Gwen Yi: The Power of Community

Here’s a short, incomplete list of what Gwen Yi did in 2014 alone:

  • Got sponsored to attend conferences at Harvard, Stanford and Brown.
  • Assumed the role of Ambassador for Mckinsey’s Youth Leadership Academy.
  • Co-authored the World Startup Wiki for Malaysia.
  • Shook hands with President Obama.
  • Led marketing for the largest TEDx conference in Asia.
  • Gave a speech at UNICEF Malaysia.
  • Went cliff-diving in Boracay in the Phillipines.

Here’s a short, incomplete list of what I’ve done in my entire life:

  • Started a blog and published to it every day since August 27th 2015.
  • Read some books and self-published my own.
  • Had twenty-plus low skill jobs.
  • Lived in two small towns.

That’s the mindset I was in as I prepared for the conversation with Gwen. She’s done, and is doing, so much. In the run-up to our talk I was thinking this is going to go one of two ways: it’s either going to be fascinating, or it’s going to be a trainwreck and we won’t connect at all.

I came across Gwen after Sebastian Marshall shared a blog post she’d written. It was called Life in Transition. I enjoyed it and decided to email her saying so. I also included some books that she might like to explore that were on similar themes. A few weeks later she replied, thanking me for reaching out. At this point, I had what seemed like a stupid idea. I’d explored her blog and done some digging. She seemed like an interesting person. So I thought it’d be good to ask if I could interview her. So I typed out the message and hit send before I could change my mind.

She said yes. I said, “oh fuck.”

On the morning of the interview, whilst setting up the mic, audio software and making myself a coffee, I was nervous. Gwen has done things that I can in no way relate to: moved halfway across the world, won awards, embedded herself in multiple communities, met and worked with people I admire. I was terrified that our conversation would be like a clammy, limp handshake.

It wasn’t. Gwen was as bubbly, curious and intelligent as her work and our correspondence made her out to be. We talked about a lot, and the insights I took from this conversation have changed my mind, and will certainly help shape my future. I hope the following interview with Gwen creates as many sparks in your brain as it did in mine.


MATT: How has your day been? What have you been up to?

GWEN: Just chilling out, basically.

MATT: Are you taking a bit of a holiday?

GWEN: Yeah. I spent the weekend mentoring at Startup Weekend so I’m catching up on work and recuperating.

MATT: What did you do there? What was that about?

GWEN: Do you know the concept of Startup Weekend?

MATT: I don’t, no.

GWEN: It’s a movement that started in Boulder, Colorado, if I’m not mistaken. It’s a safe space or platform for anyone—our youngest participant was thirteen years old—to experience what it’s like to build a startup in fifty-four hours. It’s like a mini-accelerator or incubator, but there’s no exchange of equity. It’s very community driven. There’s people like myself coming in, pro-bono, as mentors, and people who are keen to help out and share their experiences.

MATT: Who did you work with? Who were some of the people you helped out?

GWEN: It was interesting because I went to a smaller town. I’m from the capital of Malaysia, but this was in a small town, a little south of Kuala Lumpur, where I live. It’s interesting to see the contrast of ideas depending on where you’re from. One of the things I worked on was people wanting to get cheaper access to food, which involved setting up a marketplace for near-expiration food, or food that is mal-packaged or damaged, but still edible. A place to buy those products.

That was pretty cool, and I guess, quite indicative of the kind of lifestyle and values that people have there.

MATT: Do you find that people in cities tend to have ambitions and visions which are more global, rather than local? Do you think it’s easier to think on that scale when you’re in a city, surrounded by the big lights and swarms of people?

GWEN: Yeah, definitely. But even though Kuala Lumpur is one of the business hubs of the region, that mindset isn’t as prevalent here as you would expect. In Southeast Asia, if I were to generalise, not as many people have that global mindset, even though they know they should. The people who work here, who have startups here, who grow ideas here, they tend to not think as globally, and they prefer to focus on really local, small-scale problems.

MATT: Is that part of the reason why, in 2013 and 2014, you were trying to go outside of your region, to get out of Southeast Asia? You wanted to find something, or find a community, that was focused on something bigger?

GWEN: Yeah, definitely. As they say, it’s about the people you surround yourself with. I was lucky to be exposed to that mindset, that way of thinking, that lifestyle, at a relatively young age. When most people are still in their bubble thinking of the linear paths in life: college, job, work until you retire and die.

Business people locally don’t think about creating the next Facebook, or creating the next world-changing technology. They just think, “How do I feed myself? How do I feed my family? How do I move up the corporate ladder?”

In Malaysia, we call it jaguh kampung. That means, “I am the champion of my own village.” I think that because I win a village competition I’m the best in the world. A lot of people think like that. I don’t know whether it’s because of their upbringing, that their parents drill it into them: “You’re so special, you’re good, whatever you do.” Maybe it’s because the parents have a smaller world-view than myself and other people I’m exposed to? It could be that, or it could just be pure ignorance. That they think the world really is that small and they don’t want to look beyond that.

MATT: Some people get that sort of exposure and then turn their back on it. They don’t try and pull the curtain back a little more. From what I can tell, you did the opposite. You got a taste, you saw a glimpse, and you pushed on and explored, which opened up a lot of doors.

GWEN: I’ve seen that in some of my friends. We all met at this global entrepreneurship conference. It was President Obama’s Global Entrepreneurship Summit. They flew in 350 of the most aspirational young entrepreneurs from all around the world. It was like the crème de la crème from every corner of the globe, flying into Kuala Lumpur. I was 19, and because I was starting to work those circles locally, I managed to get involved and I met a new group of friends who were also just getting a taste of it.

Some, like myself, just stepped with arms wide open into it. But I’ve seen friends get a taste of it and, after a while, retract back into their shells. Decide to go for a corporate path. Or decide to go back to focusing on their studies. It is interesting to see the different kind of reactions to it. I’m still wondering why it made me act that way.

