If your tax bill caught you off guard last year, it probably wasn’t the IRS that surprised you—it was your systems.
Taxes don’t sneak up on you when your accounting, forecasting, and cash flow are in sync. But for many business owners, those three pieces live in separate corners of the business, handled by different people on different timelines. The result is a lack of visibility that leaves you reacting to problems instead of planning ahead.
Sound familiar?
You work hard all year—serving clients, leading your team, managing growth—and still find yourself blindsided by a tax bill that doesn’t match what you expected. Maybe the business was profitable, but the cash just isn’t there. Maybe your quarterly estimates missed the mark. Or maybe you were told you’d be fine, only to find yourself dipping into reserves to cover the shortfall.
The truth is, most tax surprises don’t come from the IRS, and they don’t happen because you’re disorganized. They happen because the systems you rely on—accounting, tax, and cash flow—aren’t connected in a way that gives you a clear picture. When those systems operate in silos, your financial information is always a step behind reality.
That disconnect doesn’t just create stress; it leads to missed opportunities, poor visibility, and unnecessary surprises.
The good news is that it doesn’t have to be this way. With a few intentional habits, you can move from reactive to proactive and turn tax time into something predictable, not painful.
Here are three steps you can take right now to stop guessing at your tax bill and start leading with confidence.
1. Get Your Books Current and Correct
Start with accuracy, because strategy depends on it.
Before you can plan for taxes, you need to trust your numbers. That means your books have to be clean, current, and complete. It’s nearly impossible to forecast or make smart tax moves if your P&L is behind or your transactions aren’t categorized correctly.
When we dig into clients’ systems, most tax surprises trace back to this single issue: data that’s incomplete or inaccurate. The owner may think they made $400,000, but their books say $600,000 because of double entries or uncategorized deposits. That difference can translate to tens of thousands of dollars in unexpected taxes.
What to do right now:
- Reconcile every bank and credit card account through the most recent month.
- Review income and expense categories—especially owner draws, distributions, and large purchases that can distort net income.
- Fix small inconsistencies before they compound into costly miscalculations.
A clean P&L isn’t just about recordkeeping—it’s about decision-making. When your numbers are accurate, your strategy becomes accurate too.
2. Run a Tax Projection Before Year-End
Turn guesswork into a plan.
Waiting until after year-end to find out what you owe is too late. By then, your options are limited, and your tax bill is whatever it is. But running a tax projection before year-end changes that—it gives you the opportunity to plan while there’s still time to make an impact.
Think of it this way: if you wait to talk to your tax professional after year end, you’ve already closed out your books for the prior tax year, so you can’t go back and retroactively make changes to maximize your tax savings. That’s why the best time to think about your taxes before year-end, when most of your revenue for the year is already known but you still have time to make any needed adjustments.
A tax projection is exactly how you turn that timing into clarity. It brings together your year-to-date numbers, estimated tax payments, and expected results for the final quarter to show where you’ll likely land. If you’re not sure how to calculate it, reach out to your tax provider now and have them walk you through it. Or, if you prefer to take an initial pass yourself, use your accounting data to estimate—just make sure your books are current and accurate before you start.
Then when you see those numbers clearly, you can decide how to adjust:
- Do you need to increase your Q4 payment?
- Accelerate certain deductions?
- Delay income until January?
- Invest in equipment before year-end?
- Maximize your retirement contributions?
This is the key difference between tax preparation and tax planning.
Tax preparation takes place in the Spring and is the act of preparing your taxes to be filed with the government. By nature, it focuses on reporting what took place in the past. Tax planning, however, is a proactive strategy focused on using today’s numbers to plan ahead and make smarter financial decisions now and avoid surprises or missed opportunities come tax time.
To learn more about tax planning versus tax prep, click here to read The Difference Between Tax Planning and Tax Prep—and Why Your Business Needs Both
What to do right now:
- Use your year-to-date profit to estimate your estimated tax liability.
- Compare that to what you’ve already paid in quarterly estimates.
