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24 Lessons I Learned from Meeting 100 Strangers Over 100 Days


There are so many ways to cut my lessons learned from 100 Strangers, 100 Days. Today, I’m going to give you a slice of the grander, big-picture lessons. I’ve written 24. Yes, that’s a lot. However, I probably could’ve written a hundred, and indeed, I thought about it. However, that’d be overkill, and you likely wouldn’t read it anyways.

So, here are 24. 24 because… that’s just where I decided to draw the line. Enjoy them, but please… learn some lessons on your own, too. J
  1. It doesn’t take much to start something important to you. I came up with theidea for 100 Strangers, 100 Days while hiking one Saturday morning in September. Within two hours, I interviewed my first Stranger. Within six hours, I had 100Strangers100Days.com up and running. It doesn’t take much to start, and get something off the ground. Just takes focus and commitment.
  2. It takes a lot to be consistent. The hardest part of the journey was not meeting Strangers. It was meeting one and writing about the interaction each day for 100 days. Some days, I wasn’t feeling up for it. However, I did it because that’s what this journey was about. Being consistent. Being deliberate. Meeting people. This is what separates the true doers from the wanters – executing.
  3. You can meet people everywhere. I walked up to Strangers with familiar faces around the office, Starbucks, and yoga, primarily. However, I also met complete Strangers in these places plus while shopping, walking on the street, hiking Stone Mountain, in line for a restaurant in Boston, everywhere. Meeting new faces is not as hard as many believe. Couple this with explicit networking events, and you can meet like-minded people and build new and existing circles.
  4. Things may always be awkward, but you’ll be comfortable about it. I was pretty natural, I think, at the beginning. However, I was still uncomfortable and anxious walking up to complete Strangers to ask them to share their stories with me. That was true up to Day 100. However, I only need to be confident and happy with what I’ve done, so far, for many of those feelings to melt away, and even give light to excitement. I wholeheartedly believe I can walk up to anyone today, and strike up a conversation.
  5. Each opportunity has one thing in common – you. Even when I got rejected, the next person was a new opportunity. I remember being rejected three times in one day before finding a Stranger to talk to me. But each subsequent Stranger knew nothing about the person before rejecting me. I was the only person who knew. It’s important to know what happened, but to keep positive and keep authentic with each Stranger. Think about that if you’re in sales.
  6. People want authenticity. By the end, I had a near 80% acceptance rate. More than half of those who turned me down either because they didn’t have time, or just weren’t open for the picture to be taken. Otherwise, people were very open to just talking to me and sharing their stories. I approached many Strangers who were staring at their phones or working on their computers. Yet, they allowed me to interrupt them, and many smiled as I shared my journey and asked them to be the Stranger of the Day. All of them smiled at the end of our meets.
  7. Support comes in many forms. I had several friends share my journey on their many different social media accounts, and one friend who helped me troubleshoot my website when it went down a few times. Then, I had friends who would ask me questions about how it’s going, but weren’t open to sharing with their friends publicly. There are segments of support in almost everything you do. Know who they are.
  8. Some of the closest people are the most skeptical. I was surprised I was still surprised at this. That is, when I shared #100Strangers100Days with some family and friends, they laughed at the journey with heavy doses of skepticism. They were more skeptical and teasing of the journey than others. Again, realize the segments of support.
  9. Familiarity makes everything so much easier. I did meet a lot of Strangers who I had seen before, but never spoke to, or gotten to know, them. This made introductions, obviously, much easier. Some of these Strangers with familiar faces, I’ve seen for years. I can go on forever, probably, and never say hello to these people because maybe too much time has elapsed that it’d be “awkward”. However, being late is better than never. In fact, it can help break the ice with some laughter – “so after four years of seeing each other, I’ve decided you’re safe to meet!”
  10. It can be hard to be a good listener. Sometimes, my head was running with what else was happening around my life that even listening to the Stranger in front of me for 10 minutes was hard. Couple that with the nature of this journey, I had trouble at times listening to connect and understand. I was listening to respond/ react. This made me, at times, want to interrupt. Be careful if you’re not listening and truly connecting. (I became more conscious when a Stranger mentioned how interrupting others can create silent, negative behaviors long term.)
  11. We don’t see ourselves as beautiful as others do. I took hundreds of pictures of Strangers – several takes for some. I found many takes to be great the first time, but the Strangers would laugh awkwardly and tell me they thought they were ugly. Meanwhile, I took many candid pictures by snapping pictures while they laughed or looked around. Despite many Strangers posing for the camera, these same Strangers wanted me to share their candids.
  12. Not a lot of people think about who they are, or what drives them. A lot of people paused for long moments when I asked them, “Who are you?” Many admitted they didn’t know, and had to think hard. Meanwhile, I had Strangers talk to me days after our meet to share they thought more about the question. It’s interesting how people describe who they are by what they do for work or their relationship status – typically, modes that are extrinsically influenced.
