June isn’t just the season for weddings, Father’s Day golf, and wondering why your tomato plants aren’t producing yet. It’s also prime time for a mid-year retirement checkup. Before the second half of the year rolls in with tax deadlines, RMD headaches, and year-end planning pressure, now’s your window to get ahead of the game while everyone else is busy perfecting their grilled salmon recipe.
Check Your Cash Flow
A lot can change between January and June. Maybe your income’s higher than expected. Maybe markets bounced more than your knees do these days. Or maybe your withdrawal plan quietly veered off track while you weren’t looking. That’s why a quick halftime review can be the smartest 60 minutes you spend this summer - aside from choosing the shady table on the patio.
Avoid Tax Surprises
Start with your income flow. Are your withdrawals still matching what you actually need? Too little and you risk short-changing your lifestyle. Too much and you’re sending extra to Uncle Sam, who’s never shy about accepting overpayments. If you’ve had any changes, new spending, travel, family gifts, now’s the time to adjust.
Fine-Tune Your Withholding
Speaking of Uncle Sam, it’s worth checking your tax withholding. Just because your CPA blessed it in April doesn’t mean it’s still on track. If you’re taking IRA distributions or Social Security, small tweaks now can spare you from a tax bill surprise next spring. You might not get a gold star for withholding correctly, but you also won’t get a penalty. And that’s a win in retirement.
Watch Out for IRMAA
Don’t forget the invisible hand reaching from two years ago: Income Related Monthly Adjustment Amount or IRMAA. If your income is creeping up this year, you may be setting yourself up for higher Medicare premiums in 2027. That's right - today’s decisions have long tails. If you’ve been converting to Roth, harvesting capital gains, or drawing larger-than-usual amounts, it’s worth a look to avoid future sticker shock from Medicare.
Rebalance Your Portfolio
Markets don’t stand still, and neither should your portfolio. A mid-year rebalance can help keep your risk in check and ensure you’re not accidentally betting the farm on tech stocks or tucking too much into cash that’s losing ground to inflation. Rebalancing isn’t flashy, but it’s one of those unglamorous habits that quietly makes a big difference.
Update Your Essentials
And if it’s been a while since you looked at your beneficiaries, estate documents, or powers of attorney, consider this a gentle nudge. These things are easy to ignore until they aren’t. A few minutes of review now can prevent months of drama later.
5-Star Tip: Adjust the Playbook
Here’s your five-star tip: June is halftime, and the scoreboard doesn’t lie. But you still have time to adjust the playbook. Don’t wait for year-end panic or December market swings. The best financial decisions often happen when nobody’s rushing.