For this interview, I (Charley, NYC roommate of past few years) will be interviewing Jenny with questions sourced from people who know her well.

Exciting! Thanks so much for doing this, Charley. It's been a long project (mostly due to my own procrastination), but I appreciate you taking the time.

Lets kick it off with intros.

I'm Jenny, the person behind this project, and I am a User Experience/User Interface designer at a platform innovation consultancy in New York. We make primarily mobile apps (we have in-house developers and designers) and advise the business strategy for emerging platform businesses. Before that, I was a digital marketing consultant in a big tech company living' the life of plentiful PTO and WFH (work from home) days.

Sweet. So for this project, I reached out to some of the people you've interviewed for this project and asked them if they had anything they'd like to ask you. Let's start with your background. What does home mean to you? You're from Houston, have strong ties to China, lived in Philly, and moved to NYC. Knowing you, you've thought about living all over the world. Where is home to you?

I asked a lot of people this in my 20/20 interviews, because I wasn't sure myself what the answer was. I started think about this in a Chinese context — my cousin was getting married a few years ago, and the tradition is that he, as the groom, picks up the bride at her home (presumably with her parents). But in this modern age, I have no idea where that would be for me. I love the freedom to travel but I kind of miss the quaint ideal of one place as home. The days where everyone is rooted in one place seem so far. I really liked Chiara's answer regarding this: "Home is what you carry with you."

I think the way I define "home" is defined more by mental geography than physical geography now. My cultural home is Shanghai, where I was born and always feel like an "insider", even though I don't speak Shanghainese and have only spent about 2 full years of my life there. My geographic home is Houston, where I grew up have all my memories of becoming a "real" person. And my young adult life is rooted deeply in New York. (The other day I thought about buying a NY hat and repping that instead of Houston. It was a heavy moment.)

In terms of family influence, I know that's always been a big driving factor of your personality. How has your family influenced you and the way you think?

My family is obviously one of the most significant influences on my identity. However, when you're a child living in your parent's home, there's only so much parents can tell their children to teach them. Kids, especially stubborn kids like me, don't like to listen to people telling them what to do. All of the deepest lessons I learned from my family are from observing what they did, not just what they said. The way I view the family model is that children, in some sense, always seek to emulate or reject the parents. Everything the child sees begets a decision to embrace how their parents do it, or change.

My parents were very strict growing up. I think they would think that they were very lax, but especially in comparison to my predominantly mainstream American peer group, everything they did was unfathomable to me. So when I first started getting exposed to Asian American culture a decade ago, it was a revelation for me. It was like, there's a whole group of people that grew up in similar ways that I did! When I found there were other people like me, everything just clicked. I felt like I came into my identity, and I didn't need to fit into the patterns mainstream society had set for me. I wasn't just an "Other" box anymore. So when my parents didn't let me go to sleepovers, or they were disappointed in my A-minuses, I thought, "Oh, this is just how Chinese parents behave." It helped me understand where they were coming from, and have a point of reference.

I think the best thing my parents did for me was provide me all the necessary elements for growth. They pushed me to aim for perfection and instilled a sense of ambition in me. My dad is a hustler; he's a really hard worker and that's what I admire the most. The more he works, the prouder he is, and that's a prevalent attitude that took me through my schooling. For my mom, I really admire how easygoing and optimistic she is. She often remarks that I'm more observant than either of them are, but I think that they put me in this environment where until I was 10, I was the only Asian kid in school and I was always just watching people, wondering why am I like this while others are like that. And as you get older, those issues start to expand beyond just you to the world. It's a very inquisitive way to learn. If you're never really comfortable, then you're always trying to figure out how things work around you. I also have a younger brother, who is very thoughtful and earnest and probably too nice for a young man in college. He's a bit of an old soul.

As far as your other influences, you've always been very active in trying new things. Some people take a laissez faire view of life and let things carve their own course. Do you believe in fate, or do you think people are masters of their own lives?

