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The Lightning Journey Of Timothy Phillips - From Isolation to Building Urban Communities



"Even though I had employed about 50 people, I realized I didn't have any friends, I had done nothing but work every waking hour for years and I had never really invested in myself or into friendships. On that bridge, I felt like I could disappear right now, and no one would notice. What a terrible feeling!  "Who would miss me other than my family? I let go of my sadness about the end of my company and realized tomorrow I will drive the same car, live in the same apartment and eat the same food, nothing meaningful is changing in my life except my intentions for how to spend my time right now, and that was the beginning of my search for community." - Timothy Philips


Timothy Phillips is an architect, photographer, Yale alumnus, visionary community builder, and founder of Lightning Society—a social wellness movement reviving community in urban living. Lightning Society is renowned for curating a variety of immersive experiences that encourage self-expression, creativity, and authentic human connection, including the famous Burlesquerade boat party. Business Insider dubbed it "the secret masquerade yacht party that brings together bigwigs at Goldman Sachs and Facebook to Brooklyn's DIY fashion designers and filmmakers." With over a thousand people on the waitlist, Lightning Society also operates a co-living space in Brooklyn that fosters generative relationships. They are on the verge of a huge expansion called the Lightning Society Social Campus, a nexus of ideas and exploration, a venue for incredible celebrations, and a third space for friends new and old.  


In this insightful interview with The Urban Executive, Timothy shares his journey from a disembodied childhood in the deep south to becoming a community leader and founder of the Lightning Society.  

 

The Urban Executive: Can you Introduce yourself? 

Timothy: My name is timothy, I'm the founder of lightning society. My greatest passion in life is social wellness and connecting people with the world around them. 


The Urban Executive: Take us back, when did you know you had a thing for community? 

Timothy: Honestly, I think I always felt a longing for community, but I couldn't quite put my finger on it for most of my life. I grew up in the Deep South, in an extremely depressed, very poor area in Mississippi. Even though I was fortunate to be a successful student, I never felt connected to anything. It was just me and my single mom. She worked during the day and went to school at night, and we moved constantly, following opportunities wherever they appeared. So, every six to twelve months, we would move. As a result, I had a disembodied childhood where I never formed deep, longstanding relationships. 


The world told me that success was about competing, being successful, and winning. So, I spent most of my teens, twenties, and early thirties just trying to win everything because that’s what I thought I was supposed to do. I was an architect, then I became a real estate developer. I started my first company, which was very successful. I made a lot of money, and then one day in 2008, I lost it all. Overnight I went from thinking "Oh I'm a genius!" to "I'm definitely not." 


I remember distinctly—it was a tough summer day. I was in my car, heading to the lawyer’s office to sign papers to close out the company. I had just laid everyone off, and it was a super tough time. I got caught in a big traffic jam at the top of the Williamsburg Bridge for two hours. In twenty years of living in New York City, I had never been stuck on the Williamsburg Bridge, except that one time. At first, I was frantic: "I've got a meeting; I have to get there." Then at some point, I thought, "Nothing good is waiting for me at this meeting; it’s really going to suck. Actually, nothing really changes if I'm late." It felt like the universe was telling me, "You need a timeout." My cellphone didn’t connect, and I was completely disconnected for two hours, contemplating this huge transition in my life. 


During that time, I went into meditation. Even though I had employed about 50 people, I realized I didn’t have any friends. I had done nothing but work every waking hour for years, and I had never really invested in myself or in friendships. I thought, "I could disappear right now, and no one would notice because I’ve made no difference in anyone’s life. What a terrible feeling!" I wondered, "Who would miss me other than my family?" I also realized I never spent any money on myself. Tomorrow, I will drive the same car, live in the same apartment, eat the same food. Nothing meaningful was changing in my life except my intentions for how to spend my time.” That was the beginning of my search for community. 


The Urban Executive: How did you move from exploring different communities to forming your own?  

Timothy:   I started going to everything I could possibly find. I tapped into everything: ballroom dancing, Burning Man, urban exploring with a group of friends—we’d explore abandoned buildings and discover lost parts of the city. I began bringing adventure into my life, and it was a massive turning point for me. 


I think some generational factors also played a role. I’m firmly Gen X, and in general, Gen X is the silent generation. My peers and I always struggled with self-expression. Part of what I learned at Burning Man, in ballroom dancing, and other activities was the importance of finding a space to express myself. It was incredibly rewarding. This quickly led me to ask myself, "If you could be anything, what would you be? How do you represent that to the world?" That was a huge epiphany. The Burlesquerade was my attempt to provide that sense of freedom and expression to everyone else. 



How did Burslesquerade happen? 

Timothy:  In 2009, I went to burning man. It was wonderful and liberating and the first time I had every really let myself have fun. But in those days, it was also a fringe culture that intimidated people. If you weren't comfortable with self-expression (which none of my friends were) it was really challenging. I kept trying to introduce all my friends, but they were just so intimidated by it.  


