Janet Mason 
The Tuesday after tax season ends is what I like to call “Accountant Boxing Day.” The phone’s slow down, the coffee’s still hot at 10:00 a.m., and there’s finally time to sit for a full lunch instead of survival-snacking on almonds and regret.
This year, I spent my first post-deadline afternoon cleaning out my desk drawer. You’d be amazed what turns up—four highlighters (none of which work), one ancient granola bar that may have predated the CARES Act, and a Post-it that just said, “Ask Jeff about the forklift thing??” Still no clue.
But here’s the thing: as I was tossing receipts and eating celebratory Chinese takeout, I found myself scribbling down notes for clients. Not the ones who just filed—I’m talking about the ones who could make next year easier. The ones who say every April, “Next year, I’m going to be more prepared.”
So, if that’s you—if you’ve ever said those exact words while sweating over a shoebox of crumpled 1099s—let’s talk. Not judgment. Not jargon. Just real-life things to consider for tax planning in 2025.
Let me tell you about a guy named Pete. Pete is a contractor—smart, hardworking, salt-of-the-earth kind of guy. But every April, he rolls in with a box full of envelopes, a panicked look, and absolutely no bookkeeping.
Last year, I finally asked: “Pete, what if you just used an app to track this stuff as you go?”
This year, he did. And for the first time, we filed early. He owed less. He looked… peaceful.
Moral of the story? Whether you’re a freelancer, a side hustler, or just someone with a complex financial life, start tracking now. Use QuickBooks, a spreadsheet, or even a simple notes app. The tool doesn’t matter. The habit does.
Yes, the standard deduction is higher than it used to be. And yes, it works for a lot of people. But let’s not forget—blankets don’t fit everyone the same way.
If you have mortgage interest, big medical bills, or if you give to charity like your grandma taught you, itemizing might still be your best move.
And here’s the kicker: you can’t decide that in March if you didn’t plan all year. If you want to take advantage of deductions, you have to create them. Donate intentionally. Pay property taxes before year-end. Keep those receipts organized—or at least in the same drawer.
I once had a client who sold handmade leather wallets on Etsy. She made good money, y—but her entire business ledger was a mix of Venmo screenshots and Instagram DMs.
If you’re making money outside your W-2 job—even $50 here or there—you’ve started a business, whether you meant to or not. And that means taxes.
Open a separate bank account. Save at least 20–30% of what you earn. Keep records of everything—supplies, mileage, and fees. Because if the IRS comes knocking, “I didn’t know” is not a get-out-of-jail-free card.
Also, consider forming an LLC or sole proprietorship. It’s not scary, I promise. Think of it like giving your side hustle its toothbrush—it’s grown up enough to deserve one.
You know those glossy brochures with silver-haired couples walking on the beach? Yeah, that’s not what retirement planning looks like for most people.
Real-life retirement planning is deciding in your 30s or 40s to put money into a SEP IRA, a traditional IRA, or a solo 401(k)—even if it means fewer takeout lunches. It’s the freelancer choosing to invest $6,500 this year instead of rolling the dice on crypto again.
Contributions to tax-deferred retirement accounts reduce your taxable income now, which means you pay less in April 2026. Future You will say thank you. Probably while walking a rescue dog instead of working your fifth side gig at 68.
This one’s for the W-2 crowd. I can’t tell you how many people haven’t touched their W-4 since they got hired—even if they got married, had kids, or started a second job.
That form controls how much tax your employer withholds from each paycheck. If you’re consistently getting a big refund—or worse, a big bill—you might need to revisit it.
You can update your W-4 anytime. It’s not carved in granite behind your HR person’s desk. So take 15 minutes, check your withholdings, and make sure 2025 isn’t a repeat of “Wait, I owe how much?”
When I meet with clients for tax planning, we end up talking about life—because taxes touch everything. Are you thinking of selling your house? Starting a business? Taking care of an aging parent? That’s tax planning.
If your CPA isn’t asking you those kinds of questions, find one who will. Or at the very least, you should be asking yourself.
Because good tax planning isn’t just about paying less. It’s about making sure your financial choices align with your goals, your values, and your future.
You don’t have to be doing anything wrong to get audited. Sometimes it’s just the luck of the draw—or a random math error. But you can make sure that if it happens, you’re not sweating bullets at midnight trying to find a $142 receipt for “business dinner—Taco Bell.”
Keep digital copies of receipts. Label transactions. If you’re not sure if something is deductible, ask, don’t guess. Audits aren’t fun, but they’re survivable when you’re organized.
One of my favorite moments this year was when a client sheepishly asked if she could deduct the cost of her dog’s obedience training. Turns out, the dog was a certified service animal—and yes, some of that was deductible.
Moral of the story? Don’t assume something isn’t tax-relevant just because it sounds weird. Energy-efficient windows? Solar panels? A home office in the attic that you never finished painting? All are possibly deductible under the right circumstances.
So ask the weird questions. They’re often the most interesting ones.
Look, I’m not saying you need to live and breathe taxes. Please don’t. Life’s too short.
But a little forethought now—just a few smart moves over the next 8 months—can save you hours of stress and possibly thousands of dollars next April.
So, schedule a check-in with your CPA. Automate your savings. Put “sort receipts” on your calendar once a month. And if you’ve got a business, treat it like one.
Or, you know… just wait until next April and panic-order a pizza while frantically downloading bank statements.
Your call.
