Recently we talked about how passion in your business affairs is great, but unchecked passion without proper perspective can get you into trouble. I can’t think of any better way to illustrate that point than by providing some cautionary tales from my own experience. Read on for two stories straight from my past that illustrate what not to do with your business.

Cautionary Tale #1: Social Technology Platform

Years ago I had an idea for a social technology platform. This was a real pet project for me. I was very invested in it and thinking big. I was so taken with the potential of a platform like this that I got overambitious, losing sight of the fact that you can’t be everything to everyone. Some friends cautioned me to start out going after a specific group.  (You may even have heard of a little company called “Facebook” that did this, targeting Ivy League students at first.) I didn’t listen, though. I was too passionate about what I wanted to build, I got overextended, and the project failed. All told, I lost about $2.5 million, which was a poignant reminder to follow my own rules!

Cautionary Tale #2: Military Training Facility

Having never served in the military, I saw this venture—sponsoring a state-of-the-art military training facility—as my opportunity to give back. Because this opportunity came along at a time when I was between projects, I allowed myself to be seduced by the “warm fuzzies” of doing something good. I wasn’t nearly attentive enough to the quality of the business plan. I failed to do my due diligence on all phases of the project. There came a point when I was just blindly writing check after check. I was so caught up in my noble intentions that it took me far too long to see that things weren’t coming together. Once all was said and done, I lost about $1 million.


Our professional journeys take us many places and teach us many lessons. No successful entrepreneur get where they are without a misstep or two along the way. And one of the easiest mistakes is letting the professional passion that should be your ally get the better of you. That’s what I did in the stories above.

Whatever your particular area of vulnerability is, though, you need to recognize your mistakes when they occur and learn from them. Treat them as signposts in your travels warning you which routes not to take. Your mistakes are nothing to be ashamed of unless you make a habit of repeating them. Move forward with your eyes open!

Let my cautionary tales guide you in your own professional enterprises. And if you do find yourself making bad decisions, it’s not the end of the world. Learn, and move forward stronger and wiser.


Need help with a business mistake? Get in touch with me here or on LinkedIn.


image credit: Bigstock/Tull Pradipath

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