So, what I did was that I made a burlesque themed masquerade party, if you were comfortable with costuming, you were like a burlesque person and if you weren't, you were still an actor in everyone's experience and it's really important that you show up. Streetwear however, takes everyone out of that suspension of reality, so you had to show up in an evening gown or tuxedo and a mask, and it really elevated everyone's experiences. At the end of the day, it was just a lot of really smart people who wanted to dress up and make a special experience together and it was hugely successful, the very first one was about 600 people and they exploded after that. Also, I think there was this element of bringing communities together in a positive light that was also electric for them and for me. I felt the event significantly impacted the Burning Man culture in New York City and beyond, transforming the perception and experience of the larger community. 




The Urban Executive: How did you transition from real estate development to creating Lightning Society? 

Timothy: In 2014, I was running a real estate company in Manhattan, it was at a prestigious firm, we were doing great projects but I was just so unhappy, I felt very unfulfilled. I felt like I could build a thousand more luxury condos and nothing in my life would change. I had achieved success according to the rules the world had given me, yet I was so unhappy.  

So, I went to a meditation retreat with the intention of changing the direction of my life. I remember repeating the mantra, 


"What should I do with my life?, What should I do with my life?"


The message that came back to me was that I was asking the wrong question. I needed to decide who I wanted to be and what the ultimate expression of my values was that I could represent as an example to the world. That’s not only leadership in its best form, but it also set a north star for me.


When you’re going through these moments of change, it’s very easy to get lost in the minutiae — which healthcare plan, what neighborhood, etc. But if you set this north star, you always know where you’re heading. You try things, some work and some don’t, but it doesn’t matter because, at the end of each attempt, you assess whether you’re closer or farther from your goal and note the lessons. Either way is a success because you learned something and you never wonder if you’re being authentic with yourself because you never lose track of your north star.  I walked out of that meditation with the name Lightning Society, and everything unfolded from there. 


The Urban Executive: You were transitioning from a "successful" career to full-time community building which is not the most financially viable decision especially at first, what kept you forging on? 

Timothy: I think anytime you deviate from what societies norms are, you are going to get a lot of push back. I mean I went from being "under forty, running a prestigious real estate company in lower Manhattan with a fancy apartment, to moving to Bushwick and opening a hippie commune. It was a shock for many of my friends who said "oh no, what happened!?" 


Have you ever just stumbled on a right answer that hits you to the core of your being, and there's this existential relief that comes with that? That's what I felt. I realized


"wow, this is the thing that I have been wanting on so many levels. This feels so right. "


I think that that's what has been missing in society, for most of human history we did everything in groups and then we had things like church and other spaces, they are called third spaces. They shape meaning and belonging. There was a moment during the industrial revolution where that all disappeared. In America that is when work became the source of meaning and belonging for most people and I don't think work is very good at that. 

If work is your only source of meaning you’re setting up a future when work ends, meaning and belonging end, making what comes after really hard. I've seen people struggle with that, so I believe you can separate meaning and belonging from work. Especially in a world where people are changing jobs every year or two, if work is your only source of community, then you don't really have a community. It’s super important for us to have generative third spaces where we find real connection, passions, and interests outside of work. That's where the social campus comes in. 


The Urban Executive: Can you elaborate on the concept of a "social campus" and how it differs from traditional social clubs? 

Sure! The medium of community is gatherings, right? That is what communities do. Whatever you are gathering about, if you are in a runners club you go run,  if you are in a women's circle you all meet and talk about life and womanhood. Lightning Society is actually dozens and dozens of communities. There are all these sub-circles, but broadly, everyone is aligned around a shared set of values and operates within that ecosystem and it’s great because we all have so many different groups we can connect with.  


That's why the metaphor that we are using going forward is a social campus. It's a place of ideas and a way to move from one conversation to another. 


A traditional club is basically about nightlife and beyond that, the social clubs that exist now are mostly industry related so each one is connected very directly to a particular industry like fashion, tech, media, finance, etc. I think that's intellectually limiting. Nightlife, at its core, tends to be about dating, which is inherently competitive and so is industry. Those two things together create a trajectory of exclusivity, access, and prestige, which I don't align with. The social campus, on the other hand, is intended to be broadly appealing and open, fostering genuine connections and diverse conversations beyond the constraints of any one industry.  


The Urban Executive: How would you define modern leadership in the context of community building and development? 

Timothy: What's interesting about community building is that it's distinct from corporate leadership. In a corporate setting, people follow you because they have to; you’re paying them, and if they don’t comply, you stop paying them. It’s very straightforward. In contrast, community-oriented leadership is about people choosing to follow you because they want to. They opt in voluntarily, which requires a more nuanced form of leadership. 


