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In this episode of 'Ladies Who Create', co-hosts Jess Rosenberg and Liz Meyer interview Design Director Anna Fine. Anna shares her impressive career journey with us, which spans from aspiring genetic engineer to graduating from The School of Visual Arts and thus embarking upon the design & creative industries. Anna has worked at reputable companies in advertising & tech such as R/GA, Anomaly, Instacart, and Doordash (to name a few). The conversation explores transitions in design, exploring entrepreneurship and the business of design, working from home during the pandemic, overcoming imposter syndrome, and so much more.
Creators & Guests
What is Ladies Who Create?
A podcast highlighting extraordinary women in the design and creative industry. Hosted by Jess Rosenberg and Liz Meyer.
Welcome back to Ladies Who Create, a show where we'll be interviewing the incredibly inspiring women who are trailblazing the design and creative industries. I'm your co host, Liz Meyer, a creative director and half of the data lands duo.
Jess Rosenberg:And I'm your other co host Jess Rosenberg, and I'm a creative director currently working in the tech industry. Today, we're excited to welcome design director Anna Fine, who was kind enough to share her design journey with us.
Liz Meyer:We talked to Anna about her leap from a background in science to design, navigating career shifts, the importance of continual education, and the intersection of design across different aspects of life, including furniture collecting. Welcome, Anna, to
Jess Rosenberg:the show. Welcome Anna Fine to Ladies Who Create. We're so excited to have you here. I'm excited to be here.
Anna Fine:Thank you for having me.
Jess Rosenberg:Yeah. Thanks for hanging out with us for an hour. I'd love to get into your career trajectory. You've done so many different things throughout your career from brand design, product design, agency side, non agency side. I'd love to hear from you what that journey has looked like.
Anna Fine:Sure. So I'll I'll go high level in the beginning. But I actually, growing up, wanted to be a genetic engineer. I didn't even know art was a viable career path. In fact, I was so dead set on it that I went to a STEM high school.
Anna Fine:And my mom, while discussing with her my very poor organic chemistry grades, said, you know, why are you why are you trying to be a scientist when you hate doing the same thing every day in and day out? Like, you don't like repetition. You don't like, you know, the the menial tasks of the same to dos, which is science. Like, that's that's what you do. And she was like, why don't you do art?
Anna Fine:You love art. And I was like, mom, you can't you can't make a career out of art. Anyway, fast forward a few years, made a career out of art. I graduated from the School of Visual Arts and Design and Advertising. I started out at Anomaly New York as an art director.
Anna Fine:And I worked on Google, Converse, and a couple others. And embarrassingly, I worked on the Android logo when they were looking to rebrand. I pitched for them and then realized after I got the feedback that they had spread it around Google that I had created a logo with a very phallic looking a. So that was my that was my, like, oh, I should probably learn a little bit more about branding, which actually which actually ended up being a good thing because Google asked me to join their 30 weeks program. And that's like, or once upon a time, Google Creative Lab wanted to prove that designers made great entrepreneurs.
Anna Fine:So, in their inaugural class, I joined them as an incubator accelerator program, and I attempted to make a company. I say attempt. It was, like, 6 attempts. I had I had too many ideas, and I could never find one that, like, spoke to something I just wanted to do for a long time. I was too anxious, too excited about the possibilities of all the things I could do.
Anna Fine:And so by the end of the program, I ended up, like, just going into demo day saying, hey, I didn't actually launch anything. But I've got some great learnings I can share with everyone. And within a couple weeks, I had 8 job offers, went to venture capital for a hot minute, realized it was not the temperament for me, and and then fell into fell into RGA, where I was doing a little bit of everything, branding, marketing, and product design. I helped them with a new brand product launch at Verizon that got pulled 3 days before launch and is now known as Visible. It's which is their, like, sub product, whatever.
Anna Fine:So that was something I worked on. And then my client at RGA was like, hey. You like me. I like you. You're cool.
Anna Fine:We're cool. Come work with me at Droga 5. And I was like, alright. So I went to Droga 5, where I did more of the same, mostly branding, but a little bit of marketing. I worked on the Game of Thrones campaign.
Anna Fine:And then I also worked on the rebrand and product launch for Harley Davidson. So yeah. So then from there, that was right around the time COVID hit. I was at this point, I had left Droga. I was a consultant, and I was working with Policygenius in New York.
Anna Fine:I did a, like, short term contract with them, fell into Instacart, was there with Instacart for a year, tried the startup world for a couple years, Didn't really work out for me. And now I'm currently at DoorDash. So that is the long tangent of my career. That's awesome.
Jess Rosenberg:Thank you. Yeah. That's amazing.
Jess Rosenberg:How so during COVID times, you were consulting, working from home. What was that like? Yep. Well, at
Anna Fine:first it was great. My 2020 was probably the most lucrative year I've ever had. It was I was working with Instacart. I had just completed my contract with Policygenius. I was also doing some side work with a couple smaller studios.
Anna Fine:So it was it was a lot of exciting work, actually. But after that, I had during 2020, I'd actually left New York and moved officially to Colorado. And at the end of 2020, my when my contract ended, I kinda was like, now what? And actually finding even though everything was still predominantly remote, finding work outside of the Bay Area or outside of New York City was extremely hard. So it's and it's still kind of an ongoing struggle that I'm I'm figuring out being based in Denver.
