Jessica Harllee

Jessica Harllee

Dec 21, 2020

Jessica is a Principal Product Designer at Primary, a gender-non-prescriptive, inclusive kids clothing brand. Before this, she designed at Etsy and Kickstarter, where she built software to enable independent creators, and at Modea, an ad agency.

When did you decide you wanted to stay on the IC track?

Etsy was the first place that I worked at that even had a separate IC track. I actually didn’t know what an IC was when I joined the company. I just assumed that everyone became more and more senior, and then they became a manager, and that’s just how things worked. Then when I was a senior designer, I wasn’t really sure if I wanted to go down the management track or stay an IC.

I can’t remember what prompted it, but I started having a series of conversations with my manager about the two different tracks and whether you could be in a leadership position as an IC. If I wanted to be in a leadership position on the design team, and have more responsibility, or more influence, would I have to become a manager? Would it be possible to do that as an IC?

My impression was that I needed to be a manager to have an impact. So we basically spent weeks in our one-on-ones just talking through different examples of leadership. For example, we talked about different things that I was doing that were examples of leadership and unpacked all of that.

There were a lot of examples of solid IC leadership at Etsy, too. I was able to look at other people on the design team and engineering team to understand how you could be an IC and a leader. Then I also asked my manager for his opinion on what I should do.

I remember that he tried to coach me through that conversation, so he wasn’t just outright saying “here’s what I think you should do.” But I do remember at the end of it he told me “I think you’d be happiest as an IC.”

I just remember coming out of all of those conversations with him and realizing “Oh yeah, definitely, this is the kind of thing that I think plays to my strengths. I want to keep designing. I want to keep doing these things.”

Maybe I only toyed with the idea of becoming a manager because I felt like I needed to, or that’s just what you did.

After that conversation, what did you do? Did it change the way you worked or change the kinds of things that you worked on?

Not explicitly, but I do think it changed my mindset a little bit. I was promoted a couple months later to Staff Designer, so I feel like I was probably already on the cusp of that happening. Some of the things that we were talking about I was already doing, like facilitating working groups or identifying gaps in process, or advising on strategy. I just didn’t see that that could also be something that could lead into being on the IC path.

Once you had that title, did people treat you differently? Were you invited to work on different kinds of things?

I think the title gave me the confidence and the permission to speak up more, to play a bigger role on the team and in the org. People probably treated me differently, but I think I was also carrying myself differently.

And the day-to-day is super different. My focus is less on my own work overall. I’m still doing my work, but the percentage of my time that I’m spending doing my work versus making sure that the people around me are also successful, changed. If you picture a graph, my own time on my projects was going down, and working with other people around me on their work or their projects increased as I became more senior.

Was that frustrating?

I don’t think so. I like doing my own work and I like executing on projects. I also get a lot of fulfillment out of helping other people: improving their skillset, or advising on solving problems that I’ve also encountered, or helping them figure out how to navigate different situations.

If I’m only focusing on myself or my own skillset, then that doesn’t really help anyone around me, or the design team, or the company. And I think it’s very similar in some ways to what you hear about being a manager, which is that you’re not spending as much time on your work, but it’s kind of different because I am helping people level up in my own way.

Does that make sense?

For me, there is a tension there. I understand why it’s important to be a little bit more cross-functional, or play more of a mentor role. But the time spent doing that is in direct conflict with time doing the craft: designing something, or researching, or whatever it might be. Did you find that you ended up having to work more? Did the pressures change or was it about resetting expectations about how much design work you would be contributing?

Yeah, my capacity for mentorship does change based on my workload. If I am in the thick of a really intense project, I’m probably not spending as much time proactively reaching out to people or trying to mentor or things like that. I’m focused a lot more on my own work. And if it becomes completely imbalanced, it’s the kind of thing I’ve brought up to my manager before.

And then when I do find lulls, then I can ask “what can I be doing with this extra time?” I talked about this a little bit in the Try Everything post, but I’ve gotten a lot faster at executing than when I was a more mid-level designer. And I’ve gotten really good at prioritizing my time.

What other trade-offs or risks do you think exist for people who want to continue down the IC path?

This question messes me up. I think the hardest thing for me has been just the lack of clarity on career paths, and it’s part of why I left my last job and went to a smaller company. I think managers have this really clear ladder. It seems to be pretty well-defined within the industry. There’s so many examples of managers rising the ranks and having different roles or paths that they can emulate.

But for me, I don’t have any plans to be a manager. I don’t have any plans to have reports. I’ve never done it and I don’t want to right now. And that’s fine, but because I don’t want reports, it eliminates so many roles for me.

