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The courage to speak. And the will to keep speaking.

Updated: Oct 19, 2022

Over the weekend while helping my 6th grader research Dr. Martin Luther King Jr., I was struck by an interesting fact about him. He was jailed 29 times. 29 times.

Most of his arrests were related to civil disobedience, and some were on exorbitant charges like driving 30-mph in a 25-mph zone. When he was arrested as part of the Montgomery Bus Boycott in 1956, his home was bombed four days later. Another arrest landed him in Birmingham City Jail, where he wrote a powerful letter that stated, “Injustice anywhere is a threat to justice everywhere."

MLK Jr was nearly killed 10 years before his assassination by a woman at a book signing in a department store. She stabbed him in the chest with a seven-inch letter opener. The assassination attempt was the inspiration for his last speech titled "I've Been to the Mountaintop," which he delivered the day before he was killed. In his address, he said he was happy that he didn't sneeze when he was stabbed, as he wouldn't have been present when the Civil Rights Act was passed.

The courage to speak. And the will to keep speaking.

In The Obstacle is the Way, Ryan Holiday illustrates Stoic lessons about will with a story about Abraham Lincoln and his struggles with depression. That dark despair gave him compassion for others, patience to continue to fight against slavery, and not give into hopelessness on that journey.

Holiday states, “Placed in some situation that seems unchangeable and undeniably negative, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That’s will power. But that needs to be cultivated. We must prepare for adversity and turmoil, we must learn the art of acquiescence and practice cheerfulness even in dark times. Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength. Try “God willing” over “the will to win” or “willing it into existence,” for even those attributes can be broken. True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.”

The courage to speak. And the will to keep speaking.

When I think about the leadership characteristics I strive to embody, will is at the top of the list. Cheerful grit is what keeps us committed to long-term pursuits. Whether climbing a mountain or challenging the “that’s the way we’ve always done it” mindset, the goal is to explore beyond our comfort zones to carve new paths.

The courage to speak. And the will to keep speaking.

Is this your cup of tea? Cool, would love to connect with you (but I’ll be drinking iced coffee, not tea) to geek out on leadership and business transformation. And here are a few of my favorite resources that are shaping the way I’m thinking about these topics:

The Obstacle is the Way by Ryan Holiday

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