100 Strangers 100 Days Collage

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 the idea 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

A Week After 100 Days — 80%, No But Why, and My Lessons (Yours)

It’s been a little over a week since I wrapped up my 100 Days. It’s been odd many days not “having” to meet a Stranger. I’ve caught myself a few days walking into a room, and wondering who in the room I should meet for today. Then, “Oh, wait, I don’t have to today.” My days have definitely been a little simpler without an additional priority in my day-to-day.

Beyond that, everyone has been asking me for an update on what am I doing next — I don’t know, yet. Also, what are my lessons learned? That, too, is coming. Before those happen, here are my post-journey reflections…

(I have so many more, but here’s a simple list.)

Almost 80% of the time, they say yes

Here’s an update on the acceptances:

  • No time/ in a hurry: 8 times
  • Did not want picture taken/ shared: 8
  • Disinterested: 10

So all in, I had to ask 126 people to find 100 Strangers to share their stories putting the rate at 79.37%. That’s not bad. Starting out, I didn’t have a strong feeling if this would be more difficult. However, I was a heck of a lot more nervous walking up to people.

I remember most every rejection. I just watched Jia Jiang’s TED Talk on his “100 Days of Rejection”. In fact, I was told about Jia’s journey sometime in the middle of my own. Watching Jia recount his lessons learned, I was thinking about my own journey. Specifically, I was thinking about when I was rejected, and how often did I ask, “why?” (Answer: not often.)

If no, then why?

In many cases, the Stranger who rejected me told me why (i.e. no time, no picture). However, for many of the plain “disinterested”, I didn’t get a reason, and I never asked why. I usually chalked this up to they just didn’t want to do it, or they thought I was weird. I put them into the big “disinterested” bucket because I gave them the reason. I gave them the reason that “they were private”, “they didn’t care for my journey”, or I read their facial expressions and saw, “you’re strange, get away from me”.

After hearing Jia’s talk and how he responded with rejections by asking, “why?”, it made me wish I could go back in time and do the same.

In a sales role in my professional life, I want to get better at dealing with rejections, and getting to the root of people’s rejections. There are nuggets of insights that I’m missing out on by not asking deeper questions. In several instances, I still spoke with the Strangers. However, I didn’t share their stories (those who wanted to remain private). However, I might have missed the opportunities with those in the “disinterested” bucket to learn more about people.

The “Lessons List” – Start Your Own

Everyone’s asking me for the lessons learned. I’m getting to them.

Then, I’m also wondering how many people will try to learn their own lessons, or are they looking to me for the Cliff’s Notes. Meeting the 100 Strangers required no patented process. Required no money. Demanded little time. Anyone can do this. The lessons will be my own, and though, I might paint them in a light that is best seen and understood by others, they will be mine.

Meeting a handful of Strangers today, tomorrow, over the next two weeks, and learning from the experience (and maybe making some great connections), just requires an initiative. Then, those lessons will be your own. Don’t need to blog about them. Don’t need to bust out a voice recorder. Don’t need to start with “Who are you?” Instead, your lessons and journey starts today, and can take whatever path you wish.

(This is true beyond meeting Strangers, too.)

Stranger 101, Day 101 - Meet Me

BONUS ROUND: Stranger 101, Day 101 – Meet Me, the “Doer”

So, I wanted to throw in an M Night Shyamalan-esque twist for my 100th Stranger. After all, I had a lot of different people want to get to know me better. Meanwhile, most of my meetings with Strangers was in one direction — myself getting to know them.

However, I miscalculated thinking the 100th Strangers would be the 26th. Instead, it was yesterday — Christmas. It was difficult to find someone who would interview me on Christmas Day. Note: I originally wrote a post interviewing myself from the original bank of questions waaayyy back when I started. I wanted to use that, but seeing as this journey has evolved to be more conversational, I wanted someone to interview me.

Instead, I met a terrific woman named Toccoa yesterday on Christmas Day. So today, would be my BONUS ROUND, and I asked my good friend, Don, to interview me as Stranger 101, Day 101.

I’ll let him now “be me” while meeting me as a Stranger…

When Daryl asked me to interview him, I was a tad intimidated. He’s an expert. He has interviewed over 100 Strangers. What qualifies me to interview him? Yes, I was the first person with whom he shared the idea for this project. However, I think the most important reason is that I know Daryl very well. We’ve been best friends for over a decade. I understand him on a level that many don’t, and a major key to this project are Daryl’s internal motivations. After coming to that realization, I was ready to channel my inner Terry Gross (shout-out to NPR).

Meet Me, 31

Alright. So, we have Daryl Lu… Founder of 100 Strangers, 100 Days. The first question I would like to ask you is, “Who are you?”

“You forgot to ask for my birthday.”

I have to ask you for your birthday?! You didn’t say anything! You didn’t say I had to ask! Is that required?! What is your birthday? Sorry.

“31. Actually, it’s my age, not my birthday. Alright, so who am I? Who am I…”

“I am a doer! I like to call myself a doer. Because… I love to not make excuses. When I had this idea, for example, I had the idea coming down the mountain. Then, I called you immediately. Then within two hours, I was interviewing my first Stranger. Six hours later, the website was up! So for me, I love to not make excuses. I love to inspire others.”

“Or rather, my personal mission – to change the lives/ the world for the greater through entrepreneurial endeavors. To be an entrepreneur, it’s not about ideas. It’s about execution; so, I love to do things.”


So, why this project? What inspired you to interview 100 Strangers? That’s a Stranger every single day for more than three months. Why?

“Uhh, I’ve had so many – well, I think I’m in a really great place today. And, I’m the product of the great people who put me here. That’d be inclusive of my family, my friends, even Strangers who I come into contact with and somehow form some great connections. Meanwhile, we’re getting lost in our phones. We’re not texting back. We’re not emailing. We’re not calling. We just… don’t take time out for those people we love.”

