06-08-2025
During Job Transitions, Pay Attention To Your Healthcare Benefits
John Pierce is an entrepreneur with a focus on C-Suite consulting, M&A in the RIA segment, and a builder and leader of high-quality teams.
When I left a corporate environment after 30 years to become a full-time consultant, I came to a startling realization: I'd never truly understood the value or impact of healthcare benefit packages. Sure, I paid for the benefits, and I've been frustrated when plans were changed to save a nickel. But the pain of selecting new company-provided benefits paled in comparison to what I've experienced since becoming an entrepreneur.
Leaving or losing a job is already one of life's most disruptive events. It can often lead to financial strain, emotional turmoil and a cascade of logistical challenges. So, it's no surprise that entrepreneurs often overlook the importance of securing healthcare benefits. I know I treated it as an afterthought, and it was a big mistake. The sudden loss of employer-sponsored health insurance can leave individuals and families vulnerable to significant medical costs and gaps in coverage. But the healthcare selection process is shockingly complex.
Here are three action steps to consider on your journey.
1. If terminated, enroll in COBRA—quickly.
According to KFF, about 49% of Americans under age 65 rely on employer-sponsored health plans, meaning any kind of job change can trigger a loss of benefits. Without prompt action, individuals risk unaffordable medical expenses, delayed care or penalties from lack of coverage. The Consolidated Omnibus Budget Reconciliation Act (COBRA) allows terminated employees to continue their employer-sponsored health plan for up to 18 months. While this option isn't cheap—there's a fee on top of what you paid as an employee—COBRA can be a short-term stopgap.
Keep in mind that enrollment must occur within 60 days of termination or loss of coverage. Missing this window can result in permanent eligibility loss, forcing individuals to seek alternative coverage, often at higher costs or with less comprehensive benefits. Read any termination or exit agreements you have with your employer carefully, especially the terms of possible COBRA coverage.
2. Understand your marketplace options.
After really studying and reviewing your COBRA options, explore ACA plans and check eligibility for subsidies based on your projected income. Check your state's Medicaid program for income-based eligibility, especially if your income will decrease significantly. I'd also suggest finding a local licensed insurance broker to help you compare options and ensure timely enrollment.
3. Don't think you can get by without insurance.
Just because you're healthy today doesn't mean you'll be healthy tomorrow. In the U.S., "the average cost of a 3-day hospital stay is around $30,000," while routine procedures like an appendectomy can cost an average of nearly $8,000 without coverage. These costs can lead to debt or bankruptcy. Additionally, lapses in coverage can disrupt medication adherence, leading to worsened health outcomes and higher long-term costs. Don't risk all you have by thinking you can find cheaper options later.
Securing healthcare benefits quickly after vacating a job is essential to avoid coverage gaps, mitigate financial risks and leverage time-sensitive options. That said, many individuals aren't prepared for the process because they're unfamiliar with the system. It's easy to underestimate the costs or misunderstand eligibility, especially when you're experiencing emotional overload during a job change. Don't be as shocked as I was when I got to my 'to-do' list with healthcare next up. Put this topic at the top of your list!
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