MATT: What do you think makes that difference? I think that as well as physical courage, like bravery, there’s an intellectual counterpart: intellectual courage. When you seek out ideas that are opposite to your own, when you seek out new experiences, it’s a consequence of being intellectually courageous.

GWEN: For me, I am, inherently, extremely curious. Perhaps insatiably so. I have a tendency to seek out new experiences and new stimuli that actively challenge what I believe in, or expose me to completely new realms of thought.

The best analogy I have for that is when friends say, “Don’t watch that movie. I didn’t like it.” You and your friend are completely different individuals with your own preferences, your own thoughts. What makes you think that your friend not liking that movie will result in you not liking it?

So often we’re easily swayed by the opinions and norms we see established in society. “Don’t be an entrepreneur. You’re going to go broke and your family will leave you” is an ingrained cultural belief. No one has to actively say it to you. But if you, first, don’t take notice of it, and second, don’t challenge it, you just spend your life wondering, “What if?” Not taking the chance. That’s really sad.

Personally, I feel like I need to try everything at least once for myself. I almost drowned in the ocean once. I really love deep sea creatures, so I decided to learn how to scuba dive. I had constant panic attacks in the water, but it was so worth it.

MATT: On your website, you wrote about 2013 and 2014. They were kind of like your blow-out years. 2013 was putting the building blocks into place, and in 2014, well, you just owned it. I read the beginning of the post where you put all the stuff that happened and I was like, “Jesus.” Has that trajectory continued? What have you been up to in the last year? In the last couple months?

GWEN: I’ve focused more on building hard skills, or building a repertoire. ‘13 was the building blocks, ‘14 was the blow-out, and then ‘15 was more about learning and exploration. In 2015 I learned how to code. I discovered my love for design, but I wasn’t that great at it. But it was better than backend programming.

Through that process I built my first product. It was my first time actually having a product vision, and then a roadmap. Also, I took part in my first hackathon, and won my first hackathon. I tried to build my first tech startup. Yeah, I was very tech focused in 2015.

But I’ve also been exploring my soft skills. Like what I do at Startup Weekend, capacity building for young entrepreneurs. Helping people who haven’t had the exposure that I’ve had. Bringing my experience from all these things and giving back, helping them explore how to build their position and realise it in the real world. Training and facilitation and capacity building is another area I’m really interested in.

MATT: Were those things you were focused on early on but didn’t have the opportunity to explore and pursue? Or were they things that you’ve just discovered and now you’re like, “Holy crap, I love this sort of thing,” and you’re now in a position where you can go after them?

GWEN: I think it’s a mixture of both for the tech stuff. I don’t do it so much now but, I would say, I’m more technically inclined than most girls or people my age. But just taking that first step and learning how to code was completely out of my comfort zone. I have zero math or science background. But it was something I felt I had to do. I felt like I’d maxed out my potential in other aspects and I wanted to see if I had a shot at the technical side of things.

Only two years back, if you’d asked me to code a simple static website I would’ve looked at you blankly and not known what to do. Now I have the foundation and the skills and the tools to do that easily. I literally went from zero to one.

That’s one side of it. The other side is training and facilitation. It’s something I’ve always wanted to do. I always thought it was something to be kept for later in life when I’m super rich and successful and have a lot of time because I retired at thirty. I never once thought that it would be something that I could do on the side or as a full time thing.

My passion for those things—human connection, creating experiences, facilitating growth—is something I’m exploring to see if I can actually make a career and a living out of.

MATT: So if someone approaches you and asks for help, how do you begin? What do you look for, and what do you try to impart to the people you work with? Do you have a system you work through or is it more intuitive and done by feel?

GWEN: If someone comes to me personally, how do I gauge how to help them?

MATT: Yeah. Let’s go with individuals and organisations. If it was an individual and if it was an organisation.

GWEN: I wish I had a framework. I think I should have one. At the moment it’s based on gut feel.

I first look at viability. This is a mistake all first time entrepreneurs make. They get so caught up with their idea-baby that they won’t let anything kill it. Even if the model isn’t feasible or they don’t a proper team. These are things I personally went through, and that’s why I’ve failed so many times. A lot of people either don’t want to face the facts, or they’re just so enamoured by the idea that they are incapable of facing the facts.

If it’s really hard for me to get through to you, I don’t want to work with you. I kind of tag you as a lost cause because I know it’s something you have to bang your head against the wall for, and fall flat on your face to understand, because that’s what I had to do.

Yeah, the first thing is the willingness to learn, and that’s true for the individuals and organisations I work with. I’m always happy to have an exploratory chat, but through the chat, I’m reading body language and responses. If they show signs of tuning out or not listening or brushing off what I say without asking why or following up, then I typically don’t waste anymore time with them.

MATT: Does that come from understanding that people have to change their own minds? No matter how persuasive your argument or your reasoning is, you can’t compel someone to think differently. They have to do it themselves.

GWEN: You asked this question in the email. “What is the one thing that you’ve changed your mind about this year?” That’s it. You can’t actually change someone. They need to change themselves.

I was really interested in training and helping people and all these things. I always thought, “If only they were exposed,” or “If only they were educated,” or “If only they had this or that.” I tried to give them all these things, but it didn’t work. None of it worked, and I was like “I’m wasting my time. Why isn’t anything working?”Eventually I found, I think through Tony Robbins, this amazing framework about the stages of changing one’s mind. The final stage is changing your identity. Binding to it.

For example, if you don’t smoke and I offer you a cigarette, you’ll say no because you’re a non-smoker. But if you’re a recovering smoker and I offered you a cigarette you’d be like, “I don’t want that, but I kind of do.” Once you’ve ingrained that mindset change, that identity change, it’s easy for you to say no because then the action would be incongruent with the identity you’ve adopted. I think our brains are naturally tuned to go against incongruence. So we will say no, even if we do actually want it, because that is not who we identify as.