“I think that we should also love the people who are around us in the community. So, this was to inspire others who ask me all the time how do I know so many people. How many people – great people – with all different backgrounds. It’s purely because I say hello, and then, I like to go a little bit beyond the hello, as I like to say.”

“So, this project, or this journey, has been to inspire others to connect with those around them. As well as, to show people when you have a little passion or you want to start something interesting, it’s not hard to start. The hardest part is being sustainable, but you can sustain something that is as simple as one Stranger-a-day.”

Have you, I guess, if someone doesn’t know you, have you always been the type to just go up and talk to Strangers, and get to know them? Or is this just kind of a continuation of what you’ve always done, like when you were a kid? How do you go, and approach Strangers? Were you always this extroverted?

“Definitely not.” I laugh.

“I grew up introverted. Then, I decided that – well, not decided, but I saw how hard my father worked for my family. So, I’ve always wanted to be a business owner. Then, through Boy Scouts and soccer teams, alike, and all the great people around me, I said that I always wanted to be more than just a business leader. So even though I grew up being introverted, I made it a habit of being comfortable being uncomfortable.”

“For me, that meant meeting people, and being more extroverted. Back in college, I did a Senior Design project, I made sure to volunteer for every single presentation. Not being I loved doing presentations, but because I wanted to be accustomed to that feeling. Since then, I used to be really to myself. Didn’t even want to get hugs or anything else. But over the last… oh my gosh, it’s almost been 8-10 years now!” I realize. “I now just try to meet the great people around me.”

“So, this is kind of a continuation of that. Continue that effort, but… yeah.”

It sounds like this is not just a social experiment on other, random people, but also, an experiment on yourself. Right?

“Yup! Yup…” I laugh.

What have you learned about others? And also, about yourself during this process?

“So… when it comes to others, I’ve learned that – think I have like an 80% acceptance rate. I think that’s pretty phenomenal. People are willing to say hello, and allow me to get to know them better. Even to share their story. If I was include people who weren’t comfortable with the picture, but still wanting to get to know, I think that number would probably more like 90-95%. So, I’ve learned that a lot of people are very open to meet. Just take the time to get to know them. A lot of people will get really, really super excited when you do. Especially at the end of our ‘meet’, they’re all just… glowing. They’re all just so excited. When they read their stories, they’re like, ‘Wow!’ Like they discover a little bit about themselves.”

“In terms of myself, I seem to be pretty friendly, and approachable. Or people can let me approach them.” I think about this for a moment.

“I learned that when I set my mind to it, I really do do that. Because this has added a lot of extra work – like another hour, hour and a half most days. Every single day on top of the things I already do… It hammered home more and more to me that you make the time for the things and the people that matter.”

“And no excuses. So for me, it was like, ‘Wow! I can really do this every single day, no matter how hard it is. It just takes a little bit of priorities and processes.’”

“So, I’m happy about that.”

When you started this, did you… can you talk a little about how your process has evolved and changed? Not just how you go about finding a Stranger, and doing the interview and write-up, but the kind of questions you would ask, and the kinds of responses you would get from those questions?

“Yeah, so when I started out, the first two people I started with, ‘What do you do?’ Then, I realized that both of them, they went straight into work mode. That’s maybe who they are as well, but I really wanted to get to know who they are, and let them, kind of, dictate where they want to take me.”

“So, I changed it to, ‘Who are you?’ I normally have a pen and paper, so I’d take notes. And I also had like a bank of questions to ask. So I would almost ask in a very interview-esque fashion. Over time, I started recording the voices, so it became a lot more natural. So, I’m not taking notes and stopping… stopping and starting.”

“And then, instead of just having a list of questions, I still want to get down to what drives people – like their motivations and passions. Especially as an entrepreneur, I’m very interested in that. So, the questions would start from the ‘Who are you?’ Based on the feedback there, then I would ask questions that would build on that. Maybe taking what they do, if that’s what they share. Or, what their passions are. Or, what matters to them, whether that’s family, religion, or sports, comics, video games, that sort of stuff.”

“I started getting a lot more conversational and really connecting with people. And I think a better, deeper level. I think a lot of readers have also expressed their interest in how great this kind of transformation has been.”

So, when did you start making that transformation? Was it 30 Days in, or 30 Strangers in, you started transitioning to more conversational approach? Or, did you kind of just try different things with every Stranger?

I thought about this for a second. “I think the transition to more conversational – I don’t remember. Maybe it was 20 or 30? But, it really started getting a lot better in the second half.”

So… you’ve just done/ completed a marathon of meeting new Strangers. What’s next? What do you see as the next step for this project, or is this it?

“Several people keep asking me this, and sometimes, I ask myself that. Then, I say, ‘You know what? I’m going to first, A, take a little time for myself!’” I laugh. “Not press myself to go meet someone every single day. I’m also going to let it all sink in. So, I’ll probably have a good lessons learned post, or several posts. I know several have been asking for it.”

“And… not sure yet. I might start interviewing friends. Meeting my friends on a deeper level. A lot of people have been asking me about that. Might turn some of the lessons and the approach into a book.”

“… might also make this into a TED talk. Everyone keeps asking me about that as well. So, have a few different things. Doesn’t mean they’re all mutually exclusive, or I’ll do one, and not the others. But, the next several days, I’ll probably just, at least, let it all soak in.”

Can you give us a preview of some of your lessons learned about, maybe for example, how you approach Strangers? How you get them to open up? Is there like a secret sauce or magic secret approach to doing that?

“I think the biggest approach is being open.”

