• Richie Crowley

The Greatest Personal Tragedy Is That Of A Dream Deferred.

In the summer of 2016, I wrote a reminder to myself on a blue sticky note. It was to send an email to my role model, Rich Roll, and ask him if I rode my bicycle across the country, would he have coffee with me.

As ludicrous as it sounded, I knew it would work. It was the stuff of legend.

I never sent it, and that blue sticky note lives in my journal.

In 2018, I had committed to moving to Los Angeles, and that August tasted the idea to ride my bike across the country again. I thought the headline “Man Moves Across America, From Boston to California…By Bike” was again, the stuff of legend.

I spent the fall in Boston and flew to Los Angeles on December 2nd. That’s when I moved. I didn’t even bring my bike.

For 3 years, my dream was to bike across the country, alone and unsupported, and twice I had the opportunity to realize it, and twice I walked away.

I was at-bat and struck out, looking.

In so many conversations, I’d share this dream, entertain friends and say “I’m going to do it”, but I never did.

I talked shit. I cried wolf.

Until a close friend, maybe my closest, confronted me and humbled me. They told me I have so many ideas, but I never act on any of them. I play it safe. They were right. Dreaming can be exhausting, but the energy arrives when you begin to pursue one. When you just dream and don’t act, it not only exhausts you and those around you, it defeats you. Damn, that conversation landed. Not only was I consistently letting myself down, but I was also exhausting all those who believed in me and were ready to cheer me on as I went for it.

It was time to adjust the course.

You already know the details of the ride, so I’ll spare you those, but what I haven’t shared yet is my relationship to dreams. Twice, I feel that I have lived out my dreams. First, when I played professional hockey, my childhood dream, pursued from ages 3–26, and next when I arrived home to Santa Monica having ridden every inch of America from Boston to LA by bike. Riding my bike across the country was the manifestation of my most recent dream, and the underlying story threaded through this tale of adventure is not one about physical accomplishments, but something less tangible: The tragedy of a dream deferred.

Romance unintended, I want everyone to believe they can achieve whatever they want. That they can become whoever they want to become. I want them to know that there may be obstacles, but these are only there to test us. When we meet obstacles, we are challenged to find ways around, through, and over them. Obstacles expose dreams, if we encounter one and quit, then we must confront if what we are pursuing is truly a dream. And I want everyone to know they shouldn’t be competitive with their dreams. Dreams don’t have to be grand, many are very humble, unknown to anyone before, during, or after completion. The magnitude of a dream doesn’t correlate to its importance. Dreams are unique to their creators. Your dream’s yours. Their dream’s theirs. And, it’s worthwhile to add that we all have different starting points, and are equipped with different resources. An acknowledgment that shouldn’t justify envy, doubt, or competition but recognize that we all have the same opportunity: To reach our dreams. Let’s get real on this. If a person is gifted $1,000,000 sure they have a big advantage but not over you, their advantage is simply over their dream. No matter who you are, where you come from, if you have an education, or don’t have a home, the power of belief can propel you to your dreams, but that belief must be 100% authentic. Because when obstacles arrive, only the less convicted minds will have the resiliency to persevere. The biggest advantage we can have over our dreams is our belief.

“There is only one thing that makes a dream impossible to achieve, the fear of failure.” The Alchemist, Paulo Coehlo

The process of reaching your dreams will challenge you. Like a storm, it may tear through your life. You may need to adjust how you live, where you live, how you spend, and your complete lifestyle, but all those sacrifices, are choices. Choices to invest in yourself. Choices to invest in your dreams. You’ll doubt your dream, you’ll consider quitting, and you’ll reach for a myriad of excuses that all originate from fear, but when the pain of not realizing your dream is stronger than the comfort from the safety of not pursuing one, you’ll continue. You’ll grow stronger, smarter, savvier, and with every success, your confidence will compound until YOU BECOME THE STORM thrashing through your dreams. As strong as our confidence becomes when we exercise it towards our dreams, up rises a certain sadness in the souls of those who continue to choose to defer or abandon their dreams. Beyond everlasting unfulfillment, if we continue to defer our dreams, a time will come when we are not blessed with the ability to dream anymore. We will lose our creativity, our spark, our zest. That is why the greatest personal tragedy to me is that of a dream deferred.

I don’t encourage recklessness in the pursuit of dreams, in fact, I attempt to mitigate all risks before even beginning to act on mine, but at some point, we must simply activate. A simple way to do so is to first determine if an idea is truly a dream. It takes an incredible amount of honesty to sort between good ideas, great ideas, fun ideas, and dreams. Next, is strategy. In a world where Instagram M.D.’s, life coaches, and well-written headlines champion “manifesting”, there has been a massive misdirection when educating communities on what this is. Thinking something, writing it in your journal or on your fridge, doesn’t move the needle. If you want to work at SpaceX and never send a fucking email, pitch an idea, or have a conversation, then counting your breaths till 10 while meditating on the mantra I am SpaceX is irrelevant. Dreams need water. Dreams need strategy.

Dreams deserve action.

A dream, is something unpredictable and dangerous for those who lack the courage to dream.” Hippie, Paulo Coehlo

When writing this from a state of fulfillment, it would be easy to illustrate a certain fearlessness, but that’s not true. An admission I have to offer is that my direction today has been built on a foundation of inaction and failure. For years I was a coward, not brave enough to act on my dreams. I exhausted those around me, crying wolf that I would do something personally great, and I never did. Until I did.

Until I made the scariest decision in my life and believed in myself.

What I’ve learned in the years since that decision is that if you keep creating, dreaming, strategizing, and acting, eventually a card will fall in your favor. This is not the “big break” because big breaks don’t exist, they are the result of resilient self-belief and action.

This ride had obstacles: Flat tires, wind, hills, darkness, strange encounters, and animals. There were moments where my disobedience would have meant death. Midwest winds were strong enough to throw me across a road, trucks were wide enough to send me from the road, and the desert was dry enough to exhaust my water reserves.

No pedal was taken for granted. But this ride, like every dream realized, has returned so much confidence that what I endured has been woven into the milestone.

There is safety in dreaming without action, it protects you by not inviting failure onto yourself. But without failure, there is no growth. Acting on your dreams is not reserved for the wild ones, or the reckless ones, it’s reserved for you.

There is a question I ask myself and am not comfortable asking others, but it’s this: What Did You Do With Your Life?

It’s a future reflection that addresses one’s expected legacy. When answering, I share with myself the dreams I want to have reached by the time I’m at the age where one even has a legacy.

This moment that we are in, life, is so rare. The beat of our heart, the expansion of our lungs simply indicates we are alive. For me, these actions of my organs are reminders go big, to dream, and to become the storm, for if I don’t, I accept that I am dying.

I am not writing this to hear my voice and hopefully, we never have to have this conversation again, but I am writing to be the voice, if even the only one, that agrees with you that you can do anything.

Our challenge is to not convince ourself but to believe ourselves when we say nothing is impossible because the greatest personal tragedy is that of a dream deferred. And we should not be motivated by the fear of personal tragedy but with the fulfillment in achieving a dream itself.

"Never stop dreaming” the old king had said “follow the omens” The Alchemist, Paulo Coehlo

Richie. Human


The difference between Seth Godin, The Morning Brew, and me? I respect your inbox, curating only one newsletter per month — Join my behind-the-words monthly newsletter to feel what it’s like to receive a respectful newsletter.