What I Wish I'd Known: Bernie Levv on a Decade of Solopreneurship and the Money Side Nobody Prepares You For

Bernie Levv Maloney built the independent career most people dream about. A business owner, founder of Levv Co, a Pilates mentor, and wellness researcher, she has been self-employed for nearly 10 years and shares her work with a combined audience of nearly 100,000 across Instagram and TikTok. With a six-figure brand, she shares how she stays ahead of it all.

At Sumly, we serve the self-employed, and the same story keeps coming up. The work they love is not the problem. The money and admin behind it are. Few people tell that story as plainly as Bernie Levv, a Pilates mentorship and studio-consulting business, and co-founder of Levv & Jane, a B2B medical partnerships company.

We asked her what she wishes she had known, and she got real about the parts of self-employment nobody puts on a highlight reel.

The surprise tax bill nobody warns you about

Ask Bernie what caught her off guard when she first went independent, and she does not hesitate. It was "the taxes and how exactly to categorize, organize, and save for them so that I wasn't panicking come tax season."

She has watched it happen to the people around her, too. "I've had many women tell me they owed five figures in taxes at the end of their fiscal year that they weren't expecting and weren't prepared for," she says. "Trust me, that is not a position you want catching you off guard."

That five-figure surprise is the single most common financial shock we hear about from newly independent professionals. It is almost never because someone did something wrong. It is because no one is withholding taxes on your behalf anymore, and quarterly estimated taxes are the system built to fix that.

So, what are quarterly estimated taxes?

When you have a W-2 job, your employer pulls taxes out of every paycheck and sends them to the IRS for you. When you work for yourself, that withholding disappears. The IRS still expects you to pay as you earn, so it asks you to pay in four installments throughout the year. Those are your quarterly estimated taxes.

Here is the 2026 schedule for a calendar-year filer:

The next deadline for most self-employed earners is September 15, 2026. You can confirm current deadlines and payment methods on the IRS estimated taxes page.

How much to set aside, and how to stay ahead

Bernie's approach is refreshingly blunt. "I'm a drill sergeant when it comes to money," she says. "I put a percentage of everything I make away, and I organize all the expenses so they're in categories ready for tax season."

That is the whole game in two habits. A rough starting point for many self-employed people is to set aside 25% to 30% of what they earn, since self-employment tax alone runs about 15.3% before income tax comes into play. The exact number depends on your bracket, your state, and your deductions, which is precisely why a running estimate beats a fixed guess.

If you want a simple system to stay ahead of quarterly taxes, it looks like this:

1. Set aside a percentage of every payment the day it lands, not at quarter's end. A separate savings account makes it real.
2. Categorize expenses as you go, so deductions are captured instead of reconstructed in a panic.
3. Track a running tax estimate, so you always have a ballpark instead of a shock.
4. Mark the four deadlines and pay on schedule to avoid paying penalties.
5. Bring in a licensed professional for the questions and the filing, so judgment calls are not on you.

Do those five things and the "surprise" disappears. It becomes a number you have been watching all year.

You do not have to become your own accountant overnight

One thing Bernie named that we hear constantly: the pressure that going independent means becoming your own accountant the moment you leave. "They're not necessarily wrong, and it is a lot of pressure," she says. "Money can be scary, along with all the other very scary and uncertain parts about going independent."

But she does not think it has to hold people back the way it used to. "Now, with services that streamline at least this part, it takes a load of stress off of you. I hope people feel more encouraged knowing there are tools that are accessible, inviting, and easy to have in your back pocket to make the journey smoother."

This is exactly the gap Sumly was built to close. The software is the core: it tracks your income and expenses, organizes and categorizes them for your review, keeps your books in order, and gives you a real-time tax estimate so you are never blindsided when it's time to pay taxes. It is the "drill sergeant" system Bernie built by hand over ten years, without the ten years.

And you are not left alone with a dashboard. When you hit a real question, licensed tax professionals are there as expert support you can actually reach. For people who want someone to handle the filing itself, a dedicated licensed tax pro is available on our Thrive plan. As Bernie puts it, the mix is the point: "the fact that there's the option of automation and human help is key."

That combination is what she says would have changed the game for her. "Life changing," she told us, when we asked what a licensed professional in her corner year-round, not just in April, would mean. "Even with my ducks in a row, tax season is still so much to deal with. I have a million things going on at all times. The last thing I want to think about is taxes, but they're definitely a priority."

The real cost is your time

Ask Bernie what she would hand off if she could offload one piece of the admin, and the answer comes fast: "Anything money related, and all the emails I'm constantly having to send." What she wants back is obvious. "Building pilates businesses, mentoring new instructors, managing partnerships in the health and medical space, that is what I love to do. All the behind-the-scenes stuff like organizing the money, I would love to pass off."

That is the quiet math of self-employment. Every hour spent reconstructing expenses or bracing for a tax bill is an hour not spent on the work that actually earns. "It saves money," Bernie says of the goal, "and most importantly time and effort that absolutely needs to be put back into generating revenue for your business."

Frequently asked questions

How much should I set aside for quarterly estimated taxes if I'm self-employed?

Many self-employed people set aside 25% to 30% of what they earn, because self-employment tax alone is about 15.3% before income tax. Your exact number depends on your income, state, and deductions, which is why a real-time estimate is more reliable than a flat percentage.

When are quarterly estimated taxes due in 2026?

April 15, 2026, June 15, 2026, September 15, 2026, and January 15, 2027. If a date falls on a weekend or holiday, it shifts to the next business day.

What happens if I don't pay quarterly estimated taxes?

You can owe an underpayment penalty plus interest. You generally avoid it by paying at least 90% of this year's tax or 100% of last year's (110% if you earned over $150,000).

Do I have to pay quarterly taxes in my first year working for myself?

Often yes, once you expect to owe about $1,000 or more for the year. Paying quarterly is also how you avoid a large, stressful bill in April.

How is Sumly different from doing it myself or hiring an accountant?

Sumly does the organizing for you: it tracks and categorizes expenses, keeps your books in order, and shows a real-time tax estimate all year. When you have a real tax question, licensed professionals are there as support, and a dedicated pro is available for filing on the Thrive plan. You get automation and human help without having to choose between them.

Ready to stop dreading tax season?

Bernie's advice for anyone who just went independent and feels underwater on the money side is three words: "Start with Sumly."

If the surprise bill, the guesswork, and the admin drain sound familiar, that is exactly what we built Sumly to take off your plate.

Know what you owe in real time. Save 50+ hours a year you would otherwise spend piecing together your finances.

Keep more of what you earn. Our average user saves $2,000+ a year. Sumly organizes your expenses and flags them for deductions, so you stop leaving money on the table.

Support when you need it. A team within reach for the real questions, and licensed tax professionals you can choose for the filing itself.

Bernie Levv is a paid partner of Sumly.