So yeah. You can’t change people. They have to want to change themselves first. It’s all internal.

MATT: Something that has always interested me is being able to learn, grow, and figure out where your limitations and boundaries are. How do you do that all the time? Because it’s not enough to just do it once.

When I was twenty-one, I was a typical twenty-one year old. Then a collection of factors coalesced and started me on the road I’m on today. But it’s not enough to have that reinvention occur once. It needs to be an ongoing process. How do you do that?

GWEN: I’ve recently become really interested in the idea of being in constant transition. Right now I’m in transition. I dropped out of school and I’m figuring out what to do with the rest of my life. But I’ve basically decided that, instead of focusing on my next steps, I want to focus on laying the groundwork. I’m trying to figure out what the foundation of a good life is and build on that. Instead of moving forward, I’m moving downward.

We will, in our generation, be constantly going through transitions. We’ll always be exploring. Always seeking more. All these statistics say that the average millennial will change jobs at least eight times. We’re going to be in transition and changing all the time. So to bring that back to your question, first of all, I would say you have to adopt the growth mindset. A fixed mindset says “I’m an engineer. I can only do engineer-y things. I can never do anything else.” A growth mindset says, “Yeah, I may be an engineer, but I could give painting a try. Maybe it’s my thing…”

I think that’s especially important in your early twenties because it’s so easy to get stuck doing what you’ve been good at since you were young. Yes, stick to your strengths. But often, you can distil them. For example, if I’m really good at playing video games, I could ask, why am I good at video games? Is it the strategy? The memorisation? Is it the teamwork? You distil it and find that, “okay, I’m really good at video games because I’m good at strategy and problem solving.” And I can apply that to other areas that I’m not as comfortable with, or areas I’m curious about.

Reapplying those strengths in a different context will strengthen the strength. But at the same time it will teach you analogous thinking: to learn how to apply one thing in a different context. To connect the dots and see what manifests. I think, personally, I’m pretty good at that. I tried a lot of things and figured out that skill X and skill Yapplies in context A. I never knew that. And I never would have known that if I hadn’t tried context A.

MATT: When you made the hop from Malaysia to San Francisco, was that an example of that? You found out what you were good at in your home country and your home city and thought, “I’m going to find out what happens if I take myself and my skillset and put it in an alien environment?”

GWEN: Yes and no.

When I was in Malaysia, I liked to say that my ambition had grown too big for the peninsula to contain. So I wanted to see if I could apply what I had learned here in a different context. The United States. I wanted to see, first of all, whether I could have any relevance there, where I would be a small fish in an ocean. Secondly, I wanted to see if the skills I had, or thought I had, obtained in Malaysia could be of any use.

MATT: Were they?

GWEN: Yes and no. I was quite lucky as I managed to get in some good networks that allowed me to explore my interpersonal skills, my networking skills, my connecting skills, my event organising skills. I had the opportunity to practice those things and I would say they were functioning at the level that was expected in the Valley.

On the other hand, I suffered from a lot of imposter syndrome. Like I said, small fish, big ocean. I didn’t have the opportunity to really express myself and be who I wanted to be.

I don’t know how to articulate this.

MATT: Did it feel like you were trying to play other people’s game rather than your own? You were in San Francisco and felt like you had to be what people in your network wanted you to be, rather than what you actually desired?

GWEN: I felt like if I wasn’t a CEO I wasn’t worth talking to. I don’t know whether it’s the image that’s perpetuated by the Valley or if it was my own ego beating me down. But I perceived people’s reactions to be that way and I got snubbed. People would actually turn on their heel and walk away from me if they heard I was only a student.
But you’re right. It was really hard trying to pretend to be someone I wasn’t. I also felt like a lot of what I had done back home was for naught. I had built up this incredible network, all these things back home, and then left it all behind. I’d gone to a completely foreign country, some would say the capital of the startup world, and had to rebuild everything from scratch. I didn’t have the same kind of leverage I had previously. That was difficult. I know now that I shouldn’t have relied on the Valley to build me. I had to build myself before going to the Valley. That’s why I’m really focusing on making myself more valuable to others.

Which brings me to my second answer to your question. “What have I changed my mind about this year?” It’s an appreciation for the basics. I know I’ve been talking about this non-stop but I think, especially people in the Valley, really discount the value of a good foundation.

We’re both fans of Sebastian Marshall, so you know what I’m talking about. Sebastian is meticulous about all these things. He tracks everything. He’s so intentional about everything. I think that really rubbed off on me because I’ve always relied on pure talent to get to wherever I was.

Sebastian has called me out on that too. He says, “You can’t expect to be this raw, unpolished diamond that everyone oohs and ahhs over. ‘Oh you’re so young,’ or ‘you’re Asian and you speak English’ or whatever. When you become older and pass that stage, what will you have to show for it?”

He’s right. Like I said, back home people don’t have that kind of mindset or understanding. They think that if someone travels the world and takes a lot of Instagram photos they’re successful. They don’t see the foundation or the hard work that goes into that.

The Valley has tonnes of high school—not college, but high school—drop-outs. Kids who learned to code when they were foetuses and are coding geniuses once they’re out of the womb. They grow multi-million dollar companies, but they don’t have that foundation. They don’t know how to be a good person, how to take care of themselves, how to build good relationships. It’s more than that though. How do you work effectively? How do you manage your energy or schedule your life in a way that’s fulfilling and doesn’t burn you out?

A lot of people in the Valley rush so fast into success that they don’t have a base to build upon. So when they get to the top of the skyscraper they’ve been building, one small push brings it crashing down. We’ve seen it so many times in so many stories from the Valley. “This CEO killed himself.” “That CEO burned out.” Et cetera, et cetera. That doesn’t have to happen, you know?

