creative business owners lifetime access to the tax systems, quarterly accountability, and investing education they need to build financial security.
Resources From This Episode
- Free Visual Guide to Designer's Tax Deductions (Sunlight Tax)
- Taxes for Humans by Hannah Cole
- Money Bootcamp by Sunlight Tax
- 5 Subtle Proposal Mistakes That Cost Experienced Web Designers Thousands (free guide from Shannon) – because the worthiness work around money connects directly to how you present your pricing to clients
- Web Designer Academy
Related Podcast Episodes:
- Episode 139: 13 Money Myths Keeping Web Designers Under-Earning with Financial Coach Gina Knox
- Episode 167: Rewire Your Brain & Reframe Your Beliefs with Reha Zamani
- Episode 171: From Corporate Burnout To Web Design Business Success with Amber Jones
Do web designers really need to pay quarterly taxes?
Yes, if you're self-employed and expect to owe more than $1,000 in taxes for the year, the IRS requires you to pay estimated taxes quarterly. The deadlines are typically in April, June, September, and January. Paying quarterly helps you avoid a large tax bill at filing time and potential underpayment penalties.
What business expenses can web designers deduct?
Web designers can deduct a wide range of business expenses, including software subscriptions, website hosting, design tools, coaching programs, educational courses, community memberships, home office space (if used regularly and exclusively for business), business mileage, and more. Working with a tax professional who specializes in creative businesses, like Hannah at Sunlight Tax, can help you make sure you're capturing all your legitimate deductions.
How is self-employed tax different from employee tax for web designers?
As a self-employed web designer, you're responsible for paying both the employee and employer portions of Social Security and Medicare taxes (called self-employment tax), in addition to income tax. You don't have an employer withholding from your paycheck, so you need to set aside money throughout the year and pay quarterly estimated taxes. The upside is that you can deduct business expenses from your taxable income, which employees generally cannot do.
Should I hire an accountant for my web design business?
It depends on where you are in your business journey. For many web designers, especially those just getting started, a program like Hannah's Money Bootcamp can give you the education and quarterly accountability you need at a much more accessible price point than full-service monthly accounting. As your revenue grows and your finances become more complex, working with a full-service accountant who specializes in creative businesses can be a worthwhile investment.
How do I stop feeling "bad with money" as a web designer?
First, recognize that nobody taught you this stuff. There's no tax education in schools, and many of us have received cultural messaging that discourages financial confidence, especially women. Start by getting clear on what you actually don't know (vs. what you assume you're doing wrong), finding a financial educator who gets the creative world, and building simple systems that make the information accessible. Hannah Cole's resources at Sunlight Tax are a great place to start.
About Shannon Mattern
Shannon Mattern is a Pricing Strategist and the founder of the Web Designer Academy where she helps experienced women web designers book higher-paying web design projects, charge more with confidence, run projects without overworking and burnout and break through to their next level of income and freedom.
Connect with Shannon:
- Website: webdesigneracademy.com
- Instagram: @profitablewebdesigner
- TikTok: @profitablewebdesigner
- YouTube: @profitablewebdesigner
- LinkedIn: shannonmattern
