Can you believe we’re already halfway through 2026!
I say this every June and somehow it still catches me off guard. One minute you’re making New Year’s resolutions about getting your finances organized, and the next thing you know it’s summer and Q3 is knocking on the door.
Here’s the thing about midyear — it’s actually one of the most useful moments in the financial calendar. You have six months of real data behind you. You still have six months to make adjustments before December 31st. And a few of the deadlines that matter most to retirees or near retirees fall right around now: Adding to your 401K with Catch-Up Limits, June 15th estimated tax payments, RMD planning windows, and Medicare open enrollment on the horizon.
So before summer gets fully underway and you’re too busy enjoying it to think about money (as you should be), let’s do a quick check-in. Five things. Thirty minutes. You’ll feel so much better having done it.
Six months of real data behind you. Six months left to make it count. That’s a rare and useful place to be.
1. Check Your Tax Withholding — Before You Owe a Surprise in April
This is the one that sneaks up on people, and it’s especially tricky in retirement when your income comes from multiple sources — Social Security, IRA distributions, a pension, maybe some investment income or part-time work.
Unlike a W-2 job where taxes were withheld automatically, retirement income requires you to either set up withholding or make quarterly estimated tax payments. If you haven’t revisited your withholding since last year, now is the time.
What to look at:
- Pull up your 2025 tax return. What did you owe, or what did you get back? If you owed more than $1,000, you may need to increase withholding or estimated payments now. The rule is – you need to pay at least 100% of last year’s tax liability or 90% of what is owed this year to avoid penalties.
- Check the withholding on your Social Security (Form SSA-1099) and any pension payments. You can adjust Social Security withholding by submitting a new Form W-4V.
- Review any IRA or 401(k) distributions taken so far in 2026 — are taxes being withheld? If not, you’ll need to either add withholding or make a Q3 estimated payment by September 15.
- Mark June 15 on your calendar if you make quarterly payments — that’s your Q2 deadline. Miss it and you may owe a penalty, even if you pay the full amount later.
- Note for next year – you can file form 2210 and Schedule AI – this is for filers that have more seasonal income – you can pay taxes as income is received seasonally throughout the year. It reduces potential penalites.
Why this matters more now than it used to: The 2026 tax landscape shifted with the One Big Beautiful Bill Act. Standard deduction amounts changed, and some itemized deduction rules were adjusted. If your tax situation is similar to last year but your withholding hasn’t been updated, you could be in for a surprise. When in doubt, a quick conversation with your CPA or tax preparer mid-year is much cheaper than a penalty in April.
2. Confirm Your RMD Status — and Consider Timing
If you’re 73 or older, Required Minimum Distributions aren’t optional — and the penalty for missing them is steep (25% of the amount you should have taken). Midyear is the perfect time to make sure you’re on track.
But there’s more to this than just “did I take my RMD.” The timing of your distributions across the year affects your tax bracket, your Medicare premiums, and how much flexibility you have for strategies like Roth conversions or charitable giving.
What to look at:
- Confirm the RMD amount for each account with your custodian — don’t rely on last year’s number. Account balances change, and your RMD is recalculated each year based on December 31 balances.
- Have you taken your full RMD for 2026, or at least a portion of it? You have until December 31 — but spreading distributions across the year can smooth out your tax liability.
- Are you planning to make a Qualified Charitable Distribution (QCD)? If so, do it before taking other IRA distributions. QCDs count toward your RMD dollar-for-dollar and are excluded from taxable income. (See my post on Tax-Smart Charitable Giving for a full explainer.)
- Multiple IRAs? Confirm the aggregation rules apply — you can satisfy all traditional IRA RMDs from one account, but 403(b) and inherited IRA rules are different.
Heads up: inherited IRAs have new rules. If you inherited an IRA after 2019, the SECURE Act rules apply to you, and they changed significantly. Most non-spouse beneficiaries must now empty the account within 10 years. If you’re in this situation and haven’t revisited your withdrawal strategy lately, mid-year is a good time to do it.
3. Review Your Income for Medicare Premium Purposes
This one has a delay built in that trips people up. Your Medicare Part B and Part D premiums for 2027 will be based on your 2025 tax return — the one you likely filed this spring. So the income decisions you make right now, in 2026, will affect your 2028 premiums.
I know. It’s a lot of years to keep track of. But this is exactly the kind of thing that’s worth understanding, because the premium jumps at each IRMAA tier are significant.
