27: Choose Yourself—Making up your career path as you go (ft. Abby Covert)

In which Peter and Jesse are joined by information architect and author Abby Covert, who shares her story of moving from independent consultant, to Etsy’s first (and only?) staff information architect, to product manager, and then independent author. She shares what she learned along the way about burnout and work-life balance, and gives us a peek her forthcoming book on the power of diagrams as tools for thinking.


Peter: I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

Together: And we’re finding our way

Peter: navigating the opportunities and challenges of design and design leadership.

Jesse: On today’s show information architect and author Abby Covert joins us. We’ll hear about her journey from consulting to in-house and back out again, what she’s learned along the way about burnout and work-life balance and her forthcoming book on the power of diagrams as tools for thinking.

Peter: Abby, Jesse, and I asked you here, actually, your involvement in this conversation, unbeknownst to yourself started about a year and a half ago. Well, it was, it was, it was, it was after you wrote, I choose me and Jesse and I were recording the podcast back in those– at that time. But then we ended up taking a year- long hiatus and we never got around to asking you.

So it’s now a year- plus later and you’re here. And just to make it clear for anyone listening, there was a post you wrote called, “I choose me” that talked about your kind of journey as a, I’m trying to think of the right way to frame it, journey as a practitioner, journey as a professional, trying to figure out your space within corporations and within organizations and what you learned and what you took away from that. And it resonates with a lot of the conversations that Jesse and I had had, both between ourselves, and others that had been on that we talked to in the kind of year prior. So it’s great to have you here to now finally talk about it.

Well, I guess just to kind of ground ourselves, we don’t, you don’t need to do a recapitulation of the piece, but I’m kind of curious what spurred it for you? Why, why write that? Why put that out there? What were you, what was, what was the demon that you were trying to unleash or let go of that, that got you to, I mean, there’s like 3000 words or 4,000 words…

Abby: Yeah,

Peter: It’s not short. So what was that process like?

Abby: So I think it really came down to needing to close a chapter and open a new one. And I took that really literally. Like I just, I really needed to move on from a period of time where I had very much been in flux. And my position in that company was very in flux. My relationship with myself was very in flux.

I was moving across the country. I was trying to get pregnant. Like there was just so many things going on in my life that I had sort of lost the love of writing along the way. Like I did a lot of writing as a part of my job at Etsy, but ultimately I wasn’t writing for myself anymore. And I felt like in the days after I, I left, which that piece came out about 10 days after I left, I kind of locked myself in my office and just went to town on it.

I just really needed to write the story for myself. And then I happened to be teaching a– and one of the, like people who asked questions at the end of the workshop, like thanked me for being authentic about my experience with something they had asked me about. And that was the push, that was the push that was like, okay, I’m actually going to, like, make this a piece that goes out into the world.

And isn’t just for me, ’cause I would say 80% of what I write never sees the light of day. But that piece felt like it…

Peter: So, you originally just wrote that almost like a diary entry or journal entry, just something for you to process what you thought. I see.

Abby: Yeah, yeah, no, absolutely. And then once I knew that I was going to share it, that’s where the like drawing out of specific lessons came from and like kind of formulating it into more of like a piece for others.

But yeah, no that started from, I just have a really strong journaling practice. So I create a lot of words is whether or not I use them for other people is sort of up to the context. So yeah, that, that piece really it meant a lot to me. To sort of like put a final point on something that was very ambiguous for myself and for my team as well.

But also for like people that don’t know me that well, but know me a little bit, like, it just seemed like, okay, we’re in the middle of this, like, global catastrophe, you’re at the super staff senior level. You just had a kid, what’s happening? Like where, what are you doing? You know, like what’s the story there.

And it was a really easy way for me to kind of get that out in my own words so that people could kind of take it as they would. And I got a lot of feedback from, from folks saying that it was a really helpful thing to hear and that my experience very much reflected other people’s so yeah.

Happy to, happy to be that model, I guess.

Peter: I remember blogging.

Abby: Yeah,

Do you Peter, do you remember blogging?

Jesse: Never heard of it.

So you find yourself in this circumstance where you were going through a lot of transition, a lot of change. But I get the sense that something was changing inside of you as well in this. What was changing about your view of yourself, your relationship to your career, your, your relationship to the world in this time that you were trying to capture.

Abby: Oh man, I’m going to put it real simple. I was a workaholic. It’s not the only -aholic that I was. And I am deeply in recovery from that at this point. For the first 10 years of my career, as an IA, I burned at both ends. And I wasn’t taking care of myself, like not even a little bit. And as I started to make the decision to start a family and bring another person into the world, I knew that that wasn’t the kind of person I wanted to be as a parent.

And yeah, I started to clean myself. And in that process, I realized that a lot of the way that I was practicing, the way that I spoke about IA, the sort of attitude that I had about it was very much tied to my self-esteem and the way that I felt about myself and and the workaholism was all just the place to hide it.

