One of the most under-the-radar benefits of entrepreneurship is its ability to build fortitude and make the entrepreneur a more formidable person. Challenges – particularly the crazy, unexpected ones that take on a life of their own – build character and confidence. And the unexpected surprises to the upside, the crazy good moments offer a high that’s hard to reproduce elsewhere. The charm and the challenge of entrepreneurship is dealing with the crazy things that happen and so we’ve asked some fantastic business owners and leaders to share some of their stories with us below.

Camryn Bailey

One of the craziest—and most defining—moments of my career as a service provider happened while producing the Earners Circle event for Earn Your Leisure at 40/40 Club in NYC. Our budget approval didn’t come through until 48 hours before the event. At that point, most teams would’ve postponed or scaled back. Instead, we went into execution mode. Read More>>

Andrea Bowman

One of the most underappreciated realities of entrepreneurship—especially in talent management—is that you’re often navigating chaos long before anything looks successful on the outside. The craziest thing that’s ever happened to me happened early in my career, when I had just started managing talent. Read More>>

Elizabeth Walston

There is a special joy in the revival of an old craft. Hat making was considered somewhat of a dead art for many years, as the practice of daily hat wearing fell out of the societal fashion. But like any old art, remnants are still there. Read More>>

Misha Lewis

I had been doing makeup for a couple of years when I randomly received an email from a PR agency requesting makeup for tennis champion and star Martina Navratilova!!! I was sure that it was either a hoax or they had reached the wrong artist, as I had no connection with them. Read More>>

Dianne Lawson

Being an astrologer in Topeka, Kansas and making a good living at it seems improbable. The reason why I was able to scale up and build my business was because I continually have treated what I do as a business, as well as a service to others. Read More>>