If tax season felt like a scramble again this year, it’s worth taking a moment to figure out why while it’s still fresh.
For many small business owners, tax season stress tends to repeat year after year. The pattern usually looks the same: good intentions at the start of the year, then one busy stretch after another until the whole year slips by. Taxes get delayed, avoidance creeps in, and it all turns into a last-minute crunch. That cycle doesn't happen because owners aren't trying—it's the outcome of not having a system that works throughout the year.
Most of the stress business owners feel during tax season isn't really about the money. It's about unpredictability. When you don't know what's coming, your brain fills in worst-case scenarios. The goal is to make tax season boring. The way you do that is by building a system that removes the surprises.
Step 1: Adjust your payments now, not in December
If you ended up owing more than you expected this year, it usually comes down to one thing: not enough tax was being paid throughout the year. This is the time to fix that, not in December when the year is almost over.
If you're required to make quarterly estimated payments, work with your tax advisor now to adjust them so they reflect what you actually expect to earn. If you also have W-2 income from your business, increasing your withholding from each paycheck means more tax is being paid automatically throughout the year, so April isn't a shock. (Note: this applies to business owners who pay themselves through payroll—not to sole proprietors or partners who don't receive a W-2.)
The goal is simple: spread the tax burden evenly throughout the year. One large bill landing when cash is already committed elsewhere is far harder to manage than smaller, predictable payments made along the way.
Step 2: Schedule payments in advance
A lot of owners intend to make estimated payments. But intention isn't a system. Work with your CPA to schedule those quarterly payments in advance. Put them on the calendar and treat them like rent: non-negotiable.
When it's scheduled, it stops being something you have to remember to deal with. You're not choosing whether to make a payment when cash flow gets tight. The decision is already made. That's what removes the decision fatigue and the guilt of knowing you should have done it sooner.
Step 3: Automate your tax savings
This is where most people fall back into old habits. They mean to set money aside. But revenue fluctuates, expenses pop up, and growth feels more urgent. So instead of relying on willpower, build a system that does it automatically.
Take a percentage of every dollar that comes in—20%, 25%, whatever your advisor recommends based on your situation—and automatically move it into a separate, dedicated tax account. A percentage works better than a fixed amount here because it scales with your income: when more comes in, more gets set aside; when less comes in, less does. That's how you avoid either under-saving or over-constraining yourself in a slow month.
The key is keeping that money separate from your operating cash. When tax dollars stay mixed in with everything else, your balance looks more usable than it really is, and it's easy to spend without realizing. A dedicated account makes your cash position easier to read and removes the temptation to "borrow" from your tax savings during a tight stretch.
Relay is built for exactly this kind of setup. You can open a dedicated tax savings account1, use auto-transfer rules to move a percentage of incoming revenue into it automatically, and keep those funds visible but separate from your operating cash—so when the tax bill comes next year, the money is already sitting there.
When you adjust your estimated payments, increase withholding if needed, and automate your tax savings, the unpredictability disappears. Tax season becomes a formality rather than a crisis. And that's exactly what you're building toward.
Make this the last stressful year
Once the system is in place, the goal is simple: remove uncertainty. Keeping tax money separated and automatically set aside turns April into confirmation instead of calculation, so you already know the answer before the deadline arrives. Learn how Relay can help put that process on autopilot.
1Relay is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC. FDIC deposit insurance covers the failure of an insured bank. Certain conditions must be satisfied for pass-through deposit insurance coverage to apply.
