After 18 years of running a small business, there hasn't been one "best" time, but instead a series of them. Of course, my best of times, might be hell for you. My wife used to take math classes for fun, case in point. So what are my best of times?
Figuring It Out. Learning the trade from scratch was a glorious time, breaking the code of my trade. I'm still doing it. In retrospect, I paid about as much for that education as my parents paid for my college education. My startup loss budget, AKA my informal education, was over $50,000. Figuring out the trade also included understanding customers. Some of those early customers are still with me. Some have loaned me large sums of money. One is a long time investor. Learning games was also part of figuring it out. I learned about 100 board games, several miniature games, and half a dozen role playing games. I don't do that anymore, nor do I want to, but I look back fondly on this time.
Survival. Squeaking by with a few days of cash flow made me feel lean and mean. Extra money tended to be more liability than opportunity. I remember being on vacation in Mexico and essentially bouncing a Friday payroll, rolling it over until Monday. Business as usual. We had super thin labor. We relied on December to get us out of debt nearly every year. I did this for so long, I would have told you "this" is what owning a small business is about. It is for most. It taught me discipline, but if I analyze it clearly, there's also some psychological trauma. There was a baseline of constant pressure to perform. It can be addictive.
Just a Taste. I overbuilt, over-invested, and there was a potential energy built into my business, like a large rubber band being slowly twisted. In year eight it unwound and after years of just getting by, we finally cracked the expense nut and saw net profit soar. It continued to soar for years to come. Scraping by for eight years and finally having some extra cash was glorious. It didn't feel like a reward for hard work though, it felt unearned. I did enjoy the vacations and outside hobbies this provided. It was a nice distraction from imposter syndrome.
Break Out. COVID saw my return as the sole proprietor for several months, building a new POS on my dining room table, delivering games to customers, creating an online store, and re-hiring staff to take it all over. Imposter syndrome was cured when it was just me again and I didn't fall on my face after a lot of years away from the counter. I can still do this! It gave me the confidence to work from home, plan my long term working road trips, and believe that what I built had a strong foundation. We had strong policies and an equally strong business culture embodied by wonderful employees.
The Last Day. One day I will sell the business, hand it off to my son, leave it to employees, or liquidate at a tremendous profit. They say the two happiest days of owning a boat is the day you buy it, and the day you sell it. I imagine a small business is no different. I'm another 18 years away from that day, if I'm lucky, but I imagine it will feel like victory.