In a lot of ways, I’m glad I caught myself early. I burned out and had this realisation. It’s important not just to take care of yourself. Yeah, okay, please exercise. But more than that. Get the foundation right. How do you work? How do you think? How do you manage your energy? How do you take care of yourself? All these things are important, but we don’t care about them because it’s not as sexy as making a million before you’re 30.

MATT: I am familiar with Sebastian’s work. But it’s one thing to ask those questions. The process itself feels good. It’s nice to sit back and survey your life and think, “Oh, where am I going wrong? What am I not doing effectively?” But asking the question is way, way easier than answering it.

So how do you begin to answer those questions? How do you come up with an honest assessment of your skills, or your ability to build relationships, or your ability to provide value to a community or organisation? How do you figure that stuff out?

GWEN: If I knew I would be doing it already. But I have a hunch: it’s just doing and feedback. Especially when it comes to value. That’s something I struggle a lot with because it’s so relative, right? I could think I was giving a lot of value, and the CEO could think I was giving a lot of value, but when I come to the organisation you may think that I’m complete trash. It’s hard to say.

What I’ve been doing is things that I have confidence I can do. Not necessarily do well, but do. For example, some people may find throwing a dinner really hard. They wouldn’t know where to begin, where to get people, where to host it, et cetera. But for me, that’s doable. It’s not easy. I wouldn’t call myself an expert at throwing dinner parties, but I can do it. For some people coding an entire web app is easy. For me, that’s out of my comfort zone. I wouldn’t be able to do that by myself. But others can. They wouldn’t call themselves an expert, but they can do it.

I think it’s important to start with what you can do. With something that’s really easy, doable, like dinners. You can’t fail at dinner right? You can host it and then no one comes. Maybe that’s a failure. But it doesn’t matter because it’s not something you’ve staked your entire career on. Things like that, low risk but potentially high return actions. I’m trying more of those right now because I feel like I need to build my confidence back up.

Doing and feedback. It’s a loop. Whenever you do something get feedback from the people you are doing it for. For example. let’s say I’m a budding web developer. I don’t know whether this idea I have is good or not. But I could prototype it and show it to my web developer friends, or the client who I’m doing this for free for. I can ask, “What’s bad about this? How can I improve it?” et cetera. That feedback is more valuable than any money you can get. Especially if you are new to a field or you want to improve in a skill. Rinse and repeat and eventually you get to a point where you hit some sort of milestone for success. “Out of ten clients, nine don’t want to kill me. Maybe I could start charging?” You can build a career like that.

MATT: What are some of the low risk, high return things that you’re working on now?

GWEN: I’ve started hosting these things called Tribeless dinners.

Tribeless is a concept that my psychologist friend and I came up with. In all of human history there is a spectrum of social belonging. On one end you have Tribal people and on the other you have Outcasts. Tribal people are those with very strong beliefs. They have values and traditions that they really resonate with, and there’s a group with cultural norms set up around it. It’s typically a religion or something like that. You base your entire identity on that belief and those values. If someone asks, “Oh, who are you?”, you say, “I’m a Christian.” That’s how you define yourself. You fit into the group. You completely belong. The only drawback is ignorance. You only see things from one world view. You can’t see from any other perspective.

On the other end of the spectrum you have Outcasts. Outcasts are exiled from society. They have no place and they can’t just fit in or belong, or go along with the values that society desires. This could be those heretics that you hear about in religious stories, or anyone who goes against the grain. It’s mostly a mental thing. They feel victimised. They feel like they cannot be a part of society. They are outcasts.

The Tribeless are in the middle. They are people who can fit in, but don’t feel like they belong. Typically, they’re known as mavericks or lone wolves. Perhaps they have multiple social groups they interact with. They fit in with all of these groups, and yet, they don’t feel like they belong to any of them, either. They don’t say, “I’m a librarian and a polo player.” They don’t tie their identity to all these things for whatever reason. Maybe they feel like they’re more than that, or they just don’t see the world that way.

The Tribeless are special. They function like lone wolves. But wolves, when they come together as a pack, are much stronger. These Tribeless dinners are a way for me to find my pack, and find people who are willing to share their knowledge and connections. Basically, it’s a safe space for people who share the same values. A lot of the time, the world tries to peg us down. But Tribeless is a place for people who can’t be tied down.

MATT: There’s two things I want to pick up on here. The first is that how you’re talking about insiders, outsiders and groups reminds me of labels.

You mentioned that you started this with your “psychologist friend.” It wouldn’t make any sense to me if you said the guy’s name. But because you said “my psychologist friend,” there’s something I can relate to. Labels like that make it easier for us to communicate with each other. Is what makes people Tribeless the ability to have multiple labels?

GWEN: Yeah, you have any multiple labels but not own any of them. But not just that. You’re able to actively empathise with both ends of the spectrum. You know where the Tribal person is coming from. You know where the Outcast is coming from. You’re able to take in multiple perspectives because you aren’t tied to any one world view.

MATT: That’s the second thing I was going to say. It sounds like the people in the middle can wear any mask. The mask that any group or community requires, they can pick it up, put it on, and really inhabit what the person that they’re trying to imitate would feel or think. Not in a non-authentic, fake way. But almost as a thought experiment. As a way to understand what other people are going through.

GWEN: Exactly.

MATT: So what stage is that in at the moment? Is it still a conceptual thing, or have you hosted some of those dinners already?

GWEN: We’re onto our fourth. I host it on the last Thursday of every month. I’ve already got feedback from people from other cities saying, “Can I have Tribeless dinners in my city?” That’s hard because I haven’t established it here yet. But I’m starting to think that I could come up with a guidebook, or a thing that helps other people to organise these things.

MATT: Have you heard of Jayson Gaignard?

GWEN: Yeah, I know of him.

MATT: He’s done a similar thing. For his Mastermind Dinners, he’s written a book. A playbook for them. Is that what you’d like to do?

