“My success so far has only been won by absolute indifference to my future career.” (Theodore Roosevelt)

Theodore Roosevelt is one of my favorite Presidents. He won the Medal of Honor as well as the Nobel Peace Prize. Before his fiftieth birthday he had served as a New York state legislator, the under-secretary of the Navy, police commissioner for the city of New York, U.S. civil service commissioner, the governor of the state of New York, the vice-president under President McKinley, a colonel in the U.S. Army, and two terms as the president of the United States.

In addition, he wrote 43 books, innumerable magazine articles and was hailed as utterly remarkable by many as being capable of conversing intelligently on a wide range of topics from botany to classical history. He was a phenomenal human being.

And while he was a very energetic and ambitious man, he was a not given to promoting himself or being a high achiever for the sake of elevating himself over others. Rather, he possessed a very bold resolve when it came to those things he regarded as Absolutes. He maintained a lifelong romance with his wife and from about 1876 on he taught a Sunday School class whenever the opportunity arose¹.

While I can point to several things that I find both inspiring and intriguing about Roosevelt, it is the quote I have referenced at the beginning of this article that I find especially significant when it comes to the mindset of the “artist.”

I happened upon this thought as I was watching a portion of Tolkein’s “The Hobbit” where Bilbo is approached by Gandalf with the prospect of going on an adventure. Bilbo’s initial response is an overly cautious disposition described by words and phrases such as “nasty,” “uncomfortable,” and “they make you late for dinner.” It’s the kind of sentiment represented by the antithesis of Roosevelt’s quote. Where Roosevelt proceeded based on conviction –  indifferent to how it would affect his future – others come to a standstill, paralyzed by thoughts of failure and humiliation.

Bilbo’s comments are funny, but at the same time it’s kind of tragic. Many will dream, but few will take that path that’s required to fulfill that dream. Or, some will embark on a road that seemingly justifies what is, in fact, an irresponsible and selfish perspective, believing that a myopic view that dismisses relationships and responsibilities as obstacles rather than priorities is needful in order to “claim the prize.”

Fact is, it’s not always a clear cut line. Some will dare, but only to the extent where it becomes uncomfortable and fall short of what’s needed in order to really progress. Others will be reckless and even if they do succeed, the goal they reach is enjoyed alone rather than in the company of those that matter. There’s a balance that needs to be achieved that requires both wisdom and flexibility. It’s not a callous indifference to the practical realities that are out there, nor is it a debilitating sensitivity to that which cannot be wholly known or controlled. It’s somewhere in the middle and while it’s subjective to a degree, there is one thing that can be held on to that strikes me as a practical starting point.

There was time when there was no such thing as health insurance. IRA’s had yet to be concocted. Your prospects were pretty much dictated by your ambition and work ethic. Nothing guaranteed, but nothing beyond the realm of possibility. You were not limited by your class, only by your imagination.

That was the world viewed by the pioneer and by the 16th century colonist. How would those individuals react to the 21st century entrepreneur who’s contemplating a self employed dynamic, but hesitates because they’re not certain they’re going to succeed?

I think their response would be two fold. First off, I think they would be impressed with how easily many are capsized by even the slightest breeze of uncertainty. These are people whose sustenance is affected by rainfall and sunshine. They can weed and plant and sow all they want, but at some point, they’ve got to depend on things they can’t control. I imagine they would be very willing to exchange their brand of anxiety with the kind of worry we struggle with in terms of bills and financial obligations.

Secondly, I think they would be somewhat sympathetic as far as recognizing the challenge and preparing accordingly. When they were confronted with the prospect of danger, they prepared for it. In a similar fashion, I imagine they would recommend you “prepare” however you could before you journeyed into uncharted territory

But as the conversation wore on, I imagine that both the colonist and the pioneer would at some point say “Go!” It wouldn’t be a dilemma. It would be nothing more than acknowledging the fact that you don’t progress unless you take a step forward. You’ve got try if you’re going to succeed. And If you’re going to try, then you have to accept that you will fail more than you will triumph. There are occasions when quitting seems logical. There are other times when compromising seems practical. But it’s the one who fails forward, who stays the course, who accepts the risk that ultimately breathes the air inhaled by those who genuinely live rather than exist.

Some confuse being responsible with being too cautious and others mistake courage for recklessness. Don’t be distracted and don’t be defeated. Simply keep moving forward and embrace every activity as part of the journey and know that you achieve more by being on the field than you do in the stands.

Before there was insurance, there was only life. But in the time before GEICO and in the culture we live in today, there’s a choice: Dare to win or refuse to try. I think Roosevelt said it best:

Far better is it to dare mighty things, to win glorious triumphs, even though checkered by failure… than to rank with those poor spirits who neither enjoy nor suffer much, because they live in a gray twilight that knows not victory nor defeat.²

Go get ’em!

1.”Carry a Big Stick”, George Grant, Highland Books, Elkton, MD, 1996, p170

2. “Brainy Quote”, http://www.brainyquote.com/quotes/quotes/t/theodorero103499.html, accessed November 15, 2013