Let’s talk about doing hard things that actually matter—not just for the sake of hardship, but for true transformation. As entrepreneurs, we tend to glorify the grind, but the grind only moves the needle when it’s paired with self discipline.
I’ve been obsessed with this idea for years. It’s the foundation behind my book Killing Comfort, and it’s something that’s been echoed across time by some of history’s greatest thinkers and leaders.
History Has Always Warned Us About Comfort
This isn’t a new idea. Theodore Roosevelt talked about how success doesn’t come to the man who desires peace, but to the one who faces hardship head-on. In 1906, William James said we need “the moral equivalent of war”—something to toughen us without actual bloodshed. These men weren’t just talking about national defense or heroism—they were talking about self discipline as a path to greatness.
Even Robert Falcon Scott, who perished exploring the Antarctic, left a message to his wife: “Make him a strenuous man.” That one line was his ultimate wish for his son. He didn’t say “make him wealthy” or “successful.” He wanted his son to be disciplined, resilient—someone who could handle discomfort and do hard things.
That’s what this is all about.
Why Entrepreneurs Must Choose Their Hard
You don’t need a global crisis to challenge you. In fact, when life is good, that’s when you must choose your hard. If you want your business to grow, if you want to become a better parent, partner, or leader—it starts with self discipline. You don’t become better by accident. You become better by showing up daily, doing what you don’t want to do, and doing it well.
The better you are, the better your business becomes. Period.
The Hard Things Equation
Here’s where I see people get it wrong: they treat hard things like one-off stunts. They sign up for a marathon, complete it, and think they’ve done their part. But sporadic effort doesn’t shape character. Daily self-discipline does.
I use what I call the Hard Things Equation:
Push forward against your own desire + Do it daily over decades = Real growth.
That’s how you transform yourself. Not with random, meaningless suffering (like putting a rock in your shoe for a 10-mile run), but with intentional, targeted effort.
Self Discipline Means Doing What You Don’t Want to Do
Ask yourself: What do I not want to do today that would improve my life or business?
That’s your current “hard thing.”
For some people, working out is the hard thing. For me? It’s not. I love training. I’ve been doing it so long, it’s automatic. Which means it’s time for me to move on to another hard thing.
That’s how this works. You pick one. You master it. You move on.
The Power of One Hard Thing at a Time
Trying to change everything at once is a guaranteed way to change nothing at all. Self discipline works best when you put the spotlight on one area of your life, and you pour everything into that.
Daily. Relentlessly.
When it becomes second nature, you shift to the next hard thing. And over time, you become a different person. A better version of yourself.
And that’s the secret. Growth doesn’t come from hacks, tactics, or shortcuts—it comes from discipline. From doing the hard thing, daily, until it’s no longer hard.
So choose your hard. Start today. And stick with it long enough to become someone new.
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Time-Stamped Show Notes
00:30 – Why doing hard things is a universal, historical call
02:15 – Warnings from Roosevelt, William James, and JFK on the dangers of comfort
05:30 – Why entrepreneurs must actively choose their hard
07:00 – The Hard Things Equation: push forward + consistency
08:40 – Why self discipline isn’t built through occasional challenges
10:05 – How to pick your hard thing and why one is enough
12:00 – When a habit is no longer hard, it’s time to move on
14:15 – Real growth only happens when you stop avoiding discomfort