Your Mid-Year Financial Check-In: Five Smart Moves for High Earners

Every June, I seem to have the same conversation.

Someone sits down across from me and says, “I haven’t looked at any of this since January.” They’re not behind. They’re not doing anything wrong. They’ve just been busy. Working, earning, raising kids, managing life — and suddenly six months have passed. 

That is exactly why mid-year is such an important time to pause. By June you have enough data to see what’s working. You also still have enough time left in the year to adjust what is not. 

Here are five mid-year planning moves I am discussing with clients right now.

1. Check Your Withholding

This is the most common issue I see at mid-year, and the one that creates the biggest surprises.

If you have RSUs, your employer likely withheld 22% at vesting. But if your total income puts you in the 32%, 35% or 37% bracket, that withholding may not be enough. And that withholding gap may be growing every time shares vest.

Here’s a situation I see all the time: an Amazon employee in year three or four of a grant, when larger vesting events occur, assumes everything is covered because the tax withholding happened automatically. But by mid-year, the gap between what was withheld and what may actually be owed can easily reach $20,000 to $40,000. Not because anyone made a mistake. The flat-rate withholding simply doesn’t account for the full picture.

What to do now: Pull your most recent pay stub and compare your year-to-date federal withholding against a rough projection of your total 2026 tax liability. If the numbers do not line up, there is still time to adjust withholding, make an estimated payment, or coordinate both.

If you are self-employed, have meaningful investment income, or are otherwise making estimated payments, the Q2 federal estimated tax deadline is June 15, 2026. Missing it can trigger penalties that are often completely avoidable.

2. Review Your Retirement Contributions

The 401(k) employee deferral limit is now $24,500. If you are age 50 or older, you can contribute an additional $8,000 as a catch-up contribution. And if you turn age 60, 61, 62, or 63 during the year, the SECURE 2.0 “super catch-up” limit allows a higher catch-up contribution of $11,250. 

The mid-year question is simple: Are you on track to max out by December?

If you front-loaded contributions early in the year, you may already be close. If you did not adjust your contribution percentage in January, you may need to increase it now to avoid falling short.

One change worth noting: beginning in 2026, if your prior-year FICA wages from the employer sponsoring the plan exceed $150,000, and your plan offers a Roth feature, your catch-up contributions must generally be made on a Roth basis. This is not optional. Some employer plans may still be working through the administrative details, so if you are age 50 or older, it is worth confirming with HR or your plan provider that catch-up contributions are being handled correctly.

If you have access to the Mega Backdoor Roth, mid-year is a good time to check in. Are your after-tax contributions flowing? Are the in-plan Roth conversions happening automatically, or do you need to initiate them? A missed setting can mean missed Roth dollars by year-end.

3. Consider a Mid-Year Roth Conversion

Most people consider Roth conversions a year-end move. However, mid-year can sometimes be a better time to evaluate them.

Here’s why: in January, you are guessing what the year will look like. In December, you may be scrambling. By June, you usually have several months of real income data and enough runway left to make a thoughtful decision. 

A Roth conversion moves money from a traditional IRA, SEP IRA, SIMPLE IRA, or eligible pre-tax retirement account into a Roth IRA. You pay taxes now, but the money grows tax-free going forward if Roth distribution rules are met. The key is finding the right amount — converting too much can push you into a higher tax bracket, trigger Medicare surcharges, or create other tax issues. Convert too little, and you may miss a valuable planning window.

If you had a lower-income first half of the year — maybe you changed jobs, took leave, retired, had a gap between equity vests, or experienced a temporary drop in business income — this could be an especially valuable year to evaluate a conversion.

Those windows do not come around often, and they are much easier to use when you identify them before year-end.

4. Revisit Your Insurance and Estate Planning Documents

This is not the exciting part of financial planning. But it is often the part that matters most when something goes wrong.

Life insurance: If your income, expenses, mortgage, or family responsibilities have grown significantly, your current coverage may no longer be enough to protect your family. The same goes for disability insurance — your ability to earn an income is one of your most valuable assets, and a gap in coverage can be financially devastating.

Umbrella insurance: If your net worth has increased, your liability exposure may have increased with it. An umbrella policy provides additional liability protection above the limits on your homeowners, auto, or other underlying policies. It is often one of the more cost-effective ways to add meaningful protection.

Beneficiary designations: These are easy to overlook, but they are critical. For retirement accounts, life insurance policies, and certain other assets, beneficiary designations generally control where the money goes, regardless of what your will says. That means an outdated form can create serious problems. If you have gotten married, gotten divorced, had a child, bought a home, started a business, or experienced a major change in your financial life since your last review, check them.

You would be surprised how often I find outdated beneficiaries during a first review. Ex-spouses still listed on life insurance policies. Retirement accounts that still name a parent instead of a spouse. No contingent beneficiary listed at all. Trust documents that no longer reflect the family’s current situation.

These are often five-minute fixes when you catch them. When you do not, the consequences can be significant.

5. Get Ahead on New Opportunities

The One Big Beautiful Bill Act created a few planning opportunities that are worth acting on now.

One example is the expanded SALT deduction. For 2026, the SALT cap is scheduled to increase to $40,400 for most filers, with the cap beginning to phase down once modified adjusted gross income exceeds approximately $505,000. If you itemize deductions and live in a high-tax state, this is worth reviewing with your CPA . Depending on your income, property taxes, state income taxes, and other deductions, the higher cap could meaningfully reduce your federal tax bill compared to prior years.

Trump Accounts open for contributions on July 4th. These are new tax-advantaged investment accounts for children under 18. Parents can establish an account, and contributions are generally allowed up to $5,000 per year. Funds must be invested in certain U.S. stock index mutual funds or ETFs, and the account generally cannot be accessed before the year the child turns 18.

Children born from January 1, 2025 through December 31, 2028 may also be eligible for a one-time $1,000 federal contribution. At age 18, the account is generally treated like a traditional IRA.

This is brand new, and the details matter. How a Trump Account fits alongside a 529 plan, how the investments are structured, and how the account integrates with your broader plan are all worth thinking through before contributions open.

The Bottom Line

A mid-year check-in doesn’t take weeks. In most cases, a focused conversation covering these five areas can surface opportunities, or catch problems, that make a real difference by December.

The common thread is simple: the earlier you identify something, the more options you have. Waiting until December limits your flexibility.

If you want help running the numbers — your withholding gap, a Roth conversion, whether your retirement contributions are on track, or where Trump Accounts fit for your family — book a free consultation.