Anna Fine:But it is it it's a it's a good, like, exercise in grit. And and, like, new learnings for me, I had never been without work for more than a few weeks in New York. And then here, this past year, as you know, Jess, I was unemployed for a full year. And that was an entirely new experience for me. So COVID has been both a blessing and a lot of learnings, having forced myself to move from New York and start new here and just essentially network in a whole new way.
Anna Fine:Yeah.
Jess Rosenberg:Yeah. A few times on the podcast, just in some other the guests that we've had on, we talk about the time and space between jobs and the type of effects that time and space has had for different people. And we're I'd love to hear from you on on what that time and space, how it affected you positively and maybe not positively.
Anna Fine:Okay. Well, we're we're thinking about that.
Jess Rosenberg:If the time I mean, the, the conversations we have were more so around having the time to slow down and really think about what's
Jess Rosenberg:going on with the next.
Jess Rosenberg:So maybe like positive. That doesn't have to be both with them.
Anna Fine:I'm just here real. Yeah. I would say I finally have a more purposeful sense of self. When I was in New York, it was I was the first one in to the office, the last one to leave in every job. I had no boundaries.
Anna Fine:I didn't understand, you know, like, just taking a minute to yourself. I would work, you know, 80 hours a week. And then on weekends, I would go to gallery shows or whatever because I wanted to get reinspired to help fuel me for the following week. And it was a really impactful time of my life because I learned so much. I met so many people and it, you know, it was wonderful experience, and I wouldn't change it.
Anna Fine:You know? But I I was burned out. I was I've been burned out for 7 years by the time I left New York. And I I just didn't really know what I wanted anymore, and I and it was like, the more I kept trying to do design because I that's what I told myself I wanted, the more I I just didn't want it anymore. And it actually got to the point where speaking to the negatives, I, you know, last year after after layoffs, I I was like, okay.
Anna Fine:I'm gonna I'm gonna get my portfolio together. I'm gonna do some new projects. I'm gonna make this happen, and I'll get a new job. No problem. This would be great.
Anna Fine:But after a a month or 2 of, like, just downtime and kinda getting my head right, I opened up Figma, and I almost had a panic attack. Like, I I was just that I had that much anxiety. And I was like, wow. I I need a minute. Like, I need time.
Anna Fine:And I need to figure out if this is really what I want, Which is actually why I ended up doing the Harvard program that, you know, I absolutely tweeted about.
Jess Rosenberg:Alright. That's a. Being your
Anna Fine:work. Yeah. Yeah. So it I don't know. I I think to and now that I've gone out of town to bring it back.
Anna Fine:Yeah. I you know, the positive has been I've slowed down. I I've know what I want. I have enough energy and boundaries and space and time to do the things I'm interested in, explore new things, and have, like, a a contented sense of self, which is something that I did not have in my twenties. The negative is that I had to go through a lot of hell to get here.
Anna Fine:But, you know, what doesn't kill you make you stronger or whatever that, you know Yeah. For sure. Cliche thing is. That's so yeah.
Jess Rosenberg:Thank you for that. Yeah. I relate to that a lot, the leaving New York because it was overwhelmed. There's this overwhelming drive to do more and more and not have those boundaries because also you see all of your friends. Getting all this amazing work and you're like, okay, well I have to keep up with them.
Jess Rosenberg:And every night is a hangout night. You go to a bar, you go out to dinner and everyone's spending cash and you're like, wait, what am
Jess Rosenberg:I supposed
Anna Fine:to What's money?
Jess Rosenberg:Right. Yep. Plus the credit cards. Yeah. I totally understand that.
Jess Rosenberg:I left New York as well to move upstate. Oh, where are you now? A little I'm a little bit.
Anna Fine:But Oh, my, my best friend moves upstate too. It's like an entirely different experience. It's night and day.
Jess Rosenberg:Rural. It's Yeah. Quiet. It's calm. There's no pressure unless it's internal pressure.
Jess Rosenberg:But it's, it's a different life. And I, I applaud you for leaving the stress and finding your space. Yeah. Yeah.
Anna Fine:Super wise. I I don't know. I I don't know what part of upstate you're at, but for me also just yeah. We had Central Park and we had Prospect Park and we had, you know, these really beautiful spaces. But like actually being in nature.
Anna Fine:And it's an entirely different mental health benefit than just walking through a really beautiful park.
Jess Rosenberg:So Yeah. I have a bunch of 5 acres around my house.
Anna Fine:Oh, wow. Okay. Yeah. You've got way more nature than I do. You have
Jess Rosenberg:wait, you have chickens? I did. We did. It's Oh, wow. It was a COVID.
Jess Rosenberg:It was a COVID. Oh my gosh. But, they're living at our friend's farm right now. So it's okay. I don't even wanna ask what happened to a chicken.
Jess Rosenberg:They don't want it to No,
Jess Rosenberg:no, no. They're okay. Well Oh my gosh. No. I I couldn't eat chicken several years.
