School’s back in session, and so is spending season

Welcome to Business of One,  the biweekly read for solo business owners wearing every hat, from client calls to closing the books.

The Brief

What’s happening and what it means for your business

• Back-to-school season kicks off: Retailers are bracing for one of the biggest spending pushes of the year over the next few weeks. If you sell to parents, students, or educators, this is your window to show up.
• Deadline coming: 2026 Q3 estimated taxes are due September 15, 2026. If you’ve been setting aside 25-30% of every payment like we suggested last issue, you’re in good shape. If not, now’s the time to start catching up.
• Ask the accountant: Should you pay yourself a salary or just take a draw? We break down the difference.
• Tool we’re testing: Tired of guessing what you can actually spend without touching your tax money? We tried a banking app built to fix that.
• The number: $40 billion+. That’s roughly what U.S. families are projected to spend on back-to-school shopping this year, according to retail forecasts. Every one of those dollars has to move through somebody’s business first.

The Big Idea

The Back-to-School Economy Isn’t Just About School Supplies

Families spend billions getting ready for the back-to-school reset, and that demand isn’t just for big-box retailers. Tutors, photographers, meal-preppers, organizers, and B2B freelancers (designing back-to-school campaigns) all see a massive seasonal surge.

Back-to-school is a predictable “attention economy” moment when demand is concentrated. To capture your piece of that spending, don’t scramble in late August. Take three quick actions right now:

• Package a seasonal mini-offer: Frame your core skill around the reset. Think “First-Day Mini Photo Sessions,” “Schedule Audit for Busy Parents,” or “Q3 Marketing Push Packages.”
• Pitch existing clients first: Reach out to past clients this week with a simple email: “Hey [Name], routines are resetting soon—want to get on my calendar before September fills up?”
• Set firm booking deadlines: Give clients a reason to decide now by offering early-bird pricing or limiting available slots for August and September.

Predictable demand isn’t a guaranteed payday. The demand goes to the solopreneurs who ship their offer before everyone else starts posted count downs.

Ask The Accountant

A real question from a real solopreneur

Q: I finally started making real money this year. Should I be paying myself a salary, or is it fine to just transfer money to my personal account whenever I need it?

A: This depends on how your business is structured, but the short answer is: the more you earn, the more that “whenever I need it” approach can cost you.

If you’re a sole proprietor or a single-member LLC, taking an owner’s draw is standard- you’re not required to run payroll. But if you’ve elected S-Corp status, the IRS expects you to pay yourself a reasonable salary through payroll before taking any additional profit as a distribution. Skipping that step is one of the most common red flags in an audit.

If you’re netting well into five figures a year consistently, it’s worth talking to an accountant about whether an S-Corp election and a salary/distribution split could lower your tax bill.

The key here is intention. Know which bucket every transfer is coming from, and don’t let “whenever I need it” become your entire financial strategy.

Tool We’re Testing: Relay

Relay is a business banking platform designed around cash-flow clarity and sub-account budgeting. As money comes in, it uses custom auto-transfer rules to automatically split deposits across up to 20 dedicated sub-accounts (like Taxes, Profit, and OpEx), leaving your main checking account showing only what’s actually safe to spend.

For solopreneurs and small business owners who use envelope-style budgeting, the appeal is  physically partitioning tax reserves and profits so you never have to do the mental math or rely on willpower every time a client pays.

Worth testing if: You struggle with cash-flow management and want an automated budgeting system built directly into your business checking accounts.

Around the web

Your next watch. We rounded up the most overlooked small-business tax deductions solopreneurs miss every year.

KVIA confirmed we probably shouldn’t try to wear all the hats.

This 16-year-old CEO reminds us that AI has completely flattened the playing field. 

Member spotlight

Mariah Althoff, Brand & Content Strategist

Mariah taught herself design after being turned down from a college design program, eventually landing corporate work and freelance clients like Walmart and Adobe. When other creatives started asking how she attracted those opportunities, she turned her design studio into an education brand that teaches freelancers and creatives how to build content and attract clients without chasing them.

After joining Collective, Mariah got her business structure squared away, her bookkeeping automated, and a clear system for quarterly taxes, so the financial side of running her business stopped competing for her attention with content and clients.

Look out for Mariah’s full story in an upcoming Faces of Collective highlight.

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