08/07/2025
Running a business, like waging a war, goes exactly as planned right until the moment you start.
I mean that literally. When I started my first business in my early twenties, for example, I hedged my bets by informing my boss at the time that I’d work part-time for him but do my own thing on my days off and the weekend. That way, I’d enjoy at least one guaranteed source of income as a buffer as I experimented with small business ownership.
My position was complicated by the fact that my side-hustle – manufacturing and repairing commercial signs – was also what I did in my day job. If it turned out to be successful, in other words, I’d be competing with my boss.
To my relief, he agreed. In retrospect, I realize it was because he didn’t take me seriously. About a week later, when a fellow employee informed him that he’d spotted me working on a sign for a new customer out of my own truck, he flipped his lid.
He gave me an ultimatum: I could either abandon my silly dream of competing with him and work my way up through the ranks as his employee, or else. I chose the latter and he fired me without further ado.
This, I think, is an ideal example of the vagaries of entrepreneurial life. The minute you launch out on your own, it’s all or nothing. You can’t hedge your bets or strike cozy deals which allow you to have your cake and eat it too. The advantage of such stark realities is that they force you to grow up in a hurry.
To paraphrase Samuel Johnson, when you know you might starve if you don’t perform, it concentrates your mind wonderfully.
The main thing to remember is that small business owners will face numerous unexpected challenges in their first two years of operation, testing their resilience, adaptability, and determination. The challenges will continue, of course, but by then reacting appropriately will have become second nature.
Small business owners will face numerous unexpected challenges in their first two years of operation, testing their resilience, adaptability, and determination.
