how to do hard things that actually matter

Summary

Theodore Roosevelt and JFK both got at the same idea: greatness comes from doing hard things on purpose. the version most people get wrong is treating “hard things” as a one-time event. run a marathon. do a cold plunge weekend. cool. that doesn’t actually change you.

in Killing Comfort I call it the hard things equation. it’s two parts:

1. pushing against your own desires. doing the thing you don’t want to do.
2. doing it consistently over time. years, not days.

the ultra-marathon you run once is a great story. it doesn’t restructure your identity. the daily run for ten years does. the moment a hard thing becomes a habit, it’s no longer hard. that’s the cue to find a new hard thing and start over.

how to use this:

• pick one area. don’t try to do hard things across five categories at once.
• define the daily action that’s against your current grain.
• commit to enough time horizon for it to become automatic.
• when it does, move on.

the targeting matters as much as the difficulty. hard things you don’t actually care about don’t compound. hard things aimed at the life you’re building do.

Transcript

why “doing hard things” isn’t enough

All right, let’s talk about doing hard things that actually matter, that actually move the needle, that build you into a better human, a better version of yourself, so your business can actually make progress. Okay, so I was doing some research for some content that I was putting together, and something I find interesting, you know, and I’ve been obsessed with this idea ever since I started writing the book in 2018. I started writing Killing Comfort, published it in 2020, and I’ve always been fascinated with the fact that there’s always some sort of historical context in which men of history are warning us about being too comfortable in some capacity.

So I’m going to go over these real quick, and then I’m going to dive into ultimately how to do a hard thing that actually moves you forward and not sporadic stupidity. Okay, so Theodore Roosevelt in 1899, he says, the highest form of success comes not to the man who desires mere easy peace, but to the man who does not shrink from danger or hardship.

Roosevelt was just huge on this stuff. You could go through many archives, listen to speeches, read them. He talks about doing hard things and how important it is. Then we jump to William James in 1906. He says, we must find the moral equivalent of war, something heroic that preserves honor and toughness without bloodshed. Now that was in 1906.

the historical warnings about comfort

Little did he know, World War I was coming, World War II was coming. But his main idea, now he just has like thousands and thousands of words where he expands on this topic. You can read through his speeches as well. But he talks about how war would actually harden men and make them better in some capacity because of the hardness that they got. They became more sharpened, if you will.

But he said, we don’t, he was basically saying, we don’t need war. Who wants war? I’m not going to desire a war to turn me into a tougher person or a better person. But he’s like, we need the moral equivalent of war. We need to find our hard things that are going to shape us without having to go to war. That’s what he means by that quote.

And then Robert Falcon Scott in 1912 says, make him a strenuous man. Now he was talking about how his son should be raised.

So he was trying to cross the Antarctic. He passed away in the process, but he was keeping a journal throughout the entire, entire thing. And what was so fascinating about it is he was keeping these journal entries even up until the point he knew he was going to die. And so this was one of his final messages to his wife about how his son should be raised. And he basically just like, that was it.

It was like, make him a strenuous man. That was about it. He didn’t say like, make him educated, make sure he is an explorer like me or make sure he’s an entrepreneur, which probably wouldn’t have been as much of the case or request in 1912. But it’s none of that.

He didn’t say any of those things. He’s like, just make him a strenuous man. He knew the rest of everything would work itself out. I think that’s awesome. George S. Patton, says better to fight for something than to live for nothing. Right. Like so many people are not mission oriented. He could see it back then.

what william james meant by a “moral equivalent of war”

If you don’t have a mission, you’re not trying to make an impact. You’re just going to wander in life. And so he said it’s better to fight for something to live for nothing. And then John F. Kennedy talked about this in volumes. You know, he had his famous speech where he talks about doing hard things. He’s like, we do these hard things because they are hard.

He talks about the moon landing, like we’re going to go land on the moon. Why? Because it’s freaking hard and we’re going to do it. That’s what we do as human beings. That’s how we make progress. He also has this piece that I highly recommend people read. It’s called The Soft American, written in Sports Illustrated. And he talks about the ultimate, like physical, like softness of men.

