You Filed Your Taxes Now What?
- John Piershale, CFP®, AEP®
- Apr 20
- 4 min read
Smart Moves to Make While the IRS Sleeps
You survived another tax season. Congratulations! The shoeboxes are emptied, the e-filing is done, and your CPA finally stopped giving you that “Where’s your 1099?” look. Time to toss the tax folder in a drawer and forget about it until next April, right?
Not so fast.
Just because you’re off the IRS radar for now doesn’t mean your tax return can’t still do some heavy lifting. In fact, this is prime time for smart planning - especially if you’re in your 50s or early 60s, staring down retirement and wondering how to make everything click.
Let’s walk through three things you can do after tax season that can help set you up for smoother sailing ahead.
1. Turn That Tax Return Into a Planning GPS
Most people treat their tax return like a fire extinguisher - only useful in emergencies. But it’s actually a gold mine of planning opportunities if you know where to look.
Start with your marginal tax bracket. This tells us how much you pay on your next dollar of income - and whether there’s room to do some strategic moves (like Roth conversions, which we’ll get to in a minute). If you’re sitting in a lower bracket now than you’ll be in later (say, after RMDs kick in or tax laws sunset in 2026), that’s a planning window worth exploiting.
Then, scan your return for missed deductions or quirky income patterns—consulting gigs, investment spikes, or that one year you sold a boat and somehow owed the IRS $2,300.
Your tax return isn’t just a rearview mirror. It’s a financial map - and you don’t want to drive into retirement without knowing the terrain.
2. Roth Conversions: While the Tax Sun Shines
If you’re in your early 60s, post-career but pre-RMD (Required Minimum Distribution) age, welcome to the sweet spot. You may be in a temporarily low tax bracket - an ideal time to convert some IRA dollars to Roth.
Why does this matter?
Because Roth IRAs grow tax-free, come out tax-free, and don’t force you to take withdrawals at age 73, they’re one of the few financial moves that might feel like cheating - but are 100% legal. No annual RMDs, no tax bill on growth, no awkward run-ins with Uncle Sam. It’s like tucking your dollars into financial witness protection.
Even small conversions - just enough to max out your current tax bracket without tipping into the next one - can add up over time.
Yes, you’ll owe taxes now, but with future rates possibly headed north (thanks, expiring tax cuts and ballooning deficits), this might be the lesser of two tax evils.
⭐ 5 Star Tip: run these numbers with a planner or tax pro. Roth conversions are powerful but nuanced - you don’t want to fly solo and end up in the Medicare IRMAA penalty zone by mistake.
3. Fix Your Withholdings Before They Haunt You
If you got a big refund - or worse, a surprise tax bill - your withholdings may need a tune-up.
Refunds feel nice, but they’re just an interest-free loan to Uncle Sam - and he doesn’t send thank-you notes. Meanwhile, underpaying can land you with penalties and a springtime migraine. Now’s a great time to adjust.
Here’s how to get your withholdings back in tune:
Update your W-4 if you're still working.
Adjust estimated payments if you're retired or self-employed.
And if your income fluctuates (think RMDs, freelance work, or stock sales), consider setting up a quarterly system to avoid surprises.
It’s about getting as close to “break-even” as possible—not owing, not overpaying. Just right. Like financial Goldilocks.
⭐ 5 Star Tip: Retired Doesn’t Mean Untaxed
Just because you stopped working doesn’t mean you stopped owing. Retirees can still get walloped with tax underpayment penalties if they don’t have enough withheld from IRA withdrawals or Social Security. The good news? You can often skip quarterly estimates entirely by setting up smart withholdings instead. Let the IRS take a little off the top - on your terms.
The Wrap
You already did the hard part. The taxes are filed, the caffeine-induced spreadsheet marathon is over, and you can finally open your mailbox without fear.
Now’s the time to do some low-pressure, high-impact planning while the IRS hits the snooze button until next spring.
Your future self - the one sipping wine in Tuscany or golfing on a Tuesday - will thank you.
Need help making sense of your tax return or deciding if a Roth conversion makes sense this year? Let’s chat. This is what I do, minus the jargon and pressure.
👉 Contact Me - Let’s turn that tax return into a retirement strategy.
John Piershale, CFP®, AEP®
Fee-Only and Fiduciary Advisor
John Piershale Wealth Management, LLC is an Investment Adviser registered with the State of IL and in other jurisdictions where exempt from registration. All views, expressions, and opinions included in this communication are subject to change. This communication is not intended as an offer or solicitation to buy, hold or sell any financial instrument or investment advisory services. Any information provided has been obtained from sources considered reliable, but we do not guarantee the accuracy or the completeness of any description of securities, markets or developments mentioned. The information contained herein is intended to be used for educational purposes only and is not exhaustive. Diversification and/or any strategy that may be discussed does not guarantee against investment losses but are intended to help manage risk and return. If applicable, historical discussions and/or opinions are not predictive of future events. The content is presented in good faith and has been drawn from sources believed to be reliable. The content is not intended to be legal, tax or financial advice. Please consult a legal, tax or financial professional for information specific to your individual situation.
