Better to Say 'Oops' Than 'What If...'

Leap of Faith
Leap of Faith

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I once met a man who was actually a banker/hairdresser. "I do banking for money," he offered "and hairdressing for enjoyment."

It left me thinking about our individual 'backslashes' and what would happen if we could one day explore another passion.

For me, today is that day.

I have decided to follow in the entrepreneurial footsteps of my immigrant father whom I know is cheering me on from above. In his memory, I'll be starting a company (non-PR related) with a partner to launch later this year and pursuing, well, the other American dream -- 'doing what you love.' I am jumping in with eyes wide open, heart quite full and a parachute half-launched

Yes, the 'Do-what-you-love' movement (#DWYL) is thriving -- complete with Facebook groups and reality shows like Shark Tank and Quit Your Day Job. Even commercials like this one for Prudential Insurance tap into our inner desires: "If you could get paid to do something you really love, what would you do?"

It's a weighty question, implying that, chances are, what we'd choose might be radically different than what we're currently doing. Case in point, answers included "Yoga instructor" and "pie maker," not doctor or lawyer.

It's a subject on which it seems everyone has a public opinion accessible via Google Search: "5 signs It's Time to Leave your Day Job and Become an Entrepreneur," "10 Reasons You Have to Quit Your Job," or "7 Signs You Are Not Ready To Quit Your Job And Become an Entrepreneur" and, my personal favorite, "How Quitting my Corporate Job for my Startup Dream f*cked up my life." BTW, that last one does have a happy ending.

It's a subject, however, where the only opinion that really matters is your own.

The most notable DWYL evangelist was the late Apple CEO Steve Jobs. In his now well-read graduation speech at Stanford, Jobs offered this simple analogy: "You've got to find what you love. And that is as true for your work as it is for your lovers."

Jobs was right about, well, jobs. Finding the right one is much like a finding the right partner. It's not easy, it takes time, you may make mistakes and then, even when it seemingly works, it may one day be time to say goodbye. And when you do, uncertainty, stress, finances and emotions all come into play.

Like many modern divorces, you may even occasionally find yourself missing what you had. Deciding to leave a long-held job is, in many ways, like a breakup from a partner for whom you still hold great affection. Think of it, in the now infamous words of Gwyneth Paltrow, as "Conscious Uncoupling" from your job.

I am fortunate. I am leaving a wonderful company that I have loved for a very sweet 16 years. I have been privileged to work alongside fantastic people who are now more than just colleagues; they are friends. For me, however, it is time to begin my next adventure.

Each of us must figure out our own path to #DWYL. Sometimes, it's a backslash like the banker\hairdresser, the doctor\chef, the accountant\ballet dancer. Sometimes, it's an evolution like my dear friend and colleague Steve Mallory who, while working as a marketing executive, recently wrote the No. 1 movie in America.

Or, sometimes, one day, you decide to just... [gulp]...jump.

The choice can happen early in one's career, or as Vivek Wadhwa points out in Why Middle-Aged Entrepreneurs will be Critical to the Next Trillion-Dollar Business, later in life: "The claim that only the young can effect change has been disproved not only by Apple, but also by founders, inventors, innovators, and executives at almost every major technology company, including Google, LinkedIn,, Qualcomm, and Intel." In fact, from 1996 to 2013, Americans in the 55-to-64 age group started new businesses at a higher rate than those in their twenties and thirties.

"These technologies will make it possible to create the next trillion-dollar industries and to better our lives. But they require...experience, that is why we need to get beyond the stereotypes and realize that older entrepreneurs are going to better the world."

Bettering the world; now, there's a good goal. My #DWYL involves attempting to do just that by creating and investing in a purpose-driven business and work portfolio. I also wouldn't mind showing my kids that it is okay to take risks no matter their stage in life.

I don't know if I'll be successful, but I do know that I have to try.

When I told a trusted colleague of my plans, she didn't skip a beat when offering: "Well, it's better to say oops than what if."

So here I go. Looking forward to seeing you on the other side of "what if..."