🌪️ My new book is available for pre-order! Reserve your copy.

How to live like Theodore Roosevelt, even though you probably shouldn’t and can’t

I had the realization this morning that Theodore Roosevelt did a lot of things, but didn’t do any of them exceedingly great.

Theodore Roosevelt wrote over 35 books, including The Naval War of 1812 that served as the service manual of choice on American and British naval vessels for a generation. But despite writing more words than Shakespeare, I don’t think anyone today could name one thing he wrote or argue anything was definitively “literature.” They were good but not great or at the level of Mark Twain or Kurt Vonnegut.

T.R. exercised nearly every day and lived his self-proclaimed strenuous life. But most biographies and photos of him show a burly man who was strong but not “fit.” T.R. wasn’t sporting a six-pack. His heavy diet was rich in meat and potatoes. He did many activities, too, from Judo to boxing, horseback riding to tennis, and chopping wood to long hikes in the woods. But he was never an Olympic athlete at any of them. He was just pretty good at a lot of things at a time when most American men were undernourished and took upon a life no more physically active than what their work demanded (which could be a lot in a mill or on a farm).

Roosevelt lived a very regimented, timely schedule. He lived by his stopwatch and would cut conversations short or sign a piece of paper only to whir around to whatever was next on his itinerary for the day. That’s not a bad idea, but it can also be considered rude. “Sorry, we only have five minutes and it’s 4:59.”

Much of what we know T.R. for today was his conservation efforts, national parks and reserves, and other environmental work. It was all earth-moving in scope, but it came to fruition only as a result of being president. Roosevelt became president after McKinley was assassinated, and Roosevelt was only ever Vice President because everyone else around him in New York thought he was a rabble-rouser and wanted him stuck somewhere unimportant, like the vice presidency. His presidency was defined in a time when there were no wars, either.

I do not mean to diminish these accomplishments. He did a great many things, like fight in the Spanish-American War. But this “splendid little war,” as John Hay called it, was not exactly the meat grinder of WWI or WWII. So when we start asking, “How do I live a life like Theodore Roosevelt?” you have to recognize some hard truths:

  • The competition, so to speak, against other Americans at the time was lesser. More people are better educated, nourished, and prepared today than in 1900. For a rich dude in New York, he had a fair bit of privilege.
  • T.R. had ailments, for sure, like low vision and asthma. There is something to be said for his sheer grit at just barreling past these.
  • He wrote that his intense focus allowed him to accomplish so much in a day. There is probably something to this and something most people could emulate.
  • Roosevelt had the benefit of servants, a culture that did not demand he always be a “good” father, and loads of time. You and I do not have servants, and Roosevelt would not be 2024’s definition of a “good father” since he routinely left them alone with his sister and wife.

There are some things people today could do to live a life akin to Roosevelt’s strenuous life:

  • You could read more, likely by getting rid of your TV. But let’s be real, T.R. would absolutely have had a TV in his life. His political life would have demanded it and the time it consumed would have to come from somewhere.
  • You could probably garden, write, and produce other “scholarly” things by avoiding your phone, social media, and news sites. None of which he had, but he probably would have if he could because his job would have demanded it. Only so many newspapers could have been delivered daily to the White House.
  • You could be more politically active in your local community or volunteer places. But there’s a reason boards are full of people with money and connections. And there’s a reason why volunteering is done so much by the young and old and not much in between.

The more I think about it, I’m not sure someone like Theodore Roosevelt could exist today. Perhaps the closest we have is someone like Jeff Bezos or Elon Musk, and I don’t think too many people sit around thinking, “I wish I was one of those guys. Yeah. One of the most hated people on the planet.” But they have/had wealth and they do big things with it. Like spaceships. Remember, T.R. bought a ranch in North Dakota because he was depressed. That’s quite an outlet.

No, our culture today makes living a life like T.R.’s prohibitive for most people. It’s cost-prohibitive for most of us, and I don’t think anyone would trade being a good parent for the chance to traipse around the world.

There’s also a lot less low-hanging fruit to discover. Roosevelt got to explore the Amazon simply because no one else had. Is there any part of the world short of the bottom of the ocean anyone can say that about? And we see how deep-sea explorers are doing. Space travel is another possibility, but, again, back to Bezos and Musk. T.R. took a boat. Where’s your spaceship, smart guy?

You really have to wonder what someone like T.R. could have done if he had really focused in on one or two things in his life. What could he have written if he weren’t spinning out Harper’s Weekly stories for money in between running for office? Could he have been one of America’s leading military strategists if not for timing of his age during relative peace? And, you have to wonder: could T.R. have been president if he wasn’t already wealthy? Obviously presidents have come from nothing and risen to greatness, like Lincoln. But T.R. was already most of the way up the chain.

Theodore Roosevelt was a generalist. A polymath who liked lots of things and did lots of things. That’s not a bad way to live. On the whole, he seemed to have really enjoyed his life. That much is worth emulating.

You could go further and spend more time reading, painting, writing, or otherwise producing, but this is going to come with the obvious cultural opt-out required. You’re going to have to opt out of a lot of life that most people have fallen into, including a constant need for easy entertainment, driving all the time, and being comfortable with being the “outcast” who doesn’t understand some TV show or app.

All of which T.R. got to skip right by. In some ways, it’s probably harder to live a life like T.R. today simply because life demands so much that is just different. Inertia of employers, workplaces, family obligations, and more are just different. You probably can’t live a life like T.R. And, you probably don’t want to. It’s far better to zero in on what you’re good at or be comfortable as a generalist enjoying life for what that brings.

Want to know when stuff like this is published?
Sign up for my email list.

Photo of Justin Harter


Justin has been around the Internet long enough to remember when people started saying “content is king”.

He has worked for some of Indiana’s largest companies, state government, taught college-level courses, and about 1.1M people see his work every year.

You’ll probably see him around Indianapolis on a bicycle.

Leave a Comment