GWEN: Not so much a book. Just a simple guide for people to host their own things.

MATT: When these dinners happen, how do you begin them? Do you have specific objectives for the evening? Or is it just, “get a bunch of people in a room, make them feel comfortable, and see what happens”?

GWEN: Mostly the latter. I’m a big believer in serendipity. Get the right people in the right room and magic can happen.

I think it would be cool to move to a more impact-driven model where people walk away with something. At the moment we’re getting people to contribute a theme or a conversation topic they want to explore. Then I, as the one receiving all this information, piece together a pattern in what people are saying and decide what would be a good topic for the group to talk about.

We start the dinner with introductions, and something fun, like a game. Then we move on to the meat of the conversation, the theme. Usually all it takes is one or two opening questions to get the ball rolling. Then it’s anyone’s game from there.

MATT: Kind of like what’s happened on this call. We start with one thing and then it opens up doorways to all these different things.

What’s the biggest surprise that’s come from the first four dinners? Is there anything that’s come out of it that has made you say, “Holy crap. I was not expecting that?” Or is it still too fresh, too raw for you?

GWEN: The biggest shock came from the first one because, you know, the first one is always the most nerve wracking.

It almost became a support therapy group. I was in transition and, maybe because your vibe attracts your tribe, everyone there happened to be young, burnt-out entrepreneurs as well. Everyone was sharing their stories, and asking “How do I get over that?”

That was kind of strange but interesting at the same time. I think that when you’re genuine about the kind of progress you want to make, the people who want to make that same progress tend to band around you.

That was a pretty big wow.

MATT: Have you tried to make it more future-focused? Rather than, “This is who I am and this is what I’ve been through.” Rather than people just telling their stories, have you orientated it towards the future and what they’re going to do?

GWEN: It’s interesting that you orientate in terms of chronology. For the first one, the theme itself was the future of work. But everyone became very anchored on where they were and how they didn’t know how to move past that. It’s interesting. When you try to orient it a certain way, you do get to cover some of it, but eventually the conversation flows to where the people want it to flow.

MATT: What’s the feedback from the first four dinners? Have the people that participated got back to you and told you about anything that occurred because of the dinners?

GWEN: I think a lot of friendships have been made. The dinners are quite intimate and they tend to attract people around the same age. Not necessarily from the same backgrounds, but the same interests. People who have taken the first step and spent an evening with strangers. There’s no guarantees. They have no idea who’s going to be at the dinners. The only person they know is me. It’s not like a Facebook event where you can see everyone who is attending. It really is a leap of faith they’re taking to sign up and actually attend. The big takeaways for them were the friendships, and also the surprise that they could get along so well with strangers. That they could have such good conversations in a safe space.

MATT: Most mornings, I write for a couple of hours and this morning I was thinking about our talk. Me and you, we don’t have many similar experiences. We don’t have the same background. We have similar perspectives. But I was thinking, “How the hell do you manage to connect with someone you know nothing about? When all you know is a very, very shallow, short story of their life, how do you connect?”
I don’t know if you found this from the dinners, but the only thing I could figure out was that common experiences don’t matter. You don’t even have to have similar perspectives. It goes back to what you were saying earlier. The willingness to learn and expose yourself. You just need to be open to the other person. Interested in their life, in what they’re trying to say, in what they’re trying to do.

GWEN: Exactly. You answered your own question.

MATT: So you’ve got the Tribeless dinners going on. Is that a side project for you? Or is it taking up a lot of your resources?

GWEN: No, not really. It’s a part time thing. Full time, I’m exploring what I want to do professionally. A couple of opportunities, but nothing concrete yet.

MATT: You said you dropped out of Minerva, right?

GWEN: Yeah.

MATT: Is that your second time coming out of full time education? You’ve repeated the pattern again.

GWEN: The first time it was the equivalent of A Levels in Britain. Pre-college. That’s why I was having doubts about going to college at all. But Minerva convinced me, and then that didn’t work out, so now I’m like, “I guess college really isn’t for me.” I’m a lot more certain about my path now. It’s not full of uncertainty. Before I could think, “Okay, I’m doing startup X or project Y, but if it fails I can always go back to college.” That’s no longer an option. So I’ve been discarding that student mindset and focusing: “This is my life, this is my career. What do I want to do?”

MATT: If you don’t mind me asking, what was the thing that caused you to make that decision a second time? Was there a specific factor or was it a collection of things?

GWEN: I felt emotionally and mentally compromised in that situation. It got to a point where I couldn’t bear to be in it anymore. It wasn’t like there was something outside, like a startup idea, pulling me out of school, but there was a push. I felt that if I stayed any longer I would lose myself.

MATT: What was it? Was it the pressure? The competition? Was it related to what you described about San Francisco?

GWEN: A combination of all those things.

We were under a lot of pressure and stress that I felt was unnecessary. And there was the pressure I was putting on myself. I’m in San Francisco living the dream and everyone had such high expectations of me, or so I thought. “Oh, Gwen’s in the Mecca now. She’s going to IPO in the next year” or something. It felt like I had that much pressure on me. Plus my inability to get an internship or to get a visa to even work in the country. I just felt all these things were a huge burden on my shoulders.

MATT: And you just wanted to unload?

GWEN: I wanted to find myself again. After that I came home pretty broken. I realised I had lost myself because I had tied so much of my identity to the school, to being the girl in San Fran. Having left and not knowing what to do next, I felt like my entire identity and who I was had disintegrated. I had no idea who I was and what I wanted to do anymore, what I liked or what I wanted out of my life. All these things disintegrated. I had to restart the process and try to understand what it means to live a good life and figure out the kind of life I wanted to live.

MATT: The stuff with Minerva was in the last year right?

GWEN: Yeah.

MATT: How old are you?

GWEN: I’m 22.

