Philina Fan on her journey from a fashion designer to a digital product designer at Handshake

In each episode of our podcast, we talk to amazing product builders to learn about how they work, their processes, tools they use, and things that inspire them. It's an opportunity to get a sneak peek into how other builders and makers do their jobs.

In this episode, we interviewed Philina Fan, Product Design Manager at Handshake. Before Handshake, she was a designer at Asana and Cloudfare.

In our episode, Philina shares her crazy journey from a fashion designer to a digital product designer, how she landed her first job as a designer, and how surrounding yourself with amazing people can unlock opportunities for you.

Irtefa: I'm so excited to have Philina Fan on the pod today. We're going to be chatting about a lot of the design stuff, but Philina has a really weird story of how she ended up on the digital product side. Philina was working as a designer at Carolina Herrera, which is one of the craziest, incredible high-end fashion brands in the world, and now she works at Handshake as a lead product designer. Before, she was at Asana and Cloudflare. Before we get started, do you want to talk about how you ended up here? Just curious. That's a crazy story. It's so unusual.

Philina: It is kind of unusual, and I would've never expected it. Like I would have never expected to end up working in Silicon Valley in technology. You hear a lot about people's past, they played with computers when they were young, and they were obsessed with technology. I was definitely not that girl. I was like the one that was crafting manual things. I loved sewing and art and painting and all of that stuff. So it made sense that I ended up in my previous career as a fashion designer for Carolina Herrera, which is a very craft-focused kind of brand that used to show in, and it still does show, at New York Fashion Week. So craft was a thing, and I loved all that stuff involved with that. But how I got into tech is pretty funny. I got married; that's how I got into it. I got married, and my husband went to grad school at UC Berkeley to study information. He always knew he wanted to be in technology, and because we got married, I followed him to the west coast, quit my job, and was planning to work at Gap or Old Navy or, you know, Everlane or something here.

Irtefa: Like something closer to Carolina Herrara, not like cloud computing or CDN

Philina: Totally. Didn't even know what that was, and I was like, Oh, it's fine. I'll work at Old Navy or whatever Everlane, one of these companies in the Bay Area, and it'll be great. So I came in here, and I started exploring that world, and TLDR just wasn't what I wanted to do because of the space I was in the fashion industry, and it was so interesting and creative. Not that there's anything wrong with like Gap or Everlane and stuff, but the mass market of clothing is very different from the skill set that I had in New York. So I was like, I want a new challenge. I want to do something different. And I did have friends that were interaction designers in New York and in California, and they would always be like, Oh, you would be a great person for this job. And I'd be like, No, I'm not a computer person. But then I started exploring it, and I went to various boot camp info sessions, just out of curiosity, like, what is this technology thing? What is product design?

Irtefa: These are all like product design boot camps?

Philina: Yeah, they're like those intensive 10 to 12-week ones where you put in like 40 to 60 hours. And I was like, I'm just gonna go see what this is all about. And so I started doing that, and then I was, like, this is an interesting challenge, and I think I could do this. So then I applied. At the time, General Assembly was like the hottest boot camp. This is back like seven or eight years ago or whatever. They were so hot, and I remember being like, this is the one to go to. Because they were hip, they knew exactly what they were doing, and their success rate was really high, so I just took a chance and jumped into that boot camp, and I loved it. I loved it, and it tapped into skill sets that I didn't know I had that I was good at.

Irtefa: Philina, I'm curious because you come from this, like, craftsperson background, right? Carolina Herrera makes dresses for first ladies, specifically for them, then from there to UX design. When doing this crazy boot camp, General Assembly, what about it attracted you?

Philina: Yeah. At first, I thought it was like, Oh, it's a good extension. Like I knew I was a good visual design person. I knew I had good taste. I knew that innately. I understood things in graphic design, like spacing and hierarchy. I knew that I had that already, naturally, because I went to art school and took graphic design classes. But what I didn't know was I was a systems thinker. What I found out was I could, like, really step back. You could give me a really weird problem, and I loved dissecting it and breaking it down. And creating different solutions for that. So I was a bit surprised myself. I thought I would get out of the boot camp being more of the interaction designer or the visual designer. But it was strange to discover that I was like this natural systems thinker, a natural product thinker. And I was enjoying all the UX stuff a lot more. And because of that, I discovered, Oh wow, I never really tapped into this side. I knew I was a problem solver. I did solve a lot of problems very quickly in fashion, but it wasn't like the problems that you solve in UX. I knew that I was quick on my feet and I could always get something together. And that's pretty scrappy. That part I knew already, but this was kind of solidifying that I loved these big, gnarly problems and liked being able to break them down and figure out things that I didn't even understand from scratch. And as you know, we worked together, I didn't know anything about Cloudflare right when I joined. And somehow managed to design things for Cloudflare.