And one of the quotes is the physical hardness of the past, which built a strong people is being replaced by softness. And what’s funny about JFK is he was talking about things in that piece that were like, yeah, people like parking lots are full at high schools because people are driving to school. You know, it’s like he’s like, you’re soft, you’re driving, you know, things like refrigerators, all these like microwaves, basic conveniences we have now. He was just like, I can see it.

why you must choose hard things on purpose

It’s going to make people weaker and softer. And so here’s the deal. These days, as an entrepreneur, as a human being, you need to choose your heart. I know that life is going to hit you in the face and it’s going to be hard at some point for some reason. Now, sometimes life chooses the hard for you. But when things are good, you need to choose your own heart. You really do.

And the reason I think entrepreneurs need to do this and really everyone is because the better you are, the better everything else is. And you get better by doing hard things. And so if you want a better, bigger business that makes more income and impact, you need to yourself get better, right? You need to be working on yourself and you do that through doing hard things.

If you want to be a better parent, if you want to be a better leader, you want to be a better anything. You have to do the hard things. Now, I want to talk about the hard things equation because I do think that people are trying to do hard things these days, but they’re doing them sporadically and not frequently enough.

the hard things equation explained

So if I want to run an ultra marathon, no doubt you’re going to learn something about yourself. That’s a hard thing. But I run an ultra marathon this year and then I don’t do anything for three or four years. And it’s like, yeah, I did my hard thing once. Is that moving the needle?

I mean, maybe you learn something about yourself. It was good. But is that really like transforming who you are, transforming your life? And my thought is no, it’s really not. So what actually makes a hard thing, and I have the hard things equation, and I talk about that in my book Killing Comfort, and it is first off, there are two parts. You have to push forward against your own desire and then do that daily over decades.

That’s a hard thing. So where I think hard things need to start is you have to ask yourself, do I want to do this thing? And if the answer is no, you’re pushing forward against your own desire, you are starting to shape who you are. Now, I don’t think you need to do this in every form and facet in your life.

when your hard thing stops being hard

You might just hate your life if you do it, but you should have one little area where you’re trying to build a habit. You’re trying to do something and it’s pushing forward against your own desire. Like, let’s say you never worked out and you’re like, OK, I’m going to start working out. You’re pushing forward against your own desire every day to do this new thing, to build this new habit.

So you have to push forward against your own desire. But on the same note, I love fitness. I like to train. It’s harder for me to not train than it is to train. Like, sometimes time-wise, it’s hard to find the time, but the desire is absolutely there. I always want to train. So I can’t pretend like training each and every single day is my hard thing. I just can’t do it. Like, that’s not realistic.

For some people, it is a hard thing. For me, it’s not because I’m not pushing forward against my own desire.

sporadic suffering vs. daily progress

I’m going with my desire because I’ve been doing it for decades at this point. So I need to find something else that’s shaping me, something that’s, you know, causing a little bit of friction, something I don’t want to do, maybe a new habit, something that’s just not quite there. It could be in my relationships. It could be in my nutrition. It could be something else.

But I need to do something that pushes forward against my own desire. I need to keep pushing forward. I need to feel that friction. Now, the second part is daily over decades, right? Now, eventually, you’re going to make this a habit. It will become a habit. And once it becomes a habit, I don’t think it’s your hard thing anymore because you’re not pushing forward against your own desire anymore.

how to pick the right hard thing for growth

You’re just, you kind of have a new status quo. That’s when it’s time to jump to a new hard thing. I really think you should only pursue one hard thing at a time.

Whatever that is, building a new habit, doing something in business, like chasing down leads or building a funnel or writing a newsletter, like whatever it is, push forward against your own desire, do it daily over decades. And then once it’s a habit, move on to something else. And you can do that in your business. You can do that in your personal life. You can do that in your relationships. You can do this in any area.

this is how you actually transform and build a better business

But once you realize, like, oh, I actually want to make progress, you need to put time under tension. You need to put a magnifying glass on one specific area and improve it until it’s automatic. And then after it’s automatic, you move on. Not sporadic, hard things. Like if I wanted to just do something hard today, I could go grab a rock from outside, put it in my shoe and go for a 10-mile run.

Hard thing. Am I more mentally tough? Not really. Am I dumb? Absolutely. You don’t need to put rocks in your shoe as your hard thing. You need to have a targeted area you’re trying to improve and then push forward against your own desire. Do that for daily over decades or until it’s a habit. If that takes you six weeks, six months or six years, you stick with that hard thing until it is automatic. Then you can move on to the next hard thing. This is how you transform who you are.

And whether you know it or agree or not, this is how you actually grow your business.