I stayed too long in tech, because healthcare
Here's the unexpected way I've eliminated that issue
I stayed too long in tech, because...healthcare.
I've since left tech and my wife has held down our benefits since. But in the past couple months, it became clear that she needed to leave her non-profit for a career reset and time to rest.
The problem: we needed health insurance.
Between the two of us, we’ve switched benefit ownership for years. But this time, neither of us could stomach another corporate/philanthropy job.
So we found a self-pay plan through the ACA marketplace that covers the bulk of doctor visits, urgent care, x-rays, etc. It’s not the Cadillac of health insurance, but it works.
During the sign-up process, I realized something big.
The lever we miss
In a W-2 job, your employer holds several levers over you.
Compensation is obvious. Health insurance is the sneaky one. We take it for granted until something goes wrong at work. We realize we can’t just leave, especially with kids and dependents.
I stayed in jobs longer than I should have. Not because I loved the work, but because I needed the insurance. Few people say this out loud.
Self-pay insurance is not perfect. My wife and I have a lot of privilege to be on a “good enough” plan. But the freedom we both felt taking ownership of our own insurance, reduced the stress of staying or needing to find a new misaligned job.
I’m not saying you have to switch to self-pay. Rather, I’m pointing out that supplying your own insurance removes a lever your company can hold over you. Removing that layer can shift the dynamic, big time.
Tenure
I once asked a favorite professor, “Do you have tenure?”
I needed to know how she got away with open criticism of the university.
She smiled and said, “I gave myself tenure.”
Not literally, metaphorically. She built her career so that she didn’t need the university to survive. She had other income streams, which led to her refreshing idgaf attitude. Whereas professors seek tenure to feel financially secure, she did that for herself.
And because she had options, she could maintain her value system even in a dysfunctional ivory tower.
That’s what self-pay insurance is doing for me too.
Even if I went back to tech tomorrow, I’d keep our self-pay plan. The company would still control my salary. But they wouldn’t control that lever.
Eliminating even one lever, changes how you show up. How much you tolerate, how long you wait, and whether you speak up.
It reduces the chronic loop: I need to stay for insurance.
Rationalizing bad management, moral issues — even embarrassment about your company — quiets down.
You say, “I no longer need this place for insurance.”
This is a mindset shift; it’s not about being reckless. You still need income. You still have to pay the mortgage. But health insurance doesn’t have to be part of the golden handcuff equation.
Now that my wife and I supply our own insurance, no one holds that over us anymore. We’re free agents.
The practical part
If you’re curious, we used the ACA marketplace and a health insurance broker to understand our healthcare options. The process took about 5 hours, a to z. It’s not perfect and there are gaps, but our family is no longer trapped by this one variable.
Don’t brush this off.
Look into your options before assuming self-pay insurance is too expensive. You might pay less annually than your company-sponsored plan. Regardless, the cost of staying in your tech job may be higher than the cost of leaving.
Give yourself tenure.



