Every autumn your employer hands you a window of a few weeks to change life, disability, health, and retirement elections. Whatever you pick stays in place for a year. Most people re-tick last year's boxes in ten minutes and move on, and the gaps only show up when something goes wrong.
This playbook is one page per decision, each with the numbers that matter and a checklist you can work through with your spouse or partner before the deadline.
Set up the evening
Treat enrollment like a tax return, not a software update. Ninety minutes, both adults, everything on the table.
GATHER FIRST
THE DECISIONS YOU WILL MAKE
Medical, dental, vision. HSA, health FSA, and dependent care FSA funding. Basic and supplemental life. Spouse and child life. Basic and voluntary AD&D. Short and long-term disability. Group legal. Employee stock purchase. Identity protection. 401(k) contribution rate and bucket. New benefits such as Trump Account contributions. College savings in a 529. Each has a page here.
Contributing exactly enough to capture the employer match feels efficient. It is usually a third of what a comfortable retirement needs. Decide the savings rate from the goal, not from the match formula.
Trump Account contributions: employers may add up to $2,500 a year per employee, tax-free, split across your children's accounts. That money likely counts toward each child's $5,000 yearly cap, so family room can shrink to $2,500; final IRS rules are pending. Also ask about tax-free student loan repayment (up to $5,250 a year) and a 401(k) match on student loan payments: you keep paying the loan, certify the payments to the plan, and the employer deposits a match as if you had deferred from pay. All three are optional for employers.
Add up the subscriptions, food delivery, and impulse buys from last year. Almost every household finds enough to fund supplemental life, disability buy-up, and a legal plan without noticing the difference.
Health plan and HSA
Pick the plan on total expected cost, not the premium. If the high-deductible plan wins, fund the HSA.
CHECKLIST
Coverage type sets the limit, not how you file. One spouse on a self-only HDHP: $4,500. Each spouse on their own self-only HDHP: $4,500 each, in separate HSAs. Either spouse on family coverage: one shared $9,000.
You pay the full deductible before the plan pays, so a bad year costs more. Non-medical withdrawals before 65 are taxed plus a 20% penalty. Invested balances can fall. California and New Jersey tax HSAs at the state level. A non-spouse heir owes income tax on the whole balance, so spend it down or leave it to your spouse.
Bronze and catastrophic marketplace plans now qualify, a direct primary care membership no longer blocks contributions, and telehealth before the deductible is permanently allowed.
Each $1,000 catch-up belongs to the person, so a couple wanting both needs two separate HSAs. Enrolling in any part of Medicare, including premium-free Part A, ends HSA contributions. Part A taken after 65 is backdated up to six months, so stop contributing six months before you sign up.
FSAs: health and dependent care
Flexible spending accounts save tax on money you were going to spend anyway. Unlike an HSA, what you do not spend can disappear.
CHECKLIST
Health FSA money left after the deadline is forfeited to your employer, and leaving your job usually ends the account the same day. The dependent care FSA pays you back only as money is deducted from your pay, so expect to front daycare costs early in the year, and it rarely has a carryover. Over-fund either one and the tax you saved turns into money you lost.
Your full annual health FSA election is available from the first day of the plan year, even though it comes out of pay gradually. A large January expense can be covered before most of it has been deducted.
Life insurance
Employer basic life at one or two times salary is a token. The supplemental election is where the real protection is bought, and at work it is often cheaper than the open market for people in their 30s and 40s.
CHECKLIST
Group life is exam-free only at initial enrollment and only up to the guaranteed-issue amount. Waiting until you feel like you need more usually means a medical questionnaire, and a health change in between can make you uninsurable at group rates.
Premiums often run 10 or more times a term policy with the same death benefit. Most early premiums pay commissions and costs, so cash value stays low for years, and surrendering in the first 10 to 15 years usually means a loss. Policy loans charge interest and shrink the death benefit, and if a policy with a loan lapses, the gain becomes taxable income. Indexed universal life adds caps on returns and insurance costs that rise with age, which can force much higher premiums later.
A lifelong dependent such as a child with special needs, an estate large enough to owe estate tax, or a business buy-sell agreement. For most families the answer is level-premium term for 20 or 30 years, investing the difference.
Disability and AD&D
Your ability to earn is the largest asset you own. Disability coverage protects it. AD&D is a narrow add-on that pays only for accidents.
CHECKLIST
AD&D pays for accidental death or loss of limb or sight. Illness, the most common cause of death, is excluded. Size life insurance as though AD&D did not exist.
A 60% LTD benefit on a capped salary, taxed if the premium was pre-tax, can land at 40% of take-home. Run the number before deciding whether the buy-up or an individual policy is needed.
401(k): how much and which bucket
The contribution rate matters more than every other choice on this page combined. Set it from the goal, then choose pre-tax, Roth, or a split.