I don't think it is black or white, though I sometimes tend to break down life choices into decision trees with probabilities. I think you can position yourself to have the best possible outcomes.

I guess I view change as coming either internally or externally. External events, like a car hitting you or winning the lottery, are really out of your control. Since I can control what happens internally, I like to focus a lot on self-improvement, in order to prepare myself so that I can be exposed to the best possible branches of that external probability tree. I realize that's a very rational, unsexy way to think, but for a self-appellated "creative person", I am very pragmatic.

What's the balance between what motivates you, internally and externally? If others had no expectations of you, where would you be now?

My motivation to stay creatively busy is definitely almost 90% internal, but that's not to say that most of my inspiration doesn't come from external sources. From my early years, I had a lot of time to dabble in creative things, so I got involved early with drawing, writing, craft-making, photography, coding, etc. as well as consuming a lot of great artwork, stories, and showcases of what other artists did online. I had a lot of time to myself to read and absorb all this great creative work, even on a 56K modem and all those hours I spent plugging up our home telephone line.

Honestly, I think a lot of kids start out this way. But somewhere along the way, other things catch their interest, or they get this idea that they have to be good enough to keep going. That kind of thinking is a huge hurdle. I still think everything I do isn't good enough, but it's okay, I've gotten past the point where I think it might be better to give up. I almost did, in high school when academics became demanding and again as an undergraduate at Wharton, but each time, creative work wiggled its way back in. I'm trying to be Zen about it now, and internalizing the quote by Ira Glass about beginners has given me some new life, creatively. I know I have to work through it. But still, nothing beats the amount of free, idle time you have as a kid, and I wish I could've gotten past this hurdle a little sooner when I had more time as a resource.

The fact that I held on and kept pursuing these random side projects is a little bit by accident. As a kid, I played a lot of video games and barely tried in school because it wasn't very demanding. In middle school, I started joining some very nascent afterschool club activities because I didn't want to ride the bus home, random shit like Spelling Bee, Yearbook, Geography Club, anything so that I could stay after school long enough for my parents to pick me up. But then after a while, I was like, "This is great!" I started doing more writing, web design, photography, and sinking time into stuff I consider my life's passions now.

I think I just really like the process of making things, and seeing my efforts come to fruition. It makes me proud. Having other people see what I do or use something I've made is a very minor side benefit, and I've noticed that differentiates my more artist/maker mentality from the product manager/business mentality. Great freelance artists have both the love of their work and the ego/pride to sell their name and really own their work. I'm very, very shy about showing people my work (though I am always open to constructive feedback) because I know it's not where I want it to be yet. When I get to a level I can be proud of, I hope I can start building my own "brand" as well. But that's not what I'm in this for.

Everyone's favorite topic of questioning is how you feel about your twenties. What expectations did you have, and how did you get to where you are now?

As a teenager, I never really dared to think about my twenties. I thought it wasn't that useful to think so far ahead when I didn't even know what options I'd have. I thought I would go to Stanford, but I applied to Penn's Huntsman Program (dual degree in international studies and business) on a whim. I didn't get into Huntsman, but I got into the Wharton school on a binding early admission, so I had to go. Then I got to Wharton and thought, okay, I'm in business school. I had wanted to study anthropology, but of course my parents were like, "Please go to Wall Street," and the corporate sphere of influence is quite strong at Wharton. At this time I thought, okay, I like doing these creative things, but maybe they can be a hobby and I can just have a business day job instead. However, I never realized how much your quality of life can suffer if you have a clear, committed passion and something else is constantly in your way. Sans my other interests, a career down the path I could've taken out of Wharton would've been comfortable and exciting. But it just wasn't for me. I also felt an enormous pressure to make work my life, and be defined by my occupation. I realize this isn't the same across all colleges, but this attitude was prevalent in my pre-professional school. I rejected that attitude, and still reject it, but it's hard to work within the "system" while maintaining your "soul", as they say.

