05/08/2015 04:54 pm ET Updated Dec 06, 2017

4 Unexpected Truths in Entrepreneurship


As National Small Business Week draws to a close, there is no time like the present to reflect on the advice I've collected, from life experiences and an incredibly supportive mentor base, in my years as the founder and president of a digital marketing agency. Though the company has evolved and expanded since the days of me and a lone laptop, I like to believe the entrepreneurial spirit infuses all we do and makes us a better company for it.

Whenever I'm asked to advise business start-ups, I share the only constant I know: expect the unexpected. While the tactical elements of business might be predictable, life is not. As John Lennon so wisely said, "Life is what happens to you while you're busy making other plans." Or my favorite, "We plan, God laughs."

As I age, I wish I could say I've learned from my mistakes but, for some reason, every year just keeps one-upping the last with new challenges, unforeseen circumstances, and true "game-changing" moments. Here are four statements that have become staples in my vocabulary over my years dealing with the unexpected.

"Did that really just happen?"
If you've ever said, "I've seen it all," brace yourself because you haven't. The unimaginable and uncontrollable will happen and there is no business plan in the world to stop it.

On my way out the door from home one morning, I received a phone call from my operations manager. "There is someone on the roof. Police are on-site and they are working to get them off the ledge." My heart sank. Our office is on the rooftop floor with a staff of over 50 employees. I was bracing for the worst. The young woman in distress, with whom we had no connection, entered the building early in the morning. She took the elevator to the top floor, opened up the first window she could find, and sat out on the ledge of the building. News team helicopters circled the building, police took over the office, and giant airbags were placed on the streets 20 floors down. Fortunately, the NYPD demonstrated why they are best in class and brought her off the roof to safety.

I was relieved and happy for all the reasons you might imagine on behalf of the young lady, her family, and the police. But that story could have ended differently, and I'm still not sure how you prepare for an event that could ultimately have a profound impact on so many lives that are part of your business. This is one of the more heart-wrenchingly unexpected situations I've come across over the years, but leaders must steel themselves for these unexpected doozies.

"That's just wrong."
Like many people, I tend to take things very personally and it's hard to walk away from unjust or hurtful or just plain deceitful behavior. Whether it's being stiffed on a bill or having a promise left unfulfilled, I've seen unbelievable behavior from people I never expected to behave that way.

It's taken me probably too long to realize this, but these "bad people" are simply part of the game. And while you can try your best to avoid them, they hit you when you least expect it. Distance yourself from these people as soon as possible; do not enter the long drawn-out game of retribution. Channeling your inner Tony Soprano won't get you far. Aside from attorneys, I can't name many folks that say they felt wholly satisfied after an extensive battle of revenge.

"I can't believe they did that."
Astounding, unexpected acts of everyday kindness have fueled me during critical moments in our business's history that, at the time, felt nearly impossible to overcome. Running a business is a marathon, not a sprint, so believing in the best of people is an important ingredient for sustainability in any organization.

Colleagues who give their vacation days to another. Or babysit each other's kids in times of need. Or fly long distances to mourn with colleagues suffering loss. Or vendors who offer up services to support philanthropic efforts in the community. These big and small kindnesses have a significant impact on company culture. Entrepreneurial leaders should support, reward, and nurture the unexpected moments of human greatness that are much more commonplace than one might think.

"Get home safe."
With all of the amazing treasures that comes with hiring people who ultimately become part of your workplace family, there is also the pain and hardship that life often delivers. As we all know, it's remarkable how fragile life can often be.

My most indelible moment at the helm of this company came one early weekend morning with a phone call. We lost our Creative Director in a tragic vehicular accident. I vividly remember calling each and every one of our employees that rainy morning. One call after the other, it was a grueling reminder that the lines between business and personal are far blurrier than we might tell ourselves.

"Get home safe" has become a staple in my language as a reminder to myself and the ones I care about that life is fragile and unexpected in ways we can't fully understand.

The unexpected should be the expected on any journey of entrepreneurship. It brings with it the good, the bad, and the ugly, but it sure as heck never brings dull to the party.