CHECKLIST
$72,000 is the 2026 ceiling for your deferral, the employer match, and any after-tax money combined. Age-based catch-ups sit on top of it, so the real ceiling is $80,000 at 50+ and $83,250 at ages 60-63. After-tax room is $72,000 minus your $24,500 minus the match; catch-ups do not reduce it. On a $150,000 salary with a 6% match that is roughly $38,500, not $72,000.
Roth withdrawals are US-tax-free when qualified, but the country you retire in may not recognize Roth status and could tax the growth. India, for example, does not. If a permanent move is in the plan, get cross-border tax advice before choosing the bucket.
ESPP, RSUs, and options
Equity pay is real money that arrives concentrated in the one company that already signs your paycheck. Capture the discount, then diversify without sentiment.
CHECKLIST
You already believe in it with your salary, your bonus, and your career. Adding your savings to the same bet turns a bad year at work into a bad year everywhere.
RSUs are taxed at their value on the vest date. Hold them, watch the price fall, and the tax is still owed on the higher number. The 22% default withholding (37% above $1 million of supplemental pay) can leave a bill in April. With an ESPP, a quick sale makes the full discount ordinary income on your W-2; if the stock then drops below your purchase price, you owe that tax anyway and the loss is a capital loss that offsets only $3,000 of wages a year. Selling at a loss within 30 days of a new ESPP purchase or RSU vest is a wash sale, which delays the loss. Unvested shares are forfeited when you leave.
15% is the most a qualified ESPP may offer. Plenty of plans give 5% or 10%, and some have no lookback. Read the plan summary before assuming.
Legal plan and the four documents
A will, a financial power of attorney, a medical power of attorney, and a living will. Every adult needs them; most do not have them. The group legal plan is the cheapest way to get them drafted.
CHECKLIST
Group legal is a paid voluntary benefit deducted from payroll. The attorney's work is covered once enrolled. It is still excellent value; just budget for the premium.
If you own property or expect an inheritance in another country, ask the attorney whether a US will is recognized there or whether a second, jurisdiction-specific will is needed. Two uncoordinated wills can revoke each other.
Beneficiaries
Retirement accounts, life insurance, and HSAs pass by the beneficiary form, not by the will. An outdated form overrides everything else you have written down.
CHECKLIST
A will directs only assets that have no beneficiary designation and no joint owner. For most households that is a small share of net worth. The forms do the heavy lifting.
A 401(k), IRA, or life policy cannot pay a child directly. The money skips probate, but without a trust or custodian on the form a court usually appoints and supervises a guardian of the funds, and the child can get the whole balance outright at 18. Name a trust or a custodian under your state's UTMA, and ask each plan which it accepts.
Federal law makes a spouse the default 401(k) beneficiary; naming anyone else requires the spouse's written consent, witnessed by a notary or a plan representative. IRAs have no such rule, so an old IRA form can quietly name someone you no longer intend.
Fraud defenses
Voice cloning and AI-written phishing have removed the tells people used to rely on. The defenses are unglamorous and mostly free.
CHECKLIST
Monitoring tells you after a new account has been opened in your name. A freeze prevents it. Do both, but if you only do one, freeze.
With the lock on, no money leaves the account until you unlock it through a separately verified step. A scammer holding your password and your one-time code still cannot move funds. It costs nothing and takes two minutes to enable.
Investing simply, plus an umbrella
Two habits that do more for long-term wealth than any product: a portfolio you can explain in one sentence, and liability cover for the lawsuit you are not expecting.
CHECKLIST
Studies of retail traders in options and leveraged products show most lose money, and the losses cluster in the years families can least afford them. Boring is the strategy, not the absence of one.
Adding a 16-year-old to your auto policy multiplies your liability exposure overnight. A serious at-fault accident can produce a judgment well above standard auto limits, and your savings and future wages are what a plaintiff's attorney goes after. The umbrella is what stands between them.
Kids' college: the 529
Growth is tax-free for education, and most states add an income tax deduction. The deduction is the reason to start now, not later.
CHECKLIST
Money withdrawn for anything else pays income tax plus a 10% penalty on the earnings, and your state can claw back deductions you already took. Investments can fall right before tuition is due. The menu is limited to the plan's funds, and most states give no deduction for another state's plan. A parent-owned 529 counts modestly against financial aid, at up to about 5.6% of its value.
Change the beneficiary to a sibling, cousin, or yourself, or roll up to $35,000 over a lifetime into the child's Roth IRA. The rollover needs a 529 open for 15 years, uses only contributions older than 5 years, counts toward that year's IRA limit, and requires the child to have earned income.
The master checklist
Print this page. Tick every line before the enrollment window closes.
ON THE ENROLLMENT FORM
OUTSIDE THE FORM, BEFORE YEAR-END
Mid-to-late October 2026: the IRS releases the 2027 health FSA limit and tax brackets. Late October to mid-November 2026: the 2027 401(k), IRA, and catch-up limits, plus the 2027 Roth catch-up wage threshold. Update your 401(k) election in the first January pay period so you are not leaving room unused.