The Wonder of Wandering

When I walked out of IBM at age 29, I didn’t have a clue where I was headed. I only knew that I wanted the freedom to explore life on my own terms before it was too late. It wasn’t my first time to experience a transformative revelation, but it was the first time I acted on it with a burn-your-ships finality.

For years I had taken classes on the side, trying to find my calling. (It wasn’t computer programming.) But this penchant for wandering made me uncomfortable. Stay put, keep your head down, focus on moving up the ladder: this was a surefire path to success, so I had been told. But some force propelled me to veer off the path. I did not yet recognize this magnetic pull toward life outside as a healthy creative impulse. I mainly felt like a failure. But I also worried that if I allowed the energy to fester, it would come back to haunt me later.

And so I began dabbling. I enrolled in art history and interior design courses. I took a painting class. On nights and weekends, I worked side gigs in art and fashion retail. I even organized an art show and a clothes drive for the employees in the consulting firm - anything to get me out of my cube and into creative connection with others.

At last, I settled on direct sales. What began as a random invitation to join a girlfriend for a recognition luncheon became a portal to a pivotal life experience. Without warning, I found myself wanting what she had: a sense of belonging and accomplishment, and a way to connect with others. And so I bought a starter kit for this direct sales cosmetics company and stashed this treasure in my closet, where it stayed for two weeks until I found the nerve to open up my “business in a box” and get to work. And thus began my self-inflicted saga of solo-prenuership.

My story is not unlike the story of Exodus: both the Israelites and I woke up one day (them after 400 years, me after five) to discover that we weren’t living in freedom, but servitude (theirs real, mine perceived, but you get the idea.) After being freed (them by Moses, me by makeup), we entered a period of wandering (them for 40 some-odd years, me for three). Our mutual release was followed by a protracted “wilderness” experience in which we had to learn to live off the land (them literally, me figuratively). For sustenance, the Israelites received manna from Heaven while I got by on a wing and a prayer (and manna, too).

Until now, I have avoided talking about this episode in my work history. People tend to make assumptions without understanding how challenging it is to succeed as an independent beauty consultant. Even my own family wasn’t jazzed about my decision. “Is this why we put you through college?” asked my dad. But false starts can also lead to new discoveries. That first business, which seemed like a bizarre left turn, exposed skills that I may not have discovered in time to refine had I remained in my cubicle.

In direct sales, I found an outlet for my hunger to connect with the public and an opportunity to share something of value with people across the socioeconomic spectrum. To keep my new business going, I had to sell strangers on a seemingly impossible dream on a daily basis. (Friends help, but if you’re not careful they’ll stop taking your calls.) And so it was on the strength of tenacity and ten leads a day that I earned the company’s iconic symbol of success within my first ten months. Not only did I somehow find myself driving the coveted pink car, but my achievement as the region’s top recruiter also landed on me stage at the annual convention. To my surprise, I was recognized as the number one recruiter out of approximately 2,000 sales directors.

My accomplishment was not selling lipstick; it was selling a promise of a better life, one that I believed existed even if I had no idea how to get there. Like Dorothy in Wizard of Oz, I was certain that somewhere over the rainbow dreams really did come true, and so over the rainbow I did go.

The beauty of beauty consulting was (and still is) the accessibility of this path for all, regardless of race, class and education level. This held enormous appeal to my egalitarian nature. But entrepreneurship proved much tougher than I expected, especially because in this model, you don’t succeed unless your team’s dreams also come true. Unfortunately, I found that the majority of women I recruited were unprepared for reality of the work it would take to accomplish their dreams. In a real sense, freedom became a bit of a burden for all of us.

For Americans, freedom is synonymous with life, liberty and the pursuit of happiness. It also encompasses the power or right to act, speak or think as one wants without hindrance or restraint; the absence of subjection to foreign domination or despotic government; and the state of not being imprisoned or enslaved. But these definitions were not on my mind at this time. Instead, freedom represented some place “out there” where work wasn’t hard, contentment always reigns and the rules don’t apply. The sort of freedom that soldiers fight to protect was so far beyond my understanding that I took it for granted. And so I wandered instead.

Like freedom, “wander” can mean a lot of things. It can mean to stroll or to move slowly away from a fixed point or place. It can mean leaving behind the safety of established institutions. To some, wandering connotes going morally astray. For example, when Pinocchio wandered into Pleasure Island, he was lured into some very bad behavior. And as all good fairy tales teach, aimless wandering can definitely lead to trouble. But then, so can freedom when you don't know how to use it.

To wander well, one must learn to check one’s own compass to ensure one hasn’t ventured too far off the path. That pink car I once drove was equipped with OnStar, but I never did figure out the navigation system. I was way too busy chasing the next lead and selling the dream rather than living it. On the outside I held it together, but internally I was all over the place, wondering how I could actually choose to leave behind a perfectly good paycheck for the illusion of freedom.

Not that it was all bad. Some of the women I met were cut from the same cloth as this company’s extraordinary founder, and several of those burgeoning entrepreneurs have since grown into successful businesswomen women who remain friends today. That said, by year three, merely checking my mailbox made me want to gag. I was drowning in pink newsletters I didn’t want to read and pink boxes I didn’t want to open. What was once benignly sweet had become cloying and nauseating, like an overdose of Pepto. And with that, my pink dream began to die. Freedom, for me, had became just another word for nothing left to lose.

When at last I declared defeat and said goodbye to both my team and the car, I was deep into my next calling: motherhood. Assessing the fallout of my unconventional path took awhile to sort out. But looking back, I believe I gained more than I lost in those years of wandering. Without realizing it, I had developed my own internal GPS system, an instinct that I hadn’t recognized before when I was following society’s traditional trajectory of success. Only then was I ready to leverage my new skills to sell a green dream instead.

Since 2005, I have continued to wander in search of a better way to live and better ways of doing business. I’ve written extensively about corporate social responsibility and sustainability communication, as well as my own internal conversion from consumer to sustainer. What I haven’t yet written about is how it feels to venture back into the world of full-time work. Was it real or was it a dream, those many years of wandering?

Not only was it real, I’ve got the newfound sense of freedom to prove it. Not the kind that looks like a bunch of free time to pursue my whims, but freedom with healthy boundaries, attainable goals and beliefs that I didn’t inherit so much as inspect, challenge and ultimately claim as my own. All that wandering had prepared me for the adventure of joining a team again, but this time with full grasp of my own identity and the resources of an institution. That’s another kind of freedom altogether.

In this next chapter, I’m embracing the opportunity to use the abilities I acquired in the wilderness to guide the world’s biggest brands in connecting with the public. In these rapidly changing times, there’s no roadmap for where we’re going, so leaders and institutions must rely on good counsel to help them adapt. Even Lewis and Clark needed Sacajawea to successfully carve a route to commerce. As history has proved many times over, explorers can open up new territories, but they can only take society so far. From there, it’s up to the pioneers, the innovators, the settlers and the wanderers to create a civilization.

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