Back to School: A Health Insurance Hack

More than ten years after I left teaching and nearly nine years since finishing my last degree, I am back in school!

I acquired a B.A. in International Relations, an M.Ed. in Curriculum and Instruction, and an M.A. in Security Policy Studies prior to and while job hopping to increase my salary rapidly and grow my professional skills.  My career highlight reel includes designing my own ideal job with a promotion, getting paid more without switching jobs as a result of an unexpected bidding war, and retiring with enough when the time was right for me.

But now I am headed back to school!

Usually people go to school to get the job they want, gain the skills they need to create a business, or secure a degree to earn a higher salary or get a promotion.  I have done all those things, making me a strange candidate for further education at this stage of life.

However, college students in the District of Columbia are eligible for affordable health insurance coverage for themselves and their families.  Affordable health insurance in the United States of America?  It does not sound real, but I spent a steep $934 for health insurance to cover Patrick and myself from January 9, 2026 through August 10, 2026.  At that point, I have to pay for the entire next school year, a whopping $1,600-ish.  Yes, that is $1,600 for health insurance for two people for an entire year.

The insurance is also better than my former employer’s insurance, which cost significantly more despite my employer paying for part of it.  My new out-of-pocket maximum is $2,500/individual and $5,000/family.  In other words, we will not have to pay more than $5,000 for medical costs this year.  (We also have access to the same provider network as we did before.)

That means in a given year, we would spend a maximum of $6,600 for the two of us on health insurance if we paid the initial cost of the health insurance and reached our out-of-pocket maximum.

Compare that to a plan for a family of two on the exchange: We would pay more than $20,000 in monthly payments alone for a high-deductible health plan.  The exchange rates were comparable to when we spent $1,564.26 monthly on COBRA for a few months last year.  Each month, we were paying what we will now pay in a year.  That is a huge savings for health insurance!

Other Costs and Benefits

Attending college is not otherwise free.  To be eligible for health insurance for our household for the entire year, I need to take a course in the spring semester and a course in the fall semester.  The total cost of two three-credit courses is $2,374.  This brings our total cost of classes plus health insurance to $3,974 for an entire year.  Fortunately, that is still less than one-fifth of $20,000!

In future years, I will also have the option to only take a fall semester course to qualify our household for insurance for the entire year because colleges follow the academic calendar for coverage purposes.  That means a year of insurance can be obtained for $3,002 if you opt to take only a fall semester class.  That annual rate is less than two months of health insurance purchased on the exchange.

While this is an extra cost to consider, it comes with the perk of continued learning!  I am currently enrolled in a business course at the University of the District of Columbia, and the experience of low-stress learning has been fun so far.  All of my previous college experiences included having to maintain a high GPA to keep a scholarship, going to school while working or interning part- or full-time, or both.  While I enjoyed my academic experiences thoroughly, there is something lighter and joyful about learning just for the sake of learning.  I do not need a degree or high grade.  I am not taking this to further my job prospects.  This is learning for the sake of learning.

This is certainly not the reality for most of my classmates, all of whom seem to be at different stages of life from each other.  So far, that has been part of the fun.  Sure, there are 18–22 year-olds attending college to get a job like they are supposed to do.  But there are also mid-career students attending to switch careers or get the degree to support skills they already have.  We are a diverse group with a range of ages, races and ethnicities, genders, nationalities, DC zip codes we call home, and previous business experiences.  We are also similar, experiencing the realities of living in Washington, DC at this moment in time.  Despite our similarities, I probably would not have met anyone in the class in daily life, and I am grateful that this experience has led to me meeting a group of people I would otherwise never know.

Lesson Learned: Jobs Have Fewer Perks than We Think

Health insurance is the detail that appears most when those considering early retirement remain in a job.  The prohibitive cost of COBRA or ACA plans on the exchange keeps people tied to desks for longer.  It makes sense mathematically.  If you assume health insurance for your family will cost $20,000 annually, that means you need an extra $500,000 to retire according to the 4% rule.  That is a huge amount of money and a significant fraction of wealth for most early retirees!

My experience shows there are more affordable health insurance options if you are willing to get creative.  Spending $3,002 annually means retiring with an extra $75,050, and that seems a lot more doable than $500,000.

The biggest takeaway may be how many people this could help that are on other, slower paths to early retirement.  So many people assume that alternative health insurance rates cannot be better than the health insurance offered by large employers, but my current health insurance costs less and is better than the health insurance offered by my former employer.  That stunned me.  I assumed I would have to either pay more or accept less because Americans assume that full-time employment is the only viable path to obtaining health insurance.

How many people would choose to take a class and work a part-time job that adequately supported their lifestyle but did not provide health insurance if they knew this option existed?  Especially those who have creative talents.  You could work part-time getting experience in a craft while taking a business class like me, potentially preparing yourself to open a business doing what you love in the future.

The enduring student route is not perfect for everyone.  I will have to take a fall class each year, meaning I could not travel full-time.  That said, there are affordable traveler insurance options for those who would find this approach restrictive.  For a college rugby coach, adhering to the college schedule does not change my life too much, especially since I only have to take a class one semester each year going forward.  Even if I had to take one in both the fall and spring, I like to learn much more than I like sitting at a boring job.

Regardless of your own situation, there may be options.  If health insurance is holding you back from pursuing your ideal life, explore other options.  The normalization of health insurance being tied to jobs in the United States does not have to keep you stuck.  Explore your options, and find the health insurance hack that is right for your dream life.