Tag: student loan repayment

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.

1. The dates. Search your inbox for “open enrollment” or “benefits.” The email names the window and usually the portal.
2. 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.
3. 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