“So, I know there are a few people I would see normally, and I think I’d guess – well, I know – I would judge them. Through this, this also inspires me to say instead of judging someone, why don’t I get to know them. Right?” I laugh at myself. “Instead of just going based on what I see. So, that’s been really fascinating. That’s been fun.”

“So that’s one thing. That approach of being open… being open to anything. This guy or woman can shock you in terms of the good, or could be for the bad, but either way, you don’t know. You might as well spend a couple minutes just getting to know ‘em. So, that’s a big one.”

“Other lessons… yeah, everyone… most people are willing to open up for a couple minutes. And definitely still, my heart beats a little bit still, when I think about approaching someone, but it’s… now, it’s probably more, ‘Well, heart’s beating fast! Doesn’t matter!’ Right? The whole being comfortable being uncomfortable… Being able to acknowledge that, and say, ‘I’m going in anyways!’ I think that that’s been really fun.”

“So the big lesson for that is just doing it. Just like any project or passion, just giving it a go. Doesn’t have to be ridiculously big. Can be something small. That little effort. That little change can make that person’s day, can make your day. Can change the whole week. And you don’t know if that connection’s going to be a life-long connection, either. So, could even have huge… benefits, and ripple effects.”

Interesting. So speaking of ripple effects, what are some of the most… can you give us a couple examples of some of the most interesting conversations or shocking revelations, or maybe contentious conversations that you had or interactions that you had with Strangers? Something that stands out in your mind?

“I don’t know if there’s any contentious ones. Thinking about a couple stories that they shared, their low-points. Those, for whatever reason, resonate really heavily with me. Maybe because I’m the ‘Master of Failure’ having written a book,” I laugh. “I love the motivations and passions of what drives people. A lot of times it’s the low-points that drive people. Hearing about people’s battles with alcoholism or drug abuse has been fascinating because they’re open to that. They acknowledge that. They’re okay to share that. I think that’s a beautiful thing to be confident that you’re in a better place, and you can be vulnerable to share that. And trust! You know, vulnerability and trust in me and others to share that. So, I really, really love that.”

“And, just how hard some people work on whether it’s a startup, or like, heck yesterday. I just pulled over at a Waffle House on Christmas Day. Met a mother. She works at Waffle House. She drives Uber. She drives Lyft. She does all these different things because she’s trying to provide for her daughter. Her biggest goal and aspiration is continue with college – or rather, she’s 10, so get into college, but also get her doctor’s degree. To do better than her. I thought that was something that was really beautiful because she was working on Christmas Day. She still allowed me a couple minutes before she had to go rush off to see her daughter.”

“And then, so many about just walking up to people at Starbucks, and how some of them are pursuing their passions, but you never know it. You never know they have a side gig. What can you do to help them? Because being an entrepreneur, knowing some of the stuff, it’s like, ‘Oh wow! I never knew this! Now, I can help you with some of the stuff that you have questions about. Things you have trouble with. I can probably do that. I can probably connect you with this DJ that I met the other day, and then, this DJ and four other people who are in the music industry. Would you like to connect? Seems like you guys would get along great!’”

“Even though they can be really successful in something that everyone else would be so impressed by whether it’s music, and then, they pursue something more business… 9-5 isn’t always bad. The corporate world isn’t bad. It’s still motivating. People have a lot of fun. It’s not always about the creative kind of occupations, too.”

That’s really interesting because I think part of… everyone has their own interest in your project. For whatever reason, my interest has always been for people I see around because you and I share – we share a similar network. With you going out and interviewing all these Strangers, you’ve broadened your network by at least 100 or more. And the people I see around that I don’t know, and I go to 100Strangers100Days.com, and I read their profiles. I get to know them, and I feel like, “Oh man, it’s almost like cheating” because I didn’t actually interview them, but I feel like I know so much more about them in order to engage with them. So, I’ve actually engaged with people based on your posts. Like, “oh, I know about you! I didn’t know you had five or six brothers and sisters! That’s really cool!” And instantly, the Stranger is like, “Whoa, what?! You know about me?” We’re like instantly connected in a way that I would probably have to spend a lot more time, or many more interactions with that individual. So, that’s been really cool to almost kind of cheat my way in to getting to know some people I see around all the time without interacting with them. So that’s really cool.

“Well, that’s like the whole point – to inspire connections. If I can inspire one person to make one connection, again, like, what are the ripple effects of that? You know, that one interaction can make that one person smile big for that day. Could make you smile for that day.”

It’s something you’re adept at in the business world, too. It’s good to see. You’re able to do this for just the general population. Would be interesting to see what else comes out of your creative lab with dealing with interactions and connecting people. Inspiring connections.


Anything else you want me to ask?

“Yeah, so, I like to ask the Stranger of the Day, if you could ask anyone anything, what would you like to ask? So, I think remembering Toccoa’s question yesterday, which was, ‘What can, essentially, I do or what am I doing to make the world a better place?’”

“So for me, I’m just going to encapsulate it with that personal mission which is: To change the world for the greater through entrepreneurial endeavors. So an entrepreneurial endeavors like this, 100 Strangers was just to inspire others to connect. Or, it could be helping them with their startup and being an Adviser or whatever that is, and helping them grow what they love or their passion. Or, encouraging others to write. Those types of things. So, you know, I want my entrepreneurial endeavors to be a catalyst for others.”


“And then, I think the other question, or the final question I like to ask others is what is the question I would like to ask a Stranger.”

Yeah, what is a question?

“You’d think I would have a good one at this right now. But I really kind of don’t. Everyone has some really cool questions. Some people are really interested in what is true happiness. Others, ‘What can you do to make the world better’. Before, I used to ask like, ‘What’s your biggest life regrets?’ Those types of things. Or, what’s stopping you. I think they’re all such great questions.”

