Being a Boss

There are a million things I’ve learned since starting this company, many of them around what it means to be responsible for other human beings. But the most meaningful of these experiences occurred just a couple of weeks ago when I opened my mailbox to find, tucked inside an inconspicuous white envelope, a shiny little card.

Health insurance. This little card entitled me (and our employees) to top notch health coverage, which not coincidentally comes tied to an exorbitant premium, significant deductibles, and a limited menu of services. But still, health insurance!

Now, why is this so meaningful? Of course it’s significant to be able to support our team and my family in this way. It means the business is doing well. It also feels like we’re doing the right thing here as human beings. Which is all very nice, but not the most meaningful (I’m channeling here Johnny Depp in Chocolat as Juliette Binoche gives him sample after sample of divine chocolates, trying to discern his favorite–it was hot chocolate all along, little jerk).

This next part will resonate with some of you, but not with others. When I was growing up, we often did not have health insurance. That’s what happens when you’re raised by a single mother who tried to work remotely (before it was a thing), and in the process sacrificed regular benefits (or a good salary). Even in California, which is known to have a pretty well-developed health program for people who can’t afford insurance (shoutout to Medi-Cal), we still had to pay. You may not know this, but Medi-Cal or Medicaid, or whatever it’s called in your state, isn’t necessarily free. It’s just cheaper. That’s why things like “free clinics” exist–because there the services actually are free.

After I graduated from college, I moved to DC and got my first real, full-time job working for an economics consulting firm. It was one of those perfect post-collegiate jobs that required limited brainpower (and was brutally boring . . . you SAS programmers out there know what I’m talking about), but allowed me virtually unlimited time to take breaks with my friends Andre and Dave (breaks that were often spent grabbing a second breakfast at the bagel shop around the corner or just standing outside watching Dave smoke cigarettes). 

Along with my full-time salary, I receive some kind of health insurance. I don’t know what it was, but I remember it came with this shiny little card. Up until that time, each time anyone asked me if I had health insurance, I felt ashamed. Insurance was a thing that people had and, in not having it, I was deficient. Even in college, I had the university health plan, which was a collegiate version of being on the school lunch program.

So when I got that card I felt amazing. I looked forward to doctor’s appointments, when I would stroll up to the desk, just waiting for them to ask me for my insurance card so I could nonchalantly slide it from my wallet. Of course I have insurance (hair flip). At the same time, there was always this mild sense of panic, that I was about to be outed, even though I knew that insurance card was tucked safely away, waiting to be revealed. Even now, there is part of me that feels like I’m about to be exposed as a fraud when I’m waiting to check in at a front desk. And then there is the relief that comes when I remember that I do in fact have insurance, that the feeling is just residue from those earlier years.

Fast forward to a couple of weeks ago when my very own, All Places insurance card arrived in the mail. Not only did I have insurance, but it was my own company’s plan that was covering me, my family, and my employees. It was, and I’m sure will continue to be for quite some time, magic.

--Jessie Gabriel