Taking the Path of Most Resistance

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I can’t stop thinking about something I heard this summer: “I don’t wish my children happiness. I wish them purpose.”

Honestly, it didn’t sit right when I first heard it. I mean, who doesn’t wish happiness for their kids? What the hell? But I’m getting ahead of myself.

This came up at a networking dinner in June, where the conversation somehow shifted from business and AI to parenting and hardship. Because nothing says “professional networking” quite like debating the optimal amount of childhood suffering over scotch and dessert.

Each of us had a different definition of hardship, shaped by our backgrounds and cultures. Yet we agreed on one thing: struggle matters. Pain has value. Strength is not built in comfort.

At one point, someone did remind us that children also need stillness, space, and joy. They should be happy. But then one of our hosts shook his head and said quietly, almost to himself: “For my children, I don’t wish them happiness. I wish them purpose.”

And there it was. The kind of statement that just sorta knocks the wind out of you. The kind that makes you question what you thought you knew about raising humans. The kind of statement that sticks with you all summer.

So this week, let’s talk about why purpose beats happiness every time, what happens when we chase the wrong thing, and how to build a life that matters instead of one that just feels good.

The Problem with Chasing Happy

We've all been sold a bill of goods about happiness. Somewhere along the way, we've been convinced that feeling good is the ultimate goal. That if we're not happy, we're probably doing something wrong.

But if happiness is the point, anything uncomfortable starts to feel like failure. Hard work? Avoid it. Tough conversations? Dodge them. It’s a mindset that keeps you stuck in the shallow end of the pool.

Happiness is just an emotion. It's a feeling. It comes and goes like weather. And you can't build a life on something that temporary. It’s like trying to anchor yourself to a cloud…or a toddler.

But more than that, happiness-as-a-goal creates some pretty twisted incentives. When feeling good becomes the point, you start making decisions based on what's pleasant rather than what's meaningful. You avoid difficult feedback. You quit when things get messy. You choose the path of least resistance, even if it leads nowhere.

Ultimately, you end up optimizing for the wrong thing.

Think about the last time you felt truly fulfilled. I'm gonna bet it wasn't during a moment of pure, uncomplicated happiness. It was probably after you'd done something really freakin hard. After you'd solved a problem that mattered, helped someone who needed it, or created something that didn't exist before.

That feeling wasn't happiness. I’d argue it was something deeper. It was the satisfaction that comes from living in alignment with what you value. From knowing that your time and energy went toward something that mattered.

Purpose doesn't promise you'll feel good. It promises something better: that you'll feel useful.

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The Case for Struggle

I think that the best parents don’t try to eliminate struggle from their kids’ lives. They try to make sure their kids struggle with the right things. It’s part of why I am such a fan of having your kids in sports. When our kids were growing up, they had to choose at least one sport to be a part of. That took the forms of Kung Fu, Ultimate Frisbee, and Tennis. (I guess it would have killed our kids to try and get a scholarship or sponsorship to something, but I digress).

Sport, by its very nature, causes struggle. It is a somewhat safe environment in which you can feel the joy of triumph but also the pain of defeat. And if done right, the stakes are low enough so that that pain doesn’t ruin you, it teaches you that you can overcome difficult things.

Kara Lawson, the head coach of Duke women’s basketball, has a phrase for this: handle hard better. Life never gets easier, she tells her players. You just get better at handling the hard parts. Which, if we’re honest, is both deeply inspiring and deeply depressing.

But that’s what good parents (and leaders) do. Because the truth is, our happiness-obsessed culture has forgotten something simple: the best things in life require you to go through something difficult to get them.

When you shield someone from all difficulty, you don’t protect them—you make them fragile. You rob them of the chance to discover what they’re made of. But when you help someone find their purpose, struggle shifts. It becomes something they’re willing to endure because the goal is worth it.

Purpose gives struggle meaning. It transforms pain from something you endure into something you’re willing to face, because it’s carrying you toward something that matters.

Building a Life That Points Toward Something

So how do you find purpose? How do you help someone else find theirs?

These are big questions, bigger than one newsletter, but here’s what I do know: you don’t find purpose by asking, “What makes me happy?”

You find it by asking better questions:

• What am I good at?

• What does the world around me actually need?

• What matters enough that I’m willing to work at it, even if it costs me?

Purpose tends to sit where those three things overlap. Happiness doesn’t make the list because happiness isn’t the goal. Happiness is a byproduct, not a destination.

A few ways to start spotting your purpose:

• Pay attention to what bothers you. The things that frustrate or anger you aren’t just annoyances. They’re clues. If something keeps tugging at your attention, it’s pointing toward a problem worth solving.

• Take stock of your strengths. What comes easily to you? What do people ask you for help with? You don’t need to be world-class. You just need to be helpful.

• Decide what you’re willing to give up. Purpose always comes with a cost. It demands time, energy, and attention that could go elsewhere. It requires you to say no to some things so you can say yes to the thing that matters.

You can’t think your way to purpose. You have to actually take action to get there. You find it by trying things, seeing what resonates, and paying attention to what you're willing to keep doing even when it gets hard.

Purpose isn’t a single discovery you make once and carry forever. It evolves. It deepens. It shifts as you do. But once you start living with it, happiness becomes almost irrelevant.

Not because you don’t feel it, but because you’ve traded up for something sturdier: the knowledge that your life is pointing toward something that matters.

In Conclusion

Happiness is not bad, but it is not enough. It is the frosting, not the cake. If you build your life around chasing happy, you will spend it avoiding anything hard. If you build your life around purpose, happiness will show up on its own.

When the hard times come (and trust me they will), purpose is what keeps you steady. It gives your struggle meaning. It turns obstacles into stepping stones and pain into progress. And when you know your life points toward something that matters, you do not just feel good, you feel grounded.

So if you have to choose between happiness and purpose, choose purpose. Happiness will tag along.

As always, thanks for reading,

— Derek (aka Chief Rabbit)
Oh and have something interesting you think I should write about? You can reply to this email (or any other Chief Rabbit email) to suggest it. 

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