Theodore Roosevelt was never afraid to fail. In fact, he often wore his failures as badges of honor. To him, the attempt, the effort, and the sheer pluck of involvement was what really mattered in the end, “Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much nor suffer much because they live in the gray twilight that knows neither victory nor defeat.”
Though he enjoyed many successes throughout his career, he had his share of failures. He never allowed them to stymie his sense of responsibility and calling. He was often knocked down, but never out.
In addition, he was eager to learn from his mistakes. On this day in 1905, when his administration had lost a strategic legislative battle on the floor of the Senate, he called each of the men who had led the opposition to the White House. Expecting an angry tirade or an hysterical harangue, the Senators were surprised when Roosevelt anxiously gathered them around his desk and asked for their advice. “How could I have handled this bill better? What did I say or not say to cause you to oppose it? What should I do in the future to better advance my principles?” The men were stunned. There was no recrimination. There were no lectures. There were no threats. Instead, they found in the President an eager learner—ready to accept the blame for his own shortcomings and then to try to move on and do better on another day. One of them later confessed, “I learned more about leadership and greatness in that one incident than in all my previous years in politics.”
Elihu Root, who served as Roosevelt’s Secretary of State, called him “the most advisable man I ever knew.” “If he was convinced of your sincerity,” said the Progressive leader Albert Beveridge, “you could say anything to him you liked. You could even criticize him personally.” And the author and social reformer Herbert Croly remarked that he had “never met a man so eager to learn from his mistakes—or even so ready to admit them. It was as if he had no ego.”
Roosevelt was not simply a hopeless romantic or and unrealistic optimist in this regard. Rather he was a man who was secure enough in his calling and purpose in life to remain undeterred by obstacles along the way—be they great or small. His son, Kermit explained, “Some men have a strong sense of destiny. I cannot say that Father could ever fully identify such sentiments in his own experience. But I am quite certain that he knew what to work toward. Whether he ever actually attained to it was another matter altogether—and one of little concern to him.”
For Roosevelt, true leadership not only involved a strength of character that was unafraid to admit failure, was willing to learn from error, and was quick to accept wise counsel, it also involved a sense of calling that was able to integrate such virtues into life with real confidence. For him, failure was merely the backdoor to success.