Overcoming fear, hardship and challenges to experience everything life can offer.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better.

The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly;

who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions;

who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly,…”

– The Man in the Arena: Citizenship in a Republic, Theodore Roosevelt

San Juan Heights is located near the city of Santiago in Cuba. A force of around eight hundred Spanish troops were tasked with the order of defending the position against an American attack.

The Battle of San Juan Heights began with artillery fire at the Spanish entrenchments. The Rough Riders marched towards the base of Kettle Hill, taking cover along the riverbank to avoid the returning Spanish shells.

The Rough Riders were a regiment of voluntary cavalry, one of three raised during the Spanish-American War in 1898. Its commanders were Colonel Leonard Wood and the future president Theodore Roosevelt.

The regiment mostly consisted of men from southwestern ranches who were skilled in horsemanship. Cowboys, miners and hunters, the volunteers came from a diverse range of occupations.

The Rough Riders were pinned down under a heavy line of fire and Colonel Roosevelt was disappointed with the lack of direct orders from the commanders. At last, there was an order to assist with an assault on the hill’s front. American troops began to slowly move up the hill whilst firing on the Spanish positions. However, due to the Spanish reinforcements and the steepness of the hill, it was difficult for the American troops to effectively to return fire.

Recognising this problem, Colonel Roosevelt advised the captain to issue a full-scale charge of Kettle Hill. The captain refused and repeated orders to hold the position.

Frustrated, Roosevelt declared himself the ranking office and ordered a charge up Kettle Hill. This was an extraordinary act of defiance. A man of action, Roosevelt knew how to take initiative when others, paralysed with doubt, would hesitate and hope for better odds.

“Far better it is 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 the gray twilight that knows not victory nor defeat.” — Theodore Roosevelt, The Strenuous Life

Roosevelt rode off immediately on his horse and rushed up the hill waving his hands and cheering his soldiers on to follow him. The Rough Riders, inspired by their leader and stirred with enthusiasm and excitement, sprinted up the hill after their colonel. The advance was covered by three Gatling guns and Roosevelt noted that this covering fire raised the confidence of the soldiers.

Roosevelt’s bravery paid off. Kettle Hill was taken and the rest of Juan Heights was captured shortly afterwards. The United States would go on to win the Spanish-American War, dimming the last light flickers of the Spanish Empire.

The charge up Kettle Hill was a tremendous demonstration of individual heroism. Roosevelt clearly thrived on danger and adventure. This was again obvious when he agreed to join the expedition to explore the one thousand mile ‘River of Doubt’ located in a remote area of the Brazilian Amazon basin.

The expedition started in Cáceres, a small town on the Paraguay River, with Brazilian porters, the two leaders, Roosevelt’s son, and American naturalist George Cherrie. They traveled to Tapirapuã, where Rondon had previously discovered the Headwaters of the River of Doubt. From Tapirapuã, the expedition traveled northwest, through dense forests and then later through the plains on top of the Parecis plateau.

They reached the River of Doubt on February 27, 1914. At this point, due to a lack of food supplies, the Expedition split up, with part of the Expedition following the Ji-Paraná River to the Madeira River. The remaining party then started down the River of Doubt.

‘Believe you can and you’re halfway there.’ — Theodore Roosevelt.

The expedition suffered problems from the beginning. Malaria was a constant issue, the canoes were often destroyed in the rapids, requiring days of to build new ones and there was a strict lack of food. There was also the threat that the Cinta Larga natives, who were shadowing the expedition, would kill the entire team for their goods and tools. This fear turned out to be appropriate, as expeditions in the 1920s would come to realise.

The team had only made it a quarter of the way down the river and everyone was exhausted, starving and feverish. The continuous labour that the canoes required after going through the rapids was taking its toll. Roosevelt had suffered a wound to his leg that had become infected. The party feared for his life every day. With help from rubber-tappers, men who worked in the forests to take advantage of the new rubber market in the States, the expedition managed to make it to the end.

Two men died, one drowned and the other was murdered. The murdered was left behind in the jungle and it was presumed he was dead too. Sixteen of the nineteen returned. Roosevelt was severely weakened and his health would never fully recover. He died five years later in 1919, aged 60.

The character of Theodore Roosevelt was truly astonishing. It is clear to see how he became the youngest president in the United States’ history.

To march towards certain danger regardless of the consequences requires immense steel and determination. Roosevelt was an adventurous spirit who longed for new challenges. He did not fear the unknown rather he cherished it. He dared to be great and that meant having the courage, strength and nerve to overcome the terror within him.

“There were all kinds of things I was afraid to do at first, ranging from grizzly bears to mean horses and gun fighters, but by acting as if I was not afraid I gradually ceased to be afraid.” — Theodore Roosevelt.

Roosevelt constantly spoke about not living a soft existence of pleasure and apathy. He advocated not giving into fear, for being afraid means the act is worthwhile and that beyond the fright lies a greater version of yourself. He firmly believed that by facing your fears, you gradually cease to become fearful at all and instead develop into a formidable character.

This was a mantra that Roosevelt lived by and his actions and experiences throughout his life certainly attest to it.

‘The only alternative to a shuddering paralysis is to leap into action regardless of the consequences. Action in this spirit may be right or wrong in conventional standards. But, our decisions upon the conventional level must be supported by the conviction that whatever we do, and whatever “happens” to us, is ultimately right. In other words, we must enter into it without second thought, without regret, hesitancy, doubt or self-recrimination.’

Alan Watts — The Way of Zen

Harry J. Stead

Thank you for reading!

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by 335,210+ people.

Subscribe to receive our top stories here.



Please enter your comment!
Please enter your name here