MATT: From personal experience, and from what I’ve read, it seems to be that twenty-one or twenty-two is where you first get the ability to take your head out of the sand. You pull your head out, look around at where you are and start to ask those questions. It took me a long time to figure that stuff out. Two or three years to hone in on those things.

Are there any specific things that you’re looking to do over the next year to help you answer some of those questions?

GWEN: It’s just building that foundation. The foundation is what leads to discovery. Ironically, while building this foundation and not thinking about my career or exploring opportunities, the opportunities that have come seem to be more aligned with who I am and what excites me than if I had put my head down and deliberately put all my energies into finding opportunities. That’s what I was doing in San Francisco. Trying to find a job. Trying to find, I don’t know, a way to validate my existence. Now, I’m attracting things that I feel are more aligned with me at the core, even though I still don’t know exactly what that is yet. I think that’s where the doing-feedback thing comes into play.

MATT: Who are some of the people in your life—not necessarily people you know or who are in your immediate circle—that are helping and guiding you through this transition and period of your life?

GWEN: Sebastian Marshall has had a huge role in how my mindset has shifted. I attended his programme in Chicago in August and since then he’s given me a lot of food for thought. He’s not an active mentor, per se, but I am trying to put into play the things that he has done himself.

It’s interesting because Sebastian was very like me when he was younger. Relying on his natural talent, being all over the place and not having one focus or a methodical way of doing things. He told me that I would probably bang my head against the wall for a few more years before I learn what he did. But he also said that if I had the discipline to put my head down and stop pursuing adrenaline highs I would be able to get there a lot faster.

That’s kind of the approach I’m adopting now. Yeah, my life is boring, but so what? That’s fine. Putting my head down and doing the work, as he said, will get me there eventually. I have faith in that and that’s the philosophy I’m following now.

MATT: Me and Molly, my partner, talked about building the foundation. We were talking about exercise but it applies to learning, seeking opportunities and exposing yourself. It’s that in your twenties, especially your mid to late-twenties, is when you lay the foundation for the rest of your life. If you consistently exercise or train five times a week throughout your twenties, there’s way, way, way more chance that you’re going to still be doing it when you’re sixty. It’s the same with reading and learning and thinking. If you put the structures and habits in place now, it’s way more likely that you’ll carry them on for the next twenty, thirty, forty, fifty years. And one of the most important things to learn, like you said, is that ability to handle boredom and be comfortable in a low stimulation environment.

What’s your main creative output? Mine is writing.

GWEN: Same.

MATT: Is that how you unburden yourself? Do you journal or do you prefer to blog and publish stuff?

GWEN: I’ve been actively blogging. Before I was very caught up in doing. That’s why I ended up doing those huge end-of-year summaries without any context. Recently I’ve been writing more, but sometimes I don’t know what is worth writing about. While my main creative outlet is writing, I don’t know what I should be writing about most of the time.

I have a question for you.

MATT: Okay.

GWEN: How do you decide what to write about? Your creative output is the act of writing itself, right? Or is it just about the dissemination of information and writing just happens to be your medium of choice?

MATT: That’s something I’m trying to figure out. For me, specially when it comes to career and commercial skills, I have writing down in two categories. Writing-as-selling, which is like copywriting and persuasive writing. On the other side, you have writing-as-thinking, which is what I think I’m more drawn towards.

In terms of deciding what to write about, that’s a hard question.

GWEN: Because if you don’t know what to write about—you mentioned that you write daily—what do you write about every day?

MATT: Here’s a nice way to frame it: think of scarcity and abundance. A thing I’ve seen hundreds of times is that when you’re out on a walk or a run, or in the middle of a conversation, whenever you have an idea for something you should try to capture it. Email it to yourself, write it on your hand, or always carry a notebook. Whatever.
I used to subscribe to that idea, but the more I learn, the more backwards that seems to me. It’s a scarcity mindset. You have to grab onto this thing because you’re so worried you might not have another one. But throughout the day we have thousands and thousands of thoughts and insights and experiences and questions. To write, especially in the way that I do which is very short form—a post for me will usually be between two hundred and six hundred words—I just need to capture one thought.
It’s not about asking “How do I generate all these ideas?” It’s about being receptive to all the ideas that are already there.

Imagine a raging storm over an ocean. You can’t see what’s beneath the surface. Now think about a still pond. You can see all the fishes that are swimming around. You want to attain that pond-like state where you can penetrate the surface and see what’s going through your mind. Then all you have to do is accept what’s there and say, “Okay, that’s what I’m going to write about today.”

GWEN: How do you achieve that pond-like state? Is it with meditation? I guess it’s a two-pronged question. First, how do you achieve that state? And secondly, how do you decide which fish or idea to focus on and write about?

MATT: Do you meditate?

GWEN: I’ve been trying to get into it, but I haven’t reached the point where it’s regular yet.

MATT: One of the biggest things to keep in mind about meditation is that it’s practice for the rest of your life. The meditation itself is just practise. It’s a means to an end.
I see—this is the first time I’ve talked about this to anyone—mindfulness as being closely linked with creativity because both are about acceptance and receptivity. But getting into that state is a consequence of allowing yourself to think about anything. It’s saying that it’s okay to question this, to ask that, to look for that, to take the standards right down. It’s about not constantly comparing one idea to another that you’ve had.

Then there’s the other side of it which is very important. I’ve stolen it from other people. It’s the idea of denarration.

I did some reading about you before we talked. I wanted to get an idea of where you’re coming from and the things we could talk about. It would have been very easy for me to create a story out of the pieces of your life that I know about. I could say, “Oh, Gwen’s from Malaysia and she did this when she was nineteen, and then this happened, and then this, and then she hit a low point and bounced back.” It’s very easy to create a narrative out of a life. Denarration is the opposite of that, but applied to yourself. You look at your life, at everything that has happened, and you take the story out of it.