I don’t really know what it looks like to be in the industry for 15 or 20 years or beyond, and still be an IC. There aren’t a lot of examples out there, which is also why I’m really glad to be a reader of this Staff Design series. I want to know what other senior ICs think about this stuff, too.

I don’t really know what comes next for me, and I don’t love that feeling. I’m definitely not making 5 or 10 year plans, but I don’t even feel like I know anything. When I was a senior designer, it was “cool, my goal is to get to staff designer.” And then when I was at staff, it was “okay, cool, now my goal is to get to principal.” And then now I have no idea.

I saw a really good tweet a while ago from Camille Fournier that said the problem of an undefined IC career path is actually a symptom of management problems. We talk about the lack of career clarity and lack of career paths for ICs, but actually that’s a management problem.

Because I’ve been in a position where I’ve had to write my own career ladder or define my role in some way and invent my path without a lot of support from design leadership. It’s so hard to do that.

Career ladders and leveling and org structure fall squarely within the responsibility of managers, so I just wish that I saw more design managers and leaders invested in the lack of career clarity for ICs. I want to believe that these two paths can exist, and that it can just be as fulfilling and lucrative as somebody whose career is on the management track.

The lucrative part is interesting.

I think what I mean more is lucrative in a non-monetary kind of way. Like fulfilling, or having the same amount of success. But then I ask “what does success mean?”

I don’t know. I don’t really know what success looks like. It’s so hard to articulate that.

I’ve worked at companies that didn’t have that articulation. The career ladder is pretty easily defined up until around this level, but above that it’s “to do.”

At Etsy in the design ladder we had Staff Design, and then after that it was IC 5/Principal. And for a long time, the skills matrix was “question mark, question mark”. It didn’t bother me when I was first promoted to Staff. But then later I didn’t know what I was working toward. And it sounds like you don’t, either!

So how do you know that you’re actually getting better and progressing? Usually at the higher levels, even on the management side, there’s still a little bit of ambiguity about what value you should be providing to an organization. But for you specifically, how do you know you’re getting better?

I mentioned this a little bit in the last question, but I used to rely on my title and getting promotions as a way to track progress and set goals. It took me, I think, three years to go from Staff to Principal. And I’m expecting that it’ll take longer than that to go to the next level. I think the expectation is that the more senior you get, the more time there is between each promotion and each level.

Yeah, like a logarithmic scale or something.

So I’m just not even thinking about it. I can’t really use that as this marker anymore. So then what? I am not really a 5 or 10 year plan person, so I don’t really know what my career ambitions are. I don’t know that there’s a specific title or role that I’m working toward or really want to have.

In the absence of that, some things that I’ve been thinking about as ways to quantify my progress are: am I having an impact on the business? Or is my impact growing over time? Or am I having an impact on the company, the way that we work, and what we work on? And is that scaling over time? Am I finding ways to share what I’ve learned through blog posts or interviews or coaching or mentoring or whatever? Am I scaling myself in my learnings also?

I think one day I want to be the first designer at a startup because it would be something totally different. And I would pick up a completely different set of skills than I have.

A co-founder?

Maybe. I don’t even know that I need to be a co-founder, it’s more about being the first person articulating design at a company; going from nothing to something. So I’ve never been in that position before, and I think it would be really hard.

Then the other thing is that I write occasionally, I would love to focus on that more. Right before the pandemic hit, I thought maybe I’d write a book one day. And then that idea disappeared really quickly. But I think that could be a really interesting thing to work toward.

Tell me about the writing part. It seems like the people who are writing the most tend to be the people earlier on, they’re just figuring stuff out. And then the more experience you get, the more you realize you don’t know everything. And then eventually you’re so experienced that there’s no incentive to write...what you’ve learned becomes your competitive advantage. Or you’re just busy doing the work.

But you have been writing, so tell me about how you’re thinking through that. What’s the motivation and reward?

I’ve always done it casually. I don’t do it super often, but when I do it’s because there’s something that’s been rolling around in my head for days or weeks or months. I also think about the things I wish I had been able to read when I was starting out as a designer, beyond tips and tricks for designing.

I think there’s this assumption that people who are earlier in their career make, which is that people who are further along in their career have everything figured out and they have their shit together and they know exactly what they’re doing. But I definitely don’t always feel like I have my shit together. And I try to share the times when I learned something or I grew from something. I just wish that I’d been able to read stuff like that too, when I was younger.

Your Etsy Last Lecture post was excellent. How has it been since writing that? Did you feel you accomplished what you wanted to accomplish by publishing that?

