Why I'm Stubborn

Why I'm Stubborn

Months before leaving my previous company to go off on my own as a fulltime debate and public speaking coach and eventually starting LearningLeaders, I had the chance to speak with a notably successful entrepreneur. They shared many strategic and tactical ideas, shared stories, and also pointed advice. Reviewing my notes a few months ago (which was five years since that conversation), I came across a memorable comment:

“If you aren’t getting rejected on a daily basis, then your goals for your business aren’t scary enough. If you aren’t disagreeing with yourself on a daily basis, then your goals for yourself aren’t scary enough. If everything is going smoothly, you either need to set your sights higher, or something you don’t know about is terribly wrong.”

Reflecting on this five years and a few months later, my thinking has changed a bit from when I first heard it. My initial reaction five+ years ago was, “Yeah! Yeah! Rah Rah!” It’s an exciting sentiment and one which perhaps my DNA gravitates towards naturally: evolve or die. In spirit, I want to agree with this guidance: "Always aim higher. Always challenge yourself. Always question yourself." It’s an optimistic outlook on life and one that I generally share - constantly challenging yourself to grow and improve.

Five years on, though, the word “enough” is where I hold issue with the entrepreneurial advice. The word “enough" really says to me there can never be an ambitious enough goal. At the start of a project, it is perfectly regular for others to reject your thoughts and premises. However, once a project begins to gather some steam, many (not all) of the critics will begin to slowly become converts. It’s the way of the world. At that point, you no longer have the pain of rejection on a daily basis. And the advice implies at that moment, it is the moment to create a new goal and set your sights immediately higher.

Upon hearing it the first time, this made sense to me, though I feel differently today. Working doggedly towards building a future world that you imagine to be better than the present one requires some degree of consistency. If the goal is always changing at every step of the journey, only the most ardent of adventures would stay with you on such a quest for any extended period of time. While the trail and path is unknown because it lies in front, the summit in focus should remain consistent, to whatever extent possible. It’s no wonder that most people don’t like “changing goalposts.” Once that summit is mounted, I don’t disagree with setting one’s sights further down the mountain range for a new peak. This is fantastic. Though I think it should be that moment - not the one where others stop rejecting your premise - that is the moment to fish out your spyglass and raise it to the skies again.

On the flip side, what to do if you’re halfway and realize that your goal isn’t likely to be in reach. I assume I differ from most here in my perspective: I want to continue to pursue the goal regardless if I’m behind schedule, unless mortal peril is the likely outcome. If summiting the mountain in a lightning storm is the only option, I’m against it. I’d rather swallow my pride than risk the lives of myself and my traveling companions. But if the alternative is to wake up earlier and muster an extra 6K one morning, or find a different route, then I’m game.

I find that once you are behind schedule and still doggedly determined to reach your goal is the moment you are likely to find within yourself something you didn’t know you had. That might be perseverance, creativity, or even willingness to break completely from your patterns of behavior in the past. Radically re-thinking what it means to reach a goal is the definition of innovation. How are we meant to innovate in the absence of constraints? No one can deny the journey is far simpler when the plan goes off without a hitch. But simple staircases don't fashion accomplished adventurers.