Advice for Leading a Successful Outdoor Life


Last week, I gave the address at the commencement ceremony for the Rocky Mountain School of Expeditionary Learning. It was a great exercise in trying to figure out what advice I would have given 18-year-old me a couple decades ago, based on how things have turned out so far. And, of course, asking myself, “Do I actually know anything yet?”

The full text of the speech appears below.


Greetings and congratulations, graduates of the class of 2018.

My name is Brendan Leonard. I’m an author, a magazine writer, an illustrator, a filmmaker, and public speaker. I was not voted Most Likely to Succeed in my high school graduating class. I was voted Class Clown. But life surprises us all, and today, I’m going to talk to you about success.

Two weeks ago, I was climbing Mount Shasta in California with a pair of skis on my backpack. About halfway to the summit, I sat down in the snow, enjoyed the view, caught my breath a little bit, and took a second to be grateful that what I was doing was part of my job. I would say I’m a lucky person to get to climb mountains and ski on the clock, but I don’t think it was luck that got me there—it was work. Also, I spend 95 percent of my workdays answering emails, just like everyone else. But I decided on that mountain that because I sometimes get to go on adventures and write about them for work, I am successful.

Maybe before we get any further into this speech, it’s worth noting that I drove here in a $2,500 car with 200,000 miles on it. Just so we’re clear that the word “successful” can mean a lot of different things. When I was in your shoes about 20 years ago, about to receive my diploma, I had a much different idea of what my career might look like. Also, I almost never wear a tie unless someone dies or gets married, so this is also awkward.

When I was 17 years old, at the beginning of my senior year at a public high school in a small town in Iowa, my guidance counselor, Mr. Hurst, and I sat down in his office to talk about my future. Mr. Hurst asked me, like he asked the rest of the students in my class, what I thought I might want to do after high school. I took a few guesses: optometry, physical therapy, maybe anesthesiology. Medical professions. Good-paying careers that smart people pursued, I thought. And I would probably be able to afford a nice car someday.

Here’s a thing no one tells you when you’re graduating high school: you don’t know anything about anything.

Actually, my dad very gently told me that. But at the time, I was too full of youthful hormones to listen to him. And you certainly don’t have to listen to me if you already know everything, like I did when I was your age. But I’ll tell you, the time when you don’t know anything about anything is one of the most wonderful times of your life. Certainty is low, and possibility is infinite. Enjoy it while you can. Sometimes I miss those days, and that feeling.

I still don’t know much, but a few members of your faculty are under the impression that I know a few things worth talking about, so here we are.

What I’m going to tell you today is mostly about work, because that’s what you’ll likely spend a lot of your waking hours doing over the next 45 years.

We have a popular saying in America, which goes, “Do what you love and you’ll never work a day in your life.”

I’m self-employed, which means I work for myself and I do what I love, and I’m here to tell you, that saying is a load of crap. Work is work. If it wasn’t work, it would be called fun. Even your dream job is still a job. If you enjoy about 30 percent of your work, and you can tolerate the other 70 percent, I think you’ve beaten the game. I’ve created my own dream job, and I can tell you, I only like about 30 percent of it.

Instead of focusing on doing what we love, I think we should focus on loving what we do. I have not liked 100 percent of any job, whether it’s scrubbing pots and pans or writing my weekly blog. This is an important distinction, both in work and in life.

Loving something is different than liking it. For example, it’s very probable that your parents love you. But trust me, they don’t like you 100 percent of the time.

Since I was 15 years old, I’ve been a dishwasher, a busboy, an assembly line worker, a day laborer, a bartender, a janitor, and a newspaper reporter. I’ve picked rocks out of cornfields, mowed lawns, worked on road construction crews, and once got paid to swim in a golf course water hazard and retrieve balls from the bottom. In my current job, I don’t have to clock in or clock out or wear a uniform, but I remember everything I learned in those early jobs, because some things are true whether you’re taking trash out at the back of a restaurant or writing a story for Outside magazine.

In my line of work, you hear a lot about talent, which is an idea I think we’ve mostly invented to give ourselves an excuse to be lazy. Here’s why: if you see someone doing something really well, and you say it’s because they’re talented, that means you think they’re somehow special compared to the rest of us. It also discounts the tremendous amount of work they’ve done to get to where they are.

Research has shown that talent is nothing without hard work. I choose to believe in hard work, and not so much believe in talent. I put it this way: There are no special people, just people who put in enough hard work until something special happens. I can promise you one thing: whatever you choose to do for a career, if you work hard at it, eventually, special things will happen. They may not happen as quickly as you’d like them to, and they may turn out to be completely different from the special things you imagined at the beginning, but they will happen.

I’m going to share with you six pieces of advice today: the first three I learned in my small hometown in Iowa. The last three I believe can take you anywhere in the world.

The first three things I’m going to tell you don’t require specialized training, and anyone at any job can do them, whether their job requires a Ph.D, or no education at all. These three things seem incredibly simple, but believe it or not, they’re not practiced as much as you’d think. They’ll help you stand out in school, at work, and be a better friend and spouse. These three things are: Be kind. Show up on time. And do what you said you were going to do. I believe they’re better than being talented. Because it takes zero talent to be kind. It takes zero talent to show up on time. And it takes zero talent to do what you said you were going to do.