Irtefa: Yeah. I mean, you more than managed, but the interesting thing is how going into that boot camp experience tapped into this different part of your brain that you didn't even know you were good at.

Philina: Yeah, it was really cool. And then, when I look back now, it sort of makes sense. I think about the things I liked as a child. Like I loved maths, or when I was in fashion school, I loved pattern making, which is a lot of like negotiating with fractions and fitting things together and building and constructing things. And it sort of made sense because I had always been interested in architecture too, which involves a lot of that infrastructure type of thinking or thinking about how something's engineered together. And that was stuff I always enjoyed, but never really understood that I enjoyed it until I went to product design.

Irtefa: Wow. That's incredible. And how did you get your first job?

Philina: Oh wow. I'm a very blessed human. I really believe that truly my entire life story, if we had two hours, is just full of blessings. And I think it's because I have such amazing people around me. When you're surrounded by amazing people, there's always really good energy. So what happened was everyone was looking for a job in boot camp. And they already warned you. They're like if you come from boot camp and you're not from HCI, it's going to take sometimes up to 180 days to land a job. And that is still a success in the boot camp world. So that's like six months, right?

Irtefa: Oh, is it like half a year just waiting and trying to figure it out?

Philina: Yeah, half a year. I remember being like, I do not want to be that person who waits for half a year. I was really motivated. I was like, I'm going to get this portfolio exactly the way I want before the course is over so that as soon as the course is over, I can shoot out my portfolio everywhere.

And as I said, I was very lucky. My husband was in the same sort of world. He was about to graduate, too, from his master's in info systems. He just helped me shoot out my done portfolio to people that were in the alumni circle of Berkeley from his program. He had met this girl who was a year ahead of him, they had this mentor session, and then she was a product designer, a senior one, and he just asked her, Hey, do you mind reviewing my wife's portfolio? Not even like, Does your company have a job? Just review it for her since she just finished. And she's really determined to get a job and shout out to Lizzy if she ever hears this. Lizzy Ha, who is now an amazing designer at Facebook, looked at my portfolio. And instead of just reviewing it, she gave it to her boss to look at. I think she saw some sort of potential in it that was interesting. And they were looking for designers, so she sent it to Travis, who is amazing I am still friends with him, and I got a phone call. That's like, Oh, I would love to chat with you. I saw your portfolio. I was like, Wow. And this is before graduating from boot camp. So I was really lucky.

Irtefa: Wow. So you still didn't graduate? You were still there?

Philina: I was still there. There were like two or three more weeks or something like that. And Travis is like, Oh, this is an interesting portfolio. Would love to chat with you. Would love for you to come to the office. And by the way, they worked at this company called Prosper at the time, and they're a competitor to Lending Club. So it was like peer-to-peer lending. And he's like, I've been looking for designers. And I came in, met with him, showed one of my case studies in a deck. So I did a Google Slides deck and showed my final project, and he was like, I'm going to give you a chance, but because you've never done product design before, do you want to be a contractor? And I was like, absolutely, I was in the mode that I will take any sort of opportunity just to get in the door. He offered me a contractor position, and I started immediately after I graduated.  I think I might have taken a week or two off for a little vacation cuz the boot camp was so intense, but I was like, I am ready. And, funnily enough, I started in the same week as my husband in Tech.

Irtefa: It's so beautiful. People who are listening to this or who are in a similar situation can take away a few things from you. The first thing is tapping into your network. Super important. This doesn't mean just going out to have casual conversations with people but having deep relationships and then asking for help. The second thing was, and I love this part, Hey, can you review my portfolio? It's not like, Hey, can I get a job or anything? It's a very low ask, and people should do that more. So that's incredible.

Philina: Yeah, for sure.

Irtefa: And this segues into my next question, what’s one tip or one tactical advice that you have for other designers to level up?