I decided to do consulting out of college since it was a good mix of things I enjoyed — lots of new people to meet, projects to do, places to go... and my experiences reflected that. I met really awesome people, traveled a little bit, and did a smattering of projects. Throughout that time, I started spending a lot of the "after hours work time" learning about user experience design as opposed to just graphic or web design. I was drawn to UX because it integrated all of the thoughts on cognitive psychology, human behavior, visual design, and human computer interaction — all these other areas I've been thinking about my whole life. It was also a booming field: salaries were high, and job openings were plentiful. I don't know if it will always be so high, but it was a field I wanted to learn about every day, a feeling I didn't have for anything else.

What were your expectations about living in New York, and how have they changed?

When I moved to New York right after graduation, the first year was like a college after-party. I moved here with some of my best friends from college, and we had a huge apartment where there were a million people visiting all the time. We'd stay up nearly every night watching movies and eating pizza; it was excessive and awesome. But after a while, the "what's next" question started resurfacing, and I realized I had no concept of what to do with my "twenties".

I started researching about young adulthood — I guess I'm more deliberate than I thought I was. I came across the idea of the Odyssey Years in psychological development, the idea that we have an emerging adulthood period in our development. Like in the 1800s when they realized that childhood is a phase of life, emerging adulthood was being recognized as more of a legitimate phase of life. It made sense to me biologically — we're living longer, there are older people in the workforce, and our generation in particular was well coddled by our parents so we are going through this second puberty of sorts.

What do you do with this younger class of educated adults when there's not that much room for them in the world? For people that are privileged enough to not have to struggle for survival, the question is always hanging over us: "How do I achieve self-actualization? What do I do with all this time?" It's the biggest paradox: the days are long but the years are short. I kind of think of this as a second, emotional puberty and I see people in various stages of it.

For a lot of people, this is a soul-searching decade. At the beginning of this project, when I was 23, I felt like I was at square one even though objectively, I wasn't at all. It's been a little weird because this project took two years to complete and now that I'm almost 25, I feel like I have more or less figured out what I want to do with my twenties.

What I did to get there involved a lot of introspection and honest conversations in my head about what values and lifestyles were most important to me, meeting or reading about a lot of cool people, and in particular, hearing what others thought about this decade (thus, this project came about). I also found role models I didn't know personally but whose work I deeply admired. I tended to gravitate towards illustrators, designers, and Instafamous people who were only in the process of making it big but did inspiring work — they seemed relatable, like they too once started from "Level 1".

My game plan for this "kickstarting my life" project was to meet as many people as I could, listen to their stories, and empathize. To really persevere to start and finish whatever I put my effort into. Inspiration and talent isn't enough, the follow through is really critical and I think that's what makes the difference between something ephemeral versus the kind of impact that endures.

I'm also slowly accepting the responsibilities of adulthood. I was kind of excited when I filed my first taxes, and signed my first lease without a guarantor. It was like, "Aw yeah! I've made it!" When I switched jobs for the first time, it was actually terrifying since that was the first thing I did outside of the handholding college education system. I'm noticing more and more moments where I'm switching between thinking like a child versus thinking like an adult. I'm starting to think this "young adult" phase is not a binary switch, 0r even a gradient. It's flashes here or there. Sometimes, I'll be out at night and it's 4am and I'm like, "Yassss, springtime of my youth." But most Friday nights now, really, I go home and I'm in bed by 11PM. I don't even think the "twenties" is an accurate description anymore — Odyssey Years could last until you're psychologically ready to settle down at 35, or maybe a hard life will abbreviate that soul searching to your late teens. It's not about a physical age; it's a psychological age. And eventually, I'll maybe move towards having more adult moments than child moments. And there've been a ton of moments where I was like, "Oh shit, I'm not cool anymore."

If you had to pick one life-defining moment in your twenties, what would it be?

I don't think of particularly life defining moments, because everything that I have now has been a progression. I also realize now how annoying of a question this is to ask people, sorry to all of my interviewees. Who can pick just one moment?

