Creating Wealth vs. Pursuing Wealth: The Indirect Path

Guest:

Sonja Lyubomirsky

Featuring Insights from Dr. Sonja Lyubomirsky

No one in the world has empirically studied happiness and well-being quite like my friend Dr. Sonja Lyubomirsky. A pioneer in the field of psychology, Sonja authored the first evidence-based book on happiness ever written, The How of Happiness

Sonja’s lab has led groundbreaking research on what genuinely contributes to—or detracts from—our sense of well-being.

One of her most compelling insights is that the direct pursuit of happiness, often ironically leads to less of it

Instead, it's the indirect pursuit of happiness where true fulfillment emerges. 

Indirect path? Huh? Let me explain.

The Zen Master and the Trap of the Direct Approach

I’ve spent 20 years hanging out weekly with a Zen priest. I’m into that kind of thing. The conversations are fantastic. 

I like to ask him about his old, dead teachers. They teach through riddles.

The great masters were studying life’s patterns long before we had psychology, experiments, and studies. 

When I come across a Zen story that aligns with modern research, I pay attention. 

One day, my Zen priest friend told me about this dead guy called Master Joshu. He shared a 4 line parable that immediately reminded me of Sonja’s lab.

Joshu (778–897), one of the great Zen masters, had a famous exchange with a student. The student asked him about the way to enlightenment:

            Student: “What is the way?”

            Zen Master Joshu: “Everyday mind is the way.”

            Student: “Can I approach it directly?”

            Zen Master Joshu: “If you attempt to approach it directly, you are going in the opposite direction.”

My Interpretation of what the fuck this means

If you chase happiness as a primary goal you will literally run farther away from it. 

If you focus primarily on your own happiness, you become attached to it as some kind of destination, grasping for it—and it slips right through your fingers. 

Why? Because chasing your own happiness is a focus on SELF. A focus on your own self over others always ends badly. 

Instead, my take on Joshu’s everyday mind or “the way” =

  1. Focusing on what’s truly present (good or bad)
  2. Detaching from outcomes (see actor Bryan Cranston for more on this)
  3. Aiming at the right things

This magic combination is where fulfillment becomes possible.

So, what can you aim at to execute this “indirect approach”? What’s an example of an “indirect” target that will get you going in the right direction?

That’s where Sonja’s lab comes up huge. According to Sonja, it involves focusing on one of three missions.

The Three Missions

Sonja’s research reveals three missions that, when aimed at, indirectly lead to happiness:

The Connection Mission

This could mean fostering a deep bond with your team, family, or customers. It could be a spiritual connection or simply the feeling of belonging to a community. When we prioritize authentic connections, we tap into a deep well that isn't tied to external markers like money or power.

The Contribution Mission

This involves framing your work or purpose around making a positive impact. It doesn’t matter what your job is—you can always find a way to contribute meaningfully. As Sonja points out, even a cashier who smiles and connects with customers can make someone's day better and feel a sense of fulfillment.

The Personal Growth Mission

This mission is about constantly learning, evolving, and striving to become a better version of yourself. For entrepreneurs, personal growth is an easy mission to align with because the journey of building a business is full of challenges which can be transformed into opportunities for learning and growth.

When founders focus on one or a combination of these missions—deepening connections, contributing to a greater cause, or pursuing personal growth—a kind of fulfillment emerges as a natural byproduct.

Does This Mean I Can’t Enjoy My Mega Yacht?

Jeff Bezos is building a $500M mega yacht, dressed here ready to board.

Hell no. Enjoy life’s spoils, just don’t be consumed by them. 

I don’t have a mega yacht but I rather like the idea of spending a week on one with great people. 

You don’t need to become a monk and renounce all possessions. It’s okay to enjoy the financial rewards of being a founder. It’s nice to have more influence and resources. 

But, as Sonja’s research shows, for long-term well-being and sustainability, making happiness or wealth the primary focus is a trap. Chasing it directly backfires. Hard.

The most fulfilled entrepreneurs I've observed are those who pursue a mission that’s aimed outside themselves. 

They recognize that money, power, or status will come as a consequence of their efforts. 

They are smart about getting well compensated for their efforts. 

They enjoy the hell out of their toys and good fortune.

They hold the mission dearly but the spoils loosely. 

How to Apply the Indirect Path: The Purpose-Led To-Do List

Jesse telling the story of his Purpose-Driven To Do List on the My First Million Podcast

All this talk of “paths,” “ways,” and “traps” are interesting but can feel WAY up in the clouds. 

I’m obsessed with how to apply them in real life.

One of my favorite examples comes from my friend and serial entrepreneur Jesse Pujji. Ten years into his founder journey, Jesse got clear that his deepest purpose was to unleash the potential of everyone who worked with him.

It’s not lip service. Spend any time around Jesse and you can feel how real it is for him to make people better. And, he’s not afraid to be very direct to help you get there either.

One day, as he was building his startup studio GatewayX, his executive coach challenged him to rearrange his to-do list by the people who worked for him. 

Instead of action items organized by project, client, or business, what if he reorganized them by the people he was trying to help grow?

Immediately, he noticed an energy boost. 

Suddenly, the everyday work was reframed through his mission of connection, contribution, and growth.

Organizing his to-do list through the lens of his mission created a sustainable source of energy and fulfillment.

Remember Joshu’s cryptic teaching to his student? Pursue the indirect path. 

Jesse’s purpose-driven to-do list is a modern application of the indirect path.

His work points in the direction of his bigger mission. 

In my view, that’s walking in the direction Joshu was cryptically suggesting but applied in the everyday life of the modern world.

It’s everyday action, applied in a wise direction. 

Of course it needs to show up in a motherfucking to do list. 

If it’s a real purpose, it needs to (and gets to!) permeate everything.

Indirect Paths for the Win

As Sonja, Jesse, and Joshu remind us, the indirect path involves a shift in focus—from pursuing money, status, or even happiness itself to pursuing something bigger than ourselves. 

You get to choose your own mission. But you're gonna be miserable if deep down the mission is really about yourself. 

In business, you still need to ensure you’re playing a well-chosen game to thrive long-term. That mega-yacht doesn’t just happen chasing after a small problem. 

But in entrepreneurship and life, it's a paradox worth remembering: sometimes, the best things come when we stop chasing them directly.

To go deeper on Sonja’s work, I highly recommend her website featuring her published papers and books.

Get in touch

Matt acquires or invests in cash-flowing digital businesses with $1-$5M in EBITDA.

Occasionally, he takes on advisory engagements for interesting projects. If this is of interest, feel free to share more.

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