“But I guess because I start out just about every conversation, every meet, might as well keep being my question for anyone. That is, ‘Who are you?’”

After the handshake.

I was a little surprised that our conversation flowed with such ease. We hadn’t prepared beforehand, but I felt comfortable asking Daryl about his experiences. Thankfully, Daryl helped me ask the right questions when I felt lost. Yet again, he demonstrated his natural affinity to guide. One thing I noticed about “playing” interviewer – active listening without interrupting takes work, and I wondered to myself how many times Daryl sat in my position focusing on his interviewee.

Coming out of this interview, what really interests me is not only the lessons Daryl has learned, but also how he chooses to present them. I agree that a TED talk would be an excellent way to distill his experience and findings in an easily consumable medium for a general audience.

As to what his findings will show, my guess is that the truly insightful points will be what he learned about himself. If you read closely, this project was as much about Daryl testing and discovering unknown things about himself as it was about learning more about and connecting with others. He is quite adept at hacking his internal wiring through consistent and measurable approaches. In this case, he has successfully hacked his inner-introvert to become an extrovert in unfamiliar situations. He repeatedly stepped out of his comfort zone by approaching Strangers, asking their permission to be photographed and interviewed, getting them to open up to a Stranger, and publishing a write-up. He did this for 100 straight days – a true test of consistency, discipline and stamina.

So, what’s next for Daryl? What else will he hack about himself through others? I don’t know, but I agree that he should definitely take a break first. Even if that means that he does what I tell my kids. Don’t talk to Strangers.

Okay, so that’s Don interviewing me. It was pretty fun. I definitely could have prepared myself even more for this seeing as I had this pre-determined. Much of it, I also know by heart. What was surprising, though, was how I really did go straight into my passions of doing things. I didn’t even touch on how much relationships matter. I talked about family and friends, but I feel I talked about them only in context to myself as a doer. Even as I answered the ‘Who are you’ question, I thought to myself that I should mention I’m also a family man — thinking a lot about my amazing niece who I got to spend a lot of time with over Christmas. But I didn’t. I kept this focused on this journey and my entrepreneurial drive. So yeah, I thought that was interesting.

There really was so much I wanted to say, but I wanted to be somewhat brief. (Are you shocked that my lack of brevity here is still what I consider “somewhat brief”? Me, too.) As I mentioned to a Stranger the other day who felt that he rambled, I felt he was speaking differently than “rambling”. Instead, I felt his passion through his words, and how immersed he was in sharing with me his passions and motivations. I, too, hope my passion came through, even if I kept this somewhat abbreviated.

As I said, and as Don said, I’m not sure what my next adventure is. Don’t know if this will be resurrected into the coming months, weeks, or days, and in what form. However, I’m so proud to have not only completed this goal, but to have met so many great people, and to have influenced the many people who have actually said hello and went beyond with Strangers with familiar faces. I hope this is just the beginning…

And of course, thanks again to my best bud, Don, who was also the author of the Foreword to Postmortem of a Failed Startup: Lessons for Success.

Meet me. No longer a Stranger.


2 Strangers, 2 Days Left

More Than 80% Say YES! And what happens at 100+1?

Just wrote today’s Stranger post — Meet Lindsey, Stranger 98. I’m heading into the Christmas weekend with TWO Strangers, Days left! What a journey it’s been so far. *sighing out on this one*

Updated Rejections… by the Numbers

  • No time/ in a hurry: 8 times
  • Did not want picture taken/ shared: 8
  • Disinterested: 8

Since I posted last about the rejections (from Day 86), I’ve only been turned down once more. That’s improved my acceptance rate to 98 / (98 + 24) = 80.33%! Okay, it didn’t really move the needle, but that’s okay.

Day 100… + 1?

Like I said, I’ve got 2 Strangers, 2 Days left. I’m fielding a lot of questions of what’s next. My answer = I don’t know.

I’m thinking about Kevin’s thoughts on goals and what happens once you reach that goal (Kevin, the “Family Man” – Stranger 62). Yes, I’m about to hit this mark, and I don’t know what to do next. Except, I do. So, maybe I lied a little. I know I’m going to take a few days off to breathe a moment.

This journey has been incredibly fun, but it’s also added a hefty hour/ hour and a half of extra “stuff” to do each day. It’s forced me to go outside everyday. Not a bad thing, but also, I never just chill. I don’t normally do that, but it’s a totally different feeling when you know you can’t because you have a goal to achieve.

I’d like to take a few days to gather my thoughts on this journey. Luckily, I’ve been gathering these thoughts with non-Stranger stories like this one. However, I want to take a few days (week?) to just let it all marinate in my mind. It’ll do me some good. I’d like to actually proofread the Stories, too, which I haven’t done for 70% of the Stories. I may then take little blurbs and quotes from each Story, and share to grow this audience.

Beyond that, who knows? Maybe I’ll organize my thoughts into my next book. Maybe I’ll organize my thoughts and piece together a talk, and submit to TED. I know some people who run TED locally, so that’s another route. Maybe… just maybe… I’ll keep going with another effort but approach friends (who have been asking me to do so — A LOT). Maybe I’ll put together a program for others to try their own journey to meet Strangers. Maybe I’ll do video meets/ introductions! Maybe I’ll do all of that!

What do you think? What would you like to see?

Latest Rejections, (Re-)Meeting Former Strangers, and Last 14 Days

It’s been a while since I shared some of the thoughts flowing freely in my head, so let today be the great day I share. Plus, there are only two weeks left on this journey — about as good a time as any.

Updated Rejections… by the Numbers

Alright, so here’s an update on the rejections so far. I’ve been loosely tracking these, so this is +/- 2 with a 83% confidence level. (I just made that up. Kind of.)