Philina: Oh yeah, this one is great because our industry really fosters imposter syndrome. There's just so much talent, and everyone is so intelligent, and when you start out, you can really feel that imposter syndrome, right? We're surrounded by highly successful, intelligent people like yourself. And I think one of the things that I learned early on was that your ego is telling you that you need to keep face or represent yourself in a certain way, especially if you do a career change like me, which is like, Oh, I was very successful in a previous career. Now I have to feel like I have to pay my dues again. That feeling of like, Oh my gosh, I'm slightly older, and I don't know anything, and that feeling would bother me a little bit as someone that liked to be good at stuff. But then I realized, Let's put this aside, this is a whole new chapter for you, you're now this giant sponge, and your job is to sponge up as much information as you can in the first couple of years, and it's going to be hard. It's not going to be easy because you still have to produce things, right? So I remember thinking, I will look at these opportunities as learnings no matter what.

So I didn't care how dumb my questions were. I mean, I kind of cared because I have an ego, right? But I was like, No, I'm going to ask this because it's going to make me better. And it's going to make me a better product designer because I'm going to be surrounded by other people who have more experience than me that can teach me. And if I don't ask these questions, I'm not humble, and I'm not showing my vulnerability; I'm just going to sit here in this corner, put a shell on and pretend that I know what I'm doing. And it’s something that worked for me.

Irtefa: It's so cool. The first step that you mentioned is actually acknowledging that this is very normal. This is going to be hard. You have to be a sponge. But another interesting thing that you mentioned is the way you can take that knowledge now and action it into your day-to-day work is by asking more questions. Be more vulnerable. Like, these are things that you can actually do to be a better designer and get over that imposter syndrome and get over your ego and be better.

Philina: Oh yeah, for sure. I remember having one on ones with Blake. Blake, as you know, is the head of design at Cloudflare, who also really believed in me, and from the beginning, he hired me, knowing that I was this rough diamond that he would have to Blake. Shout out to Blake Mattos. So he also saw some potential in me when he hired me for sure. And I would have straight-up convos with him on our one on ones. And I'd be like, I feel so worried. I feel so incompetent. I feel like I'm not doing well. And I remember him saying, The fact that you're aware of that says you're gonna be a good designer.

I remember him saying that it's going to be okay; this is part of the journey. And he's like, You're humble. You ask questions. You're always trying to improve yourself. And those are the things that I look at for a designer that's going to be successful. He would always tell me, I knew you were going to go far. I'm not bragging about myself. These things he said to me made me feel reassured that I was in the right role and doing the right things. So that's a huge thing that I learned, and its helped me throughout my entire product design career.

Irtefa: Yeah. When you're getting started and going through a transition like that, having people around you who see that passion and that talent in you and encourage you to go down that path makes such a huge difference. And it sounds like Blake was one of those people during your journey. So one of my favorite things to ask because, by asking this question, I also created my Amazon wishlist, what books helped you get better as a designer?

Philina: Oh, what books? There's one that I really liked, especially when I was really feeling that imposter syndrome and also being a woman and a minority. I know that in tech, I'm not a super minority, but in this world, I'm an Asian woman, and there's a certain type of behavioral expectations that get into people's heads and stuff. So one of the things that was recommended to me by one of my favorite managers at Asana, she's amazing, was this book called Playing Big by Tara Moore. It's a great book, especially for a woman who wants to be a leader and who wants to learn how to be confident. She's trying to tell you to play big. Reach for more than you think all the time is the general gist of it. It's not like leaning in, but it's more like putting yourself out there and making yourself bigger than you really are. And it's a self-fulfilling prophecy. You will become big. So that message was really great in that book. And in general, she's like a life coach, so you can go on her website, you can see all these amazing tips on like how to handle life and be more confident. So that's a great book. And then another one that has helped me is the Designing Your Life book, using the design process to design your own life. And that goes beyond just your design career.

Irtefa: Who's the writer?  Folks, we'll add these to the show notes.

Philina: That's a good question. Let me quickly look into it. Oh, it's Bill Burnett and Dave Evans. It's pretty famous. The sub-headers are how to build a well-lived, joyful life using the design process basically. And I went through all the exercises. It’s basically like, where are you now? Do you want to build to find your way? It gives you tips on how to get unstuck when you feel stuck sometimes. And then it's essentially saying that if you design your whole life, it proliferates into every single part of your life, and all of it works together to get you to a place that you want to be.

