How One Notebook and 44 Pilgrims Inspired Me to Approach Strangers for a Connection Challenge

Behind the scenes: How tapping into courage brought not one, but two projects to life

In the fall of 2014, I spent about a month walking the Camino de Santiago 500 miles across Spain.

To set the scene a bit, I had two outfits: one inside my backpack and the other on my body. After each day's 6–8 hours of walking, I'd shower and hand wash that day's clothing, such that it would hopefully be dry before the sun went down. I'd eat and then sleep each night among fellow pilgrims in a room full of bunk beds.

The walking was quite meditative, and I soon began to keep a running list in my head (and later on paper) of the lessons I was learning. In time, these thoughts became this reflection:

In the second half of that month, I found myself wondering what others might be gaining from this walk as well. The idea arose to interview pilgrims at the end and ask that very question.

Now, there are many ideas that pass through my mind. Often I'll visualize said idea occurring and get so lost in what ifs and far-fetched scenarios/details, that all of a sudden I'm miles away from the very action that's necessary to bring said idea into the world. There's always a first, simple step, but instead of making that movement I love to think, and think, and think myself far away from where I must begin, allowing the idea to remain a thought and nothing more.

For whatever reason, though, I felt a strong pull to actually do this one, to see this idea through. In part to prove to myself that I could do it, and part because I knew getting over that hump of fear would be good for me.

So the day after I finished the Camino, I bought a small notebook in a tourist shop. Now I had paper for pilgrims to record their thoughts!

With this notebook and one of my pens, I walked towards the street where the pilgrims were waiting in line for their certificates of completion—exactly where I'd been the day before.

But who are you to do this?, my internal dialogue started up.

You're not a reporter, you're not doing a project, you're not writing a book—how are you going to explain what you're doing this for?

As I turned the corner, I could now see a police standing near the back of the line of pilgrims. Oh great. There hadn't been any sort of security person in the area when I'd arrived yesterday.

I have a modest fear of authority figures—especially of them telling me "no" or that I'm doing something wrong—so seeing this policeman surveying the line was an extra hurdle to something I was already fearful of doing.

Was he going to think I was cutting in line? Would he even let me do my survey? Would I need to first explain to him why I was there?

As I got closer and closer with each step, my internal fear continued talking.

What are you going to say, "I just wanted to ask people, so I’m asking people?" That’s not going to cut it. Who do you think you are?

Now I was right next to the line, policeman just to my left, and…

…my feet continued moving at the same pace, carrying me all the way back to my hostel, straight to the bar where I promptly ordered a glass of wine.

I hadn't been able to do it.

I felt a bit disappointed in myself, but not all hope was lost. Perhaps with some liquid courage I could go back and start interviewing pilgrims!

The barman told me he couldn't serve wine at this hour, something about that part of the bar being closed, so he gave me a caña instead, a small beer. I sat there alone drinking it in the hostel's empty bar.

And then it started to rain.

The rain immediately washed away the day's remaining courage, so when I finished my beer I headed up to my room. Yes, my very own (tiny) room with my own bed and bathroom—the first time I've had this luxury in a month! I let my sore body snuggle into the warm bed, and slowly streamed Gilmore Girls on my old iPhone using the hotel's Wi-Fi. Comfort at last!

Luckily, the story does not end here.

The next day, I gathered up my courage once more and decided to try again.

This time, there was no police man surveying the line. Yes! With one hurdle gone, my feet led me right to the back of the line, where I nervously began:

"Hi, I'm Rebecca, and I just finished the Camino two days ago. I learned many things, and I'm curious what you learned from walking the Camino. If you want to share, here's a notebook where you can write what you learned."

I had a sample page that included the info I was looking for: name, age, location, and what you learned while walking the Camino.

My heart was really pumping and nerves were flying at the start. I'd first ask what language they spoke, as my questioning limited to English, Spanish, and surprisingly enough, French. (My French was sooo elementary at this point in time, and I hadn't envisioned using it. But when I reached the first French speakers, I gave it a shot anyway, butchering everything on the spot, but apparently I managed to get the idea across—communication success!)

