People doing a cheers with wine.

Why You Should Treat Everything in Life like a Date

How my failures in business mirror the standard dating experience.

“If your first business had done well, do you think you’d still be doing it today?” she asked. “I’ve never thought of that,” I said. “But yes, I probably would.” I don’t aspire to build businesses for their own sake. I build businesses in the hopes of creating the one. Of creating something that is fulfilling, something that I love.

My wife and I started dating in high school. We’ve been together ever since. Because of that, entrepreneurship has always seemed to take the place of dating in my life. I’d start a business, hoping it would work out, but for one reason or another, it wouldn’t. Then I’d be sad for a while. I’d mourn what could have been. I’d start another venture. Things would go well, but the honeymoon phase would soon end. That business would close. I’d be sad once more.

I’ve founded app startups, watch brands, and a razor company. I’ve done freelance writing and web design. All in the hopes of it being the one. Sadly, none of them worked out. One had too expensive of taste. Another was too needy. I proposed to one and got rejected. Another was puppy love that faded. And another was just a poor fit.


A Break Up with a Silver Lining

The watch brand was a particularly painful experience. It was… I don’t know… maybe my third or fourth entrepreneurial attempt. I was becoming desperate. If I don’t have success in business soon, it’s never going to happen! This one has to work!

It started off passionately. I spent time on it before work and before bed. I gave it everything I had. But after six months, it was over. The expenses were too large and the potential was too small. That was the end of PΛTH (the name of my watches). It was at this point that I swore off entrepreneurship altogether. My wife and I were getting married in a few months. I didn’t want the distraction of a new business pulling at me during that time.

So instead, I sulked. Like a heartbroken teen, I cried and complained. I was angry and frustrated. Why do I keep failing?! 

The wedding arrived. It was awesome. Several weeks later, post-honeymoon, I met up with a friend. We had a conversation that left me entrepreneurially inspired. The next day I started what became my blog, QuickBooost. I’ve been building QuickBooost ever since. That was three and a half years ago. Is QuickBooost the one? It’s too early to tell. After all, I didn’t propose to my wife until we had been together for nearly a decade. QuickBooost and I are still taking it day by day. We have our ups and downs. Our good times and bad. But I could really see myself settling down with this one.


Dating in All Things

When I was asked whether if my first business had succeeded I’d still be doing it, I had never considered the question before. But as I paused for a moment, I realized that I would. Because the business is a means for me. The end is fulfillment. If that first business succeeded and I was fulfilled in building it, we’d still be together. Same goes for my second business, or my third, or fourth. Same goes for QuickBooost. If it fulfills, I stay. If it doesn’t, I walk away.

Consider your career through this lens for a moment.

Did you go on a lot of dates before choosing your path? Or, in desperation, did you choose the first one that offered you a contract? Did you commit to something that paid the bills but to this day hasn’t made you feel fulfilled? Let’s spin this out even further. Look at where you live. Before purchasing the home that we’re in now, my wife and I looked at 20 different places. It took months. We didn’t lock in the first one with running water. We wanted to find the right one for us. Which we did.

Look at the food you eat.

Do you enjoy your meals? Or do you simply go through the motions? Have you tried branching out in the past only to be burned (literally)? Have you played it safe, never daring to try anything that isn’t pasta? Or have you spent the time to find those things that light you up? That both taste good and make you feel good?


Moving Forward on the Dating Circuit

Dating is really just trial and error. You go out with someone. It’s terrible. You learn and try again with someone else. It’s better but still awful. You learn from it. You get clearer on what you want. The next date goes better, but it’s still not a match. Eventually, you find someone that you enjoy being with. That fulfills you. You commit. You’re now in it together. It’s not always easy, but you iterate along the way. You continue to learn, adjust, grow.

You start a business. It fails. You learn from it. You start another business. It fails. You learn from it. You start another business. It works, but you hate it. You learn from it. You start another business. It’s everything you’ve ever wanted in a career. You commit. It’s not always easy, but you iterate along the way.

  • You start a garden;
  • Try to lose weight;
  • Attempt to get a book published;
  • It’s all dating. It’s all trial and error, learning and growing.

You get to decide when you commit. You can either see it as a process and keep going until you find the one, or you can let desperation make that choice for you. Will desperation give you the career you want though? The body? The home? The spouse? Possibly. I never wanted to find out. Shutting PΛTH down was excruciating. Swearing off entrepreneurship was brutal. But the alternative was to force a business that didn’t have the legs.

It was painful to walk away. But QuickBooost wouldn’t be here if I didn’t. I made the right choice. Have you?

Want to hear more from me?