open enrollment Archives

Your Open Enrollment Checklist: A Treasure Hunt for the Pay You Didn’t Know You Had.

Monthly Money Man on October 17, 2026

Let’s be honest: the benefits packet is the one document in your life designed not to be read. So today, we’re not going to read it cover to cover. We’re going to hunt it.

Here’s how I get excited about a topic that can feel dull. I stop seeing a match or a tax break as a “benefit” and start seeing it as a prize. When I find one, I’m paying myself in the thing I value most, which for me is time and adventures with my kids. That employer match? It’s a paid-for week at the beach.

So picture this. I walk into your kitchen, set your benefits packet on the table, and say, “There’s a free trip to Hawaii in here. You just have to find it.” You’d read every page. The prize really is in there. It just comes in dollars instead of plane tickets. So before you start, decide what yours is. A family trip? A spa day every month for a year? Pick it now and keep it in your head while you hunt. (Can’t decide? Borrow mine, or take the spa day.)

Open enrollment is the yearly window, usually a few weeks in the fall, when you pick or change your workplace benefits for next year. This open enrollment checklist turns it into a treasure hunt: three steps, about 45 minutes, and a coffee at the end that’s, in a very real sense, already paid for.

You’ve already scouted the terrain. Over the last two Fridays, we looked for hidden money in your benefits package and put HSA vs. FSA side by side. Today, we go get it.

Open Enrollment Checklist, Step One: Grab the Map and Pick Your Trail

Every hunt starts with a map. Find these three things first. It takes about five minutes.

The dates. Search your inbox for “open enrollment” or “benefits.” The email names the window and usually the portal.
The portal. Log in once now, even if you’re not ready to choose. A forgotten password on deadline day is no way to start a hunt.
The “what’s changing” summary. It’s the only part of the packet that’s actually new, so read it first.

Put the deadline on your calendar with a reminder three days early. And remember, doing nothing is still a decision. Many health plans roll over on their own, but some benefits, like a health FSA (a pre-tax account for medical costs), usually don’t. You have to sign up again or the money stops.

Now Pick Your Trail

The number that jumps out in the portal is the monthly deduction, and it’s the least complete one. Three numbers matter, in trail terms:

Premium: your trail pass. It comes out of your paycheck every month, whether you hike or not.
Deductible: the stretch you hike on your own before your guide (the plan) shows up to share the load.
Out-of-pocket maximum: the most the trail can charge you in a season. After that, the plan pays.

Here’s a made-up example with two plans. These numbers are hypothetical, and I’m assuming the plan pays 80% after you hit the deductible.

	Plan A	Plan B
Premium per month	$350	$200
Premiums per year	$4,200	$2,400
Deductible	$1,000	$3,500
Out-of-pocket maximum	$4,500	$7,000
Total cost: a year with almost no care	$4,200	$2,400
Total cost: a year with $3,000 of care	$5,600	$5,400
Total cost: a worst-case year	$8,700	$9,400

The plan with the scarier deductible (Plan B) costs less in two of the three years. Plan A only comes out ahead in the worst-case year, and only by $700. The real question is whether you could cover that $3,500 deductible. That’s where the cash cushion we built back in February earns its keep.

Before you commit, run both plans through last year’s actual medical spending, and check that your doctors and prescriptions are covered. A cheaper plan is no bargain if your pediatrician is out of network.

Step Two: Dig for the Treasure

Every open enrollment checklist should include these four finds. Each one comes from your employer, the government, or both. Keep a tally as you go.

Treasure 1: Your 401(k) match. This isn’t technically part of open enrollment, but you’re already logged in, and it’s often the biggest find on the map. A match means your employer adds money when you contribute. Look up the match formula in your plan summary and compare it to the percentage you’re contributing now. If you’re already getting the full match, that treasure is already in your pack. If you’re not, you’ve just found money that’s been sitting there.