The second man I asked was from Middleton, Wisconsin—I kid you not! (I am from right around there, too. The world is always small.) He worked at the school where my mom used to teach in Madison. What a splendid connection I almost never had!

As you can imagine, the more people I asked, the easier it got.

It was like, look, I'm doing this thing, and here's a notebook full of all the other people who have participated too.

Some people kindly declined, and that was totally fine! It didn't feel like rejection in the slightest—I just moved on to the next people in line.

Some wanted to know why I was doing this, and I said I'd share it on my personal blog. One person asked for the URL, so I gave it to them.

When I finally reached the front of the line and had spoken to 44 people, I was done.

It had wiped my energy for the day, but it felt so incredibly rewarding to make these connections and to interact with all of these people. It was also satisfying to see the idea become action, to overcome my fears and prove to myself what I knew all along.

I have not pushed myself like that very often since, but I know I am capable, it will be fulfilling, and the very first time is the most difficult. It's best to just get it over with quickly like a bandaid, ripping it off before those what-ifs and doubts ever have a chance to arise, allowing the beating heart of your live idea to take their place instead.

And while this would be a fine ending, I must share how this day had an impact in my life more recently. So once again: The story does not end here.

I began writing this very reflection in January of 2017. Reading my own words energized me to take action on another project involving strangers—an idea that had come to me as a response to the U.S. election in November. It was a way for people to connect face-to-face with others outside of their social bubble, to bridge the gaps and increase understanding.

The idea? The 5-in-5 Connection Challenge: Challenge a stranger to find five similarities with you in five minutes—the more obscure the better—and write down your findings in a Venn diagram as you go.

I let the idea "simmer," which in this case simply meant that I let the doubts come in and freeze me. Is this totally stupid, or could it be a real thing? Would it actually help change anything? Would anyone else do it?

Over time I shared the idea with two others, saying each time, "I know I need to just do it, just try it and see what happens."

But week after week went by, and I took no action.

And that's how I found myself on the morning of January 18: Yet to test out this idea I’d been "incubating" for far too long, five days away from leaving the country for three months of travel, and writing about my experience interviewing pilgrims in Santiago de Compostela.

It wasn’t until I revisited the sensation I’d experienced two and a half years earlier, that I was propelled to action.

"I know I am capable, it will be fulfilling, and the very first time is the most difficult. It’s best to just get it over with quickly like a bandaid."

As I typed those words they really hit me, and in that moment I knew it was now or never. The sun was out—a gift during a Wisconsin winter—so I left the reflection incomplete, packed up my backpack with my journal and notecards, and walked the 30 minutes to our small town's only cafe.

I ordered a tea and sat down at a counter in the back, taking in my surroundings.

Nearly everyone there was there in groups. Duh, people come here to meet others! I wasn't about to interrupt a business meeting or a group of friends. Plus, people act differently when they're among friends versus when they're alone—I had imagined this as a one-on-one experience. What if no one came to the cafe alone while I'm here?

I opened up my journal and started writing. There was a girl to my right who was eating a sandwich alone, thumb scrolling on her smartphone. Maybe I would ask her. Did she have five minutes to spare?

As I was building up the courage to ask, she stood up and left. All right, she's out.

The door opened and some more people arrived, waiting in line to order. One man looked like he could possibly be by himself, or possibly be with the people he was standing near.

I surveyed the front counter out of the corner of my eye as I continued to write in my journal. Then, the man in question picked up his plate with a sandwich and started looking for a place to sit. He was alone. Since I'd been looking up, we made eye contact as he glanced my way, and before I knew it he was headed in this direction.

As he passed behind me, he said "Writing in a journal?"

That's when I knew he'd be my first connection challenge participant.

He sat down two spaces to my right and we made a bit of small talk. Then I made the ask: "Do you have five minutes to do a challenge with me?"

"Sure, what is it?"

"We have five minutes to find five things we have in common."

He was on board! I scribbled out a Venn diagram on a notecard, then realized I'd forgotten to ask his name.

