3 Surprising Lessons I Learned From Spending 100 Days Getting Rejected By Strangers

My heart pounded as I knocked on the stranger’s door in front of me.

I was wearing a swimsuit and holding a beach towel and I felt ridiculous.

At the same time, I also felt like a little kid again. I tried to quiet my mind and channel my inner 7-year-old but I was quickly losing my mental battle. I switched tactics and tried to reassure myself that no one would mind if a child knocked on their door and asked to use their swimming pool. But I hadn’t been a child in over 20 years. I was a 29-year-old man with a magnificent mustache.

The voice in my head screamed at me that this was a terrible idea. I was about to turn and run away when the door opened. Suddenly, I felt like I was in a nightmare. I put on my best smile and said:

“Hi! My name is Gregory and I was wondering if I could cannonball in your swimming pool?”

A shocking response

Time slowed down as the man who opened the door stared back at me. He was silent for what felt like an entire minute. Then, he suddenly burst into laughter. With a smile on his face, he said, “Sure, why not!”

As we walked to the back of the house where his pool was, I told him my story. I shared that I was on day four of a 100-day challenge where I would try and get rejected by strangers in outrageous ways. I explained that this adventure was inspired by an incredible book, appropriately named Rejection Proof.

When we got to his pool, I asked if he’d take a video of me jumping in. He was totally onboard and he filmed a short video of my jump. In case you were wondering, it was perfect cannonball form.

When I got home, I posted the video on Instagram. I’ve always loved sharing my strange life experiments online because I get to see who resonates with my weirdness. But nothing could have prepared me for what was going to happen next.

350,919 views

Over the course of the next few weeks, my Instagram video blew up and was watched by over 350,000 people. I know this is peanuts compared to some instances of internet virality, but to me this was mind-blowing.

It was as if the entire city of Anaheim, CA (population 342,000) had all watched my video. Or that three football stadiums (the largest in the NFL holds 100,000 people) showed it on the Jumbotron during half-time.

I was elated by this kind of unexpected response because it validated the secret reason I had embarked on this 100-day adventure in the first place. My real reason for subjecting myself to this ridiculous amount of #strangerdanger was to test a personal hypothesis.

Lesson #1 — The universe rewards bold action

I’ve always loved the phrase “Fortune favors the bold.” It evokes a sense of adventure and confidence and it also seemed to be a true statement.

Every time I mustered up the courage to do something bold, my life seemed to immediately improve. Whether it was talking to strangers or finally taking action on something that scared me, the universe seemed to reward me for getting out of my comfort zone.

Thus my hypothesis was formed:

The universe rewards bold action.

As I started to think more about this phenomenon and break down “Fortune favors the bold” into its component parts, I realized something.

We can’t control what happens to us in life (i.e. fortune), but we can control how bold we are being. And if we turn up the dial on how bold we are being, our fortune (i.e. what happens to us) must also increase.

This was the hypothesis that I set out to test — that taking bold action leads to great things because the universe rewards bold action.

Lesson #1 is that I found this to be irrefutably true.

Lesson #2 — Being weird is how you find your tribe

One of the early “rewards” during my journey was meeting Brad. Brad is the creator of Discover Connection, which just became your favorite YouTube channel. His videos feature him and his friends asking strangers for outrageous things like if they can cook dinner for them in their home or if they can use their shower.

When my Instagram video started blowing up, I began to ask people for ideas on what to do next. In total, I asked over one thousand people for ideas.

At first, I was surprised that so many of the suggestions were similar. But once I met Brad and checked out his YouTube channel, I realized that people had been recommending that I do the exact same things that he had already done.

I want to slow down on this point for a moment. Not only was it insanely serendipitous how I met Brad (I’ll explain this in a moment), but the fact that I got to meet the person who was unknowingly influencing so much of my journey was crazy. The only way I can make sense of this is to refer back to lesson #1 and claim that the universe was rewarding my bold action.

When the student is ready, the teacher appears.

A serendipitous connection

To make a long story short, I was introduced to Brad through a friend. We were catching up on the phone and I started sharing about what I had been up to with my 100-day challenge. My buddy responded by saying that he had the perfect person for me to meet (Brad) and that he had actually just moved into a house with Brad a few weeks ago!

When Brad and I jumped on a Zoom call, we instantly hit it off. It takes a certain type of person to be willing to ask strangers for outrageous things, and I’d be surprised to meet anyone willing to do so that Brad and I didn’t like.

A few months passed and Brad was in San Diego (where I live) to see a friend. We went on a walk together and bonded over our shared love of human connection. I loved learning more about his mission and his motivations for creating Discover Connection. Getting to spend time with him certainly felt like a reward for my bold action and it also led me to discover lesson #2:

Being weird is how you find your tribe.

What does weird mean?

I define “weird” as fully leaning into the activities, topics, and ideas that light you up. The things that you can’t stop talking and thinking about. I believe that leaning into this “weirdness” is the fastest way to find your “tribe” or the people you are meant to meet.

Contrast this with what most people do. They only engage in topics and activities that other people deem “cool” and then lament about how they can’t find anyone interesting to surround themselves with.

Being weird applies to making new friends as much as it does to finding the love of your life. It doesn’t take long to find your people if you are unabashedly authentic and open about the weird idiosyncrasies that light you up.

This is the best way to find your people.

Being weird is how you find your tribe.

Hundreds of people

Throughout my 100-day challenge, I interacted with hundreds of people. I particularly loved asking couples for strange things because they would always look to each other to answer before answering themselves. Their spoken and unspoken communications were hilarious.

Before I share the final lesson I learned from my challenge, let me share more about the things I asked for.

I asked strangers if I could:

• Bake cookies with them
• Give them a piggyback ride
• Play leapfrog with them
• Do the Macarena
• Race them down a slide at a park
• Have them push me on a swing set
• Have them lift me up at sunset like Simba from The Lion King

I had a “can I drive this” phase where I asked the mailman, Amazon delivery driver, and FedEx driver if I could drive their trucks. I even asked construction workers if I could operate an excavator and drive their steam roller.

I mostly received polite rejections, but I did save four dollars at the post office by asking if they had a discount for men with incredibly good mustaches.

It turns out, they do!

Lesson #3 — We are all desperately craving connection

Each bold ask I made was as unique as the person I was asking it to. After hundreds of uncomfortable situations and a lot of laughter, this is the biggest lesson I learned:

We are all desperately craving connection.

Even when people said no to my outrageous requests, we still shared a memorable moment. Nine times out of ten we both left with smiles, laughing about the epic story we now had to tell. I get a lot of joy from imagining the people I met talking to their friends later that day.

“You won’t believe what this random guy asked me today!”

Whether someone said yes or no, I’d always offer them a high-five as I walked away. Just this little act of connection made them smile and reminded me how much we all crave human connection.

The pandemic took away so many of the small, seemingly insignificant interactions with strangers we used to have. But after spending 100 days talking to strangers, I realize just how important those interactions are.

They remind us that we are all here together on this giant rock hurtling through space. There’s a reason that a small smile from a stranger passing on the street feels exhilarating. There’s a reason an unexpected high-five can make someone’s day.

We are all desperately craving human connection. And if you want to start making the world a better place, all you have to do is start interacting with strangers.

Bonus points if you ask them for something outrageous!

_

If something came alive in you while reading this, I dare you to take action:

1. Book a discovery call to learn more about embarking on your Hero’s journey
2. Join my newsletter to stop hating your Monday Mornings