Treasure 2: An employer deposit into your HSA. If you pick an HSA-eligible plan, some employers add their own money to your Health Savings Account. If yours does, that’s a raise you have to opt into. Look for a line in your benefits summary about an “employer contribution.” Last Friday’s HSA vs. FSA article explains how the account works and who it fits.

Treasure 3: Tax savings from your HSA. Money you put into an HSA goes in before income tax, so you pay less tax this year. For 2027, the IRS limit is $4,500 for self-only coverage and $9,000 for family coverage. This treasure doesn’t arrive as a check. It shows up as a smaller tax bill.

Treasure 4: Tax savings from a dependent care FSA. If you pay for daycare, before- or after-school care, or summer day camp for children under 13, this account lets you pay for it with pre-tax dollars. The family limit is $7,500 per year. Parents are often surprised how much of their summer camp bill qualifies.

The Bonus Round: Check the Box

Here’s why there’s a bonus round. The most common reason free money goes unclaimed isn’t that it’s complicated. It’s that nobody checks the box. I know someone whose employer offers a perk that could be worth thousands of dollars a year. All it takes is checking a box and following a few steps. Year after year, the box stays unchecked.

So scan your benefits menu for these. No employer offers them all, so tick the ones you find and ask HR about the rest.

☐ A company stock purchase plan (ESPP). It lets you buy your employer’s stock at a discount, up to 15% off under the most common type of plan. Plans like this are common at larger, publicly traded companies and rare at private ones, so yours may not have one. One caution: your paycheck already depends on this company, so read the rules on when you can sell before you sign up.
☐ Student loan help. Some employers pay toward your student loans, and up to $5,250 a year can be tax-free.
☐ Tuition reimbursement. Classes and certifications can qualify for that same $5,250 tax-free limit. It’s one shared limit, not two.
☐ Commuter benefits. Pre-tax money for transit or parking, if you commute.
☐ Employee discounts and perks. Search your portal for “perks” or “discounts.” My wife and I get a discount on our phone plan and our gym through work. It’s about $20 a month, which is like a free streaming subscription. It only counts because we’d have bought both anyway. If a perk lets you buy and resell something, read your employer’s rules first. Terms vary, and resale income can be taxable.
☐ Wellness rewards. Some plans give premium discounts, gift cards, or gym reimbursement for a checkup or health screening.
☐ Free counseling and telehealth. Many employers include a few free counseling sessions and low-cost virtual doctor visits.
☐ Free or low-cost life and disability insurance. Basic coverage is often included. Confirm it, and name your beneficiary.
☐ Family perks. Backup child care, adoption or fertility help, and paid parental leave.

Add anything you find to your tally in Step Three.

Step Three: Count Your Gold, Then Click Submit

Now the fun part. Grab a sticky note or open the notes app on your phone and tally what you found. Here’s a made-up example.

The assumptions: a $60,000 salary, an employer match of 50 cents on the dollar up to 6% of pay, an HSA contribution of $100 per paycheck across 26 paychecks, a $500 employer HSA deposit, $3,000 of summer camp and after-school care, and a 12% federal tax bracket. Yours will differ.

Treasure	Example	Your number
401(k) match (6% of pay is $3,600, and 50% of that)	$1,800	$____
Employer HSA deposit	$500	$____
HSA tax savings ($2,600 at 12%)	$312	$____
Dependent care FSA tax savings ($3,000 at 12%)	$360	$____
Stock purchase plan (ESPP) discount, if your employer offers one	Not counted (varies by plan and stock price)	$____
Other bonus finds (student loan help, perks)	Not in this example	$____
Total free money	$2,972	$____
Per month	about $248	$____

Now translate it into your prize. In this example, about $248 a month is worth roughly a spa day every month for a year. If your prize is a trip, $2,972 is a real head start on a family beach week. Whatever you picked at the top, that’s what you just found.