Jess Rosenberg:And then even now, I'm like, I don't like it. It, it feels well. It
Anna Fine:feels Yeah. Yeah. My mom had a did a similar thing. We we went to dinner one time. She my dad ordered venison, and right above them was, like, a deer head on the wall.
Anna Fine:And my mom was just like, How? How are you eating that right now?
Jess Rosenberg:Oh my gosh.
Jess Rosenberg:It's scary. Yeah. I I actually have a, you know, as you know, I was very intrigued by the Harvard course that you took. Oh yeah. Yeah.
Jess Rosenberg:Yeah. I'm just, I'm really fascinated by the idea of essentially going back to school in a way. And even if it's not like a whole master's program, it's just like that continuing education and realizing when you need to further your knowledge and Yeah, just like, how did you find it? Did it do anything helpful? All the things.
Anna Fine:Yeah. So I had seen a couple of my friends go back to school and that was something that I also, I had talked with my parents about for years going back to school and maybe getting my MBA, especially because I worked in advertising for a very long time. But when I got laid off and I was I could I saw the economy and, like, people struggling to get work, I was like, well, maybe now is a good time to go back to school. But I don't know if you know this, but an MBA program is anywhere from a 100 k to 200 k. And I was like, that is a lot of money I don't have right now.
Anna Fine:So I thought, okay. Well, let me at least let me dip my toe. I haven't been in school in 15 years. I taught I taught at SBA for 6 years, but I I hadn't been in school. And so I was like, alright.
Anna Fine:I'll I'll give it a shot. And if it's if it if I enjoy it, if I like it, you know, maybe it's I can get a loan and go to school. I did like it. I did enjoy it, but I decided not to go to school. For the record.
Anna Fine:But, yeah, I I I looked into several programs. And the Harvard one was the one that because it's an online certification program, it was only one that people, like, actually took seriously. Yeah. So I was like, okay. I'll I'll do that.
Anna Fine:And then I looked at their various programs, and there's something called Core. And Core was essentially, like, your basics in in business. So economics, finance, and data analytics. And they they wean you, into it a little bit. I did, like, my they do it by, like, weeks.
Anna Fine:So they'll do modules for different classes, different weeks so that you kinda, like, build up. And I did the fast track, which was a lot of work. In hindsight, I probably should have just done the module per week. But I, yeah, I I started out with data analytics, and I was like, oh, this is easy. I got this.
Anna Fine:And then the next week was finance, and I was like, end economics. So I was like, oh, no. I don't I don't got this. My dad, fortunately, is he's a CPA. He works in he's a c chief financial officer.
Anna Fine:So he, like, he helped me kinda get the basics a little bit. There were definitely a few nights of me crying. It was like back like flashbacks to middle school with my dad trying to teach me math going, I don't understand that. But he was a trooper. He was very, very like, very patient with me.
Anna Fine:And I and I did eventually get it. And ironically, finance was my ended up being my best class. And which I I never ever thought I would say that. But the the best part about it was I and and part of the reason I was able to cure my burnout honestly was because of this class. I I sudden I I went into it trying to understand why businesses are the way they are.
Anna Fine:Why when I present them meaningful, viable options, they go with some bullshit that they choose the, like, dumbest idea, but, you know, the easiest to implement or the fastest or whatever. And I'm like, why? Because if you do it right, then, like, there's there's a better return of investment. So why are you doing this? And so I I don't know.
Anna Fine:I I I went in with that mindset, and then every single module that I as I learned more and more, I was like, okay. Now I get why this company does x, or now I understand why. When I presented these things, they chose y. And the more that I understood the business logic of the their decision making, the more I understood that I was doing design wrong. I was coming to at it with a fervor to give them the best, most beautiful solution every time.
Anna Fine:And when you do that, you're you're you're trying to fit a square peg in a round hole. Like, they have a very specific thing that they need done, and they have a very specific budget for that. And no matter how great an idea is or no matter how beautiful something is, they're never gonna retrofit it in there. They're just not. It's not good business.
Anna Fine:A lot of what I came from New York advertising, hustle, and bustle, It's extremely competitive. It is always like whatever you present is a representation of you and you alone. And so everything I did, I will put in extra hours and extra time and extra effort to make sure that it was always the best potential representation of me. And then I did this program. I was like, oh, I I literally burned myself out.
Anna Fine:I kept trying to push a wall, and that wall was never gonna move. And so I just changed my perspective. And all of the things where I was, like, especially in product when you're doing these, like, little baby things, little baby changes that seem menial and and, like, unimportant. Suddenly, I I understood the importance, the incremental network effect that happens, the, you know, economics of these smaller changes and why they have such large impact financially and for, you know, consumers. And so I kinda just it was like the mental shift I needed to to go back into design with a with a fresh perspective and a better understanding of my peers who are non design partners.
Anna Fine:And it made it easier for me to communicate and work with them and meet them where they are. So, yeah, I think it was worth it. Okay.
Jess Rosenberg:I think that was like an amazing advertisement For Harvard Core. For Harvard Core. I you
Anna Fine:know, I you could take the girl out of advertising, but you take the advertising out of the girl.
Jess Rosenberg:But that, I mean, that is always been a struggle for me to speak the language as like a creative that wants to make an and very wants to always make the weirdest, most interesting work. That is like the core of my company. Make data weird. Yeah. That is interesting.
