The fifteen minutes that move five figures
Open enrollment is a tax decision wearing an HR costume. At your income, the default election is almost never the right one, and it's the one most people click.
A hypothetical client, but a conversation I've had many times.
Let's call her Dana. Anesthesiologist, mid-forties, married to a software developer, two kids in middle school. Last November she opened her benefits portal, scrolled for about eleven minutes, and clicked the button that said keep my current elections.
I don't blame her. Most benefits portals run to a dozen screens of plan names that sound identical, written for legal defensibility rather than your comprehension, and the decision lands in the busiest month of her year.
Here's what those eleven minutes bought her over the next twelve months: a health plan she'd chosen four years and two promotions ago; no health savings account, because that plan wasn't eligible for one; a disability benefit that would replace only a fraction of what she earns, and would be taxed on the way out if she ever claimed it; and a deferred compensation election left at zero in a year she was in line for a large bonus.
No single one of those is a dramatic mistake. Each is a small shrug when making the selections. Together, in their bracket, they moved the household's tax bill by five figures.
Think about this for a second. Open enrollment is the one financial decision of the year with total control, a hard deadline, and no market risk. I can't tell you what your portfolio will do next year. Your benefits portal is deterministic: you choose, and the outcome follows. Give it more than eleven minutes. This is one of the few decisions where your money moves exactly as planned because you decided it should.
I can't tell you what your portfolio will do next year. Your benefits portal is deterministic: you choose, and the outcome follows.
MONEY YOU CAN STILL MOVE
The HSA is a retirement account pretending to be a health plan
If your employer offers a high-deductible plan paired with a health savings account (HSA), an account funded with pretax dollars and spent on qualified medical costs, and your cash flow can absorb the deductible without strain, it deserves a much harder look than it usually gets.
The HSA is the only account in the tax code with three advantages stacked: contributions reduce your taxable income, the balance can be invested and grow untaxed, and qualified withdrawals come out untaxed. A 401(k) gives you the deduction now and taxes you later. A Roth does the reverse. The HSA is the only one that does both. Depending on your current marginal income tax rate, the first advantage alone could prove meaningful enough. Every dollar routed through the HSA is a dollar that would otherwise have been taxed at the top of your bracket.
The part most miss is that you don't have to spend it. Reimbursement from your HSA has no deadline. You can pay this year's medical costs out of pocket, keep the receipts in a folder, leave the HSA balance invested for two decades, and reimburse yourself later entirely tax-free. Used that way, it stops being a health account and starts being the most tax-efficient retirement account you have access to.
Two honest caveats. This only works if paying out of pocket doesn't strain you, and a high-deductible plan is the wrong choice if your household has predictable, ongoing high medical costs. Run the total cost of care under each plan, not just the premium difference.
Check this one thing.
Most HSA balances sit in a cash sweep by default, earning close to nothing. Moving the balance into the plan's investment options is usually two clicks inside the portal, and it's the entire difference between a health checking account and a retirement account.
Deferred comp is a bet on your own future tax bracket
If your employer offers a nonqualified deferred compensation plan, an agreement to pay you part of this year's compensation in a later year, open enrollment is frequently the only window you get to make the election, and the deadline is usually well before the money is earned.
The mechanics are straightforward. You defer income at today's marginal rate and receive it later, ideally in a year when your rate is lower: a sabbatical, a step down to part-time, the gap between your last paycheck and the start of Social Security. The spread between those two rates is the return. Get the timing right and it can be substantial.
There's a risk here that is genuinely different from your other accounts, and it's the one that gets glossed over. Unlike a 401(k), deferred comp is an unsecured promise from your employer. If the company becomes insolvent, you're a general creditor standing in line. That risk tends to be small at large, stable employers. It isn't small everywhere. Size the election to a number you could lose without changing your long-term plan.
One more thing that surprises people: the distribution schedule is largely locked at the moment you elect, and changing it later is heavily restricted. Decide when you want the money before you decide how much.
Sixteen questions to ask HR
Everything in this article, condensed into questions your benefits team can answer in one email, with space to write their answers down.
THE COVERAGE YOU ONLY NOTICE ONCE
Group disability covers less of your income than you think
The most consequential number in your benefits package isn't your salary. It's the share of your income that your disability coverage would actually replace if you couldn't work. For high earners, that number is almost always lower than the headline percentage suggests.
Three things shrink it, in sequence. First, group long-term disability is usually calculated on base salary, so bonus, partnership distributions, production-based pay, and equity compensation are often excluded entirely, and for many professionals that makes up a noticeable portion of what they earn. Second, there's typically a monthly benefit cap that a high salary blows through long before the stated percentage matters. Third, if your employer pays the premium, the benefit is taxable income when it's paid to you.
Do the math on your own numbers rather than trusting the brochure percentage: base only, then the cap, then tax. For a lot of the households I work with, the answer lands well under half of what they actually live on. That gap is what a disability would cost your family, and it's usually the single largest uninsured risk on the page.
Two moves during enrollment. Elect any buy-up coverage your plan offers, which is generally inexpensive relative to what it protects. And where the plan allows it, consider paying the premium with after-tax dollars. You'll give up a small deduction now, but the benefit can come to you tax-free later, which is usually the better trade when you're limited to a maximum payout of 60% of your gross pre-disability income. An individual own-occupation policy bought outside work can cover what remains, and it goes with you if you change employers.