A quick honest note. Not all of this lands as spending money. The match goes into your retirement account, the HSA deposit is for medical costs, and the tax savings show up as a smaller tax bill. It’s all real, and it’s all yours. That’s the point of the hunt: money that was already yours to claim makes room in the rest of your budget, now and in the years ahead.

Before You Click Submit

Beneficiaries. Whoever you named on your life insurance and 401(k) years ago gets that money. Take two minutes to confirm the names still match your life.
The confirmation page. Screenshot it or save the PDF. When your first January paycheck arrives, compare the deductions to what you chose.
The lock-in. Most choices are locked until next year unless you have a qualifying life event, such as marriage, a new baby, or losing other coverage. Those windows are often short, around 30 days, so check your plan’s rules.

This Week’s Climb: Go Buy the Coffee

Before your deadline, block 45 minutes. Work through your open enrollment checklist (the map, the trail, and the four treasures), then write down your free money number.

Then go buy the coffee. The fancy one. The fall one you’ve been eyeing, with the foam art and the cinnamon on top. Maximizing your benefits is how you give yourself a little more room, now and later, and a little room is what lets you enjoy the occasional treat without the guilt. You didn’t skip the coffee to afford it. You found the money first.

Booking the spa day or the trip is optional. Maybe your free money goes toward that credit card balance or your cash cushion, and that’s the climb too. The point is knowing you could. Competence gives you choices, and having the choice is what makes the money feel like yours.

That’s the whole hunt. By the end of it, you’ll know one more thing about your paycheck than you did ten minutes ago.

See you at the top.

Monthly Money provides general financial education for informational purposes only. Content, examples, calculators, and resources are not financial, investment, tax, legal, accounting, retirement planning, or personalized advice. Before making financial decisions, consider speaking with a qualified professional who can review your specific situation.

Last reviewed: October 2026

HSA vs FSA

Monthly Money Man on October 9, 2026

Last Friday, we pulled the car over to look for hidden money in your benefits package. I mentioned your HSA or FSA election and promised we’d put the two side by side. Here we are.

Both accounts let you pay for medical costs with pre-tax dollars, which means the money skips income tax on the way in. Same trick, two very different accounts. The HSA vs FSA question trips up almost everyone, because the names are one letter apart and the rules are not.

Here’s the shortest version I know.

An HSA (Health Savings Account) is like a backpack with medical expense money you own and carry from job to job. An FSA (Flexible Spending Account) is like a locker your employer rents you for one season to hold medical expense money. Let’s open both.

HSA vs FSA, Side by Side

Here’s the whole comparison in one place. It’s the screen most people wish their benefits portal had.

	HSA	Health FSA
Who owns it	You. It stays yours if you change jobs.	Set up through your employer. Generally stays behind if you leave.
Special plan required?	Yes, a high-deductible health plan (more below)	No
Limit for 2027	$4,500 self-only, $9,000 family	2026 limit is $3,400. The 2027 limit is expected this fall.
Unused money	Rolls over every year, with no deadline	Use it or lose it, with limited exceptions (see below)
Can you invest it?	Often, once your balance reaches a minimum	No
Changing the amount mid-year	Generally yes	Generally no, unless you have a qualifying life event
When the money is available	As you contribute	Your full yearly amount is typically available on day one

Two rules trip people up.

First, you generally can’t contribute to an HSA while you’re also covered by a regular health FSA. A “limited-purpose” FSA that covers only dental and vision is the usual exception.

Second, “use it or lose it” has a couple of softeners, but your employer chooses which one. Some plans let you carry over a small amount (up to $680 under the current rule). Others give you a grace period of a couple of months. A plan can offer one or the other, not both, and some offer neither. Your plan summary will tell you.

What “High-Deductible” Actually Means

To use an HSA, you have to be enrolled in a high-deductible health plan, or HDHP. In plain English, that’s a plan with lower monthly premiums where you pay more of the first bills yourself.

