The First Question Everyone Asked me When I Left Finance

The Surprising Obstacle Holding Talented Folks Back from Entrepreneurship

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When I left finance over a year ago, I conducted a “farewell tour” of sorts with colleagues, friends, acquaintances, clients, and other professionals I had met over the decade and a half. When they learned that I was going to try my hand at entrepreneurship, 99% of the time I was asked the same question:

What are you going to do about health insurance?

I wasn’t entirely surprised, in fact one of my wife’s pre-conditions of my foray into entrepreneurship was that nothing change about our Health Insurance. A very legitimate concern, which I shared.

I too had asked around (you can’t ask HR these questions directly) prior to my resignation. And I learned that COBRA, during which you keep your existing coverage verbatim, lasts for the 18 months. The cost is no joke (and it’s highly dependent on your prior employer’s coverage) but nothing changes for 18 months.

Yet it still feels terrifying when I get the bill each month. I immediately pay it off that day. Given that I get this recurring feeling each month (and I just got it for July) I’ve tried to unpack these emotions and see how they reconcile with my learnings over the past year.

1. Health Insurance is Confusing AF

Remember those “open enrollment” sessions? Or the never-ending pieces of paper that come in the mail? (You can’t tell if it’s a bill or a statement.) Or these random stub amounts from bill collectors that you just pay off because it’s too cumbersome to call them during work hours.

I think that certain startups (Oscar) are tackling this UX/CX nightmare, but the entire system is pretty fucked up so I can’t say I’m super optimistic.

2. Coming Out of Pocket Sucks

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Irrespective of the amount, particularly if you’ve never done it before. As “prepared” as I was for entrepreneurship — and I came into it with a decent amount of savings — nothing can prepare you for the feeling of watching your bank account go down. Every. Single. Month.

The irony is that it’s not rational, it’s highly emotional.

I had “modeled” out my expenses for the upcoming year, multiplied by 1.5x and assumed 2% investment return and in theory was TOTALLY OK with the ending number. But it doesn’t fucking matter.

Which is why doing this deep self-awareness work becomes even more important.

3. It Always Comes Back to Fear ?⚰

Charting a new path for yourself is Scary AF. There’s uncertainty. There’s noise. There’s lack of structure. There’s cash burn. There’s haters (luckily, very few in my case).

Because of this uncertainty, we tend to mis-read, or even worse, over-estimate our fears. Bringing it back to COBRA, this cuts to a deep fear of our own well-being (which probing deeper, often is related to our fear of death). This is despite the logical part of our brains knowing that we’ll be fine. Tim Urban summarized this beautifully in his post on Elon Musk with the following graphic:

The fear of missing a COBRA payment falls in the green zone (4–7) — “it’s not actually dangerous” but we mentally ascribe it to the “actually dangerous” zone.

Throughout this journey — the 4 Pillars of Introspection have been indispensable to categorizing obstacles and challenges into the right bucket. The funny thing is that it’s all in the blue and green zone. There’s very little red in the journey. But tell that to the emotional brain — the monkey mind. ???

Thanks for reading,


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Khe Hy is the creator of Rad Reads, a publication dedicated to Being your Best Authentic Self. The four pillars are frequently covered in the Rad Reads Newsletter, delivered each Saturday AM. Subscribe Here!

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