After 20 Years, We’re Still Asking “Why Not?”

On New Year’s Day, the content marketing company I started with my wife in a spare bedroom turned 20 years old. I had spent the previous few years working for a small newspaper, writing everything but the obituaries and Dear Abby, and enjoying the process of learning how every facet of society works. A sideline gig writing a few freelance articles for a rural electric cooperative expanded into a risky opportunity: I could quit the newspaper and try to parlay my freelancing into a full-time career.

My wife and I had two small kids (a six-year-old daughter and a three-year-old son), no savings to speak of and no experience running a business. We sought counsel from friends and mentors. We prayed. We weighed the options with all the logic we could muster. And then, with one contract and a prayer, we took the leap and launched WordSouth. While we’ve certainly had our ups and down, like any small business, we’ve never regretted that decision.

I was listening this weekend to @jonnastor on his most excellent podcast, “Hack The Entrepreneur,” where he interviews some of today’s leading entrepreneurs and digs deep to find their best business hacks. He always begins his interviews with this question:

“As an entrepreneur, what is the one thing that you do that has been the biggest contributor to your successes so far?”

With the impact of our company’s 20th birthday fresh in my mind, I began to wonder what I would say in that moment. If I was a guest on Jonny’s show, how would I respond to this question?

The answer came quickly. “Never stop asking ‘why not?’”

Imagine the decision we faced in 1995. Leaving a secure job was a big risk, at least on the surface. Why would we do such a thing? “Why” was the wrong question. How about “why not?” Why not leap into the unknown, where you’re forced to work hard and learn new things and stretch yourself beyond what you’ve ever done before — and then know that there’s still no guarantee you can take care of your family? Why not let go of the trapeze for the first time, knowing there is no net below you, leaning on the skills you know you have and the guts you think you have to get you to the next bar?

Why not?

That willingness to take on new challenges, to dream outlandish dreams then go for them, has served us well. Why not try creating a collaborative publication involving rural telecommunications companies across several states, even though the industry had never seen anything like it? Why not turn our company culture on its head and include more remote workers than local office workers, in order to better serve clients in surrounding states?

And now, as we run hard and fast into a new year, why not take on some extreme initiatives that we have never been ready for (and may not be ready for yet)?

There are plenty of good answers, of course, to “why not.” Because it might not work. Because it could cost us money. Because it could make us look stupid. Because it could fail to earn new clients. Because it could cost us existing clients. Because it could cause good employees to leave or become disengaged. No matter what the project may be, there are always potentially negative outcomes that an entrepreneur must consider before blindly jumping out of the plane, ripcord in hand.

We’ve been asking “why not” for 20 years, and have no plans of doing otherwise as we enter a new decade. We plan to celebrate our big birthday by tackling some big projects that have big potential to strain our operation. But the opportunity for positive things for WordSouth is just too great to let the negative “what ifs” overtake our thinking.

So, Jonny, that’s how I’d answer your first question.