  13. It’s not rambling, it’s sharing a passion. I remember running into a Stranger weeks after we met, and he felt that he rambled on during our meet. I told him that’s not how I felt at all. Whenever someone put me on a path and carried it, I liked that a lot. They shared what was on their mind, and in many cases, they shared their passion. Their excitement helped spur a little bit of a monologue, but that was a great thing to hear. Not everyone allows his/ herself to have a passionate monologue.
  14. You’ll never be yourself as long as you’re being what everyone wants you to be. A recurring theme I heard from others, and one that I lived the premise of through this journey, was being comfortable with who we are. There were Strangers who kept their passions from loved ones because they didn’t believe friends and family would appreciate the passions like they did. Meanwhile, as I mentioned above, I had my own skeptics from friends and family. If I was truly worried about what others thought of this journey, I probably would’ve stopped this long ago, let alone not started. Don’t be like everyone. Don’t mind whatever “weird” is. Be yourself. 
  15. People are acutely interested in whatever true happiness is. I asked the Stranger of the Day if s/he could ask anyone anything (effectively, the next day’s Stranger), what would s/he ask the Stranger? A very common question was what happiness meant, and what was “true” happiness. I’m not sure why that was so common. Was it because they wanted others to think happy thoughts? Was it because they weren’t sure what made them happy? Were they looking for inspiration for what happiness really is? A question for another Stranger. J
  16. People just need moments. People need moments to connect. People need moments to escape. People need moments to get in gear to talk about themselves – what drives them. People need a few minutes to set the day-to-day aside. It doesn’t take long or need extraordinary effort to do something or to achieve a smile. It just takes one moment.
  17. Every meeting was just a snapshot in time. Important to recognize we’re all dealing with different things at any given time. I remember a couple Strangers who shared how you never know how others are really doing. Being nice requires no money or skill. Opening a door with a big smile can transmit energy. Someone might have just sold an important life memento of a loved one while burying a best friend. Take a moment. Live in the present. And recognize the power of a single connection right now.
  18. Look up and connect. Over time, the journey became more engaging. Yes, I got better at the approach, but really, our conversations started to flow as my style evolved. At the beginning, I took notes with a pen and paper and a bank of questions. Over time, I stopped asking set questions except for the first question – “Who are you?” Then, I let the conversation flow from there. I then used a voice recorder, so I can look up during our entire interaction, and let the conversation flow. Readers recognized this shift, and responded accordingly telling me how the stories were much funnier, more engaging, and just flowed so much nicer. Let this be a lesson as you’re around others and you have that itch to look down at your phone.
  19. Small goals can work against your much grander goals. Goals are a funny thing much like a Stranger once told me about reaching goals. I kept my eye on Day 100. By doing so, I also had “pocket” Strangers – referring to something like a “pocket veto”. In this case, I knew there were Strangers around that I had seen enough that breaking the ice and engaging them would be really easy. With that, I wouldn’t meet them unless I knew I may have a “difficult” day coming up – like, I would be extremely busy, or would not see as many people. So, I saved these Strangers for difficult days, just in case. What this really did was give me too much comfort and delayed the grander ambition to make connections. Be aware of those goals and those metrics you measure.
  20. Get to know people to break biases and judgements. I caught myself a couple times looking at someone and making a snap judgement. When I realized I made a negative judgement, I told myself to go ask that person to be the Stranger of the Day. I wanted to force myself to get to know people, and beware of snap judgements. Each time I did this, I discovered something great about the person.
  21. People think you need a novel concept to start something. You don’t. A lot of people (friends and Strangers) were amazed by this journey. They were inquisitive about how this journey came about. They were fascinated about the stories. They then thought they couldn’t do it, or they could never think of a journey like this. Here’s the thing – meeting Strangers is not novel. Writing about them is not novel. I just wrapped it all up in a package, and did it. It’s almost always about execution, not the idea.
  22. Each connection is a connection that can change lives. I had several friends who read about a Stranger they had seen before, and then, they actually went to meet the Stranger. They used the Stranger story as a foot in the door to get to know the Stranger even better. I’ve even connected some because of business synergies. The most obvious connections are sometimes hidden in plain sight.
  23. People are great. People are beautiful. You can connect with anyone. To the point above, we all have some amazing story somewhere in us. The people around us are not that strange after all. The people around us are not as foreign after all. We are all connected in some way, and you’ll find that when you take a moment and say hello, and go beyond the hello.
  24. You’re sometimes never really ready, but you kind of assimilate to whatever success looks like just by doing. This lesson kind of wraps up a lot of the entrepreneurial lessons above. That is, the level of effort I put into this was a lot more than I originally thought. Had I known this, I’m not sure I would’ve started. I was nervous walking up to some Strangers, but once I put my feet together or said hello, there was no turning back. Sometimes, the best thing you can do is to fire before you ready yourself and aim. Happily, I’ve found I’m pretty good at this whole make-it-up-as-I-go-along-and-learn-and-adapt thing. Just go.
“There are no strangers here; Only friends you haven't yet met.” – William Butler Yeats

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