If you’re not nice to people or don’t act with integrity, they leave. They can’t always walk away from a job, but they can easily walk away from a community. I’ve learned that effective community leadership is more of a conversation. It’s about making people feel safe and appreciated. If you do that well, it’s incredibly powerful. 


We all have a desire for belonging. People want to be part of something that represents their values and feel appreciated for their contributions. Opportunities for this kind of connection are rare, which is why Lightning has been so successful. We excel at creating a space where people feel valued and supported. 


Personally, I’m not the greatest artist or event producer, but I’m good at supporting others and helping them shine. That makes them feel good, and it creates a positive cycle. That’s what modern leadership in community building is all about: fostering a supportive environment where people can thrive and feel connected. 


The Urban Executive: How do you navigate between collective decision making and what needs to be done? 

The Urban Executive: I think real leadership is getting out of the way mostly. There can be a tendency to micromanage, I've certainly done that in the past and it's not productive actually. Because I might be faster than one person at a thing, but I'm definitely not faster than two. If you don't trust people, then they don't grow. You end up setting a system that don't actually scale. What I do with my team is that I start with a bunch of intentions,


"This is where we are trying to go and these are the things that are really important to honor along the way.” 


And then I pretty much just let them go and check in once in awhile. If they need me I’m always ready to help or give an objective opinion but mostly I try to stay out of the way.  

In terms of our operational system, we have robust spreadsheets and ways of doing things that have all been figured out. Especially for creatives, it really helps because all the nuts-and-bolts stuff just works so they don't have to think about it too much. They can focus on the creative product. Then you just create the space for things to go really well and really badly at the same time.  It does, and it's awesome! We've never had a big giant failure. We've had incidental things go wrong. But in general, if you are doing anything mission driven, I think people put so much heart into it much more than I could ever reasonably ask for and so I certainly see and recognize the commitment that everyone is putting in and being anything other than completely supportive and kind would just feel terrible 


The Urban Executive: Most community experiences are quite euphoric, you go to the event, and you have this wide experience, when you return or the event lasts longer than a certain time, it quickly becomes chaotic. Lightning coliving loft, currently accommodates 18 people with diverse personalities and lifestyles with a waitlist of over a thousand people. How do you create systems that sustain happiness in a way that is not euphoric but daily

My first positive experience of community at scale was Burning Man. It is euphoric.  It is a manic state. Burning man is a moment not a place. It would be hell to try and live that way all year round. Over the years, I went a several times, and then at some point I wondered


“How do I distill the things that I value most about this experience and make it a calm and generative experience?”


For me burning man is not about the party, I'm really not that interested in big giant parties anymore. What I love about it is taking a break from all of my daily stress and work and having these deep generative conversations.  


That's what our coliving house is. It's just calm and quiet and we've done a really good job of making the rules work effortlessly. I don't think it's right for everybody but I think it's right for a lot more people than one would imagine. It’s harder to have two roommates than it is to have eight because with eight everyone understands that you have to have good communication and transparent rules. I wrote a house manual that breaks down everything in our ‘mutual agreements.’ To make it work, you must have a clear understanding about what everyone is committing to and if you can look at those agreements and say, this doesn't work for me then that's great, that's them doing what they're supposed to do.  


Lighting society is known as a community that fosters a space for self-expression and authenticity, can you share a moment that truly embodies the lightning experience?   

Sure! If I had to pick a single thing that is a core value that everything else comes back to is daily acceptance. I think in general; we all have a certain amount of anxiety about not fitting in, we've all experienced loneliness, we've all experienced the discomfort of not being able to fully be ourselves. Fundamentally, that's not something you can fix for yourself, you can't give yourself belonging and acceptance, it only comes from the group around you and that is your community. To me that is the core of social wellness. What we do is we build that into everything.


The event that most embodies this for me is the Lightning Salon. It is basically just an open mic and yet people show up and do unbelievably cool things that are spectacular to watch. People are so brilliant and amazing that I'm always blown away with their talent and creativity. It is so heartfelt and everything about it is just so wonderful. One woman, who was ethnically Mexican, had a long-standing frustration that much of Mexican pop music was misogynistic or at least is not kind to women, one way or another. So she rewrote the songs to celebrate women and when she sang them, we were so stunned.  


There was another guy is a professional musician. When he came, he told us about a song that he had written for his mother on her deathbed. It was beautiful song that meant everything to him. It embodied and memorialized their relationship but there was nowhere to perform it, you don't just pull that out when you are performing in a bar. But in the context of community of course it made sense. So, he shared the song with us and it was breathtaking.  And it doesn't always have to be so amazing.  Another friend of mine used to played the guitar in college but now he's in his thirties and he hadn't made space for his creative self in a long time. So, he got up and he just played songs he wrote in college, and it was amazing. He's the big giant guy with big giant beard, but when I looked up there, I saw twenty-one-year-old him, and it was adorable.  

It's a place where people can safely share something intimate and feel appreciated. That's how you build trust at scale, and trust is what defines community. 


 

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