Week 20: Why Health Insurance is an Underrated Career (and Side Gig)

I recently received an interesting invitation. My sister-in-law, who works as a high school counselor, asked if I’d participate in their career fair. She suggested I present myself as an “entrepreneur,” which honestly made me laugh a little. None of my businesses are huge. I run continuing education courses, I built a quoting spreadsheet (Stella), I do some writing, consulting, and a few other projects. Nothing flashy. But collectively, they’ve created something pretty valuable: ownership.

And that got me thinking about what I actually want to tell these students.

Let me start with this: I do believe in college.

Not because it magically guarantees success (it doesn’t), but because it’s still the entry ticket to a lot of industries. Fair or not, many employers expect a degree. College teaches you how to think, how to communicate, how to manage deadlines, and how to navigate systems. Those skills matter.

So no, I’m not anti-college. The time, money, and effort spent there can absolutely be worth it. But…

The part I really want students to hear is this: Don’t wait until after college to start building something of your own.

The reality is, there isn’t much company loyalty anymore. You can be a great employee, well-liked, productive… and still get laid off. Businesses make decisions based on numbers, not feelings. That’s just the world we live in.

You probably won’t work at the same place your entire career. And that’s okay. But it’s smart to have something you own. A side business. A skill you can monetize. A platform that doesn’t disappear if someone else changes their mind.

Call it a side hustle, a side gig, or a long-term plan — it doesn’t matter. Ownership gives you options.

From a personal standpoint, I’ve spent a big part of my career on the carrier and vendor side of the business — working for insurance companies, general agencies, and third-party administrators. I also spent about ten years working directly for an agency selling insurance.

But about 17 or 18 years ago, starting around 2008, a friend asked me to help his small business find health insurance. He only had a handful of employees, mostly family members. A pretty small group. But also not a lot of work.

They’ve stayed with the same insurance company the entire time, only want PPOs, and prefer HSA plans, so the renewals are pretty easy. There’s also very little service work throughout the year. I literally spend about 3 hours a year maintaining the business.

On average, I make about $400 a month in commission from that one group. It fluctuates a little based on enrollment and premiums, but let’s call it roughly $4,800 a year.

Now do the math:
$4,800 a year × 17 years = over $80,000
From one small client. With minimal ongoing work.

And here’s the key part: even while working for other companies, I’ve always been allowed to keep this client (I negotiate it upfront). That’s ownership.

That’s the kind of thing a young person with a license could easily stumble into. And over time, it can turn into something meaningful.

We always tell young people to invest part of their income. But what if they didn’t need this money to live on? What if they just set it aside? What could that grow into over 30 or 40 years?

One or two clients like that could compound into a significant part of someone’s retirement income. And most people never even think about that possibility.

This is why health insurance is such a practical side gig — even while you’re in college.

• You don’t need a college degree to become an insurance agent. You can start now.

• You only need to pass one licensing exam. A short prep class (usually a few days) is enough to get ready.

• You don’t have to buy inventory.

• You’re selling something people already need.

• You earn a percentage of the premium – usually about 4 or 5% for health insurance, more than that for dental and vision.

• Income can recur month after month, year after year.

You help someone enroll. You get paid. As long as they stay on that plan, you keep getting paid.

Over time, those small commissions stack up. Add a few clients each year and suddenly it becomes meaningful money. Not overnight success, but steady, compounding income.

And once you’re licensed, it’s yours. You maintain your licnese by taking a few continuing education classes per year (no test required!), but you’re not tied to one employer. You can build this on your own terms. That flexibility is rare.

Now let’s say you actually like the industry.

When you graduate, there are tons of opportunities:

• Agencies

• Insurance carriers

• Sales

• Account management

• Compliance

• Operations

• Analytics

• Benefits technology

Health insurance touches everything — employers, hospitals, government programs, HR, tech platforms. It’s a massive ecosystem. Jobs aren’t hard to find, and many of them pay very well.

You don’t have to be a hardcore salesperson either. There are a lot of different paths inside this space.

Let me switch gears for a second. A lot of agents quietly wonder, “Did I choose the right career?” Perhaps the better question is, “What doors has this career opened that I didn’t even notice?”

Many of you also have kids, nieces, nephews, or younger people asking, “What should I do with my life?” If so, this article is for you too.

Health insurance isn’t glamorous. It’s not what kids say they want to be when they grow up. But it’s stable, it’s needed, it pays well, and it creates options. That’s a powerful combination.

Health insurance isn’t just a job. It’s a platform. You can start small, build slowly, pivot when you need to, stack income over time, and create real independence. What begins as a side gig can quietly grow into something much bigger. In a world of layoffs, AI, and constant change, owning something — even if it starts small — is one of the best forms of career insurance there is. And if you’ve got a young person in your life asking about careers, this might be a conversation worth having.