Jess Rosenberg:To think about the business side of it all. They are paying you and there is a reason why they're paying you for that work. Though it does make me wonder why hire the weird the weird designer in the first place? I just but maybe that's why I should go and take those classes.
Anna Fine:I mean, I don't think, I don't think it's necessarily saying, you know, homogenize and and to take away the weirdness. I just think, you know, it it puts it in a perspective of if you do the weird, what what is the risk management for weird? And what what is the opportunity for reaching a new audience with weird? I mean, Duolingo does it phenomenally. Right?
Anna Fine:Yeah. They do. So it's not it's not no to weird. It's just positioned weird in a way that it provides them a business opportunity. And I think that's Yeah.
Anna Fine:That Yeah. I don't know. We like that.
Jess Rosenberg:Think about like the fact that a lot of I don't know. When I I studied design in undergrad and we weren't we didn't have to any business classes.
Anna Fine:They're in either.
Jess Rosenberg:You would imagine that, like, the the trajectory of a design graduate is they become a designer for a business, or they are working with clients to deliver design for a business. And the fact that we don't learn that, or we didn't learn that in school just blows my mind. 100%.
Anna Fine:I mean, I don't know about you, but like we are like our whole thing was concept, concept, concept. You know? Yeah. You need to be conceptual. You need to have a point of view.
Anna Fine:You need to like, all of the things that make designers great. Don't get me wrong. But it doesn't it doesn't necessarily, to your point, address the issue at hand, which is you have a company paying you Yeah. To meet their needs. Yeah.
Jess Rosenberg:So Yeah. Especially in advertising. It's like start my career working in advertising. It was so concept heavy that I felt like a lot of creatives, even myself and sued it back then, like early on in my career. We just wanted to make like the craziest, most fun work possible.
Jess Rosenberg:And sometimes it felt like we weren't even thinking about actually advertising the benefits of the product. Which is also wild. We're like, we're just going to make this super creative and fun and weird, and it's going to attract attention, maybe get awards. But is it actually advertising that the product does and why people should care?
Anna Fine:Yeah, that last bit, like every agency I worked at was when we pitched anything, you showed them the headline of the award that, you know, like, this x will won an award for yada yada idea. And it was, like, without fail, because you had to sell the vision of winning awards. But to in the defense of advertising, which is something I never thought I'd say by you. But a lot of the marketing people internally on their end are also looking to win those awards. They're also looking to kind of make a big splash.
Anna Fine:Yeah. And so, you know, it's incumbent on them to be thinking about the product benefit. But, yeah, I don't know. I can't believe I just defended advertising.
Jess Rosenberg:I know. I mean, it's like a career decision at that point. It's do you want to further your career, get an award and then move on to the next place? Or do you want to sell incrementally This, you know, 0.2% more Cheetos. I don't know what it was.
Jess Rosenberg:What I'm talking about, but you know, or 2% more SaaS You know, subscriptions next year. So it's that that should be a CEO driven.
Anna Fine:Yeah. I
Jess Rosenberg:mean, I I mean,
Jess Rosenberg:I Yeah. Right. On the on the notion of creating weird for weird sake, I do give Liquid Dust a lot of credit for creating the brand they created out of a like, incredibly probably the most commoditized product in the world. Yep. And then that is a master class alone in disruption, in my opinion.
Jess Rosenberg:And they're selling tons of commoditized water in the form of just, you know,
Anna Fine:very there are like it. I was going to say there's dedicated sections to liquid death in my grocery store.
Jess Rosenberg:Oh, yeah. Same.
Anna Fine:Yeah. Yeah. It's it's it's very impressive. Yeah. That and Chobani.
Anna Fine:They did a really good job of taking very commonplace things and just making it something desirable. Totally. Yeah.
Jess Rosenberg:Yeah. Yogurt. How do you do that?
Anna Fine:How do you make those?
Jess Rosenberg:I'm curious, like, for those who might not be able to take, you know, a class like this or a course like this, What are some things you could suggest or advise on how designers can learn how to become more business savvy or speak the language of business in their design practice?
Anna Fine:Interesting. There are there are a couple YouTube channels that are really great. In fact, I referenced them a lot to learn the things I wasn't learning in the Harvard program because they expect you to kinda have a baseline knowledge of anything related to business. And I was coming at it from art school, so I was like, I don't know what any of this means. But there are a couple of YouTube channels that are pretty great.
Anna Fine:I admittedly am blanking on exactly what they are right now. I do have them saved in my YouTube channel so I could send them to you after. But there's a couple of podcasts on economics in particular that are pretty great. That's my biggest thing is, honestly, just listen to some of the podcasts, like, even more recently, the morning brew guys. They are doing a lot of like projection type, you know, forecasting type work.
Anna Fine:Which to me, when it before that class, I was like, I don't even know what any of this means. But I think the more you listen to it and then maybe even ask chat GPT, hey, can you explain what these things are? The more you kinda, like, gauge what is happening. I actually, admittedly, also use a lot of chat gpt to learn. Yeah.