Yeah, I definitely do. That was originally a talk that I gave at Etsy. There were over a hundred people there. I think it was just really cool hearing from a lot of my coworkers about how some of the things that I experienced were similar to things that they experienced. I always find that really special. And that really motivated me to share it.

A side goal of mine when I was writing the talk was to also share it online. And that was pretty wild, too. Seeing the response from that was overwhelming. It was people telling me that this was exactly what they needed to hear for whatever reason. That was really special.

I think writing can be a way to capture a moment in time, the things that you’re thinking about, and the things that you’re stressed about. I also occasionally will write in a journal and look back at what I wrote later and just say “man, I was so unhappy and I didn’t even know it.” Reflecting back on where I was at, when I was writing the Etsy last lecture has been pretty interesting. It’s wild to see how much I’ve grown.

It’s such a cool artifact to have.

Speaking of things that you don’t know or things you’re working on...what’s your relationship with the hard skills now that you’re pretty far along in your career?

There are definitely areas that I want to grow in, or want to get better at. I think yearly reviews can be helpful for identifying that kind of stuff. Sometimes that’s the kind of thing that I will talk with my manager about: “Hey, I want to work on projects where I can flex my research skills, or get better at this skill” and then work with my manager to find a project where I can do that.

I think it’s interesting talking about hard skills because I feel like I was working on hard skills at Etsy, but in ways that I wasn’t super aware of. At a bigger company, a lot of what you talk about is not just the projects and the work, but also the practice of design. It just comes up a lot. And so I think I absorbed a lot. Even if I wasn’t learning a specific skill myself, a lot of my coworkers were and I was absorbing that.

While I do feel like my hard skills developed a ton at Etsy, at a bigger company there are people who are specialists and you can ask them for help. Like animation, for example: I don’t think I ever animated something when I worked at Etsy. We had people who were really good at animating. So whenever animation would come up, those were the people who animated stuff.

When I started working at Primary, there was one project I was working on, maybe the 404 page, and we said “Oh, wouldn’t it be cool if this thing started animating?” And I realized: I am the person who has to figure that out. No one else here is going to figure this out. There’s no animation expert. It’s going to have to be me.

And so something that has been really interesting for my hard skills is working at a much smaller company. I was the only product designer for the first six months I was here. My hard skills have totally transformed because I just had to figure stuff out. Now I can do CSS animations and I’m leading the work to make the website more accessible. And we just did a huge rebrand and had to totally define a design system from scratch. And I got to figure all of that out.

I don’t feel I was always in that kind of position at a bigger company.

I love that: intentionally putting yourself in a position of accountability or a position where the buck stops with you.

Yeah, totally. The other thing I’ll say about hard skills is going back to what we were saying earlier about helping mentor other designers and other people. As I’ve become more senior, I’ve also become less concerned with my own hard skills as much as I’ve become more concerned with improving the hard skills of people around me. Like “okay, now I know how to do animation, but now you’re going to do animation too.” I want to make sure that I’m not the only person who knows all this stuff, and I’m finding these opportunities to help level up the skillset of people around me and help them improve their hard skills.

It’s almost a meme when you talk to people further along where they might say “my design work happens in spreadsheets and docs, I’m beyond the pixels.” And there’s truth to that. I may be being a little harsh. So how important do you actually think it is for you to stay sharp with your hard skills? Because as you get higher, scope will changes, and you will be in spreadsheets and docs a lot more...

I mean, it is important because I’m still executing. I’ve still got to do the work, which is again different from being in a manager’s position where they are coaching people on the work but not executing it themselves.

I think it becomes less about the hard skills, because it becomes so much more about all the other skills too – the soft skills or whatever you want to call it. Right?

I can’t just be really excellent at executing design. That isn’t enough to promote somebody to be in a Staff or a Principal level. I think it becomes more and more about all of the other skills that you have that help you to enable other people or solve the right problems. I don’t think it’s that hard skills don’t matter as much, but that other things also really start to matter. So you have to do all these things.

What have you learned so far about avoiding burnout?

Sometimes it’s unavoidable. I’ve learned that I’m a better designer when I have work-life balance. I can quickly get burned out when I don’t have work-life balance, so I don’t do side projects. I try to be good about taking time off or taking mental health days. I don’t have my work Slack on my phone, or my work email on my phone. I don’t answer stuff after a certain hour. I just won’t do it. I try to set a lot of boundaries, especially during the pandemic too. The pandemic has been hard on my mental health, as it has been on everyone.

