Starting your own business is a bit like setting off in a dinghy down the Mississippi—exciting, unpredictable, and, at times, terrifying. My wife and I took that plunge when we decided to work as independent contractors. That meant companies would pay us, but we had to figure out everything else—health insurance, taxes, payroll, and all those benefits that working for an established company provides. It was a kick in the pants, a push away from the directions our parents had given us, into the unknown.

As with most things in life, I turned to my friends for advice. “What business structure should I choose?” I asked. The overwhelming response: an S-Corp. It was supposedly the best fit for two independent contractors making (hopefully) over $80,000 a year. Simple enough. So, I did what any modern entrepreneur would do—I searched for help on Thumbtack. I hired another veteran, Connie, to handle the formation of our S-Corp. Anyone willing to take a call on April 16th—tax day—has to be organized. For $180, she set up: our EIN, corporate documents, election of a small business, and state Department of Revenue filings. One phone call in, and I had already surrendered a bit of my independence. No more TurboTax; now, I had a recurring expense for professional tax filing.

I asked Connie, “Do you take the federal and state taxes out of the payments from the companies I work with?” Of course not—why make it that easy? Instead, she referred me to a payroll service. So, after setting up a business bank account with a credit union, I added payroll administration to my growing list of responsibilities. Another necessary ally in the battle of self-employment.

Next came insurance—because nothing says “I’m a business owner” like signing up for multiple policies. We got umbrella insurance, professional liability, general liability, and even medical and dental coverage for our one employee (me, for now). Each policy brought its own admin portal, its own customer service lines, and, of course, another recurring expense. But hey, they’re all tax deductions, right?

Since my wife was both the co-owner and sole employee, she couldn’t have a business-provided HSA. That was one thing she had to set up separately, which was a small relief—I had enough programs to manage. Instead, I found myself stepping into a different role: webmaster. It was a throwback to my younger years and a chance to write, something I’ve always enjoyed.

Fast forward two years. The business we started has completely transformed. The contracts ended, the payroll services were canceled, and all the insurance policies were dropped. My wife, battling health challenges, could no longer work, which led to some incredibly lean months. I had to reinvent myself. Instead of project and capture management, I focused on something more meaningful: helping veterans get federal small business credentials and assisting them with disability claims.

It was a tough pivot. To make ends meet, I worked part-time at three different large retailers while also working on commission-only deals. The financial anxiety was relentless, but so was my drive to provide for my family and uphold my responsibilities. Slowly, through persistence and the kindness of others, things started to turn around. Former clients and friends began reaching out, and I found my footing as a fractional professional service provider in sales and operations.

After more than a year of working for commission only, I’m finally seeing the fruits of that labor. The journey has been anything but easy, and I’ve had moments where I wondered if it was all worth it. But as they say, “A soldier ain’t happy if he ain’t bitchin’.” So, I guess that means I’m happy. I’m happy.