Anna Fine:So yeah. It's it's a it's such an easy resource to to get the information you need. And and the best part is I literally would say, explain whatever to me, to as if I were a 5 year old. And they'd break it down. And I was like, oh, I get it.
Anna Fine:So basically I had to be a 5 year old to learn economics.
Jess Rosenberg:That's amazing. That's my most common prompt in chat GPT. It's the Yeah. Yeah. Didn't ever go
Jess Rosenberg:like on 5. I'm sorry. It does.
Anna Fine:Yeah. It but it it works so well because otherwise it's it's this very complicated thing that I'm like, I don't know what any of that what are those words? It's a string of words that means nothing to me. Really give
Jess Rosenberg:me the CliffsNotes on what this thing Yeah, exactly.
Anna Fine:Listen, I'm a millennial. We come from SparkNotes and Click Notes. Okay.
Jess Rosenberg:I wish there was something like that for like social media and like navigating algorithms and stuff like that. Cause that's my one of my current things. I'm like, I can't figure out There
Anna Fine:are so many memes. I don't and they'll they'll be like, they'll all of a sudden, out of nowhere, people were saying, Delulu. I'm like, where what is Delulu? And then now I know. Delulu.
Anna Fine:But I didn't know what Delulu was. I didn't know what it was. I had to go on TikTok and figure it out. It was an investigation.
Jess Rosenberg:Yeah. It takes so much time. Well, I admittedly just looked up what DeLulu is and now I feel like you've been running under a rock.
Anna Fine:Oh, you've just been DeLulu about DeLulu. That's all. It's okay.
Jess Rosenberg:I think you're safe. Delulu is a specific demographic. It's not I don't need to.
Jess Rosenberg:Don't worry. The fun mouth willing to say, the lulu. It
Anna Fine:is fun. I particularly liked when I first came, I was like, Zolulu is the Zolulu. And I was like, oh,
Jess Rosenberg:that's cute.
Anna Fine:That is so fun to say.
Jess Rosenberg:That is cute. It's nice. That is cute.
Anna Fine:There's a furniture designer, Yedrick Halibala, which is also a really fun name to say. And I just every every I have a piece of his, and every time people ask him, like, it's Halibala.
Jess Rosenberg:And he chatted. And it.
Anna Fine:Yeah. It's it's like it's it's actually a problem because I'm I, like, wait for people to ask about it. I'm like, oh, that? Palo Bala.
Jess Rosenberg:He's been putting research link that too. We're gonna I'll do it long length here.
Jess Rosenberg:Maybe the There you go. Same way to talking about hobbies
Jess Rosenberg:and furniture and collecting. I wanna hear more about that. Yeah.
Anna Fine:So fun fact, my great grandfather was a furniture designer and maker in Denmark. I did not know this until I was, like, 16. My grandmother and I walked into a furniture shop while we were looking for something for my parents' house, and she started crying. And I was like, what happened? I like I I immediately went into, like, overprotective granddaughter mode.
Anna Fine:I was like, what did I do? What's going on? Please tell me how I can help. And, and she just she's just pointed to this table and she started she just was like hysterical. My mom goes, oh, that was your aliphos or like your great grandfather's.
Anna Fine:And I was like, my, wait, what? I was like, what is it doing here? Why is this furniture here? And they were like, no, no. He made it.
Anna Fine:And I was like, that's insane. Why has no one ever told me this? Anyway, fast forward to COVID. I left New York. I finally had space, and I had a place of my own.
Anna Fine:And I was like, I get to decorate. I get to really decorate. And I just I looked into my grandfather's work and the people he worked with Hans Wagner, Charles Eames, like, all the great. And I was like, wow. I I need to learn more Like I need to learn more about these people And the I just went deeper and deeper and deeper into like, this weird place where now I can walk through a vintage place and be like, that's yada yada designer made in yada yada year.
Anna Fine:Amazing. And yeah. So and and that kinda just spiraled into other things, interior design, And, like, the overlap of graphic design with furniture design in particular was just so appealing and intriguing to me because it is form and functionality as a marriage, which is very much what we do. And so I was, like, so intrigued by their philosophies, particularly Finn Jule, who's a favorite designer of mine. He's Danish mid century designer.
Anna Fine:And he, he just, his whole thing was, yeah, it needs to be comfortable coming from a time period where functionalism was extremely private prevalent. It was, you know, is does it work? Does it, like, does it fit feel fine? Great. Then you're if it's ergonomic and it works, then that's all you need, Which is very much like what Hans Wegner is known for.
Anna Fine:And Fenuel said, screw that. I want it to be beautiful and artful and but also comfortable. So he would hand carve every single piece, like on his own and make these, like, gorgeous sculptural pieces. So he actually, one of his chairs, the chieftain chair, is I think still the highest priced or highest sold chair at at auction at a $120,000. Wow.
Anna Fine:Yeah. So it's it's like a weird niche hobby of mine, but it just it it was like something sparked inside of me. Now I can't I can't turn it off. So do you
Jess Rosenberg:do you collect old furniture now as well?
Anna Fine:I have a problem. Yeah. I'm actually trying to sell a good chunk of
Jess Rosenberg:it. That's why you have a job,
Jess Rosenberg:you know? That's
Anna Fine:Yeah. Yeah. Well, now now I do.
