This morning began like most every morning. My wife and I lazily blinked awake around 830. We grabbed our phones and scrolled through the internet until our dog bugged us to go outside around ten. We ate a hearty breakfast of bacon, eggs, and avocado toast, took a walk, and opened our shop at noon.

It’s a good life—one that we worked hard for. We’ve had to sacrifice a lot to make it happen. Not that we lost anything we’d mourn. I have spent zero time wishing I could go back to twelve-hour parent-teacher conferences or administrative micromanagement.


But every once in a while, I remember some details that do sound a little nice.

Such as this morning, when my old dentist’s office left a voicemail saying that we had a $7 credit on the account from our last appointment—four years ago.

Since losing our job, we’ve also lost our employee benefits. And let me tell you—we had some great benefits. We had a matching 401(k), incredibly cheap copays for dental and vision (we actually bought contacts!), and health insurance that didn’t suck.

And let me tell you: it’s far easier to let someone else take care of those things for you than do it yourself.


When your employer gives you a benefits package, you’re still paying for those things out of your own pocket, albeit with some help from your employer. But when you just get a check from your payroll department, it’s easy to ignore just how much you’re paying for them.

And as the saying goes, ignorance truly is bliss.

Owning our own business, we’re on the hook to pay all of these costs manually. And even though we might be making more now than we were teaching, writing a check for $250 each month feels like a lot more money than having that same amount withheld across your paychecks. Not to mention that working for yourself means you have to give up the lower rates of group plans, so you’re paying more for insurance anyway, even for a less comprehensive plan.


With our old plan, we had a $25 copay for doctor’s appointments. Our new plan doesn’t pay a thing until we reach the full price of our deductible. It’s good to have in emergencies, but it’s pretty useless for moderate illnesses.

And truth be told, replacing our old benefits package has been a long and stressful road, filled with ignored illnesses and out-of-date glasses prescriptions.


But if you were to ask us if we would want to trade the freedom and flexibility of being self-employed to have the extra peace of mind of a comprehensive benefits package that someone else has to deal with, the answer is a resounding hell no.

Being an entrepreneur means taking full control of your own fate—and that includes the stress-inducing parts. But if you can deal with the long, dark months of pinching pennies and working through the night, picking an insurance provider is easy.

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