  • No time/ in a hurry: 8 times
  • Did not want picture taken/ shared: 8
  • Disinterested: 7

That’s not too bad, right? I mean, including today’s Stranger 86 + the total rejected (23), that’s a 78.90% acceptance rate. When I started, I didn’t have really have expectations of what this number would be. Thinking hard, close to 80% seems pretty darn good.

Nice to Meet You! …Again!

So today, I saw… a bunch of former Strangers. I run into some of the (former) Strangers a lot. Some, I’ve actually become good friends with. That’s pretty cool. One former Stranger today, shared with me feedback from our meet, and feedback he received from sharing his story. It was fascinating, and also, in line to some of what I’ve shared previously.

  • His girlfriend commented to him that she didn’t know he was so smart. I was intrigued by this because I got this from just a few minutes of talking to him. Maybe she’s that smart. He then let on how he doesn’t always share some of the passions he has, and the literature he reads. He didn’t believe that she would appreciate this so much, but he does share in her passions. I thought that was interesting, too. Though, I’m not surprised because he’s a great guy, and seems to align to his partner’s interests. However, I encourage him to share more of his with her.
  • His friends didn’t know much about his passions. They were surprised by his depth. He commented how he often kept things pretty “high level” or at the surface. Much like his girlfriend, he didn’t feel they would appreciate this (maybe even not understand his passions). I, again, encouraged him to let them make their own decisions, not he make decisions for them. Being vulnerable means handing over the keys and trusting the other will, at least, respect who we are, if not share in the passions we have. The bond that’s formed by opening up more is a powerful one, and you don’t get that without creating a deeper connection.
  • You can’t always be so open and talk about “deep” things all the time. As much as I love a good talk, high-level “superficial” stuff is great banter and keeps conversations light. Not every conversation needs to get so deep like I go with the Strangers. That’s important. Let others in and be vulnerable, but don’t go deep every time. That’d be like always sprinting whenever you put your running shoes on. Maybe you want to jog. Maybe you’re just walking around the grocery store.

Our brief talk today covered this bit, but it also re-triggered a comment I’ve been receiving a lot. That is, what about friends? To this former Stranger, his friends didn’t even know his passions, or how much he loved to challenge himself intellectually. In my case, I have a lot of people (friends included, but not all) asking me to do a friends version. It makes sense I don’t know the driving forces of many of my friends. Though, I try to ask deeper questions. So, maybe…

Otherwise, I’ve had three other former Strangers reach out in the last 48 hours with a lot of excitement about not only their stories, but also how their stories were received by others. Much like the former Stranger above, these three shared so much excitement about how great it was to think about these questions. They were happy to have shared their passions. They enjoyed reconnecting with friends after posting on social media. This excitement and glow is pretty common, I feel, and it’s truly inspiring me to continue on… which brings me to…

The last 14 days!

Today was Day 86. 86 Strangers, I’ve met and gotten to know. Wow. The first 50 took a while to get to, I feel. However, the last 36 have been flying by. It’s been something amazing and radical to be a part of.

I’m real curious what happens with the next 14 days because I won’t be in the office as much — which has been a great source of Strangers. I run into so many Strangers with familiar faces. Meanwhile, Christmas may be a tricky day to find a Stranger depending on what’s open and who I can run into.

On that point, I’ve been speaking to several friends about this recently — I’m really not fazed to talk to someone, even a complete Stranger now. I’ve found that confidence where “hey, this is a cool project, and I want you to be a part of it” just rolls off the tongue. (No, that’s not really what I say, but I’m paraphrasing.) It’s fascinating to me because I really am not worried as I walk up to complete Strangers… even groups of people. Maybe it’s the responses and feedback the former-Strangers are sharing with me that is instilling in me this drive and confidence. Their enthusiasm and interest (like the former Stranger above) is enough for me to run on. This energy shows me how this journey will resonate with the right people — the people I’m interested in attracting and inspiring.

So let’s see how the rest of this journey goes, and let’s see where this heads next. Or rather, where I head off to next. Before that happens, I’ll just keep meeting people. One Stranger and One Day at a time.

A New Question

Today’s Day 69. I’ve already met today’s Stranger — TK. I asked him a new question that I hadn’t ever asked before that was kind of an interesting one. In fact, I thought of this while sitting down with Carling, Stranger 22, this morning — “Who are you not?”

I pretty much ask every Stranger “Who are you?” Perhaps just as interesting is considering who someone is not based on who they are and what they do.

Consider what you do or who you are today. Why and how are you not really that person? Like the “who are you” question, the person being asked can put him/ herself on whatever path they want. This is similar to a question I’ve asked before, “what is a common misperception about you?”

For me, I interpret this question as what others may think of me and, more importantly, why I am not someone I can see myself as. So who am I not? I am not a workaholic. This probably comes up today on Thanksgiving, as I was sitting at Starbucks tip-tapping on my computer (much like I am now). This exact moment last year, I was sitting outside a Starbucks drinking my cup of iced green tea while making revisions to my first manuscript of Postmortem of a Failed Startup.

My holidays are like non-holidays. My weekends are like weekdays. I “work” each and everyday. To the extent how much is a different matter. However, I love what I do. So am I actually at Starbucks “working” all the time? Am I meeting with friends talking about their websites and building their brands all the time, and is that work? Doesn’t that make me a workaholic? I’d say, “no.”

What I do, I do because I love. Sure, there are moments that I work. However, I also spend a lot of days like today, Thanksgiving, writing and perfecting my craft. It’s not work much like I don’t view my leg workout this morning work. Last night I was at yoga. That’s not work. Writing and reading is not work. It’s what I love. It’s like a sport. It’s like my meditation. Striving to improve and challenge myself is my sport, and how I do that is in many ways. For some, what I do may be work. For me, I view it as something so much more… enthralling. I’m doing something so beautifully and innately me. What I do stretches my imagination and creativity. What I do challenges how I did things before.