Early on in my career as a writer, a couple magazine editors told me stories about brilliant writers who were impossible to work with. They wrote incredible stories, but caused the editors headaches by missing deadlines and being completely unreliable. These editors impressed upon me that they’d rather work with a reliable writer than an unreliable writer any day, no matter how brilliant they were. Since no one had accused me of being brilliant, I decided to be reliable. I didn’t miss deadlines, I turned in the stories I said I would write, and I tried to be pleasant to deal with. And it worked, just like it’s worked in every job and gig I’ve had. I’m not sure Phil, my boss at my first high school dishwashing job, knew his expectations were so similar to a New York book publisher, but they turned out to be.

Think about it this way. If an airline isn’t on time, we’re unhappy. If an airline doesn’t do what it said it would do, like deliver our checked baggage to the city we’re flying to, we’re unhappy. If an airline isn’t kind to us, we’re unhappy. If an airline fails at any of these three things more than once, we take our business elsewhere. So, if you expect these things from a business, shouldn’t you expect them from yourself?

That’s the end of my practical advice for you. My final three pieces of advice are very impractical, because I believe impracticality is the principal element of a fulfilling life.

Being that this seems like a very good, progressive high school, I assume most of you have been told by at least one person that you can do anything you want to do in life if you dedicate yourself to it, and that you should reach for the stars. This is true.

If you’ve ever told someone about a goal that reaches for those proverbial stars, you may have also noticed that most people respond by advising you about the huge odds against actually reaching the stars, and that maybe you should think about something more practical. For example, the odds of you becoming an astronaut are not good. But the odds of you becoming an astronaut are much better if you don’t listen to people who tell you how hard it is to become an astronaut, and instead choose to focus on the necessary steps to becoming an astronaut.

So I advise you first to dream big. Look past typical job titles and find people doing something similar to what you want to do. You have more information at your fingertips than anyone in the history of the world, and someone is out there doing things that most of us didn’t think could be done five years ago. And they’re not being practical about it at all—they’re dreaming big, like you should.

My second piece of impractical advice to you is to learn how to persist. Big dreams come from inspiration, but making dreams come true requires work. Getting inspired will get you about five percent of the way to your goal. The other 95 percent comes from grinding it out, and it will not be fun sometimes. You’ll want to give up, and you’ll find a million reasons to justify giving up. Persistence is a very simple skill: all it requires is not giving up.

On a whim over the past three years, I have become an ultrarunner, which means I’ve run 50 miles in a single day on four different occasions, and 100 miles once. Although I don’t advise it because it’s not what most people call fun, it does provide a pertinent illustration of dreaming big and persisting. The dream is: an idiot, such as myself deciding that they want to run 50 or 100 miles.

Running 100 miles requires a lot of steps—226,000 steps, according to my watch. In my experience, about 10,000 of those steps are fun. The rest of those 226,000 steps are pure persistence, through blisters, foot and leg pain, chafing, indigestion, fatigue, sleep deprivation, and sometimes mild hallucinations. I’ve discovered that it’s a lot like wanting to be a writer when you grow up, or, I’m guessing, being an astronaut or even a small business owner: you have a dream one day, and then you spend years working toward it, many times only motivated to continue by a faint memory of that first dream of seeing yourself cross a finish line, or sign a book deal, sit in a space shuttle, or on the opening day of your shop. You start because of a dream, but you finish because you become good at talking yourself out of giving up. This is persistence. People may call you stubborn—that’s OK. Stubborn is just a dirty word for driven, and driven people get things done.

My final piece of impractical advice for you is this: Practice gratitude as much as you can. It’s scientifically proven to make you happier and help you live longer. I think we have a very screwed up definition of wealth in this country, and we’d all be better off if we had some perspective. I know this, because I’m rich. But I’m rich only because I think that if you can afford to pay someone else to make you a cup of coffee, you’re rich.

We spend a lot of our lives on social media nowadays, and it’s very easy for us to compare ourselves to others and wish we had more, or to be jealous of someone else’s life that looks perfect, instead of being grateful for what we have. In my line of work, I meet a lot of people who spend large chunks of their lives hopscotching around the world, and if I compare my own career to theirs, it would be easy to feel unsuccessful. But I have perspective, and getting to spend a workday climbing a mountain means I’ve been successful beyond anything I thought was possible during my senior year of high school—even if I’ve still never owned a car that didn’t have 100,000 miles on it when I bought it.

So, as you end this chapter of your life and begin a new one, I encourage you to dream big, to work hard, and to be kind. Show up on time, follow through, and teach yourself to persist. Most of all, don’t look at someone else’s idea of success and assume that’s what you want. Success is different for everyone, and in my experience, has nothing to do with the amount of money you have in the bank or a shiny new car. If you focus daily on evolving as a person and improving as a person, success is a moving target. And that’s a good thing.

Wherever you go from here, I encourage you not to try to be a success in 20 years, or 10 years, or even five years. Try to be a success tomorrow, and the day after that, and the day after that, until all those days add up into years. I wish you not luck, but whatever it’s called when your dreams, work, and persistence add up to something that looks like good luck. Thank you.



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