Jess Rosenberg:Yeah. You got out called Anne of Sines. Right?
Anna Fine:Yeah. It fine fines. Just to make make things difficult, you know? A little alliteration there. But, yeah, I I'm actually oh my god.
Anna Fine:This is just to prove how cool I am. I'm a Gen z scene. I have started a TikTok, and I am going to be talking through a lot of the overlap of this, like graphic design and furniture design and interior design and all that. So
Jess Rosenberg:That's awesome. Yeah. No, that's great. You're the gift card handle.
Jess Rosenberg:Yeah. More people need to be sharing this their like deep knowledge about the things that they're passionate about. I mean, it what you should do.
Anna Fine:You should be sure. I agree. Although I will say like when people meet me and they're like, you like furniture? Like, it people don't it doesn't register. They're like, why would you like furniture?
Anna Fine:And it's honestly just industrial design. Like, it's it's product design. Right. But it's premise and funk like, being functional versus, like, something more tactical or utilitarian.
Jess Rosenberg:So I don't know. That's actually not surprising to me at all. Actually, it makes sense. You're a designer and you care about beautifully designed things. Feels like a perfect.
Jess Rosenberg:Yeah. It seems like a natural interest
Anna Fine:to me. I appreciate that. Yeah. I will tell that to the many people that said that's a little weird.
Jess Rosenberg:I mean, if it was like, you know, lazy boy type furniture, I'd be like,
Anna Fine:Yeah.
Jess Rosenberg:Go to Bob's Furniture on the weekend and just hang out.
Anna Fine:That's that's just a question of taste. I bet. You never know.
Jess Rosenberg:Yeah. So they're, they're tasteful, well designed furniture.
Anna Fine:Yeah. Yeah. Yeah. And, and just like art history around it. Because it actually.
Anna Fine:Furniture. And fashion in particular are, like, very good indicators for transitional periods in art history. So it's if you if you know kind of like the the silhouettes, the lines, the kind of qualities of those particular time periods, you can actually see a direct correlation into the art period as well and, like, how it kinda transitions accordingly which I also find fascinating
Jess Rosenberg:That is fascinating
Jess Rosenberg:Have you watched the new look on Apple TV yet? No. What is that? It is a really well done. It's not a documentary.
Jess Rosenberg:It's actors scripted, but it's about Dior and Chanel and some of the other great fashion greats during World War 2 and right after. And it's so well done. Okay. A bunch of really well known actors and actresses are in it, and it's really good.
Anna Fine:Okay. That's going on it's called The Look. I'm gonna write it down.
Jess Rosenberg:The New The New Look. Okay. I love me writing right now.
Jess Rosenberg:These too mainly because of, you know, the design and the art direction, but like when you involve Sashin into it, particularly designers that, you know, you admire, that's cool.
Anna Fine:Agreed. Speaking of art direction, I love, have you seen Severance also on Apple TV? Yes. I as soon as I
Jess Rosenberg:You can tell us spoilers.
Anna Fine:I don't mind. I will, I will not tell you spoilers, but you absolutely have to watch it because it's extremely well written, but are you familiar with Jacques Tati? French director from the fifties sixties.
Jess Rosenberg:Yes. Yes. He made
Anna Fine:a movie called Playtime. That's probably his best not well known work. As soon as I saw Severance, it was like the style, the coloring, the like, the symmetry of the of the it was all, like, I I immediately said to my ex at the time, I was like, that that's Jacques Chatit. It has to be like, who's who's art directing this? And then it was Ben was it Ben Stiller?
Anna Fine:I think it was, who was the director. Was there? Yeah. And it and he actually said I was super inspired by Jacques Tatis and that's how it came to be. And I was like, there you go.
Anna Fine:Yeah. Well, there you
Jess Rosenberg:go. That's sweet.
Anna Fine:Sorry. Inside baseball. Yeah, sure.
Jess Rosenberg:Now I'll have to go watch playtime and just make the the references.
Anna Fine:Yeah. It's it's a very it's an artsy movie. There's no talking at all for the record. So it's it's purely aesthetic, but it's beautiful.
Jess Rosenberg:Yeah. Nice.
Anna Fine:Yeah
Jess Rosenberg:I saw you were talking about something else. I'm gonna edit this out, but I was I thought you were talking about something else. There's a show on HBO, And I thought it was I'm talking about that. Severance I've seen. I've binged the whole thing.
Jess Rosenberg:3 days and I became severely depressed. So I I know.
Anna Fine:I know. I'm like waiting for the 2nd season. And I
Jess Rosenberg:I really came to, like, Mary,
Jess Rosenberg:like, why is she not out? Yeah. Yeah. It was actually 2022. Oh, was it?
Jess Rosenberg:So our frame of time,
Jess Rosenberg:because they're in really fast.
Anna Fine:Listen, listen, 2020 to 2024 is just a blur. It's a blob of time. It's all one year to me. Yeah.
Jess Rosenberg:And a long. Yeah. Yes. Yeah. Should we talk a little bit about imposter syndrome?
