What Would This Look Like if it Were Easy?

Reading Time: 3 minutes

1 Big Idea

This week I’ve been thinking about how often we make life harder than it needs to be.

Whenever I’m facing something challenging – a long run, a heavy lift, a few hours of deep work – I can almost feel myself bracing for it. Like I’m preparing for battle. I tense up before I even begin, expecting it to hurt, expecting it to be a grind.

And usually, because of that, it does.

But I came across a simple question that’s been stuck in my head for the past few weeks:

What would this look like if it were easy?

The point is that most of our struggles aren’t battles against the external world – they’re battles inside our own heads.

This is something Timothy Gallwey talks about in The Inner Game of Tennis: when a player tenses up, overthinks, tries too hard to be perfect, their performance collapses.

So, it’s not that the task itself is impossible. It’s that our resistance to the task creates the friction.

For example, when I go for a long run, I normally go into it thinking ‘this is going to suck’. But, when I asked ‘what would this look like if it were easy?’, I approached it differently.

I paid less attention to the distance and the pain, and more to just enjoying the act of moving.

The point is, hard work can feel great if you stop dragging emotional baggage into it.

The dread, the tension, the weight — most of it isn’t in the work itself. It’s in the stories we tell ourselves about the work.

We imagine how painful it’s going to be. We brace for the worst. We carry an invisible heaviness into things that might otherwise feel light, or even enjoyable, if we let them.

When I started asking, what would this look like if it were easy?, it didn’t change the nature of the work. The run was still long. The weights were still heavy. The deep work still demanded focus. But something in me shifted. I stopped carrying so much resistance into the experience.

Instead of counting the miles left to run, I paid attention to the rhythm of my breath and the feeling of my feet moving across the ground. Instead of bracing for exhaustion, I softened into the process and let my body do what it was capable of doing.

And what surprised me most was this: often, the results were better. I moved more smoothly. I lasted longer. I enjoyed it more. Not because I was trying harder, but because I wasn’t fighting myself every step of the way.

It reminded me of something Josh Waitzkin wrote in The Art of Learning — that true mastery isn’t about forcing harder or grinding more. It’s about finding ease within the struggle. The best performers aren’t the ones who strain the most; they’re the ones who move through difficulty with the least internal resistance.

So, this week, whatever you’re facing — the workout you don’t feel ready for, the project you’re dreading, the conversation you’ve been putting off — pause for a moment.

Ask yourself: What would this look like if it were easy?

3 Weekly Lessons

#1 You Become Free the Day You Stop Imitating

The philosopher Michel de Montaigne said ‘the greatest thing in the world is to know how to belong to oneself’. Most people copy by default. They dress like others, think like others, chase the same goals as others. But freedom doesn’t come from rebellion or contrarianism. It comes from original self-possession. From knowing what you value without needing external permission.

#2 Slowness is a Superpower 

In a world that rewards speed —-fast news, fast reactions, fast everything – slowness becomes rare and powerful. The best decisions, the best relationships, the best work, all come from patience, not from racing. The Stoics called this ataraxia: calmness even amidst chaos. Move quickly, but don’t rush.

#3 A Brilliant Question to Ask Yourself

“If you were a character in a book, what would your readers be yelling at you to do?” – Eliezer Yudkowsky

5 Things Worth Your Time

A collection of links and other stuff I think are worth sharing.

◾️ The Days are Long but the Decades are Short: An interesting read from Sam Altman, who shares some life advice from his 30th birthday (over a decade ago).

◾️ The Martian: I rewatched this movie yesterday and Mark Watney’s advice after surviving on Mars really resonated with me: “At some point, everything’s gonna go south on you… everything’s going to go south and you’re going to say, this is it. This is how I end. Now you can either accept that, or you can get to work. That’s all it is. You just begin. You do the math. You solve one problem… and you solve the next one… and then the next. And If you solve enough problems, you get to come home.”

◾️ The Mundanity of Excellence: A fascinating paper arguing that excellence isn’t about “special talents”. It’s about doing simple things, savagely well, over and over again.

◾️ How I Find Happiness: A very honest video that explains how Jason Silva crafts his own experiences that help him grow and be happy.