Chapter 1: The Challenge Begins

As I stood at the entrance of a stranger's home, my heart raced. Clad in a swimsuit and clutching a beach towel, I felt utterly foolish. Yet, there was also a sense of childlike excitement bubbling within me. I tried to calm my thoughts, channeling my inner seven-year-old, but anxiety threatened to overwhelm me. I reassured myself that no one would mind if a kid knocked on their door to ask for a swim. But I wasn’t a child anymore; I was a 29-year-old man sporting a splendid mustache.

Just as I was about to flee, the door swung open. In that moment, I felt like I was living a nightmare. I plastered on my best grin and asked, "Hi! I'm Gregory, could I cannonball into your swimming pool?"

A Surprising Response

Time seemed to stretch as the homeowner stared at me in silence. After what felt like an eternity, he erupted with laughter. “Sure, why not!” he exclaimed with a smile.

As we strolled towards the pool, I shared my story. I explained that I was on day four of a 100-day challenge dedicated to getting rejected by strangers in the most outrageous ways. This journey was inspired by a remarkable book called Rejection Proof.

Once we reached the pool, I asked him to film my jump. He happily obliged, capturing my flawless cannonball.

When I returned home, I uploaded the video to Instagram. Sharing my quirky experiments online has always been a joy, allowing me to connect with others who appreciate my eccentricities. But nothing could have prepared me for the whirlwind that followed.

Viral Sensation

In just a few weeks, my Instagram video racked up over 350,000 views. While this may seem minor in the grand scheme of viral content, to me, it felt monumental. It was as if the entire city of Anaheim, CA (with a population of 342,000) had viewed my video, or three NFL stadiums had showcased it during halftime.

This unexpected reaction thrilled me and validated my underlying motivation for embarking on this 100-day escapade. My true aim was to test a personal theory.

Lesson #1: The Universe Rewards Bold Action

The phrase "Fortune favors the bold" has always resonated with me. It conjures a sense of adventure and assurance, and I’ve found it to be true. Whenever I gathered the courage to act boldly, my life seemed to improve almost instantly—whether it was initiating conversations with strangers or tackling fears head-on. Thus, I formulated my hypothesis: the universe rewards boldness.

Upon reflection, I realized we cannot dictate what happens to us in life (i.e., fortune), but we can control our level of boldness. If we amplify our courage, we should expect our fortunes to grow accordingly. This hypothesis proved to be undeniably accurate.

Lesson #2: Embracing Your Uniqueness Leads to Connection

One of the first "rewards" I experienced during my challenge was meeting Brad, the mastermind behind Discover Connection, a YouTube channel that features him and his friends making outrageous requests of strangers, like asking to cook dinner in their homes.

As my Instagram video gained traction, I sought input from others on what to do next, asking over a thousand people for suggestions. I was intrigued to find that many recommendations echoed the antics Brad had already filmed.

This connection felt serendipitous. I met Brad through a mutual friend, who suggested we connect after hearing about my challenge. When we eventually spoke over Zoom, we instantly clicked. It takes a unique individual to approach strangers with bold requests, and I found that Brad and I shared a mutual appreciation for such audacity.

A few months later, we met in person while he was visiting San Diego. Our shared passion for human connection deepened our bond and reinforced my second lesson: embracing your uniqueness helps you find your tribe.

Understanding "Weirdness"

To me, being "weird" means fully engaging with the activities and ideas that ignite your passion—those subjects you can’t stop discussing. I believe that leaning into your "weirdness" is the quickest path to discovering your community. In contrast, many people only pursue what is considered "cool" and then lament their inability to find interesting company. This principle applies to both friendship and romantic relationships; being authentic about your quirks is essential for attracting like-minded individuals.

Interactions with Strangers

Throughout my 100-day challenge, I engaged with hundreds of people. I particularly enjoyed asking couples for peculiar requests, as they often exchanged glances before responding. Here are some of the outrageous things I asked:

• Can I bake cookies with you?
• Can I give you a piggyback ride?
• Can we play leapfrog?
• Can I do the Macarena with you?
• Can you push me on a swing?
• Can you lift me up at sunset like Simba from The Lion King?

I even went through a phase where I asked delivery drivers if I could operate their vehicles. While I mostly received polite refusals, I did score a $4 discount at the post office by inquiring about discounts for those with impressive mustaches.

Lesson #3: The Need for Connection

After countless bold requests and laughter, I learned a profound truth: we all yearn for connection. Even when people declined my whimsical asks, we still shared memorable moments. More often than not, we both walked away smiling, armed with a delightful story to share later.

I find joy in imagining the conversations that ensued after my interactions. “You won’t believe what this random guy asked me today!” Regardless of their response, I always offered a high-five as I departed—a simple act that brightened their day and underscored our shared human experience.

The pandemic stripped away many casual interactions with strangers that once filled our days. However, after 100 days of engaging with others, I recognized the significance of these moments. They remind us that we are all on this planet together. A smile from a stranger can be uplifting, and an unexpected high-five can turn someone's day around.

To foster a better world, all it takes is initiating conversations with strangers—bonus points if you ask for something outrageous!

Conclusion

Hi, I’m Gregory, a professional coach dedicated to helping individuals craft stories worth sharing. Here are three steps to enhance your life immediately:

1. Schedule a discovery call to explore your Hero's journey.
2. Subscribe to my newsletter and say goodbye to Monday morning blues.
3. Join Medium to fill your mind with uplifting ideas.

Chapter 2: Embracing Rejection

This TED talk by Jia Jiang reveals what he learned from his 100-day rejection challenge. Discover how facing rejection can lead to personal growth and unexpected opportunities.

In this TEDx talk, Jia Jiang shares surprising lessons from his journey of seeking rejection. Learn how embracing discomfort can transform your life.