Irtefa: That sounds like it's a book you don't necessarily have to read once when you're like 10 years old. Anyone at any age can read this book and get something.

Philina: Oh, totally. At any time, too, you could repeat it. I know people who have reread it. I've reread it a second time. I read it the first time, maybe like five years ago. And I definitely reread it this past year, actually, during Covid, just to assess if the direction I had put five years ago was still valid or if I had to pivot depending on where I am right now. So it's great. I have it just sitting on my shelf, and I pull it out sometimes and read a section. There's like a whole part about failure too, which is really useful for people who are type A and want everything to be perfect. You know.

Irtefa: Working with you, I do remember a glimpse of that. What are some podcasts you're listening to or YouTube channels you're watching, or Tedtalks you're following?

Philina: Podcasts. I love How I Built; of course, that one is so good. It's always so interesting. I love hearing about how people build from nothing into something big, and I'm sure you relate since you're building something really big.

Irtefa: I love stories like that.

Philina: Me too. I love those stories. I've always loved them, and it's in my genetics too. Like my grandfathers are entrepreneurial, and I think that's why I've always admired people that can grow something from nothing. I'm really impressed by that. What else do I listen to? Honestly, every single morning I listen to The Daily.

Irtefa: From New York Times?

Philina: Yeah, from New York Times. And I will just get a gist of what's happening in the world. I try not to get too sucked into the media given everything that's happening these days, but I at least like to have a sense of what's happening, and getting that every day is good, especially because I'm juggling like five things at the same time. And then a good design one is 99% Invisible by Roman Mars.

Irtefa: Love it. Yeah.

Philina: Yeah. And I went and watched him record a podcast live. He did one at Adobe, and we got to sit in the audience, be quiet, and watch him do one of his episodes. He's really interesting and a super smart guy. And he talked about his process after that. So that was interesting. And that one's always on loop for me as well. So I would say those three, I have more, but those are at the top of my mind.

Irtefa: I have a question. You said that your grandfather was an entrepreneur. What did he do?

Philina: Yeah, my grandpa, like in the fifties, forties when everyone was leaving China. Cultural revolution and all of that stuff. He escaped Shanghai. My grandmother was saying that she grew up in this one room with like nine people and bunk beds. My grandfather basically started out from nothing and built up this manufacturing business.

Irtefa: Nice. And is this in Hong Kong?

Philina: Yeah, this is in Hong Kong. This was the era when you could really be entrepreneurial. Hong Kong was still a fishing village. People were coming in from all over China and creating their own businesses. So he was manufacturing a lot of things like fabric. He was involved with fabric, butcher's cloths, and stuff like that. And from there, he got into real estate, which is a very Hong Kong tycoon entrepreneurial thing to do. Get your money and buy property. I’ve watched my grandpa grow his business into what it is.

Irtefa: When I hear this story, first of all, it's super inspirational. We should do a podcast with him.

Philina: I wish; he's unfortunately already long gone. He would be great to talk to, though.

Irtefa: Rest in peace. The apple doesn't fall too far from the tree. Like he started in manufacturing, textile, and fabric. Same. So I'm looking forward to your next real estate adventure. I don’t know, maybe you'll start a company around real estate, or maybe you'll get into it.

Philina: I do like real estate, I have to say. I don't know if it’s because it's in my blood. But I enjoy a good open house.

Irtefa: Before you say goodbye. I have one last question. We are in the intersection of building, and I like to ask all the folks who get on the pod, as a designer, you're constantly working with product managers, engineers, and other stakeholders. Any advice for them to work better with product designers to get the best out of the team?

Philina: Yeah, I think this is probably really cliche, but now that design is getting more prominent, I do feel like one of the best ways to work with a product designer is to have them there at the beginning. That world where you get handed off like a BRD or whatever is over now, and it's really important that design is there at the table while you're doing all the product strategy as well, given that you can start off on the right foot where everyone is on equal grounds and contributing equally to a project.

Irtefa: You know, it's interesting you say that. I'm seeing a lot of companies these days, too, doing exactly what you said, but they would start the company with the design co-founder, so it would have that culture from day one and continue to foster that as the company grows. Super helpful. Philina, thank you so much again for joining the pod and sharing your sage advice. Really appreciate your time, and we'll talk soon.

Philina: Thanks for having me. This is really cool.

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