The Gift of Disillusionment

Why losing faith in the world frees you to find true, lasting contentment within

Are you still hoping that the conditions of your life will one day satisfy your deepest longing?

Caveat: Don’t believe anything I write in my newsletters. See for yourself if what I say is true in your experience. If it is, keep it. If not, throw it away.

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Dear Friend,

Being contented was easy as a kid.

Step outside and into the wonder of nature. Collect quartz, explore an ivy-covered ravine, or create mud balls and let them dry in the sun.

But as I grew older, what I thought would bring contentment became much more complex. By high school, I thought it meant wearing the right clothes, having the right haircut, listening to the right bands, spending time with friends, riding the right bike, excelling in sports, lifting weights, chasing girls, reading self-help books, eating a clean diet, attending parties, saying the right things, avoiding the wrong ones, having adventures, getting others to like me, succeeding in school, and getting into to the right college.

Later, it further expanded to include finding the right job at the right company, earning and saving money, living in the ideal town and neighborhood, having a perfect apartment and furniture like in Fight Club, taking cold showers, driving a cool car, enjoying hobbies, traveling, climbing mountains, living in a walkable community, reaching the age of 100, and earning an advanced degree.

I did all these things (well, all except turning 100), hoping for lasting happiness. To some extent, they worked—but only for a short time.

Since childhood, I had dreamed of owning a Porsche. Driving one off the lot for the first time was exhilarating. I felt cool, important, and powerful. However, as time passed, the excitement faded. I began to worry constantly about when the car would break down next. I disliked the attention from other drivers who wanted to race. I also felt like a fraud. Who was I kidding? I was making $18,000 a year ($54,000 today) and could barely afford it.

Landing my first marketing job at a Fortune 500 company was thrilling. I engaged in exciting work, collaborated with smart colleagues, and earned a good salary. However, I felt deeply insecure and was compelled to prove my worth daily, leading me to work long hours and weekends. My boss would inundate me with dozens of ideas all at once. Yet, I hadn’t learned to say no or push back, which overwhelmed me. The constant stress drained me, and when the dot-com bubble burst, I was let go along with half the staff.

Going out for drinks with friends was fun, but it was costly and left me feeling awful the next day, and I didn’t appreciate feeling pressured to drink to cope with social anxiety or conform to social expectations. I just wanted to spend time with my friends.

But my pursuit of lasting satisfaction went beyond material things.

I yearned for a partner who would love, laugh, and cry with me—someone I could depend on through good times and bad. Yet, my first serious girlfriend cheated on me, my ex-wife left me, and my current relationship has been straightforward, then complex, and only recently straightforward again.

I longed for a community where I felt welcomed, like in Cheers—“Where everybody knows your name, and they’re always glad you came.” Yet, everywhere I lived, I always felt like an outsider looking in.

By the time I turned 32, I felt profoundly dissatisfied and deeply disillusioned. Is this all there is to life? I wondered. Making money and buying stuff? The Western approach to happiness wasn’t working. Surely, someone, somewhere, across time must have figured out a better way to live.

That’s when I started seeking answers from the East.

The Illusion of Perfect Conditions

After experiencing the freedom of yoga, I realized what I had been doing wrong: trying to control the conditions of my life—my car, my job, alcohol, relationships, and money—so that they would always be just right for me to feel happy.

However, conditions are constantly changing. They are an unreliable source of enduring satisfaction and well-being.

I want to be consistently healthy and live a long life, but I'm aging and will inevitably get sick and die. I desire to be reliably attractive, but my hair is gray, silver, or falling out, and my belly fat no longer responds predictably to sleep, diet, and exercise. I hope for a beautiful yard, but the plants often grow too short, too tall, too bushy, or require excessive water.

Can you see the problem?

You and I expect the conditions of our lives to offer lasting satisfaction that, by their very nature, are unreliable. We anticipate that the things that please us will continue, and we become upset when they do not.

I thought lifting weights six days a week and eating five meals a day would help me look and feel better. I felt stronger, but the effort was unsustainable, and once I stopped, my body reverted to its default ectomorph size.

I thought gutter guards would save me from yearly cleanups, but now I clean shingle gravel off the ground instead of out of the gutters. I believed that weed fabric would keep my yard pristine and save me hours of spring weeding. Yet weeds still sprout on the north side of the house. I thought that having a complete wardrobe would satisfy my longing. Instead, I'm never content: clothes go out of style, my tastes change, and moths eat holes in my wool sweaters.

That doesn’t mean you should throw your hands up and give up on improving your life. Naturally, you need shelter. You need food and clothing. Just know that nothing outside of you can fulfill your heart’s deepest longing.

The Necessity of Disillusionment

Today, what brings me joy isn’t a car, a job, or the ideal circumstances. It’s the realization that contentment isn’t something to pursue—it’s something to uncover.

Without disillusionment, you will continue seeking lasting satisfaction outside yourself. You will never see the pot of gold you’re sitting on—the presence, the depth, the stillness within all of life—that Eckhart Tolle discusses in The Power of Now.

The universe doesn’t care if your heart is fulfilled before you die.

But you do. Deeply.

It’s like a child who constantly seeks love from a parent, yearning for affection they never received and never will. Not because the parent doesn’t care, but because they don’t know how to express it.

Similarly, the world will never provide the lasting fulfillment you desire—not because it is against you but because it was never able to do so in the first place.

Disillusionment is not the end—it’s the beginning. It’s when you stop expecting life to please you and satisfy your deepest longing.

And you finally start searching in the only place where true contentment is to be found.

Inside.

Keep welcoming disillusionment,

Ryan

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Momo, a Goldendoodle mix.