Career & Finance

What to Do When Insurance Is the Only Thing Keeping You at Your Job


Insurance is no joke. It can be confusing and potentially a huge financial and energetic cost to you and your family, especially when you really need to use it. 

Being on a group plan within an organization is an attractive benefit to many. Not only are group plans often much cheaper than individual plans, they can also save you administrative time by simplifying the selection and claims processes. Hearing terms like COBRA (Consolidated Omnibus Budget Reconciliation Act, what you may get if you leave your job), and the marketplace (aka Obamacare and The Affordable Care Act), if you’d need to purchase a plan on your own, can stir up anxiety for a lot of us.

All that being said, insurance should not be the sole reason to stay in a job that is no longer serving you.

If you feel like insurance and benefits are a pot of gold dangling over your head, it may be time to think about how much it’s holding you back. I remember days where I’d say, “I can’t leave my job because my benefits are SO good” — and really, I had the best of the best in PTO, insurance, stock options, travel rates, and 401k. But I wasn’t happy. I was stressed out at really unhealthy levels way too often.

But eventually, I got over the whole, “I can’t leave because I have amazing insurance” conundrum. How?

Baby steps.


Explore what life would be like without your current job.

Exploring the potential upside to your career and life (allow yourself to think about it, without the cost of insurance shutting you down), if you were to leave your job for freelance, consulting, entrepreneurship or even another company that may not have strong benefits. What could your dream job and life look like? What would you be doing for a living? How would you feel each day? What goals could you achieve? A lot of the time, we don’t allow ourselves to think about the upside because society (or our practical minds) tell us it’s not smart. Stop denying yourself mental freedom and allow yourself to dream!


Understand what the real financial cost of that benefit is to you.

Learn about your options if you were to leave. Once you have real numbers, you can more objectively evaluate.

What would these options realistically cost you? What is the worst case scenario? Add the costs to your monthly/annual budget using a tool like Mint to help you see the reality of it. Would you need to give anything up? Think about what monthly costs would go down as a result of being happier in your new job. Dining out, takeout, extravagant travel, massages, medical costs, and shopping are all things I hear might decrease as a result of being all-around happier and less stressed-out at work. There are also resources that can help you decide whether entrepreneurship may be the right path for you.

As an example of someone who left corporate America to start a business, I can share that I now spend a lot more on my monthly premiums than I did in corporate America (like 2.5-3 times more), but the number of times I go to the doctor per year has declined. Am I breaking even? Probably not, but the benefit to me of flexibility, autonomy, creativity, and endless opportunity is worth it to me. If the benefits outweigh the cost for you, saying buh-bye to your benefits will be a lot easier.


But what should you do if you really need your benefits for a while and you’re not happy where you are?


You can start by evaluating your current company and role.

For some, career dissatisfaction stems from a company culture problem — take some time to evaluate how a different culture may really help you find more intrinsic satisfaction while you’re at work. For others, it may be that your role doesn’t play to your strengths anymore. Get clear on the kind of work you’re good at, and the work you enjoy most. Then ask your manager for more work that you do enjoy, or perhaps offer to take on a side project.


You can also look outside your job for more satisfaction.

Volunteer for a cause you care about, make more time for friends during the evenings or take on a new hobby on the weekend. Maybe team up with a friend to start a side hustle? Feeling more connected to the people around you is sure to pay dividends on your overall well-being.


Try to alleviate the burnout.

And if you’re tired and feeling burned out by your work and the daily grind, focusing on self-care may need to be #1. Commit 10 minutes a day to start a journaling practice, download a new meditation app, or check out all the free content out there from incredibly inspiring women like Brené Brown, Marie Forleo, Susan Hyatt, Gretchen Rubin — many of them send out daily inspiration! Finally, don’t be afraid to ask for more flexibility  — sometimes working one day from home can make a huge difference. 


Wherever you are on your career journey, know that you’re never stuck. There’s always a way to make a change, and increase your career satisfaction, whether you’re ready to give up your great insurance or continue benefiting from that perk.