One times salary isn't enough
Employer life insurance usually defaults to a multiple of base pay, and the free tier is typically small. For a household carrying a mortgage, two children who'll need education expenses covered, and a lifestyle built on two incomes, that amount rarely covers the first few years of necessities, let alone the next twenty of aspirations.
Supplemental group coverage during enrollment has one real advantage: it's often guaranteed issue up to a limit, meaning no medical underwriting. If your health has changed since you last shopped for insurance, that can matter a great deal in what you might pay for private coverage. Otherwise, weigh it carefully.
Group supplemental is generally priced in age bands that step up as you get older, and the coverage ends when the job does. Level-premium term insurance bought individually tends to cost less across the full period you need it and stays with you regardless of where you work.
The practical approach for most people: take the free base coverage, use guaranteed-issue supplemental if you have a health reason to, and carry the number that actually matters outside of work.
THE HOUSEHOLD VIEW
If your spouse also has a window, stop deciding separately
Two working professionals with two benefit packages generally make two independent decisions, and end up with overlap in some places while exposed in others. Putting both packages side by side on one table for an hour is the highest-return hour of the whole season.
What to compare:
The total cost of covering the family under each plan, not the premium alone: premiums, deductible, out-of-pocket maximum, and whether your actual physicians are in network.
Whether either employer's plan is HSA-eligible, which can be reason enough to consolidate onto it.
Whether splitting the family across both plans makes sense. One spouse on their own employer's plan, the other spouse and the children on the second. This occasionally costs less than putting everyone on either plan.
Dependent care flexible spending accounts, which are limited per household rather than per person, so two full elections can create a problem at tax time.
Whether you're quietly paying for two identical legal plans, two identity theft subscriptions, and two accident policies.
One trap worth naming, and it's distinct from the ordinary fact that a spouse tier costs more than employee-only coverage. Many large employers now add a spousal surcharge: an extra monthly fee that applies only if your spouse could have enrolled in their own employer's plan and joined yours instead. It's commonly $50 to $200 a month, and it usually reaches you as an innocuous attestation question asking whether your spouse has other coverage available. If you're both going on the same plan, find out what this would cost before you elect rather than on your first pay stub of the year.
Equity compensation doesn't wait for December
If part of your pay arrives as restricted stock units, options, or an employee stock purchase plan, several decisions collide in this window, and the portal presents them as if they were unrelated.
The employee stock purchase plan is the clearest one. It buys your employer's stock through payroll at a discount, and on pure economics the discount is difficult to beat with anything else in the package. The complication is concentration: your salary, your bonus, your unvested RSUs, and now your savings are all tied to the same company. For most people the sensible route is to participate fully and sell promptly: take the discount your employer is offering, then resist the urge to get greedy by holding the shares.
Then withholding. RSUs that vest are typically withheld at a flat supplemental rate, which for many high earners sits below their actual marginal rate. The gap doesn't disappear; it shows up in April. Enrollment is a reasonable moment to look at the coming year's vesting schedule and adjust withholding or estimated payments before the shortfall compounds.
Finally, these elections interact with your retirement plan. Front-loading 401(k) contributions to hit the annual limit early can cost you part of an employer match if your plan doesn't true up at year end, and many don't. Check yours before you set the contribution rate.
THE TEN-MINUTE CLEANUP
The perks tier is small money you've already been offered
Below the headline benefits sits a tier most people scroll past. A prepaid legal plan often costs less for the year than an hour of an attorney's time, and covers exactly the documents high earners keep postponing: a will, powers of attorney, healthcare directives, a basic trust review. Identity theft protection and credit monitoring cost a fraction of what the same services cost retail, and your potential for exposure scales with your assets. Beyond that: backup child and elder care, commuter accounts, wellness credits, tuition assistance, and pet coverage.
Beneficiaries: five minutes, highest stakes
Beneficiary designations override your will. A retirement account or life insurance policy pays whoever is named on the form, no matter what your estate documents say, and no matter how carefully those documents were drafted. The most expensive estate mistakes I see aren't sophisticated ones. They're a rollover from a job three employers ago with an ex-spouse's name still on the form.
While you're already logged in: confirm the primary and contingent beneficiary on every retirement account and every insurance policy, and make sure a contingent is actually named rather than left blank. On that topic, check whether minor children are named directly. A trust is usually the better recipient, because an insurer will not write a check to a nine-year-old, and the alternative is a court-supervised guardianship you didn't choose.
Do this even if you change nothing else.
Beneficiary review takes five minutes, costs nothing, and is the only item on this list where the downside of skipping it is measured in someone else's life rather than your own tax bill.
What I'd actually do this week
Pull last year's confirmation statement and your last twelve months of medical spending. You can't evaluate a plan without knowing how you used the old one.
Calculate what your disability coverage would actually pay: base only, capped, after tax. Write the number down.
If an HSA-eligible plan is available and the deductible doesn't frighten you, model the total cost both ways and check where the HSA balance would be invested.
Get your spouse's package on the same table as yours before either of you clicks anything.
Review every beneficiary designation, including the accounts you forgot you had.
Open enrollment rewards attention in a way very little else in your financial life does. There's no forecast to be wrong about and no market to wait on. There's a form, a deadline, and a set of choices that are entirely yours.
If you want a second set of eyes on your package before your window closes, that's a conversation I'm glad to have. Bring the summary of benefits and last year's confirmation, and we'll work through it together.
Sixteen questions to ask HR
Everything in this article, condensed into questions your benefits team can answer in one email, with space to write their answers down.
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