Power Moves: How to Stop Losing at Taxes (Before Next Season Steamrolls You)

Well, congratulations. You made it through another tax season without lighting your return on fire or throwing your laptop across the room. That’s worth celebrating… sort of. But before you break out the champagne or start pretending taxes are over until next spring, we need to have a little talk.

Because if you walked away from tax season feeling scammed, shocked, or just plain annoyed, I hate to break it to you, the problem probably wasn’t tax season itself.

It was everything you didn’t do before it.

That’s not a dig. That’s me, standing on a financial soapbox with a giant neon sign flashing “PLEASE PLAN AHEAD.” Because tax season isn’t something you survive. It’s something you win—but only if you start thinking about it long before April rolls around again.

So let’s do that. Let’s get your tax life together while no one’s watching, while the IRS isn’t breathing down your neck, and while you’ve still got time to make moves that matter.

First, if you keep owing every year and acting surprised by it, we need to talk. For my W-2 folks—your paycheck isn’t lying, but your W-4 might be. Adjust it. Use the IRS estimator. Make the changes now while your refund isn’t a twisted fantasy you hope for in vain.

If you’re self-employed or freelancing, I love you, but please—open a tax savings account. Label it “IRS Ransom Fund” or “Do Not Touch Unless Being Audited,” whatever makes you respect it. Then commit to putting aside 25 to 30 percent of your income into that account, like your financial peace depends on it. (Because spoiler: it does.)

Now let’s talk about those receipts you swore you’d organize. No more piles. No more mystery charges you can’t remember. Get yourself a system—QuickBooks, a spreadsheet, a shoebox you’re not ashamed of—and use it. Because the IRS isn’t interested in your memory; they want documentation.

And while we’re here, let’s stop acting as if taxes are only about what you owe. They’re also about what you keep. Retirement contributions? That’s not just future-you stuff; that’s this year’s tax deductions. You don’t need to be on the verge of retirement to benefit from a traditional IRA, 401(k), or SEP IRA. You just need to care enough to act while there’s still time to make a difference.

Let me level with you: the smartest people I know don’t just file taxes—they plan for them. Mid-year. Late summer. Definitely before Halloween. They sit down with someone smarter than them (hi, your accountant) and ask the questions most people avoid until it’s too late:
Am I on track?
Should I delay income?
Should I prepay expenses?
Can I afford this write-off, or am I just playing financial make-believe?

Listen, the tax code isn’t trying to screw you over—it’s just trying to get you to behave in ways the government likes. So, behave. Deduct your home office (if it qualifies). Track your mileage. Max out your HSA. Use what’s already been written for your benefit, instead of letting it haunt you at year-end like the ghost of unclaimed deductions.

And parents—yes, you can hire your kids. If they can TikTok, they can help you market. If they can organize a Fortnite tournament, they can file your invoices. Pay them, write it off, and sleep easy knowing you just legally reduced your tax burden and taught your kid something real. You’re not gaming the system, you’re finally understanding how the game works.

Oh, and if you’ve been running your business as a sole proprietor for five years because it’s “easy”—I get it. But “easy” gets expensive. It may be time to grow up financially and look at an S-Corp. Yes, it requires more structure. Yes, you’ll need help. But the tax savings could make you weep with joy (or regret you didn’t do it sooner).

Now let’s get to the part that still grinds my gears. That whole Beneficial Ownership Information mess? Yeah, that. Small business owners were told to hand over sensitive data or face brutal fines. So we did. Out of fear. And now, after all the panic and compliance scramble, FinCEN has started backing off—at least for domestic businesses. So, what happens to all the data we already handed over? Is it deleted? Filed? Floating around in a digital purgatory? Who knows? The government certainly won’t tell us.

But that’s the game, isn’t it? Rules change. Deadlines move. And if we’re not ready, we get trampled.

So here I am—on my knees, if I have to be—begging you: don’t wait until next tax season to care about your money. Do something now. This month. This week. Open the savings account. Schedule the accountant meeting. Track your expenses like you want to keep your money.

If a recession is on the horizon—and let’s be honest, the economy’s got that “we need to talk” energy—now is not the time to be sloppy with your finances. This is the time to tighten the belt, cut the fat, and get real. With the government. With your business. And especially with yourself.

You don’t need to be rich to play this game well. You just need to be aware, consistent, and a little bit stubborn. You don’t need to be a tax wizard. You just need to stop pretending you don’t have time for this. Because next April is coming, whether you like it or not—and your choices right now will decide if it’s a slap or a sigh of relief.

Please, for the love of your future self: make the smart move. Start today.