Five questions to answer before summer gets away from you

Here’s what I’ve noticed over the years: many people start the year with good financial intentions.

By June, life has moved on.

The goals from January are still sitting in a drawer somewhere (literal or mental), and summer is about to make things even busier.

I don’t say that to make you feel bad. I say it because nearly half of Americans actually have a written financial plan.1

But here’s the opportunity: right now, before vacation mode kicks in, you have a small window to make a few proactive moves that could save you potential headaches later. It doesn’t require a financial overhaul.

Just five honest questions.

1. Am I on track with my tax withholding?

The IRS specifically recommends a mid-year withholding check2 — and for good reason.

If your income changed, you picked up a side project, or your filing situation shifted, your withholding from January may not match your reality in June.

A 10-minute check now could be the difference between a manageable April and an unpleasant surprise. (The IRS provides this estimator tool that makes this easy.3)

2. When was the last time I looked at my beneficiary designations?

This one catches people off guard.

Beneficiary forms are easy to forget because you usually fill them out once and move on.

But life changes fast — marriages, divorces, new kids, new jobs, old accounts you haven’t touched in years.

And here’s the important part: the beneficiary designations on retirement accounts and insurance policies generally override what’s written in your will.4

Which makes this one of those small tasks that can have a much bigger impact than people realize.

3. Is my insurance actually ready for summer?

Before you book the flights and load up the car, it’s worth a quick look at what’s actually covered.

Does your homeowner’s or renter’s policy cover what you’d need it to while you’re away?

Is your auto coverage current?

If you’re traveling internationally, does your health insurance apply?

These aren’t fun questions, but they’re a lot more fun to answer now than after something potentially goes wrong.

4. Am I making the most of my tax-advantaged accounts this year?

June is the halfway mark.

If you’re contributing to a 401(k), IRA, or HSA, now is the time to check whether you’re on pace to contribute what you intended.

This is especially worth checking for HSAs. The money never expires and grows tax-free — which matters more than people realize when you consider that a single person age 65 today could spend over $170,000 just for healthcare in retirement.5

Small adjustments now can add up over the back half of the year.

5. Could I write down what last summer actually cost me?

Most people can’t — and that’s the point.

Summer has a way of quietly running up the tab. Last year, household spending hit its highest growth rate of the year during July, driven by travel, dining, and recreation.6

That’s not a reason to stay home. But if you can’t ballpark what the season cost you last time, it’s worth a few minutes of honest math before this one starts. Even a rough number gives you something to plan around instead of reacting to.

You don’t need all five answers today.

But if any of these questions made you pause, that’s worth paying attention to.

Research consistently shows that people who work with a financial professional feel significantly more confident about reaching their goals.7

A mid-year check-in is one of the most productive conversations you can have.

If you’re unsure if you’re being asked questions like these with your current plan, reach out to schedule a call to see how our team may be able to help.

Warmly,

Barry

Sources

1. CNBC, 2025 [URL: https://www.cnbc.com/2025/09/25/no-financial-plan-how-to-find-the-right-advisor-for-you.html]
2. Internal Revenue Service, 2025 [URL: https://www.irs.gov/newsroom/irs-encourages-taxpayers-to-check-withholding-now-for-next-year]
3. Internal Revenue Service, 2026 [URL: https://apps.irs.gov/app/tax-withholding-estimator]
4. Trust & Will, 2025 [URL: https://trustandwill.com/learn/beneficiary-designation-vs-will]
5. Fidelity Investments, 2025 [URL: https://newsroom.fidelity.com/pressreleases/fidelity-investments–releases-2025-retiree-health-care-cost-estimate–a-timely-reminder-for-all-gen/s/3c62e988-12e2-4dc8-afb4-f44b06c6d52e]
6. Bank of America Institute, 2025 [URL: https://institute.bankofamerica.com/economic-insights/consumer-checkpoint-august-2025.html]
7. CFP Board, Financial Planning Longitudinal Study, 2026 [URL: https://www.cfp.net/news/2026/01/cfp-professional-advised-americans-experience-greater-financial-preparedness]