Business Creators Solve Problems—Starting with This First One

Your First Opportunity to Think Like a Business Creator.

You’re considering leaving your stable, predictable corporate job to pursue something more meaningful. Exciting, right? But then—gulp—you remember: I have to pay for ALL of my health insurance. 

Suddenly, that daydream feels a little less dreamy. I get it. That moment of sticker shock can feel like a showstopper. You’ve been used to your employer covering most of the cost, and now, in your daydream, the burden is fully on you. It’s overwhelming, frustrating, and—let’s be honest—one of those things no one really talks about when they say, Follow your passion!

We All Have to Tackle This One

Here’s the truth: this is one of the biggest concerns for aspiring entrepreneurs. You’re not just imagining it, and you’re definitely not the only one grappling with it.

Moving from W-2 employment to self employment is a shift in mindset and responsibility. Suddenly, things HR used to handle—like benefits —are now your job.

That’s a big deal. It’s completely normal to feel a little (or a lot) overwhelmed.

I remember looking at healthcare exchange plans. It was like shopping for my dream home: trading off parts of the dream to stay within my financial plan.😔 The system wasn’t exactly designed with business creators–my phrase for bootstrapping entrepreneurs–in mind, and figuring it out felt daunting at first.

A New Way to Look at It

But here’s the good news: You have more control than you think.

Entrepreneurs don’t just inherit problems—we solve them. Instead of seeing healthcare as an insurmountable hurdle, think of it as your first exercise in business problem-solving. Because that’s what entrepreneurs do—we explore, negotiate, and adapt.

Here are a few ways to tackle this:

• Look beyond the exchange – A broker can help you find options beyond what’s listed online. Private plans, group associations, and innovative health-sharing models might be available to you.
• Factor it into your business model – Just like rent, software, and business development, healthcare is a cost of doing business. And as your revenue grows, it becomes a smaller percentage of your income.
• Plan for the transition – Whether it’s using COBRA as a bridge or finding a short-term plan, you can treat this as part of your startup strategy. Because that’s exactly what it is.

Here’s the Bigger Picture

Right now, you’re solving one of the most crucial challenges every entrepreneur faces—handling uncertainty. The fact that you’re reading this, thinking through your options, and preparing for this shift? That’s exactly what separates successful entrepreneurs from those who stay stuck in “what if?” territory.

If healthcare has been the thing holding you back—know this: You’re capable of figuring this out. And when you do, you’ll have already built resilience (or a concept I’ve been exploring recently: antifragility). It will serve you in every other challenge ahead.

What other showstoppers besides healthcare are you still figuring out? Send me an email at pierre @ pierrebradette dot com. I read and respond to every email.

To your success,

Pierre

Certified Professional Coach

Photo by Pim Chu for Unsplash