Jess Rosenberg:And you'll be bringing this one up, you know, quite a bit with our guests just because it's it's such a common, you know, feeling, especially amongst creatives, especially, you know, in fields where female representation might be lacking a bit more. I'm curious how you, you know, experienced imposter syndrome and how you navigated through it and maybe even some late tips and tricks to overcome it.
Anna Fine:That's it's it. Imposter syndrome is so it's so tough because like, it creeps up on you when you least expect it. And then once it's there, it's so hard to, like, course correct. You know? I for me, imposter syndrome manifested differently at different points in my career.
Anna Fine:When I was in my mid twenties, imposter syndrome came about because I very quickly leapfrogged from, like, from lower to mid level to a director level. I it was, like, overnight. And I was very fortunate to have people around me who believed in me and wanted me to to succeed and and saw leadership qualities that would afford me those roles. But when you're when you're 25, 26, and you're at a director level at a very large company, and you're the youngest design director there, it's and a woman on top of it. It's extremely intimidating.
Anna Fine:And I remember what my my mentor slash boss. She she was also the head of design at the company that I was at. And she she said, you know, what's going on? You see him in your head lately? Like, where where where you at?
Anna Fine:And I explained to her. I was like, I just don't understand how to navigate this because, all of a sudden, I'm I'm not seen as a peer. I'm seen as a woman. I'm not seen as, like, a a partner. I'm seen as a director.
Anna Fine:And I don't I don't know how to how to be that in a way that without coming off. Am I allowed to say bitch? Because I that's that's what's leading up. Okay. I don't know how to be that without coming off like a bitch.
Anna Fine:Because every time I would talk, like, these men would pull me aside and be like, you don't you don't talk to us like that. And I'm like, like, what? I'm talking to you like I would talk to anyone. You know? I just I expect quality.
Anna Fine:I expect a, you know, a certain threshold just like any of my mentors and my directors would have expected of me. And and I I was, you know, I was, to be fair, I was mimicking my my managers, my directors, and and personality and tone and everything. And she said to me, she was like my my man my manager. She said, you know, you're now at a point in your career where it's not about the work. It's about who the work is coming from.
Anna Fine:It's about being a woman in a workplace. And it's not fair. And I'm not gonna tell you it's gonna be easy. But you have to figure out how to navigate this. And I can tell you definitively that mimicking the men in your life is not gonna work for you.
Anna Fine:And I was like, well, crap. What do I do? You know? I because I mean, we do like we talked about earlier. I didn't have a known sense of self.
Anna Fine:My identity was my job. Mhmm. So if I didn't have someone to mimic, then what do I how do I be a director at you know? And so I had crazy imposter syndrome because I was just like, I I don't know how to do this job. I don't know I don't know who to who to be for this job.
Anna Fine:I just I I I got put here because I had these soft skills that they saw in me, And I don't know how to. Leverage them. And anyway, TLDR, I ended up just becoming the director I wish I had and and ended up being exactly right. It was, in fact, the one thing I def in all of my reviews, everyone said that, like, the people who reported to me said I was a great director, a great manager. And that was probably the most fulfilling feedback I'd ever gotten.
Anna Fine:So for that, I'm, like, grateful I went through it More. But on the flip side, I I had imposter syndrome because I did leap frog. Because I did skip over steps. And later in my career, late twenties, early thirties, I was very appear like, very aware of the things that I had not learned because I skipped many steps. And I saw my peers who had this very in-depth knowledge of things that I didn't.
Anna Fine:And I had to I had to start over. I had to be willing to kinda, like, recognize that it wasn't just impostor syndrome. It was like, I didn't have skills that I needed. Mhmm. So I had hard conversations with people I respect it.
Anna Fine:And I said, what am I lacking? What do I need to do? And it's never easy to hear it. It's never easy to hear that you've got faults and, you know, things that you could do better. But I've always felt that it's better to hear the hard stuff and fix it than to let the unknown go by, and it bite you in the ass later.
Anna Fine:So I did. I I just went back, and I I started learning again. And in fact, I'm at DoorDash. Even though I was a design director for 7 years, I'm, you know, lower senior product designer, relearning things that I didn't learn in my in my earlier career. And, you know, I have to there are times where I'm, like, chomping at the bit because as as someone who has been at a higher level, I recognize, you know, you know, inefficiencies and gaps and things that, like, I wanna fix.
Anna Fine:Mhmm. But as someone who's said, okay, I'm gonna I'm gonna pull myself up by the bootstraps and start over. I'm, like, pulling myself reeling myself in and saying, okay, Observe, learn, focus on the education, and and you can get to that again. Like, that's that's never that's a skill you know you can do, so just keep going. So anyway, has a long tangent to say, ask the hard questions, expect the hard answers.
Anna Fine:Because if you have imposter syndrome, likely it's your innate gut feeling that there is something you're lacking and you don't know what it is. Totally. And it's not to say that you're incapable. It's not to say that you can't do the work. It's just it's a it's a gap in in your ability to do the job even better or to have better knowledge of the thing that you're trying to do.
Anna Fine:And so talk to people. Yeah. And then and then fix it. I love it.
Jess Rosenberg:It's also asking yourself the hard questions. It's like asking other people, but you're really like, there's part of it that's so introspective and just stopping and like going inward to realize what those, those signals are telling you.
