My First Date

Sometimes business is a little like dating. Let me explain. I went on my first date when I was in 7th grade. It was typical middle school stuff. I had a crush on a girl in my class (I will call her “Monica”) and was flirting with her, so she had her best friend ask me if I liked her. I said “Yes”. A few days later Monica casually asked me what I like to do on weekends. I told her I usually go to the Fun & Games arcade on Saturday mornings. She said she sometimes goes there also. I said, “Great, maybe I’ll see you there”.

I was not sure if this was now an official date, or just idle chatter, but since I really did go to this arcade most weekends, I figured I would go as usual and hope she showed up. I woke up that Saturday morning, and it turns out it was a gigantic snow storm. Hardly any cars were on the road, and I worried the arcade might be closed. I told my parents I wanted to ride my bike there, and they thought I was crazy (I did not tell them about the “date” because I was not sure it even was one), but after some nagging they gave in and let me go.

Just as I got to the arcade, I saw Monica riding up on her bike. I was overjoyed. We walked in together, but then I had no idea what to do. I was not sure if I should play video games with her, or if we should do our own thing and just meet up every now and then. It was awkward, but in a sweet way. We played some together, some apart, but felt connected just being there. After around an hour or so her dad came to pick her up (so she wouldn’t have to ride her bike home in the snow), and by then it felt like a real date.

We ended up going out for a year and a half and were madly in love with each other. We were voted best couple in our school. We wrote dozens of long notes to each other, we held hands on romantic walks, and talked (via notes) about having our first kiss (she was nervous about it, so it never really happened). Then she broke up with me over the summer. I am not sure why; she may have met somebody else. She ended it over the phone (there was no texting or emailing back then), even though we had promised if we ever broke up, we would do it in person. We also had said if we ever broke up we should meet when we were 30 and catch up. That never happened either. But, those 18 months were some of the most exciting and intense times of my life.

My first few years of running my own business were kind of like this. Everything was new, every day was filled with adventure. A whole new world was opening up to me. I didn’t really know what I was doing, I just learned as I went. Sometimes I lost, sometimes I won. One door would close, but another would open.

After around ten years in business, I felt like I had pretty much seen it all and done everything. This was not a bad thing, just different. Kind of like being married after ten years. Good and comfortable, but lacking the thrill of your wild and crazy days.

Some people have a mid-life crisis and change everything. Some people get divorced and start over. Some people suffer in silence. The good thing about the business world, at least on the Internet, is that it is never too late to change direction. “Pivoting” a business is now considered trendy. Expanding by buying other businesses is looked at as a healthy way to grow. Starting multiple companies is considered smart and entrepreneurial (think Richard Branson, Elon Musk, Mark Cuban, Donald Trump). Much like the dating world, the Internet is filled with endless opportunities. You just need to put yourself out there to take advantage of them.

Update: Writing this blog posting inspired me to write a song about Monica: