Undaunted by Difference: How to Go Your Own Way, Smiling

Who am I? Who do I want to be? How should I spend my time?

Questions we’ve all heard, thought, and yet, still intimidating stuff. Existential inquiries like these can cause even the most grizzled philosophical veterans to cringe because the truth is that even those on in years continue to struggle with the answers. Who we are and who we want to be is often a moving target, and as a result, so is how we should spend our time. The answers aren’t static, they continue to change as we grow as human beings. Further complicating the issue is the fact that discovering our personal answers to these questions is only the journey’s starting point. Once we figure out who we are, who we want to be, and how we should spend our time, we learn that the grand challenge really is living the discovery.

"What man actually needs is not a tensionless state but rather the striving and struggling for some goal worthy of him. What he needs is not the discharge of tension at any cost, but the call of a potential meaning waiting to be fulfilled by him."

-Viktor E. Frankl

Take a vignette from my own life. One that repeated itself more mornings than I’d care to admit.

As sunrise crested the horizon, one eye cracked open, and anxiety stretched its legs before working its way to settle into its usual nook in my gut. I tugged the sheets tighter, fighting sunlight and the thought that I had to get up and get ready to be somewhere else, as I had many days this past year. About an hour later, my feet hit sidewalk, edging their way toward the office to wait patiently and board a packed but silent elevator—21st floor please—to open office doors and be greeted by the familiar echo of “How are you doing?” “Good” without any elaboration on either side. As I sat down in my chair, heads ducked unceremoniously into offices, and the thrum of fingers on keyboards began to rise as if on cue. Leaning back, I reflected on what life might look like over the next forty years, collecting bi-weekly paychecks from a high rise as money-manager “on his way to the top.” As I turned my head away from reflections and toward the glowing blue screen atop my desk to welcome my Monday flood of tasks, a thought slipped into my head: “Forty more years… is this really all there is?”

At this point, I was fresh from school, ready to put my fancy degrees to work and impress the world. It didn’t take long to find that the whole thing I had been building to, the corner office in a high rise, was a trap. I wanted to do something way different. But I still struggled to cut the corporate cord. Paychecks were steady and so was rent, plus, what would my friends say? How would I explain all those years of schooling and tuition to my parents? I finally had a sense of who I was and where I wanted to go, but it was turning out to be stupid hard to act on the discoveries. This is perhaps the greatest challenge of the aspiring entrepreneur, and unfortunately, among the least discussed: simply doing something different.

“The moment one definitely commits oneself, then providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one's favour all manner of unforeseen incidents, meetings and material assistance which no man could have dreamed would have come his way. I have learned a deep respect for one of Goethe's couplets: ‘Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it. Begin it now.’”

-William Hutchison Murray, The Scottish Himalayan Expedition

How much have you thought on the big questions above? Are you diligently working on the answers or have you begun to implement them?

If you still count yourself among the former camp, take comfort: many of us choose our path because it is what our parents chose, what school recommends, or simply because it’s the path everyone else is walking. The truth is that most of us are just trying to keep pace with our friends, or, once we’re a little older, to “keep up with the Joneses.” Noises emanating from the unknown tend to sound awfully scary, and besides, who are we to know better than the rest of the world? There’s a certain coziness to hopping onboard the bus for a field trip with a pre-scheduled itinerary. The fact that you are now critically considering your answers is the important part. Don’t live your life on autopilot.

If after some meditation, you decide that the cleanly-graded, safely respectable path is the way for you, then bravo. Well done. Does becoming a doctor or lawyer or holding down that corner office with cushy retirement package seem the right way? By all means, full steam ahead. Self-discovery is a journey that requires courage and thus deserves commendation—not to mention the fact that that there is no “right” destination.

That said, you can also stop reading this blog post here, you’ve completed your task for the day.

If, however, you find the traditional path somewhat lacking in style, purpose, or excitement, take a line from the late and great Billy Mays: “But wait, there’s more!”