There were a few times in 2013 where I was acutely aware of my increasing independency and "transformation" into being an adult. I felt like 2013 was a low year for me, where I wasn't ever deeply satisfied or complacent (the way I am now or I was in most of college). But that discomfort and feeling of isolation was also kind of... profound? I ran a lot that year, and the first time I ran ten miles (my PR at the time), it was... almost spiritual. I was a chubby kid growing up. I never even thought about running. I used to have to walk two blocks to go home from the bus stop (the short blocks), and I'd be like, "Aw man can I get a ride?" But in 2013, I had nothing better to do so I started running a lot. After the pain subsided, it cleared my mind and felt so thrilling to go so far.

I never thought I could do that. It was weird because I always thought I could do anything I put my mind to. I was truly privileged to grow up with parents that expected that of me, friends that believed that of me, and so I thought that of myself, but I never applied it to anything physical like running. My body just seemed to be a constraint... but then I did it! I ran so much that I came to love it. That was such a win for me; it made me think, maybe I can do anything...

There was another time that summer when I was staffed 50 miles outside of Boston and had to carpool with this woman I wasn't that fond of and she would just talk and talk and talk. We'd have to drive those 100 miles round trip every week and I'd listen to her rattle on, not particularly enjoying her company. It was such a weird summer. It was a very cool summer in Boston, and when it rained, the roads were slick and reflective like glass. It was usually her that drove, so while she would talk about every extended family member's shenanigans, I'd gaze out the window, finding myself chuckling at her stories sometimes. When the sun broke through the rain, the sun-showers fell like golden ribbons. There was a double rainbow. And all I could think about was the absurdity of it all — I never thought I'd be somewhere random in Massachusetts, driving through this surreal weather with this unlikely companion. I felt this strange sense of awe in the beauty and absurdity of the moment, in how my life at that moment was absolutely unlike anything I thought my life might be when I was younger. It made me think, wow, I could end up anywhere. Do anything. It was liberating. I felt like I was being freed from something heavy. I keep that in mind a lot now; I don't ever want to become immune to awe.

What's the most disappointing lesson that you've learned in your twenties?

Maybe that you never find "it". I don't know what young people think they're looking for, but the second you're outside the gates of an educational institution, there's no clear finish line to cross. It's also very bittersweet to see people go their separate paths, once we've crossed the gate from college onwards. At every milestone, paths start to diverge and people go their separate ways down different careers and lifestyles and cities, but part of me always wants to cling on to the feeling of "togetherness", the opposite of loneliness as Marina Keegan so aptly described (I still revisit this piece regularly) that I felt in college and while growing up. We all know this is coming, but it doesn't make it any easier.

How do you feel about your close friends moving away? How does that affect your relationship to where you live?

This is a very apt question, since you, Charley, are leaving and the person who asked this question (Jing!) is also leaving me for the West Coast. It's a very hard adjustment (though understandably less of an adjustment than you folks who moved). My college after party year (Year 1 out of college) was like the best parts of college, except we were earning money and set loose in this big playground of a city. But eventually, the idea started dawning on me, "Maybe I should grow up and leave Neverland." With these moves, it's a little like we're all being ejected from the party, or outgrowing Neverland. But I hope I never outgrow these friendships.

I have this mental model of friendships (I have a lot of mental models) that friendships are inputs of proximity, shared interests, shared experiences, serendipity, and a number of other factors. But I think of the nature of those friendships in 4 dimensions. There are the 1-D acquaintances I meet once in one occasion and never see again (the "dots"). There are the 2-D friends I know through one limited context, like maybe working together on a team but that doesn't continue when the context is over (the "lines"). There are 3-D friends who I know well and have a comprehensive, more rounded understanding of who they are as people — I've seen them through their ups and downs (the "spheres"). And then there are the 4-D friendships, who transcend time and space (the... 4D equivalent of a sphere). They are the people who can pick up the phone and ask me for a favor after not talking to me for 6 months and I will bend over backwards to help them. It always feels good talking to them, no matter how long. I try to visit them whenever I can, but if I can't, I know it's okay. I look forward to growing older with those friendships.

