Work · Your first weeks on the job
Choosing your benefits
New job, short window. Put the enrollment deadline on your calendar (job plans must give you at least 30 days after a life event like marriage or losing coverage, but otherwise you wait for open enrollment). Get each health plan's Summary of Benefits and Coverage and compare premiums times 12 plus the out-of-pocket max, and check your doctors are in network. Under 26, compare with staying on a parent's plan. Contribute enough to get the full retirement match, and know the vesting schedule: you can wait up to 3 years (cliff) or 6 years (graduated) to own all of the match.
You'll need
- Your benefits packet or enrollment website login
- Each health plan's Summary of Benefits and Coverage (SBC)
- A list of your doctors and prescriptions
- The retirement plan's Summary Plan Description, or a page explaining the match and vesting
Do it like this
- Find the enrollment deadline and calendar it. Outside your new-hire window and yearly open enrollment, you can generally only change plans after a life event like losing coverage, moving, marriage or a baby. Job-based plans must give you at least 30 days for those. Source: HealthCare.gov4 Some plans also have a waiting period before coverage starts, generally up to 90 days. Source: DOL7
- Get the SBC for every health plan. Job-based plans must give you this short, plain-language summary so you can compare plans side by side. Source: HealthCare.gov3
- Compare the whole cost: premiums times 12, plus the deductible, copays, coinsurance and out-of-pocket maximum. Source: HealthCare.gov2 See Premiums, deductibles and out-of-pocket maximums for a worked comparison.
- Check the network. Ask whether you can keep your current doctors. Source: DOL7 Out-of-network care doesn't count toward your out-of-pocket max. Source: HealthCare.gov2
- Under 26? You can usually stay on a parent's plan until 26, even if you're married, not living at home, not claimed as a dependent, or turned down your own job's coverage. Source: HealthCare.gov5 Compare costs with your parent before you decide.
- Know your vesting schedule. Your own contributions and their earnings are always yours. The employer's match may not be: plans can make you wait up to 3 years to be 100% vested (cliff), or vest you gradually from 20% after 2 years to 100% after 6. Source: DOL8 Leave before you're vested and you may lose some of the match.
- Look at the extras. A Flexible Spending Account (FSA) lets you set aside pre-tax money for deductibles, copays and prescriptions, up to $3,300 a year, but you generally lose what you don't spend by the end of the plan year (your employer may allow a grace period of up to 2½ months or a carryover of up to $660). Source: HealthCare.gov6 Pick dental, vision, disability or life insurance only if you'll use them.
401(k) match vesting
The two federal schedules employers can use for matching contributions; plans can be more generous. Source: DOL8
| Years worked | Cliff vesting | Graduated vesting |
|---|---|---|
| 1 | Can be 0% | Can be 0% |
| 2 | Can be 0% | At least 20% |
| 3 | 100% | At least 40% |
| 4 | 100% | At least 60% |
| 5 | 100% | At least 80% |
| 6 | 100% | 100% |
Safe harbor and SIMPLE 401(k)s vest required employer contributions immediately. Source: DOL8
What a match is worth
A made-up example: you earn $30,000 a year, and your employer matches 50 cents per dollar on up to 6% of your pay. Your plan's real details are in its Summary Plan Description.
| Your contribution | You put in | Employer adds |
|---|---|---|
| Contribute 0% | $0 | $0 |
| Contribute 3% | $900 | $450 |
| Contribute 6% | $1,800 | $900 |
| Contribute 10% | $3,000 | $900 (match stops at 6%) |
Questions to ask HR
- When is my enrollment deadline, and when does coverage start?
- Can I get the SBC for each health plan?
- Are my doctors and prescriptions covered in network?
- What does the retirement plan match, and what's the vesting schedule?
- Am I automatically enrolled in the 401(k), and at what percentage?
- Is there an FSA or HSA, and does the company contribute?
- Part-time? Am I eligible? Plans may cover part-timers who work at least 1,000 hours a year, about 20 hours a week. Source: DOL8
See it done
Video by Khan Academy Nonprofit
Benefits explained
Full title on YouTube: “Benefits explained | Employment | Financial mathematics (TX TEKS) | Khan Academy”2024 · Checked October 3, 2026
Video won't load at school or work? No problem. Everything you need is in the steps; the video's just a bonus. Watch it on YouTube later.
If it doesn't work
- If you miss the window, ask HR when the next open enrollment is, and whether a life change lets you enroll sooner.
- If you picked the wrong plan, you can usually change it at the next open enrollment.
- If you leave the job, COBRA may let you keep the job's health plan temporarily, and you can compare Marketplace options. Source: DOL7 Your vested retirement money can stay in the old plan or roll into a new plan or an IRA. Source: DOL7
Good to know
The details, if you want them. Tap a line to open it.
Waiting to join the retirement plan
Federal law lets plans require you to be 21 and have a year of service before joining, though many let you in sooner. Source: DOL8
FSA vs. HSA
You can't use an FSA with a Marketplace plan. An HSA works with high-deductible plans. Source: HealthCare.gov6
Learn the words
Take it with you
Printable cardDownload card (PDF)Sources
- HealthCare.gov If you have job-based insurance
- HealthCare.gov Out-of-pocket maximum/limit
- HealthCare.gov Summary of Benefits and Coverage
- HealthCare.gov Special Enrollment Period
- HealthCare.gov Staying on a parent's plan
- HealthCare.gov Flexible Spending Accounts
- U.S. Department of Labor Changing jobs and job loss
- U.S. Department of Labor What you should know about your retirement plan
Lesson W4.4 · Last checked October 2, 2026 against the sources listed.
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