That’s one part of denarration. But the more important part, which relates to creativity is—sorry for rambling.

GWEN: No worries, this is really interesting.

MATT: Think in terms of words. When you wake up in the morning, if you live with someone, you talk to them with words. Then most people will go on email, Facebook, Twitter, Instagram. Blah, blah, blah, more words. Then you drive to work and put the radio on. More words. And you listen to the news on the radio. More words. Then you get to work and you’re talking to people, interacting with clients and colleagues. More words. Then you drive home, radio on. More words. You might read in the evening, or watch TV, or listen to music. Then you say goodnight to your partner. Your whole day you’re being overloaded with words.

But words are building blocks for narratives, right, for stories? So denarration makes it easier to attain that pond-like state. Does that make sense?

GWEN: Like a silent retreat?

MATT: A little bit. You know you were talking about low stimulus? It’s just about being very mindful of the stimuli in your environment. I think that’s the simplest way I could put it. I probably could have saved us five minutes there.

GWEN: The words thing, you don’t notice that.

MATT: I find that idea very helpful. Obviously meditation is a way to do that, to practice being still and not stimulated. But it could just be as simple as twice a week, maybe on a Monday and a Friday, taking half an hour for free time. For thinking time where you have no stimulus whatsoever, and you just sit with a pen and a notebook. Where you have nothing to feed off. Where there’s no external stimulus so you have to go internal and find out what’s going on.

That’s something I do a lot and it’s how I prefer to function when it comes to creating and working and thinking.

GWEN: You know how some people think inwardly and some people think outwardly? I’m the kind of person who thinks outwardly. I get my best ideas from talking to people and bouncing ideas of them. The idea may not come from that person, but it’s the act of talking things through it that gives me insight. Even now I’m making that realisation about myself from talking to you. I’m thinking, “I’ve never tried that and I think I will.”I think it’s really interesting to schedule two days a week. How long do you schedule it for?

MATT: I don’t think the specifics matter. It’s more the intention behind the time that you’re setting aside. Five minutes can be just as fruitful as five hours, you know? As long as you’re aware of what you’re trying to do, just a little block of it is enough.

GWEN: I have no idea if I would be able to get anything out of something like that. I probably would.

MATT: That’s the problem. Part of it being free time is that there’s no expectation of getting anything from it. Do you see what I mean? Don’t view it as a productivity hack or a way to one-up your thinking. It’s just something that you have no expectation of getting a return from. And because you don’t have any expectations, it’s more likely to actually yield something, you know?

I think that idea extends to relationships. If you try and build a relationship with an agenda, thinking “I want to get something from this person”, you’re way less likely to get whatever it is you want. But if you go in honest and open, not thinking about what you can get from it, you’re more likely to get something. Does that make sense?

GWEN: Yeah, I love that. I can’t remember who said it, but there’s this idea: “A relationship should be a place you go to give, not to take.” I love that.

MATT: Yeah, that’s a massive thing when it comes to creativity and mindfulness. I think mindfulness is huge. It’s something I wish I would have found earlier. Probably a good thing I didn’t because I wouldn’t have been able to appreciate it.

There’s another thing I wanted to ask you. Entrepreneurship and building companies, doing the sort of thing you want to do, up until recently has been very male dominated. There’s two things really. What are the cultural and gender-related differences you found going from Malaysia to San Francisco and back again? Are there any things that stood out?

GWEN: Not really.

Culturally, San Francisco definitely has a more advanced culture in terms of knowledge sharing and skill exchange. I wouldn’t say that’s a fault of Malaysia and the surrounding area. There just isn’t as much tech talent with the know-how and experience here to give back. The culture is growing here, but I would say people are a lot more willing and able to help in San Fran.

In terms of gender, I don’t feel actively discriminated against because I don’t think of myself as a woman-entrepreneur, or a woman-community-builder, or a woman-anything. I’m just an entrepreneur. I’m just a community builder. Maybe it’s not that I’m not personally phased by being the minority in a room. I’ve always hung out around guys, for example.

I think, in general for women, if you want to fit it or stop feeling discriminated against, you have to recognise that a lot of it is internal. We need to stop thinking, “Oh, I need to get some sort of special privilege before I can speak up,” or “I need to get permission before I can show my worth.” That’s not the case. You need to take that power for yourself.

I don’t hold very strong feminist views. With anything in the world, you could say, “Oh, you were nineteen when you started doing all this. Did it phase you?” Obviously it phases a lot of people and that’s why few people do it. That’s the same for whatever, if you’re a woman, if you’re a minority, if you’re a different skin colour, if you’re young. It’s about stepping up and knowing that you will fail. But at least you did it and that’s more than can be said about other people.

MATT: Do you think that applies to skillsets as well? That people who don’t have the expertise to compete in a field should just go out and try shit anyway?

GWEN: Exactly, because you never know what’ll happen.

I’m doing this course now, and I think everyone should do it. It’s called “Learning How to Learn.” It’s by this professor of mathematics called Dr. Barbara Oakley. It’s a very meta thing. Learning the techniques of how to learn better. Barbara talks about her own experience, how she was, like me, completely math and science illiterate. It’s only when she went to this class in college that she discovered her love for math and science. Now she’s got a freaking Ph.D in it.

What you may think you’re good or bad at doesn’t matter. You never know if you don’t actually try. It’s especially true skill-wise. Especially in this new economy where most skills are things people have never done before.

The closest thing to an experience designer is a graphic designer. They make things look pretty. But that’s not enough. UX design is so much deeper than just making things look pretty. Yet in terms of a professional skillset, most schools don’t have a UX design course.

Our academic institutions are not preparing us for this new world of work where the demand isn’t for old school skills. It’s for these newfangled skills that not many people have, or that people have had to learn by themselves with bootcamps and courses.

MATT: Was that mindset part of the reason that you came out of Minerva? Was it because you didn’t think they were teaching the right thing, or preparing you for the right thing? Did you find that you could do it on your own more effectively?