As I’m typing this, I’m recalling the many times I’ve described my day-to-days to others, and their responses echoed to the familiar — “that sounds exhausting!” I’m smiling and laughing at this right now because some days, yes. But so are my morning workouts — just as my best bud and workout partner would say as I huff and puff after a set. I push myself to the limits because I thrive on that. But it’s a different type of exhausting than working the 90-hour-weeks in a cubicle crunching spreadsheets. (That could be your sport, but it’s not mine.) One of my passions and indeed sports is self-improvement and self-challenges. I strive to be the best… in all the things that matter to me.

To me, it’s all game, and I want to have fun. I want to win — which is to be better than I was yesterday.

Thoughts on Day 58: Skepticism, Race, and My Approach

I haven’t approached a Stranger for today, yet. However, I’ve been meeting all sorts of people including friends who are curious about the journey. Meanwhile, I’ve been thinking a lot about this journey, so wanted to share some of these thoughts with you — skepticism, race, and considering altering my approach.

My social circle is the most skeptical

Up to yesterday, here’s my “rejection” rate in meeting a Stranger each day:

  • No time/ in a hurry: 4 times
  • Did not want picture taken/ shared: 8
  • Disinterested: 5

Add together the 57 Strangers I have met, and that means I’ve approached a total of 74 with a “success” rate of 77.0%. I don’t get incredulous reactions about this journey as you might think. A good number of the 57 Strangers are skeptical at the beginning, but they just start having fun with our encounter.

Yet, I get the most skepticism and incredulity from my family and friends. Despite knowing I’m this guy who just “does stuff”, I’m a writer, I’m an entrepreneur, etc., they’re all so skeptical about this. Yes, I’ve even been teased, goaded by my own family and friends about it. I have to keep my straight face and share my vision and purpose for this journey to set in so they can put their skepticism aside — at least, momentarily. Curiously, most of my women friends are totally for it, and love the idea. The men… are split, but mostly 80-20 where 80 represents the skeptical.

They eventually come around, though. Or at least, in front of me they do.

This whole experience reminds me of several entrepreneurs telling me to not share initial ideas with friends and family unless they really understand me or can add value. For some reason, those closest to us tend to be the most skeptical and, sometimes, the more likely to reject an idea. Perhaps because they want to protect me from potential heartache or some financial struggle. They want the best for me, right? Still odd.

Perhaps this is also why when I have a good idea or just an idea I’m excited about like this one, I know who the first people are that I talk to. Then, when my idea is in-flight do I share with others.

The great racial undivide

I was talking to another friend — though, we’re not “close” — about the journey. He and his fiancee didn’t know about this journey till I told them then. I shared with them a few stories where people have really opened up about how race has affected them. Especially given the recent election, race is a hot topic (again).

I try to vary the demographics of the Strangers; though, I stick to my normal day-to-day so perhaps it’s not as varied as it could be. In any case, I have found so much commonality and other poignant points with each Stranger I’ve met. My friend pointed out how this journey can be great to also bring communities together by showing the similarities we have as humans and people of this “community” and how everyone has some fascinating story behind them.

My friend then shared how he’s encountered racism as a Muslim Indian to which I shared my own encounters. The crazy thing is that we don’t encounter typical “racism” all the time like derogatory remarks, but they happen quite often whether through seeing my black Tom’s shoes and thinking they’re karate shoes. Or when someone realizes I can speak Mandarin and exclaims, “whoa! I didn’t know you could speak Chinese! You’re like so un-Chinese!” What does that even mean? Do I have to talk a certain way? Eat a certain food? Dress a certain way all the time for people to realize I’m actually Chinese? Or maybe that I don’t look Chinese. I look more Korean or Filipino.

Of course, I’m also the first to bring up how I’m a “ninja” in something (a moniker that was given to me long ago regarding my adeptness in Excel or in supply chain) or maybe that I’m great at math. Sometimes, I point these out just to keep myself laughing about it all… and before anyone else points it out.

And yet, when I’m speaking to so many Strangers, we’re just talking with one another just as people who run into each other. There’s no racial divide between us. We’re just two people talking. We can open up about race in our talks like we have, but for those few minutes, we’re just two people talking — no matter the sex, race, income level, etc. Maybe there’s something to this whole talking and listening to one another like we’re Strangers…

Hi, can I ask you a random question?

I’ve been asked by my skeptical peers how do I approach people. So with that, here’s essentially my “script”:

Hi! Can I ask you a random question? [“yes…” with a healthy dose of skepticism and curiosity]

I have a passion project I’m working on on the side called 100 Strangers, 100 Days. If you can imagine what that means, I’m essentially meeting 100 Strangers over 100 days. Today is Day [#], and I was wondering if you’d like to be today’s Stranger. [some say yes, while others listen for more…]

What this entails is me asking you questions about your motivations and passions, and you can take whatever picture you want, and I put this on my website 100Strangers100Days.com.

This is my way of inspiring people to connect with those around them. I feel like we look down so much at our phones that we neglect to say hello or get to know the people around us… some that we see every… single… day in our offices or at the coffee shop. We see them, and we may do the courteous thing and wave or smile or say hello, but we know NOTHING else about them. So I want to inspire communities to connect.

Are you interested in being today’s Stranger?

Now, I have this script down pretty darn well. Though it’s been working at 77.0% success, I find myself wanting to improve on this… not the “rate” but more about the success. I’m a big proponent of Simon Sinek’s teaching of starting with why (I’ve mentioned his Start With Why book often to Strangers). My script is actually the opposite of what Sinek espouses. The approach is actually very much what we normally do — start with WHAT (I have a passion project…) then flow into HOW (asking you questions about…) before ending with WHY (my way of inspiring people…).

