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Jobs That Offer Health Insurance After You Retire


If you’re aiming for early retirement before age 65, it’s crucial to explore your healthcare choices. Some employers extend healthcare benefits to those who retire early, making the search for health coverage more manageable. If you’re pursuing early retirement, here’s a list of jobs worth considering.

A financial advisor can help you create a financial plan for your early retirement goals.

3 Types of Jobs That Offer Health Insurance After You Retire

Government Jobs

As a federal worker, you have the option to access healthcare via the Federal Employee Health Benefits (FEHB) program, as long as the following conditions are met:

  • You are eligible for an immediate annuity under a retirement system applicable to Federal civilian employees.
  • You have been consistently enrolled (or covered as a family member) in any FEHB plan(s) for the 5-year span leading up to the commencement of your annuity, or for the entire duration of service since your initial chance to enroll (if this period is less than 5 years).

An immediate annuity means your regular payments kick in within 30 days after you retire. Even if you delayed getting it after leaving your job, an annuity you get through the Minimum Retirement Age (MRA)+10 rule in the Federal Employees Retirement System (FERS) is still considered immediate.

The word “service” refers to the time you spent in a job where you could sign up for benefits and the government helped with the costs. You don’t have to be in the same health plan the whole time. Times when you had non-FEHB plans don’t count for the five-year or first-opportunity rule, except if you were covered by TRICARE – that counts as long as you’re still under FEHB when you retire.

You can sign up for FEHB within 60 days after you first become eligible and the government will help pay for it.

Education Jobs

Educational service workers, such as University employees, have the opportunity to access health insurance benefits post-retirement. For instance, the University of Michigan offers retiree health benefits based on the average cost of the two most affordable plans, considering enrollment. Your retirement date and age determine your maximum contribution, while your health plan choice, Medicare status and coverage level influence the amount you pay.

If you’re a Johns Hopkins University employee, as another example, the university extends medical and dental coverage to eligible retirees and their dependents and matches the benefits received by active employees. The subsidy provided by JHU is calculated based on your age and years of service.

Part-Time Jobs

Exploring part-time employment post-retirement can bring both financial rewards and the added advantage of healthcare benefits. Many companies understand the significance of providing healthcare options to their employees and extend these benefits to part-time staff as well. Here are four examples of companies that prioritize the healthcare needs of their part-time workforce:


In Seattle, Costco employees who work over 23 hours per week for 180 days qualify for healthcare coverage administered by Aetna. Part-time workers can also access an affordable dental plan covering preventive care and certain basic procedures, in addition to basic vision care.

Employees can take advantage of an in-house pharmacy for prescription needs, with a separate prescription plan featuring low copays, distinct from the primary health insurance. The specific details of payroll deductions for health and dental plans are clearly outlined in Costco’s exclusive Rate Benefits Booklet.


If you’re a part-time employee at UPS and eligible for TeamstersCare, you have access to basic health plans covering preventive medical, dental services and even a vision plan—all without any personal financial contribution, thanks to UPS’s current collective bargaining agreement. Unlike other part-time benefits, these plans don’t require deductions from your paycheck. Depending on your role, you may also have the opportunity to enroll in union-administered plans subsidized by UPS, but be sure to check with UPS for the latest information, as these options may be subject to change.


Nonexempt individuals working at REI in Seattle, putting in approximately 20 hours or more per week, are eligible for all the health insurance plans REI offers. This includes medical and dental coverage, though it’s important to note that the specific coverage amount may vary depending on the plan you select.

Chipotle Mexican Grill

Part-time employees at Chipotle may be able to choose between two medical coverage options. California employees usually have more options to choose from.

The first option, labeled Anthem Preventive Plus, features lower premiums but provides less extensive coverage. The second option, Anthem Hourly PPO, involves higher premiums but offers more comprehensive benefits. Furthermore, hourly part-time workers at Chipotle can also consider supplementary dental and vision coverage, although the precise details of these plans are private too.

Alternatives to Employer Healthcare Plans in Retirement

Retired woman working part-time at a grocery store

Many companies don’t offer healthcare benefits to those who retire. If you need to secure health insurance after retiring, exploring alternative options that ensure you have the coverage you need for peace of mind during this significant life transition is essential. Here are seven common alternatives to get healthcare with early retirement:

  • COBRA: Allows continuation of employer-provided coverage for up to 18 months after leaving your job, though costs increase as you pay the full premium.
  • Health insurance marketplace: Affordable Care Act (ACA) plans with essential benefits. Enrolling during open enrollment or special periods provides access to standardized and comprehensive coverage options.
  • Medicaid: If your income drops, you may qualify for free or low-cost healthcare coverage through the federal Medicaid program, with mandatory and potentially additional benefits varying by state.
  • Private health insurance: Purchase plans directly from insurers or brokers, but it can be expensive without ACA subsidies. This option allows you to tailor a plan to your needs but requires careful budget consideration.
  • Short-term insurance plans: Temporary coverage for gaps before Medicare eligibility, providing a short-term solution with fewer benefits compared to comprehensive ACA plans.
  • Spousal insurance: If your spouse has employer-sponsored coverage, explore options to join their plan, ensuring you remain covered through your spouse’s employment.
  • Membership organization benefits: Some groups, whether secular or religious (e.g., AARP, Medi-Share) offer healthcare coverage and discounts, granting access to specialized plans through your membership. Be sure to see if the benefits meet ACA standards before enrolling.

Remember to assess each option based on your specific circumstances, considering factors such as cost, coverage and eligibility.

Bottom Line

Retired editor doing freelance work

Whether your current employer provides healthcare after retirement, you still have several options worth exploring. Working part-time for a company that extends healthcare benefits to part-time employees supplements your income and ensures you maintain the necessary coverage. If you need more clarification about the available choices or which option aligns best with your needs, consulting with a financial advisor can help guide you in the right direction.

Tips for Retirement

  • Navigating the potential expenses while you save and invest can be challenging. A financial advisor can help create a tailored financial plan aligned with your objectives. SmartAsset’s free tool matches you with up to three vetted financial advisors who serve your area, and you can have a free introductory call with your advisor matches to decide which one you feel is right for you. If you’re ready to find an advisor who can help you achieve your financial goals, get started now.
  • Uncertain about the funds required for retirement? Use SmartAsset’s retirement calculator to estimate your necessary savings, ensuring you’re prepared for any healthcare expenses that may arise unexpectedly.

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