- Work with your accountant to model different year-end scenarios.
A tax bill isn’t unpredictable—it’s just invisible until you look. The earlier you measure it, the more options you have.
3. Talk to Your Tax Advisor Before Year-End
Make your final tax moves of 2025 count.
There’s still time to make smart moves that can directly affect your 2025 tax position—but only if you take them before year-end. Once the New Year arrives, most opportunities are off the table. The end of the year is when strategy becomes action, and the best way to make those moves confidently is by talking with your tax advisor now—not in the spring.
A quick year-end check-in can uncover opportunities you might otherwise miss. Ask about how new legislation, including the One Big Beautiful Bill (OBBB), could affect your 2025 strategy. OBBB includes several provisions that may shift deductions, credits, or contribution limits—so understanding those changes early can help you make better decisions now.
It’s also the right time to review your retirement planning options. Many business owners miss out on valuable tax advantages simply because they wait too long to set up or fund their retirement accounts. If you don’t have one in place, explore options like a SEP IRA, Solo 401(k), or traditional 401(k) before the year closes. If you already have a plan, make sure you’re contributing enough to maximize deductions and stay aligned with your broader cash flow goals.
What to do right now:
- Schedule a short meeting with your tax advisor to review 2025 projections and recent or upcoming legislation.
- Ask specifically how the One Big Beautiful Bill (OBBB) could impact your business next year.
- Review your retirement plan setup, contribution limits, and compensation structure—there’s still time to adjust before year-end.
The goal isn’t to overhaul your strategy overnight. It’s simply to stay proactive, to understand what’s changing, where you can still take action, and how those decisions fit into your bigger financial picture. That’s how you move from reacting at tax time to leading with clarity year-round.
Bonus Tip: How to Spot When Your Systems Are Out of Sync
Even well-run businesses can fall out of rhythm. The signs aren’t always obvious, but they tend to show up in small ways that eventually create bigger problems at tax time.
Here are a few red flags to watch for:
- Your bookkeeper and tax preparer don’t communicate regularly.
If you only connect your accounting and tax data once a year, there’s a high chance important details are getting lost or miscategorized.
- Your reports tell you what has happened, not what’s coming.
You have historical financials, but no forward-looking cash flow or forecast. That means you’re running the business by looking in the rearview mirror.
- Your P&L looks healthy, but your bank account doesn’t.
If profits are up but cash feels tight, something isn’t aligned between how revenue is recognized and how money is actually moving.
- Your estimated tax payments are based on last year’s results.
When your business grows or changes significantly, relying on old data can leave you underpaid and surprised.
If any of these sound familiar, your systems are likely just a little out of rhythm. The fix isn’t starting over—it’s creating better connection. When your accounting, tax, and cash flow processes communicate, your numbers start reflecting what’s actually happening in your business, not what happened months ago.
And when that alignment happens, everything else—cash management, tax strategy, and decision-making—gets easier.
From Reactive to Predictable
Tax surprises disappear when visibility, timing, and cash planning work together.
Clean books give you visibility.
Early projections give you control.
Cash rhythm gives you confidence.
The difference between reacting to your tax bill and planning for it comes down to one thing: connection. When your accounting, forecasting, and cash flow are in sync, taxes stop being a guessing game. You’re not reacting anymore—you’re leading.
At Stride, this is the rhythm we build with every client. But whether you work with us or not, the principle stays the same: taxes aren’t just about compliance—they’re about clarity. And clarity is what gives business owners control.
Ready to take control of tax season? Schedule a call with Stride to see how proactive planning can support your next stage of growth.
About Stride Services
Stride Services is a comprehensive financial partner for MSPs, providing outsourced bookkeeping, tax, and advisory services designed to improve clarity, support confident decision-making, and eliminate financial fire drills. Whether you need monthly accounting support or proactive tax guidance, Stride helps you stay on track and plan for what’s next.
To learn more, visit www.stride.services.
Casey Seaborn: Email
LinkedIn: Casey Seaborn
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