For 2027, the IRS says an HDHP must have a deductible of at least $1,750 for self-only coverage or $3,500 for family coverage. The plan’s out-of-pocket maximum can’t be higher than $8,700 for self-only or $17,400 for family. In your portal, look for the words “HSA-eligible” next to the plan name.

Here’s the part the brochures skip. A lower premium only saves you money if you can handle the deductible when a bill shows up. If a $3,500 deductible would land on a credit card, that cheaper premium isn’t cheaper. This is where the cash cushion we built earlier this year earns its keep.

A Simple Way to Pick One

Here’s how I’d walk a kitchen-table client through the HSA vs FSA decision. Two questions.

1. Does my employer offer an HSA-eligible plan? If not, your answer is the FSA (if one is offered). Skip to the sizing tip below.

2. Could I cover that plan’s deductible from savings without reaching for a credit card?

If both answers are yes, the HSA is worth a serious look. An HSA can give you the best of both worlds: the tax break up front that you’d get with a traditional account, and tax-free withdrawals like a Roth, as long as the money goes toward qualified medical costs. On paper, it’s one of the most tax-advantaged accounts available. It isn’t a replacement for a Roth, which has its own strengths, like flexibility, and for many families the two work side by side. And the HSA is yours forever. Some employers also deposit money into your HSA, which is a raise you have to opt into.

If either answer is no, a traditional plan with an FSA is a perfectly good place to stand.

Sizing an FSA. Because unused money can disappear, start with what you know is coming: prescriptions, orthodontist payments, glasses or contacts, regular copays. Add those up, then round down. You can always spend more on eligible items, but you can’t easily get back money you over-elected.

Sizing an HSA. Many people start with a per-paycheck amount that doesn’t pinch, then raise it later, since you can generally change an HSA contribution during the year.

What to Click in the Portal

Once you’ve picked, the clicking takes about five minutes.

Log in and look for “Health Savings Account,” “Flexible Spending Account,” or a menu called “Spending Accounts.”
For an HSA, enter an amount per paycheck. As a hypothetical, $100 per paycheck across 26 pay periods adds up to $2,600 for the year. Check whether your employer adds a deposit of its own.
For an FSA, enter a yearly total. The portal divides it across your paychecks. Then find the carryover or grace period rule in your plan summary and put the spending deadline on your calendar.
Save or screenshot the confirmation page.
In January, watch for an activation email or a debit card for the account.

One reassuring note: eligible expenses go well beyond doctor visits. They include prescriptions, dental work, vision care, and many over-the-counter medicines. Your plan administrator keeps the full list.

This Week’s Climb

Before your deadline, answer two questions on a sticky note: Does my employer offer an HSA-eligible plan? and Could I cover its deductible from savings? Two yeses point you toward the HSA. Anything else points you toward a modest FSA.

That’s the whole HSA vs FSA decision, and it took you a few minutes. You now know one more thing about your paycheck than you did before you started reading.

See you at the top.

Last reviewed: October 2026

Hidden Money in Your Benefits Package

Monthly Money Man on October 2, 2026

The Pull-Over

It happened to us in Cades Cove, in the Smoky Mountains. A photographer had her camera trained on something in the trees, and we pulled over to ask what she’d found. “An owl,” she said, and pointed. We looked exactly where she was pointing and saw branches. She pointed again. More branches. It took almost a full minute for our eyes to adjust before the owl just appeared — feathers patterned so perfectly into the bark and shadow that it had been staring back at us the whole time. I still have the picture. It’s the closest we’ve ever gotten to an owl in the wild, and it only happened because someone who knew exactly what to look for pointed us at the right spot.

Open enrollment works the same way. Every fall, your employer hands you a packet or a portal login and says, essentially, “it’s all in here.” And it is. But most of us glance at it, see a wall of acronyms — the branches and shadows of 401(k)s, HSAs, and LTDs — and move on, the same way we nearly drove right past that owl.