The 2026 IRMAA income thresholds (for reference):
| Individual MAGI | Joint MAGI | Monthly Part B add-on |
|---|---|---|
| Up to $106,000 | Up to $212,000 | $0 (standard premium) |
| $106,001–$133,000 | $212,001–$266,000 | +$69.90 |
| $133,001–$167,000 | $266,001–$334,000 | +$174.70 |
| $167,001–$200,000 | $334,001–$400,000 | +$279.50 |
| $200,001–$500,000 | $400,001–$750,000 | +$384.30 |
| Above $500,000 | Above $750,000 | +$419.30 |
Note: These are approximate 2026 figures. Confirm current thresholds at medicare.gov or with your financial advisor.
What to look at:
- Estimate your 2026 MAGI now — salary, RMDs, Social Security (85% is taxable for most), investment income, Roth conversions. If you’re close to a threshold, there may be time to adjust before year-end.
- Are you planning a large Roth conversion this year? Roth conversions add to your MAGI and can push you into a higher IRMAA tier. Model it before you execute.
- Did your income drop significantly in 2025 vs. 2023 (the base year for 2025 premiums)? If so, you can file Form SSA-44 to request a reduction in current-year premiums based on a life-changing event.
4. Give Your Investment Allocation a Quick Checkup
I’m not suggesting you make big moves — reacting to short-term market noise is almost never a good idea, and I’m certainly not going to be the one to tell you to do that. But a midyear check on your allocation takes twenty minutes and can surface drift you didn’t notice happening.
Markets have moved. Your portfolio probably has too. The mix of stocks, bonds, and cash you set a year ago may look quite different today — and if you’re in or near retirement, that matters more than it did when you had decades of runway.
What to look at:
- Pull your current allocation across all accounts — IRAs, brokerage, 401(k) if still active. Look at the total picture, not each account in isolation.
- Compare it to your target allocation. Has it drifted more than 5–10 percentage points in any direction? If so, it may be time to rebalance — ideally within tax-advantaged accounts first to avoid triggering gains.
- Check your cash position. In retirement, holding 1–2 years of expenses in cash or short-term reserves reduces the need to sell equities in a downturn. With yields still relatively attractive on high-yield savings and money market accounts, this is worth revisiting.
- Review any concentrated positions. A single stock or sector that’s grown to represent a large portion of your portfolio is a risk worth acknowledging.
A gentle reminder about rebalancing: Rebalancing inside a traditional IRA or 401(k) has no immediate tax consequences — you’re not triggering capital gains. Rebalancing in a taxable brokerage account is a different story. Be mindful of the tax impact before you sell, especially if you’re sitting on significant long-term gains.
5. Make Sure Your Documents and Beneficiaries Are Current
I put this one last because it’s the most likely to get skipped — and it absolutely should not be. This is the most important item on the list for your family’s sake, even if it’s the least exciting one for yours.
Life changes. Documents don’t update themselves. And beneficiary designations — on IRAs, 401(k)s, life insurance, and annuities — override whatever your will says. If your ex-spouse is still listed as the beneficiary on your IRA because you never updated it after your divorce, that’s where the money goes. Full stop.
What to look at:
- Confirm beneficiary designations on all retirement accounts, life insurance, and annuities. Log into each account directly — don’t rely on old paperwork. Custodians lose forms.
- Review your will and trust documents — when were they last updated? A major life change (move to a new state, marriage, divorce, death of a beneficiary, significant change in assets) warrants a review with your estate attorney.
- Is your healthcare proxy and durable power of attorney current and accessible? The people named in these documents should know where they are and what they say.
- Are your important documents stored and accessible — both physically and digitally?
You’ve Got This
I know this list can feel a little overwhelming when you see it all together. But here’s the truth: you don’t have to do all five of these in one sitting. Pick the one that’s been nagging at you — the one you’ve been meaning to get to — and start there. Then come back for the rest.
Midyear is a gift. It’s a built-in checkpoint that most people blow past on the way to summer. The fact that you’re here, reading this, means you’re already doing better than most.
Small adjustments made in June are worth a lot more than big scrambles in December. Trust me on that one.
As always, I’m not a financial advisor and none of this is personalized tax or investment advice. For your specific situation, please work with a qualified CFP or CPA. But consider this your friendly nudge to actually have that conversation — before Q3.
Quick Recap: Your Midyear Money Checklist
- 401k catch-ups: Are you saving the most you can for retirement?
- Tax withholding: Are you on track? Any estimated payments due?
- RMD status: Have you taken distributions? QCD planned?
- Medicare / IRMAA: Is your 2026 income on track to stay in your target tier?
- Investment allocation: Has your portfolio drifted from your target?
- Documents & beneficiaries: Are they current, correct, and accessible?
