How Loss Can be Positive — Theodore Roosevelt

Matt Lively
The Startup
Published in
3 min readJul 24, 2019
Theodore Roosevelt, 26th president of the United States. He claimed that his self-reflection in seclusion after devastating loss was “the most important educational asset” of his life.

The vast majority of people will experience major loss in their lives. Loss of loved ones, relationships, or major goals can be devastating to our sense of self and orientation in the world. But tremendous loss can be positively transformative. Loss and grief have served as crucibles for great figures in our history, and the best way to look at loss, especially when you’re experiencing it, is by viewing the transformative effects it can have on you and your capacity to impact the world. Personal loss empowered Theodore Roosevelt to effectively change and lead America. The source material for the following quotes and story is Doris Kearns Goodwin’s Leadership in Turbulent Times, a book that has personally influenced me and contains other presidential stories of resiliency, loss, and triumph.

On February 14, 1884, while Theodore Roosevelt was working as an assemblyman in the Albany legislature, both his wife and his mother died. Their unexpected deaths plunged TR into an emotional abyss, and that day the avid diarist wrote only “a large X”, and the words “The light has gone out of my life.” TR was always an unusually energetic person, but his grief threw him into a manic frenzy to pass reform legislation, working at a pace that shocked his peers and soon burned himself out.

The city boy moved to the Western frontier to mourn, and later, he would learn, to grow. His two years as a rancher riding his horse “sixteen hours a day” helped him to experience “his own healing, growth, and self-transformation.” He later acknowledged this period as “the most important educational asset” in his life. Coping with his loss in his own way, through backbreaking frontier labor and rigorous contemplation, allowed TR to explore the darkest parts of his soul. He emerged from his Badlands experience as a changed man. Its commonly agreed among TR scholars that this experience allowed him to be “able to interpret the spirit of the West as he did.” It is true that TR’s time as a frontiersman allowed him to relate to more Americans and to his time, made him a better military commander and made him more electable, perhaps it was critical to him becoming president. His loss and subsequent growth enabled him to lead reform, conservation, and other political efforts much more effectively because he better understood both himself and others. But the deeper message we can extract is that his experience of coping with loss gave him a much more primal and intimate connection with the human condition, and a much greater understanding of the universe and his role in it.

Theodore Roosevelt built the Panama Canal. He brokered the end of the Russo-Japanese War. He passed the Pure Food and Drug Act and established the Forest Service. He was an author, conservationist, explorer, historian, naturalist, policeman, politician, military officer, amateur ornithologist, boxer, and president of the United States. He was a recipient of the Nobel Peace Prize and the Medal of Honor. He was educated at Harvard and then Columbia Law School. He was, by all accounts, a renaissance man who spent his entire life learning as much as he possibly could. With all of that considered, we must give weight to the fact that he considered his two years being transformed by his profound sense of loss as his “most important educational asset.” Everything exists in pairs; the universe is dichotomous. From loss can come great, tremendous growth and gain. If we actively let it.

Matt Lively is an aspiring popular historian, to see his upcoming posts about history and future publications, you can subscribe to his blog here. He is launching his first book this September. Subscribe to be among the first to receive a free copy!

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Matt Lively
The Startup

I’m Matt Lively, a writer & grad student at UChicago. I post historical anecdotes or general articles related to leadership, history, and general life lessons.