I want to reverse the script and see if I can get people pulled into this calling, this journey. Not sure when I will flip this script (almost literally), but I will soon, and I’ll let you know how this goes.

Rules of Engagement

So who’s a Stranger? Who do I talk to? Where? How do I choose them?

  • Anyone who I don’t know anything about, or I just know a name. Nothing more (other than the obvious if they work somewhere, gender, etc.).
  • I won’t go anywhere so far out to meet a Stranger. We have so many Strangers in our daily lives. I can stick to my typical flow, and meet people I see all the time, but know nothing about other than a face.
  • The Stranger must not have read a Stranger post before — it keeps the conversation spontaneous and fresh.
  • The Stranger must be open to a picture. This helps drive authenticity, and shows that the “everyday” person. Doesn’t matter if by picture time the person does a yoga pose or whatever pose that actually hides the face. The person must be open to the picture from the beginning, and then, the pose can happen any way s/he wants.
  • I “randomly” pick the Stranger. Can be at a coffee shop or the top of a mountain. I can wait hours in the same spot, and will pick whoever I choose. I try to be diverse, and even if the person “looks” like s/he will reject me, I try. I want to trust the Stranger will allow me to ask the question.
  • I have a “bank” of questions that I will draw from that reside largely in my head. I don’t ask the same questions, but hope my meeting with the Stranger will help draw the right questions.
  • There’s just about no rules for the pose for the picture, nor is there a rule for what the Stranger can ask tomorrow’s Stranger. I’ll play moderator, as needed.
  • No real format to how I post details from the meeting, but I hope it’s in a way that reflects our meeting, the Stranger, and what allows readers to best experience the meeting.

Lessons Learned From the First 44 Days

Early lessons from my first 44 days on 100 Strangers, 100 Days… Why 44? Because I’m 23 days late. Whoops!

  • I have been rejected due to…
    • No time/ in a hurry: 4 times
    • Did not want picture taken/ shared: 5
    • Disinterested: 3
  • The project resonates with people in many different ways, especially the stories of the Strangers
  • Starting out, people kept saying this reminded them of Humans of New York. Didn’t know what that was, but after I checked it out, I can definitely see similarities. The team behind HONY is doing great. Just as many people have noticed, my approach is much different and my purpose is, too. I want this to go a little deeper into the Stranger.
  • Several Strangers have reached back out to me days after our initial meeting to share with me
    • How the post was received by others, especially their friends — some responses:
      • “I never knew I had so many friends!”
      • “My family and friends loved it!”
      • Long-lost friends who typically only see social media shares got to re-experience their friends as they are today bringing back lots of emotions and reconnecting with each other
      • Hundreds of social media “Likes” and “Shares”
      • Many comments to the individual’s posts
      • Many Strangers are GLOWING as they tell me how others spoke to them afterwards
    • How they wanted to think more about a few of the questions, and wanted to share their thoughts after much thinking
    • Not many people ask these “deeper” questions, and they feel invigorated and excited to be able to think about them, and share
  • I’ve had three Strangers ask for edits for what they provided (a couple other times because I mis-typed)
  • Four Strangers asked me questions back
  • I have several friends who have shared their answers to some of the questions because they wanted me to know about them
  • Several people (friends and others) have asked me if I would consider asking friends because they’ve realized they don’t know the motivations and passions of some of their friends. Instead, many of their conversations revolve around work, sports, or kids
    • Friends are asking their friends some of these questions to now get to know each other better
    • (My “Rules for Engagement” post will come soon)
  • One coworker said to me, “Daryl, I might steal your idea… not for 100 days, but for a few”. This, because he wants to make more connections with those around him. My response is that it’s not stealing… it’s not a project that I have some crazy keys to. Anyone can do it. That’s the beauty of this
  • Recording the interview vs. taking notes during the interview helps make the conversation flow better
  • I have thoughts and initial “wants” of where I want this conversation to go — namely, talking about passions and motivations. However, I want the meetings to flow more than they did earlier when I felt like it was too much like interviewing. So, I let the Strangers tell the story, and put me on the path they want to go down while I nudge them in the direction of where I think this project resonates with my own purpose. In many ways, this is like actively practicing persuasion and listening skills
  • I catch myself seeing some people all the time, and though, I feel they would be open to talk to me, I wait to. I wait to because I look at them as my “safety” Strangers for when I may be time-crunched or unable to find a Stranger (or get shot down a bunch). I look for more real cold Strangers as much as possible so I can have the “safety” Stranger who has seen me before for later
  • I do try to meet many Strangers in the morning so I do NOT feel the pressure later in the day of “oh, crap, I better find someone! Time’s running out!”
  • I’m still scared to approach Strangers
    • There are days when I’m walking around, and I see so many Strangers about. However, I’m scared to approach any of them because I’m acutely aware of being vulnerable to rejection or being thought of as a “weirdo” for making such a request to talk to me
    • I’m nervous talking to certain people. I’m trying to figure out exactly what and who, but a common “type” of person is the 20-something to 40-something white male. I’m feeling this odd “high school” feeling where I was intimidated by the popular jocks around school. I’m nervous of talking to them, and being ridiculed. That never really happened in high school, mind you; however, I never really put myself in that position. Movies had always had these “cool kids” on a pedestal while making me feel “inferior”. It’s a silly thing to think about now as I do mostly what I want, and I’m doing great. However, it’s a feeling that has been there from so long ago
    • I have caught myself looking at someone thinking, “now, that’s a weirdo”. It’s me judging them. I realize I’m judging them, and instead of judging them by their looks, I should get to know them — this has been great, and I hope to continue to hit home in me to stop judging others
  • 100 is a lot of people and a lot of days

About 100 Strangers, 100 Days

Why this project to meet Strangers?