And so setting these boundaries with work has been really important, and just spending time away from the computer. When I am experiencing burnout, I really have to have honest conversations with my manager. I wrote about this in my last lecture, but every time that I tried to pretend I could handle something that I couldn’t, or when I was super overwhelmed, it totally backfired. And I got even more burned out and it was just a total disaster. So I’ve learned to reach out to my manager when it’s happening. And then I have to work with them to deal with it, whether that’s changing the staffing of a project or helping me reframe the work that I’m doing. There’s a lot of ways that a manager can help. But my manager can’t help me if I’m not being honest about how I’m doing.

And then there’s a framing thing, too. I really like the concept of circles of control. Basically, if you imagine that you’re at the center of a circle and there’s concentric circles around you, the things that are immediately surrounding you are the things that you have the most control over. And the things further out you have the least control over, or basically don’t have control over at all. So I can control myself. And there are certain things that I can influence like my work or my immediate team.

But then further out, there’s just going to be a lot less that I can do something about. It can be easy to get caught up in the stress of things that are totally outside my control, and it’s not worth my energy. When I was a more junior designer, I would definitely get caught up in those kinds of things really easily. And I’ve learned, or tried to learn, what kinds of things are worth being stressed about and what things are not.

As you’ve grown, has your definition of what is in each of those circles of control changed?

I could give you an example: one thing that came to mind as you were describing the rings was career ladders. When I first started, I said “Oh, this is a thing that somebody else has shaped and I need to just go along.” But now recently, I have conversations with my manager where I can actually influence what the ladder should be. Like, “Oh shit, I can say words that might actually change the requirements here.”

Totally. One hundred percent. In some ways I’ve seen more of the nuance in what kinds of things are in or out of that circle, the career ladder being an example. I’ve seen that it’s something that I can have an impact on, and that I can provide feedback on and help shape. But at the same time, I’ve also seen that if there’s no career ladder for Principal designer or whatever’s beyond Principal, that’s actually not on me to define. It’s on me to ask for that and request that, and there should be a job description I should know that I’m working toward. But it’s ultimately also the responsibility of design leadership and design management. And so I shouldn’t be writing a career ladder, but I should be asked to provide input. And I have been in a position where I was asked to just write it. And I think that’s where my boundaries are.

One thing I’m picking up is that you are particularly proactive in your relationship with your managers. Where did you learn that? Or how did you figure out to do that?

It’s come from having good managers and not-so-good managers. It’s come from understanding what makes for a good relationship and a healthy relationship. For example, one manager that I had when I was becoming Staff would ask for input and my opinion on process and projects and how the team was running. I became comfortable with speaking candidly. And then my feedback would help shape things. That outcome started rewarding that behavior, I guess.

But also I felt really comfortable with him. We built this really great, trusting relationship where I felt I could come to him with pretty much whatever, and it wouldn’t be held against me and he wouldn’t judge me for it. So I think that helped set my expectations.

I’ve talked to a lot of ICs who will be having problems at work or with their projects or in their careers and they don’t think of their manager as a resource for those things. And they’ve probably been burned by bad managers before, or don’t have any expectations around what a good manager could be like. The IC-manager relationship is so important, especially at the senior level. And when you have a great relationship with your manager, it can really unlock a lot for both of you, right? You need each other. So I feel like I can’t be a good IC without also having a good relationship with my manager. And also demanding a lot from my manager, because I need them and they need me.

I also read a lot of management books, because I also think you should know what to expect from your manager. Understanding what to expect can help you shape the kinds of conversations that you have with your manager. Knowing what their job is can be really helpful for understanding, too.

I think I’ve just seen the power of good and bad management.

You know what that reminds me of? In the whole “should designers code?” debate, I feel like it’s basically settled is: you gotta be able to work with engineers. And part of working with engineers is just having empathy for the things that they’re doing.

And so as you were talking about reading management books, I’m sitting here thinking: “Should designers know how to manage?” That is a valid thing to be able to empathize with, or at least understand their perspective and speak their language.

Yeah, totally. It’s exactly like working cross-functionally. If you know the kinds of things that people care about, and the kinds of things that motivate them, and the things that they’re held responsible for, it can help you have a stronger relationship with them, right?

Same with engineers. If you know the kinds of things that they care about, then you can use that language to talk to them. And I think management in some ways is no different.


I don’t always feel like I have my shit together. And I try to share the times when I learned something or I grew from something. I just wish that I’d been able to read stuff like that too, when I was younger.

As I’ve become more senior, I’ve become less concerned with my own hard skills and more concerned with improving the hard skills of people around me.

I can’t be a good IC without also having a good relationship with my manager, and also demanding a lot from my manager. Because I need them and they need me.

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Staff Design is a project by Brian Lovin