Jenny Wen — Pathways to Design

UW/UX
UW/UX Posts
Published in
5 min readMay 14, 2018
Jenny Wen

Jenny Wen is a product designer who is currently working at Dropbox on the Dropbox Paper team. She graduated from Systems Design Engineering at the University of Waterloo in 2017, after studying Planning for 2 years. Previously, Jenny has interned at Square and Shopify doing product design.

You can follow her on Twitter: https://twitter.com/jenny_wen

1. What got you interested in product design?

Throughout elementary school and high school, I was always interested in art. I started making websites at a pretty young age — making Neopets store themes, Myspace profiles and Piczo sites, but I never realized any of this could amount to any sort of paying job. When it came to applying to university, I was kind of all over the place, and didn’t really know what to do. I applied to a few schools for graphic design, and also half-assed applications to some architecture schools. I ended up in urban planning at Waterloo because I wasn’t totally ready to commit my life to only graphic design, and Waterloo seemed like a place where I could participate in the co-op program and figure out what I really wanted to do.

While I was in the Planning program, my favourite classes were the urban design classes because I realized you could use buildings and cities as a medium for solving complex, human problems. I liked the idea of designing for people and being intentional through a design process. I ultimately jumped ship to Systems Design Engineering because I didn’t feel like the Planning program was fast-paced enough for my liking and I wanted to do something a little more math and science-y. Going into engineering, I didn’t have a career outcome in mind, but I think I had a better idea of what I didn’t want to do. In my first co-op term, I found an internship on the internal job-board titled “UI/UX Designer” and ended up landing that gig. It helped me realize that design could be more than the visual part of something, but that it could be something that requires interdisciplinary thinking. That’s probably one of my favourite parts of product design.

2. How did/do you practice your craft?

In university, I practiced design at every chance I could outside of school. I got my footing by going to hackathons, freelancing, and designing for different clubs and groups (like UW/UX and Hack the North). I also knew that one of my distinct disadvantages as a designer was that I wasn’t in design school. So, I read a bunch of design books to supplant the theoretical stuff I could be learning in design school, but also made sure that I was always involved in some sort of design side project, so I could be applying that theory, as well.

Now that I’m working, design is less of a hobby than it used to be. At work, I set quarterly OKRs (objectives and key results — just a fancy way of saying goals) that are pretty objective and are targeted towards specific skills I want to be better at. For example, this quarter, I want to get better at visual design, and I’m doing that by working on a visual-design-oriented project, as well as getting coffee with 3 different designers who have worked on visual-heavy projects at the company.

3. What were some of the biggest learnings of your early career?

Well, I’d definitely still consider myself to be “early career”. Throughout my internships, I think I learned a lot of “hard skills” like interaction design, visual design, prototyping, etc., because these were things I didn’t learn in school. I thought that maybe in my first year working full-time, these would be the sorts of skills I’d improve most in.

Almost one year into working full-time, I think the most important skills I’ve gotten are not actually hard skills, like I thought they would be. Instead, I think a lot of my learning has been in how to work with other people, be transparent and communicative, and how to give people critical feedback (which I’m still working on!). It sounds kind of fluffy and not that satisfying as an answer, I know. I’ve found this especially working at Dropbox (which is a really collaborative place to be a designer), I have to work with other designers, engineers, writers, PMs, researchers, marketing, etc., all throughout the design process. I’ve found that regardless of how good my design work is, it can make the end result so much better if I’m really diligent about how I work with other people. Examples of this are: getting writers, researchers, and marketing involved in the right parts of the design process, doing enough back-and-forth with engineers as they’re building, working closely with PMs to set our team’s roadmap with the user in mind, and so on…

4. What are some of the differences in being an intern and going full-time?

First one ties closely to what I just mentioned about working with other people, and that’s building and managing relationships with the people I work with. I find that I’ve needed to make it a priority to give people critical feedback instead of putting it off since I know our working relationship needs to last longer than that of the length of an internship.

Secondly, having to manage my own goals has been a big difference. I think I started out working having all these grandiose goals because I thought that they were just things you needed to become a good designer. Stuff like, being loud in the community, making killer animations of micro-interactions, illustrating things, etc. While I think those are all valid things to work on, I’ve had to step back and really think about what being a designer means to me, and what parts of the design skills framework I really want to hone in on, instead of spreading myself thin. I’m still trying to figure this one out.

That’s all for this week’s design blogpost. Let us know what you thought or if there’s anything else you’d like to hear about here:

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