Jess Rosenberg:You'll love that. Yeah. I've dealt with similar stuff. I've definitely leapfrogged. Too many times.
Anna Fine:Way too many times. No, it's great. It's great in the moment. Cause you're like I'm doing awesome. I like I'm I'm succeeding.
Anna Fine:I'm successful or whatever. But then like you look back and you go, well, shoot, I, I didn't learn these little nuances that actually make all the difference.
Jess Rosenberg:So sometimes people are looking for jobs and they've been at this higher level, but then now they're like, well, maybe I wanna take a step back. Maybe I wanna be IC again. Maybe I don't wanna be a manager. How do you go into those conversations with a new company and lay it on the table and explain that in a way that makes them wanna take a chance on the the overqualified candidate?
Anna Fine:Oh, God. I heard that so many times. I Yeah. I I wish I had a a really good answer. The only thing I did was I was honest.
Anna Fine:I was like, look, I can do all of these things, but I can also limit myself. I the phrase I regularly use is, I will fill the space you give me. So if you give me a lot of room, I'm gonna take all of it. But if you give me a very narrow purview, I'm gonna stay in my lane. And so I said, if you need me to be a hyper focused individual, I will do that.
Anna Fine:But I will do that with the background knowledge and awareness of someone who comes from a more a wider, more expansive perspective. And that seemed to have worked. I mean, like I said, it's not it's not a great answer, but I it was just it was honest, which, you know, I think, nowadays, especially with how many people have been laid off, I think that's kinda where people are starting to fortunately come from as a place of honesty, which is I need a job, I've gotta pay my bills, or, you know, I'm, yeah, I'm more capable than this, but I fully recognize that that's not necessarily something that I can I can fulfill at this point in time because the demand isn't there? And I think we should be more that way. I think, you know, I I don't necessarily think we should be giving all of our cards to businesses because they would undersell us.
Anna Fine:But I do think, you know, coming from a more honest place and being honest with each other and respecting each other's boundaries is very much like a positive out of all of this.
Jess Rosenberg:Yeah. That's a, common thread that I have personally heard, like overqualified, overqualified, but then Is it supposed to just be a ladder? Are you supposed to just be climbing up this mountain? And what is the peak? Is it I mean, I already Yeah.
Jess Rosenberg:What does the peak look like? What, Why can't you take little side note down the way? You know?
Jess Rosenberg:I think I've seen a pattern like of candidates who might come off as overqualified for roles and as they don't particularly lean into the honesty upfront being like, hey, I know I've led teams and whatever, but I really miss being hands on. I wanna be an IC again. If they skip that, then the hiring manager recruiter is going to deem them as, as overqualified. So for those that are looking to be more hands on again, it's such an important step to lean into beginning is just making sure they know that this is what you're signing up for. Otherwise, you'll be labeled as overqualified and then, you know, not consider.
Jess Rosenberg:The honesty part is huge. I agree. You know we're right at time, so
Anna Fine:Yeah. We are. Wow. I talk too much. I'm sorry.
Anna Fine:I'm a No. It's alright. Equation person.
Jess Rosenberg:We wanted you to talk a lot and hear from you. And it was
Jess Rosenberg:so hard. You're fascinating. You've had such you're young and you've had such a full career already. What are you gonna do? Like what are the next 20 years?
Jess Rosenberg:So let's just think about it like that. Objectively from the outside, we're like, wow.
Anna Fine:You've pumped so much.
Jess Rosenberg:I'm such a fan girl of yours. I'm just gonna say, keep tweeting. Feeling so mutual. Keep putting yourself out there and just being you. And I love you're just like, so unapologetically yourself and I love that so much.
Anna Fine:Thank you. Yeah. I really appreciate that. Because you know, there are times where I'm like, I'm a lot. Like, we bite too much.
Anna Fine:Thanks. But it's always nice to hear that.
Jess Rosenberg:No, I think for women, it's I don't know. I feel like, especially in tech and like in our industries, women are supposed to be a certain way, but that's complete bullshit. Like we should be the way that we wanna be and our ourselves and nothing else. So
Jess Rosenberg:Yeah. I've been very I've been very quiet over the past couple of years because I'm like, where where do I fit in anymore? What is my voice supposed to be? And it's just become so cloudy and almost losing Twitter for a minute felt sad in a way that I couldn't grapple with. So, you know, it's.
Jess Rosenberg:I think a lot of people have kind of lost their voice and are now trying to find it again. That's why I'm
Anna Fine:I think, I think. Yeah, I think you're right. And it wasn't just Twitter. I mean, it was COVID plus Twitter plus the economy, plus war, plus, you know, all of these things. And it's in a world that is so hyper saturated with chaos and a lot of.
Anna Fine:Just stress thrown at you. Who are you in that? You know?
Jess Rosenberg:Yeah. It's hard. Do you want to add to the noise or do you want to just like step back and be like, Oh. All right. I'm gonna try to live a life over here.
Jess Rosenberg:Maybe. Yeah. You know?
Anna Fine:Yeah, exactly. Yeah. I mean, I. I'm, I'm a hermit in my house most of the time. So, you know, that's how I protect my piece, but I, you know, I have lots of pretty furniture, so it makes it worth.