By Christopher Krzus, CFP® / Wolfstone Wealth
We’re already past the halfway point of the year, which makes this a useful time for a mid-year check-in. If you’re earning six figures or more, a few things often line up around now: Q2 estimated taxes are due, RSU vesting is frequently in progress, and there’s still enough of the year left that decisions made today can actually change the outcome. Wait until December, and many of these windows have already narrowed.
Here are five areas worth a closer look right now.
Re-Check Your Estimated Tax Payments
If any part of your income is variable — bonuses, RSUs, K-1s, or side business earnings — mid-year is a good moment to confirm that your withholding and estimated payments are still tracking what you’ll likely owe. Underpayment penalties are avoidable, but the problem is that no one sends a warning before the bill (and the interest) arrives the following spring.
RSU Vesting: Don’t Default to Autopilot
When RSUs vest, the automatic response is often to sell enough shares to cover the taxes and move on. That’s not necessarily wrong — it’s just not automatically the best move either. Before that sale happens, it’s worth pausing to look at your current tax bracket, whether there’s room for a Roth conversion this year, your overall capital gains picture, and whether you’re holding more company stock than you’d actually choose if you were starting fresh.
(For a deeper look at vesting schedules, withholding gaps, and related planning points, see our guide on Understanding RSUs.)
Is This a Good Year for a Roth Conversion?
Mid-year has one practical advantage that year-end doesn’t: enough visibility into the year’s income combined with enough time left to act. With roughly half the year known and half still ahead, you can size a conversion to fill lower tax brackets without spilling into a higher one. By December, you’re mostly working with whatever numbers are left.
Maximize What’s Still Available in Tax-Advantaged Accounts
HSA contributions, 401(k) catch-up contributions (if you’re 50 or older), and backdoor Roth strategies still have runway left this year — though less than it may feel like in July. If you own a business, it’s also worth checking whether there’s additional room for retirement plan contributions or other deductions before that window closes. (This kind of sequencing – including the backdoor Roth pro-rata rule – is core to our Tax Planning work.)
Fund (or Add to) a Donor-Advised Fund Before Year-End Pressure Hits
If charitable giving is part of your plan, contributing to a donor-advised fund now rather than in the December rush locks in this year’s deduction while giving you more time to decide where the money ultimately goes. Very few people make their best giving decisions in the final week of the year.
None of these moves require overhauling your entire financial picture. They are simply high-leverage adjustments that are easier to make while there is still time for them to matter. For high earners, mid-year is often one of the better moments to step back and look at the full picture instead of reacting to whatever arrives next.
Frequently Asked Questions
Why does mid-year tax planning matter more than waiting until year-end?
By mid-year you generally know a good portion of the year’s income but still have time to act — sizing a Roth conversion, adjusting estimated payments, or funding accounts. By December, many of those options have already narrowed.
Should I sell my RSUs as soon as they vest?
Not automatically. Selling enough to cover taxes is the common default, but the better move depends on your tax bracket, any Roth conversion room, and how concentrated your position in company stock has become. It’s worth a specific look before defaulting to a sale.
Is it too late in the year to do a Roth conversion?
Mid-year is actually one of the better windows. There’s enough visibility into the year’s income to size it reasonably well, and enough time left before December 31 for it to be completed cleanly.
What tax-advantaged accounts should high earners revisit mid-year?
HSA contributions, 401(k) catch-up contributions for those 50 and older, backdoor Roth contributions, and — for business owners — retirement plan contributions or other business-related deductions.
Not sure which of these applies to your situation?
That’s exactly what the first conversation is for. Schedule a 20-minute introductory call — no paperwork, no pitch. wolfstonewealth.com/contact | 630-640-3582