This month, we’re going to pull the car over. Finding the hidden money in your benefits package isn’t about reading every page of a 40-page PDF. It’s about knowing exactly what shape to look for — and this week, we’re only looking for one thing.

What You’re Actually Looking At

Before we go looking for anything, let’s translate the field. Most benefits packets use the same handful of terms, and nobody ever stops to explain them in plain English:

401(k) match — your employer puts money into your retirement account when you do. Free money, but only if you contribute enough to claim all of it.
HSA (Health Savings Account) — a tax-advantaged account for medical expenses, often paired with a high-deductible health plan.
FSA (Flexible Spending Account) — similar idea, but the money usually doesn’t roll over year to year. Next week’s Financial Friday puts the HSA and FSA side by side so you can tell which one you actually have.
Life insurance election — many employers offer a base amount free, plus the option to buy more at a group rate.
Short-term and long-term disability (STD/LTD) — income replacement if you can’t work due to illness or injury.

You don’t need to master all five this week. You just need to know they’re out there in the field, so next time you’re in your HR portal, you recognize the shape.

The One Thing Worth Pulling Over For

Out of everything in the field, we’re only stopping the car for one animal this week: your employer retirement match. Most people know it as a 401(k) match, but if you work in a school, hospital, or for a nonprofit, yours is probably called a 403(b) — same idea, different name.

Here’s why it’s the owl worth pointing at. A typical employer match looks something like “50% of what you contribute, up to 6% of your pay.” Translated: if you make $60,000 a year and contribute 6% ($3,600), your employer adds another 3% ($1,800) — free, every single paycheck, for as long as you work there.

Most people glance at their 401(k) once during onboarding, pick a number that feels reasonable, and never look again. Years pass. Raises happen. The contribution percentage never moves with them. And the match percentage sits there, in the portal, the whole time — same as that owl in the trees, not hiding, just unnoticed.

This is hidden money in your benefits package in its purest form. It’s not a discount or a maybe. It’s dollars your employer has already budgeted to hand you, and the only requirement is that you ask for them by contributing enough to trigger the match.

How to Actually Go Look This Week

Here’s exactly what to do — give this ten minutes before Friday:

Log into your employer’s HR or benefits portal (common ones: Workday, ADP, Paylocity, or a link from your payroll stub).
Find the section labeled Benefits, Retirement, 401(k), or 403(b) — it’s usually its own tab, separate from health insurance.
Look for two numbers: your current contribution percentage and the employer match formula (often written as “X% up to Y% of pay”).
Do the math: are you contributing at least enough to hit the match ceiling? If your match caps at 6% and you’re only putting in 3%, you’re leaving half the match on the table.
If you’re under the match ceiling, raise your contribution percentage right there in the portal — most systems let you change it in a few clicks, effective your next paycheck.
If you’re not sure what any of this means on your specific plan, call the HR benefits line or your plan’s customer service number (usually printed on the portal’s home screen) and ask one question: “Am I contributing enough to get the full employer match?”

That’s the whole task. Not a full financial plan — just one number, checked against one formula.

What Else to Notice While You’re Parked There

Once you’re in the portal checking your match, a few other things are worth a glance — not a deep dive, just noticing their shape so you recognize them later: your HSA or FSA election (next week’s Financial Friday covers both, side by side), whether you have any free base life insurance you haven’t confirmed, and your beneficiary designations, which people forget to update for years at a time.

You don’t have to solve all of it this week. You just have to know it’s there.

This month’s move: Log into your benefits portal, find your 401(k) match formula, and make sure your contribution is high enough to capture all of it. That’s the whole climb for this week — one number, confirmed.

Monthly Money provides general financial education for informational purposes only. Content, examples, and resources are not financial, investment, tax, legal, accounting, or personalized advice. Before making financial decisions, consider speaking with a qualified professional who can review your specific situation.