I’m in a great place in life — doing well with… a lot, and as hard as I’ve worked, I realize that much of my success is because of the people I know. Those people tend to have very different backgrounds, stories, and approaching work and life in different ways. I have many friends and colleagues who see the same, and they wonder how I know such varied crowds. Simple — I go beyond a “hello”. Yes, I’ll walk right up to Strangers just to meet them if they draw my eye just because.

Everyone is fascinating and has some story to tell. I’m fortunate and grateful to have met some really amazing people. These amazing people have shaped who I am, and I’m proud of who I am and who I am becoming. I have looked at relationships as incredibly special to me – a realization surfaced from my time at Emory. That is, how much people and connections mean to me.

Yet, I still catch myself seeing many of the same people day-to-day, and I may nod to them and maybe say, “hi”. However, I know nothing else of them. Then, I look all around me and people are staring so intently at their phones not realizing the glorious stories just in front of them.

In fact, this project really sparked in me as I was hiking down Stone Mountain in Atlanta one morning. As I was hiking down from the catching the sunrise, I noticed a man next to me who was walking alongside me for the last 5 minutes. I said to myself, “I might as well say hello”, and then, the light bulb came on. I thought about taking all that I have learned about connecting and meeting Strangers into a blog. Two hours later, I met my first Stranger. Six hours later, this site was born.

This project is to help unearth the fascinating stories of people around me (around you). I’ll outline a few of the purposes of this project below.

(Oh, and ironically, I didn’t end up meeting the man walking beside me. I was caught up in this idea. Next time.)

Why 100?

For whatever reason, the number 100 crept into my head for both 100 Strangers and 100 Days – had a nice ring to it. I thought about 30 days, but that didn’t seem very ambitious. 50 just sounded like an odd number. So 100 Strangers. 100 Days. Let’s go.

My motivations for this project that I started Saturday, September 17th. I should be wrapped up with my 100th Stranger on December 26! How wild is that?

So what are the rules for a Stranger?

I’ll detail this in a future post. 🙂

What are the purposes of this project?

  • To inspire connections. I want people to get out from their cellphones texting and “Snapchatting” to get to know people around them. Myself, I see so many people in my office, but do not say hello. I may say, “hi”, or give a friendly nod, but that’s the extent. I want to connect, and I believe we should all connect as social organisms. Plus, serendipity is a wonderful thing.
  • To motivate action. Like I said, 100 days is, I think, ambitious. I thought of the idea for this and within two hours, I was interviewing my first Stranger. Within 6 hours I had the website up. I want others who have passions or questions or a project in their heads to turn those questions to answers… to turn ideas into reality. I’m an entrepreneur because I execute. I want others to realize it’s not hard to start something magical.
  • To challenge myself. I wrote Postmortem of a Failed Startup: Lessons for Success last year. This could very well be another book down the line for me. That, and I want another personal/ passion project other than the passion for the startup I work for.
  • With 1 Stranger per 1 Day, I want to show it’s not hard to get out of our comfort zone. Just one little connection per 24 hours. It’s an exercise not to rush 100 connections, but to illustrate it’s possible on a consistent basis.
  • Show the world we can be compassionate and vulnerable. I can ask some deep, personal questions to which I hope to hear truths. I want to challenge others to be vulnerable to not just answering questions to me, but to sharing their story with the world (and their picture). It’s an incredible thing to ask, but I want to ask to let others make that choice… not me make that choice for them (which I have a terrible tendency to do – make choices for others). It’s a trust thing.
  •  To encourage us to get to know those who we don’t consider Strangers. I have friends now sharing THEIR answers to questions like they were Strangers. They want to share with me! Meanwhile, I have friends now asking THEIR friends these questions because they want to know what motivates them. It’s exciting to watch as we consider how people around us could be Strangers in some way, too.
  • To change the world for the greater through entrepreneurial endeavors. I have no idea where this is going to go other than 100 Strangers… 100 Days. I may ask some more friendlier faces as I realize, too, that some familiar faces are just surface-level connections. As I said earlier, I want deeper connections, so maybe I go beyond Strangers. I don’t know if this will be a book. I don’t know if this will amount to anything “commercially viable”, but I’m good with that. I hope this journey motivates bigger effects on us as a community, as a nation, as a race. We all have common threads as well as beautiful differences. I want us to embrace each other and the effects of this journey for greater aspirations whatever they may be.

What do I want out of this project?

Outside of the purposes above… nothing… Kind of. A few of the points in the purposes above are a little lofty because connections are great, but inspiring others to connect on a deeper level makes sense if the connections are sustainable. But then again, not every connection needs to be life-long… perhaps one or two will. Perhaps finding the deeper motivations of a friend will shape the rest of that friendship. Hard to say, but I hope!

For me, this isn’t destined to be a book or a podcast — what many have suggested to me. I just want this to be “organic”. Meaning: I don’t really know what I want it to be. However, I want to move from Day to Day, Stranger to Stranger. I want to be present in my meetings, and I want to learn. That’s my only goal beyond inspiring and motivating others. For me, maybe this will change me for the greater which I’m sure it will.

Who am I?

I’m just a regular dude trying to do extraordinary things one “inflection” point at a time… hopefully, change the world for the greater through entrepreneurial endeavors. If you want to learn more, feel free to contact me. Also, you can learn more about my motivations and me at www.EntrepreneurialNinja.com.

Closing notes.

So stay tuned and check out these beautiful Strangers on http://100strangers100days.com – I’m on Day 12 today. Also, you can follow the journey via Twitter @StrangersXDays or Instagram @StrangersXDays or follow the hashtag #100strangers100days!