Open Enrollment: Three Clicks Worth Real Money

Sometime in the next several weeks, an email will land in your inbox announcing that open enrollment has begun. Most people give that portal ten distracted minutes, click whatever they clicked last year, and move on. Fair enough, it is built to be boring. But for high earners, a handful of those clicks quietly move more money than almost anything else you will do this fall. So this issue is your walkthrough, written before the portal opens instead of after it closes.

CLICK ONE: THE HSA YOU KEEP WALKING PAST

Two versions of this miss show up constantly. The first is not maxing the HSA. The second is sneakier: picking a plan that is not HSA eligible while your household is healthy, which locks you out of the account entirely for another year. For 2026 the limits are $4,400 for self only coverage and $8,750 for family coverage, with an extra $1,000 once you are 55. The HSA is the only account in the code where money can go in untaxed, grow untaxed, and come out untaxed for medical costs, and every retirement eventually has medical costs. My frame is simple: the healthy years are the saving years. If your cash reserves and the rest of your personal finances are in good order, using those years to pack the HSA is one of the better trades the portal offers. That order matters, reserves first, then optimization, same as always.

CLICK TWO: THE ESPP AND ITS CLOCK

An employee stock purchase plan sells you company shares at a discount, commonly 15 percent, and that discount is real compensation. The mistakes come in two flavors. Some people sell too quickly and give part of the benefit back: unload the shares too soon and the discount is taxed as ordinary income instead of getting the friendlier treatment that patience earns. Hold two years from the offering date and one year from the purchase date, and the math improves, with the growth taxed as long term capital gain. The second flavor is the opposite: contributing the maximum while already holding a pile of company stock from RSUs. Longtime readers know how I feel about that basket. The ESPP percentage you pick in the portal is not just a savings rate, it is a concentration decision, and it deserves the same two sided question as any stock: if this doubles, what changes about your life, and if it drops by half, what changes?

CLICK THREE: THE IRA THAT EXISTS FOR NO REASON

This one is not in the portal, but enrollment season is when people fiddle with their savings, so it earns its spot. A pattern I see over and over: money flowing into an IRA every month while the employer plan sits nowhere near its $24,500 limit. For a high earner, a traditional IRA contribution usually is not even deductible, so as a standalone move it makes no sense. And a Roth IRA does not need to be funded just to have another account. Here is the sentence you will rarely hear from someone in my industry: it is completely fine to not have an outside IRA if you are not putting the annual max into your employer plan. The employer plan has the higher limit, the payroll convenience, and often the better tax result. Accounts are tools, not collectibles. There are situations where a deliberate nondeductible contribution is step one of a larger strategy, and that is a real conversation, but it is a planned conversation, not an autopilot deposit.

A SIMPLE EXAMPLE

Marcus is 41, a director in Dublin with a healthy family, reserves in good order, and RSUs vesting every quarter. His enrollment took twenty minutes this year instead of ten, and three things changed. He moved to the HSA eligible plan and set the contribution to the full $8,750, money that was going to be spent on premiums for coverage his family was not using. He set his ESPP at a percentage his concentration could afford rather than the maximum, and put the two dates, two years from offering and one from purchase, on his calendar next to the vest dates already living there. And he stopped the $625 a month that had been drifting into an IRA on autopilot since his twenties, redirecting it into his 401(k), which had never once hit its limit. Same paychecks, same total savings. Every dollar just has a better seat now.

THE WHOLE IDEA

Open enrollment is a planning event wearing a paperwork costume. The defaults in that portal are nobody’s plan, they are just last year’s clicks compounding. Ten intentional minutes, reserves first, HSA considered, ESPP sized to your concentration, employer plan maxed before any account gets funded out of habit, sets up an entire year of money. The portal opens soon. Walk in with a plan instead of a memory.

CLOSER TO RETIREMENT? FILE THIS AWAY

The years right before retirement are the heaviest saving window the tax code ever hands you, and enrollment season is when you claim it. At 50 the catch-up contribution adds $8,000 on top of the $24,500 employer plan limit, and from 60 through 63 a higher catch-up of $11,250 applies instead. The HSA adds its own $1,000 catch-up at 55. One deadline hiding in the fine print: HSA contributions have to stop once Medicare enrollment begins, so the last pre-Medicare years are the final chance to fill that account. If retirement is three to five years out, these are the boxes worth an unhurried look before you click confirm.

WORTH A READ

401(k) limit increases to $24,500 for 2026 (IRS.gov)

About Publication 969, Health Savings Accounts (IRS.gov)

Topic 427: Stock Options (IRS.gov)

Your enrollment email is a few weeks out. If you want a second set of eyes on the choices before you click submit, reply anytime. Twenty minutes of intention beats a year of undoing.

Curious what working together looks like? There is more at jcsretirementtaxadvisors.com, and if a conversation sounds easier, you can grab 30 minutes on my calendar whenever it suits you. No pressure, just a conversation.

Know someone who should be reading this? Forward it along, that is how most people find me. And if this was forwarded to you, one subscription at buckeyeretirementbrief.beehiiv.com gets you both briefs: retirement on Mondays, equity comp on Thursdays.

Jesse Stacy MTAX, CFP®, EA

JCS Retirement Tax Advisors

This newsletter is for education only and is not tax, legal, or investment advice for your situation. The example is illustrative and simplified. Plan features, ESPP terms, and HSA eligibility vary by employer, and contribution limits shown are 2026 federal figures.