Everyone moving does change how I interact with people on a day-to-day basis. In the "College After-party" years, there was never a lonely moment where I wasn't mandatorily hanging out because everyone lived there. I'm an extroverted person, but I definitely grew up with my own time, so it put a lot of pressure on me to always hang out. Now it's a different since everyone is more spread out, and I have to make that active effort. But I also have to relearn how to be satisfied and content alone by myself again, and not let that creeping FOMO that ravaged me throughout college creep back.

How did FOMO affect you before? Do you still have it?

The biggest fear I had in college was FOMO. I did a lot of stuff in college, to the point of ridiculous exhaustion, but I think I was afraid of missing some part of the experience that would be transformative. I often prioritized socializing over personal time, so that whenever I was out, I'd feel guilty and want to be in doing work or something for me, but whenever I was in, I'd wonder what I was missing out on outside. I was afraid of missing friendships that were being formed, or memories that were being made without me, even though I might even think it was a waste of time or I knew I needed to do some work. It's better now, but I still have a little FOMO, though it's mostly transformed into FOWT... Fear of Wasting Time.

New York is such a fun city to meet people in, full of lots of stuff to do like going out to cool restaurants and festivals and such. But to me, it just seems so consumptive. I have another mental model about creation versus consumption that I started thinking about this when I saw a statistic somewhere about how over 90% of content on Tumblr is re-blogged and not original. I want to be in the 10% of content creators. If I go too long without doing creative work, I feel lethargic. Going to festivals and eating out and exploring is great and fun, but at the end of it, I feel empty. I have a low threshold to excessiveness and decadence, maybe from my more modest means while growing up, and it eats at me a lot.

So I'm afraid of missing out and forming those friendships and memories, but I'm afraid of not fulfilling my potential. That causes a lot of cognitive dissonance for me. I think of myself as a creative, prolific individual and maybe some people think that of me too, so when I'm not putting out work, I'm acutely aware of how hypocritical I'm being. That cognitive dissonance drives me the most crazy, I think, more than any extrinsic fears of losing my job or something. Maybe because I trust my social network and trust myself in that regard. Maybe it's a fear of not being who I want to be.

What's the background to this project, and why did you want to do it?

As I've said, I wanted to hear about how others are answering the "what now" question. I was sitting with Jing and Rajit in our post-college dorm, and we had all these conversations about life obligations and financial views that made me realized that even though I knew these people so well, we still had such different views and even more different formative experiences. I really wanted to hear more. For this project, I tried to pull from a variety of friends in different fields or just likely to have different worldviews, but it mattered a lot to me that I talk to actual friends and get to know them on a deeper level. (More 3-D and 4-D friends!) I was also inspired by The Great Discontent (beautiful interviews about creativity and design) and a blog called The Billfold that writes tongue and cheek about personal finance from these unique personal perspectives. I've learned a lot from everyone I spoke to. This project was truly a blessing, and it was a combination of all these different goals I was striving for — creating unique content, deepening existing relationships, telling great people's fascinating stories, and presenting that content in a beautiful way. It took a long time, a lot longer than I intended (my fault), so it really was a labor of love. Each interview took 1-2 hours, plus 2-3 hours of editing. But I'm so grateful for everyone who spoke to me and so happy to see this finally come together.

Last question — if you had to spend the rest of your life in only one city, without being able to travel anywhere else in the world, what city would it be and why?

Probably New York. Solid pedestrian transportation, everything comes to you, and there's a lot of good late night pizza and ramen.

But in all seriousness, I would love to see the world or live elsewhere eventually, but New York City is special to me. It's a living beast that keeps changing and evolving. Living here is like being in a long, committed relationship that demands constant adaptation. To quote Maugham, "We are not the same persons this year as last; nor are those we love. It is a happy chance if we, changing, continue to love a changed person." I'd like to take that happy chance. ■