"I'm Rebecca, by the way. What's your name?"

"Woodie."

I wrote each of our names on the two circles of the diagram, fingers shaking.

My hands continued to tremble as I went into my backpack to pull out my phone and set a timer, adrenaline overflowing.

"Are you ready?"

"Okay, go!"

What an adventure those five minutes were! He is not from Wisconsin, but rather from Tennessee. Later we discovered that we had both learned piano as children—first similarity. Then, Woodie had just read The Artist's Way—in which the author shares her Morning Pages practice, while I had that book on my to-read list, and had just started an 100-day project of daily writing because of reading about Morning Pages! We both journal—that was the second similarity I jotted down.

He is a father and his wife passed away in 2012, I am single and spent the previous year living in France. He doesn't live in my town, but had come to the cafe that afternoon to do some sketching (because his girlfriend sketches). I'd just taken up travel sketching / watercolor painting. Third similarity!

He works remotely (programming) and was going to sketch at the cafe and then wander walk around town. Wander walking, that's one of my beloved activities—fourth similarity found!

Our fifth was Spanish—a language he used while living along the Panama Canal while in U.S. military service from '69–'74, and while traveling in South America. My tie to the language is my B.S. degree and the two years I lived in Spain.

We had five before the time was up, and kept chatting for nearly a half an hour before he left to continue his afternoon in town. He was so thrilled at the connection—as was I. Who would have thought a venture into town would bring this?

I asked if we could take a picture before he left, to document the project.

After he left I basked in the joy of that human connection. This is why it pays to bring your ideas to life! I told myself, This is why it's worth it to be a little uncomfortable and do something your fear isn't 100% on board with!

How lucky that on the exact day and time I finally decided to act, Woodie had chosen to come into town, to this cafe. I couldn't have asked for a better first participant! It was almost too easy, we had so many similarities.

I started working on some thank-you notes I'd brought along, proud that—if nothing else—I'd broken the seal and invited one person to do the challenge that day.

A bit later, I saw my opportunity for ask #2: A younger-looking guy had come in and was sitting behind me alone. At first it looked as though he might be waiting for someone, but after a little time observing I gathered up courage and approached him.

His name was John, he was in his early 20s, and has traveled a lot internationally for mission trips. We also got to five within the time limit—if you count both having a sister in her early 30s as a valid similarity.

I was surprised how shaky my fingers were at the start; this Venn diagram was way lop-sided because of it!

It was another exhilarating experience—and John seemed excited about the idea. "This could go viral," he said afterwards, "You should make a video!"

While a viral video is not on the horizon, I'm about to return to the states in just under two weeks, and continuing this project is high on my priorities.

It pushes me out of my comfort zone; connects me with real, live, breathing human beings; plus it's a fun creative challenge to come up with questions to ask while on a time crunch. Not to mention, I never know who I'll meet or what I'll uncover.

I was on such a joyful high that afternoon in January, from the adrenaline of approaching these strangers, of finally doing something I'd been thinking about for weeks and weeks, and especially from the serendipity of human connection.

Bringing that idea to life reminded me yet again to take action.

So for my future self, I'll remind you once more: Bring your creations into the world! Let them be uniquely you and splendidly imperfect. You're here to do whatever you damn well please while you have this precious life, and you have the magical ability to create. Use it! Have fun with it and alter the very Earth on which we live by releasing your small creations into it, whatever they may be.

You never need a reason or credentials for starting a project, either. Curiosity and personal interest are more than enough! A bit of fear is usually a good indicator that this is the very thing you need to do or make. And you can be the one to take the first step and bring it into the world, how cool is that? You're a human, inherently creative, beautifully a work in progress.

And now, it's up to you. Does the story end here?

If there's an idea you've been incubating in your mind, a song you have yet to share, a story you want to tell, a project you've been considering, let this be your sign. You'll never feel "ready"—do it now! Share it now! Create it now! Rip off the bandaid to kick out doubt, and take the first, simple step today.

From 44 pilgrims in Spain to two strangers at a cafe in Wisconsin, let your own creation continue the story.