Want to build your own e-commerce boutique, start a roofing company, or translate ancient Sumerian glyphs into witty bumper stickers for the modern consumer? Kudos to you on your personal discovery as well. Learning that you want to become an owner instead of just an operator, truly feeling that you want skin in the game for your work decisions as well as your personal life, you’ve officially opted to join the ranks of movers and shakers. The world needs people to dream up highways before the engineers can set to work building them. It’s a sexy way to go. Of course, you should also realize what this means. That highway you’ve dreamt up? As of yet, it only exists in your imagination. Mentally prepare, then, as you take the first cut through the trees only to hear the quiet sniggers of strangers and friends spectating the idiot who seems hopelessly lost in the forest.

“Never give in. Never give in. Never give in. Never, never, never—in nothing, great or small, large or petty—never give in, except to convictions of honor and good sense. Never yield to force. Never yield to the apparently overwhelming might of the enemy.”

–Winston Churchill

As you’ve likely surmised, one of the greatest challenges of going your own way in business is unrelated to cashflow or any other accounting metric: it is the eight-hundred-pound gorilla of feeling different. Humans are hierarchical creatures by nature, so in making the decision to carve your own path, you’ve chosen to walk the mental minefield of “but Jack and Jill are doing,” and as you take your first steps into the fray, you will inevitably nose a few of these buried treasures with your big toe. Social comparisons, for the founder, can create an awful paradox wherein you feel simultaneously fulfilled by your work, but emptied when few understand it. They can instill a brooding sense of loneliness that strikes when people recognize your difference; an insidious gap that, at its worst, can make you question the worthiness of your cause—especially in the startup stage. Our job, as entrepreneurs, is to become experts in combating this special flavor of fear.

“What really frightens and dismays us is not external events themselves, but the way in which we think about them. It is not things that disturb us, but our interpretation of their significance. Stop scaring yourself with impetuous notions, with your reactive impressions of the way things are; because things are not as you suppose."

-Seneca

The truth of navigating social and professional differences, fortunately, isn’t so bleak. Revisit the following thoughts whenever you feel loneliness in the pursuit of your dreams:

1.       Bravery is conquering fear, not its absence.

The fear of difference is natural. We all check ourselves against our peers and keep up with the Joneses. We need some way to measure our value, to know where we stand, to feel important. The differences between us and our neighbors strike us more than the similarities, and it’s natural to wonder if we’re in the wrong when things don’t match up. Don’t let it deter you. Press on anyway.

2.       You are not, and have never been, alone.

Far from being alone on your journey, loneliness while working toward self-determination is a hill which great minds have climbed for thousands of years. It’s a hill they still climb today. A good number of these heroes have even recorded journals of their journey for you to use as a guide along your ascent. So, recognize your impression of loneliness as just that, merely an impression. On this path strides the greatest company you’ve ever had.

3.       Resources for strengthening your resolve abound. Utilize them.

Take a few examples I’ve read over the years. Tim Urban has a phenomenal blog on navigating self-conscious tendencies, where he illustrates with a twist of humor the way we have evolved to crave inclusivity and how to surmount these “Mammoth” instincts that often mislead us today. Tim Ferriss has generously compiled an archive of Seneca’s wisdom, one of the greatest of the Stoic thinkers, to train your mind to temper judgment and take reasoned action. Seneca’s tools are far from the ivory tower and are written for use in everyday life, as showcased through his letters of counsel to a young friend, Lucilius. Another great resource in this this vein is the personal journal of Marcus Aurelius, the last of the Good Roman Emperors. Tools for growing your mind, strengthening your resolve, and finding inspiration are available like never before. Make the most of it.

My friends and I have a fun Sunday hangover game: try and remember something embarrassing someone else did last night. We can’t, most of the time. Thinking back, we realize we were too caught up in what we did or said ourselves. It’s a wonderful cure for anxiety. Remember that when you strike out on your path. If everyone is only thinking of their own actions, who really cares what you do?