GWEN: Yes and no. I can’t speak generally about Minerva because a lot of people get a lot of value out of it. I can only speak for myself and say that I had a lot of practical experience before going in, so it’s not fair for me to say that it’s not useful or helpful. For an eighteen or nineteen year old, there’s no way he or she would have learned those things before, so of course, it’s helpful.

When it comes to Minerva, or any college really, you need to know where you stand and what that college can offer you. Because if you are just buying into the whole, “I need a degree” or “formal education is the only education,” then you’re wrong.
Another layer to the foundation I’m trying to build is the habit, like you said, of lifelong learning. By being in college, we are perpetuating the myth that learning stops once you graduate, which is not true anymore. I figured I might as well get used to learning how to learn on my own.

MATT: What sort of thing are you reading about and learning now? What books have you read and been influenced by recently?

GWEN: I haven’t had too much time for books recently. But one I liked was by Ryan Holiday: The Obstacle is the Way. His book is about how to view problems in a new way, and it’s been really interesting for me to try and change my perspective.

MATT: So what’s your obstacle? What’s the impediment to your progress at the moment?

GWEN: I would say it’s my lack of a community that can hold me accountable. I’m building Tribeless and all these other communities, but I don’t have a core group of people who are relying on and pushing me. It’s like co-living: when you have a bunch of people staying together, they benefit from each other’s energy and learning and work.

I don’t know if I actually need that, but I feel like I need that. Like Sebastian says, I’m not used to a low stimulus environment. I wouldn’t say I’m extrinsically motivated, but it’s a lot easier to concentrate when everyone around you is working.
That’s the same concept Sebastian has with his Ultraworking group. I really believe in that, and he believes in that too, but it’s difficult to find and build a consistent group of people to do that with.

In the new year, I’m going to be a lot more deliberate about that and try to seek people like that out, without running around the world. All these programmes: “Come co-work on an island for three months” or whatever. Previously I would have jumped at the chance, but I’m trying to get used to a low stimulus environment. I’m trying to figure out how to get that accountability but in a way that’s sustainable.

MATT: That’s the great opportunity we have now, right? At the moment, I live in a small town. Maybe twenty thousand people. I grew up in a slightly bigger town. And like you said, it’s difficult to keep yourself accountable when you’re not surrounded by people working just as hard as you. I haven’t figured out a way to do it yet but it seems to me, and obviously to you, that there is a way to do it. We’re so connected now that it’s just a problem that can be easily solved when the right system, or the right structure, when someone comes up with the right way to do it.

GWEN: That’s one thing I really want to figure out in the coming years.

MATT: That’s the difficulty. We’re very, very connected. You’re on the other side of the world from me right now, but we’re just having a conversation.

GWEN: Yeah, it’s crazy.

MATT: But at the same time, we’re becoming increasingly isolated. We have all these tools to reach out to people and build relationships and maintain relationships, but at the same time, people like me and you are being forced to do more and more things off our own back.

It’s a hard tightrope to walk upon. No one’s compelling you to do what you’re doing. No one’s sat on my shoulder telling me to do what I’m doing. It’s very difficult, in the absence of an external person or group, to keep that going.

GWEN: Exactly. I guess that’s why it’s important to have some form of accountability, or as I like to say, community. Because accountability comes from the sense of responsibility you feel to someone.

MATT: So in your mind, it’s almost like community equals responsibility, which equals accountability? Is that what you see?

GWEN: Yeah, because you feel responsible to your community right? Even on the smallest scale. Your nuclear family or neighborhood or school, all these things are communities. Maybe it’s your sense of identity, maybe it’s something else. Love perhaps. But something ties you to that community and so you feel responsible for it. You want to make it better. You feel dedicated to it. All this contributes to you going out of your way to uplift that community.

MATT: That’s one of the things Stoicism talks about. It talks about, not so much local, but global responsibility.

Right, here’s a question: Can you keep yourself accountable if you only have global responsibility? If you’re completely isolated from family and friends and communities like that, can you keep yourself motivated with just the abstract ideas of improvement and growth and learning? Is that enough to keep you going?

GWEN: I love this question. Is it a philosophical question, or is it contextualised to me?

MATT: A bit of both. It’s contextualised to me as well. It’s both practical and philosophical.

GWEN: Well, what do you think? For me, that’s completely impossible. I think a lot of people, a lot of science actually, has proven that to be impossible.

A lot of the time we do try to be globally motivated. This ties back in with the opening question: “How do you develop a global mindset?” Well, people always say, “think global but act local.” When you act local you’re tying your actions, your impact, to tangible things. To things you care about, to things that you see around you, to the things you interact with on a daily basis. That extra connection you feel with all these things intensifies your ability to do good and have an impact more than if you were motivated by abstract notions alone.

Imagine I said to you, “Please, go fight for justice.” You’d be like, “What do I do to fight for justice?” Instead, imagine I say—Sebastian gave me this example–”there are houses in your area that need to be painted by the government, but they won’t do it because it doesn’t give them any value.” You go paint the houses right?

It may seem like such a small action, that it doesn’t have any impact at all. But if you look at it it’s actually a manifestation of seeking justice. If there were no houses to paint, how would you act on that idea of justice? How would you fight? Unless there was another house you could paint on the other side of the world. That’s a global way of looking at it. You’re fighting for justice on a global scale because you left your hometown to come to Kuala Lumpur. But you wouldn’t feel as deep a connection for the people and the houses here. The houses in your hometown, you feel a connection to them, you grew up around them.

I think these things are the main motivators when the going gets tough. When everything is falling down around you, when your belief is shaken, it’s your connections and your relationships, your responsibility to these things, that keeps you going. That’s why I think community is so important, especially today.

It’s like roots. It’s understanding and appreciating how your immediate surroundings impact your life.