You know, just if I work really, really hard, no one will notice that I also don’t know what the fuck is going on around here, just like everybody else. So yeah, I would say that’s the biggest thing is I like consciously reduced my working hours. That was like the first big decision was, as an independent consultant, can I do way fewer hours and still make enough money that I can live?

And that became a really interesting challenge for me. I had a couple- year period where I like heavily focused on time as sort of a material in my life. Because I, I figured that was the, that was the way forward. That was the thing that I had, was I had the time, I, you know, I wasn’t committed to raising a family yet. I was free. I lived in New York City and could do what I wanted with my 24 hours. And I really used that to figure out like, what do I actually want to do? And writing my first book came out of that. Like I stopped burning both ends for other people, and I continued to burn at both ends for myself.

So it was sort of like, step one, learn that when you remove other people, all your problems are still there. Step two: actually deal with yourself. So yeah, why did I write a book called How to Make Sense of any Mess? Spoiler alert! I was the mess, you know, I was the one that I fun and that book, like, I, it did it, it made sense of my mess.

And yeah, that’s, that’s kind of how we got to where we are now.

Jesse: And so you have, as part of this, you made the choice to step away. So I guess you, as, did you choose to step away from a full-time in-house role in order to create this space for yourself? Or was it the other way around that having stepped away, you discovered the potential there for you.

Abby: I think that all of the work I had done on myself still did not keep me from recognizing until it was very, very late in the burnout cycle. That something was very bad for me, in terms of my position. I had a lot of factors that had nothing to do with the actual output of my role, that was the emotional weight of that job and that organization.

And that was all kind of mixed up in the emotional weight of everything that was going on in, in 2020. So I think ultimately, I needed the skills I had already learned about myself and this tendency to put other people first to put the work above my, my own needs. I needed that skillset to finally recognize it.

But ultimately like I needed– I hired a coach to help me to leave that job. Because that was a huge decision for me to sort of like jump into this expansive, just space for myself to figure out what was next, instead of go find another job and jump to the next thing, which was my tendency before.

So yeah, it was a lot of, a lot of careful preparation that could not keep it from still being a bit of a firestorm at the end. So it was, yeah, it was a fun, dramatic moment in the arc of my life, for sure.

Peter: I’m wondering what it’s meant for you to put, to do what can appear selfish in terms of putting yourself first, but doing it… well, in what appears to put yourself first in order that you can actually show up for others again, but in a way that you want to. And I’m wondering kind of how you, how, how you’ve navigated that.

Abby: Oh gosh. Well, okay. First of all, the word selfish being a bad thing, I think is like a cultural problem. I also think that selfless is a real cultural problem. So there’s something about being like full of oneself that like I’m getting comfortable with. And I feel like, um, making decisions for your own interests is not selfish.

It’s not a way to please everybody, that’s for damn sure, but it’s not actually selfish. What’s selfish is hiding what you actually want from other people and slowly resenting them because you’re not getting what you want. That’s selfish. So I don’t know. I feel like there’s there’s a lot to unpack there.

You know, like I want to be full of myself. I want to make decisions in my life that are full of what myself wants and if that makes it so I can’t have a corporate job, I’m very fortunate to be able to make that decision that like, yup, that’s what it means right now. And so that’s what I’m doing right now.

Peter: Yeah, I think I’ve made a similar decision. I’ve been independent for the last three years at Jesse’s made a similar decision in his independence for the last couple of years, but I still work with a lot of design leaders who clearly feel beholden to a context that they’ve almost found themselves in.

” Oh, I can’t leave this organization. I’ve hired all. these people. They need me,” or like, “but I don’t like my job, but I don’t know what else would I would do, but I have to earn money for my family, but I have…” like, and many of these concerns are legitimate, but there’s a navigating that selfish to selflessness is a challenge I mean, clearly, that everyone has.

Abby: Yeah, those are all valid challenges, all challenges that you have to really like go deep inside of yourself about the stories you’re telling yourself about all of those things. Like, okay, you hired a team and now you don’t like the job running that team. Is it really, like, you, just by hiring those people, you’ve made a decision for your whole life that you’re going to be in a job you don’t like, like if you were to survey those people about what they wanted for their friend who was in that position, would those people give that friend that advice? Probably not. If they were in that position, would they give themselves that advice? Would their loved ones? Probably not. So, yeah. I feel like in a lot of cases, it’s, it’s stories that we’re telling ourselves that we really have to confront.

I mean, there’s, there’s valid reasons to stay in a job that you don’t like. There’s also a lot of people that are in jobs they don’t like, because they don’t think that they have the opportunity to leave. They’re either not presented with the opportunity or they’re not ready to look for it. Or they’ve been looking and they haven’t found the right thing yet. You know, those are all valid paths. It’s just which one are you?

Jesse: Yeah. I mean, I think that there is a certain amount of inertia that sets in. It’s definitely something… so, in my leadership coaching work, now I’m working with people one-on-one where they’re navigating exactly this territory of the trade-offs between where I am now, where I want to be, can I create that here? Or do I need to go somewhere else that’s going to serve me? How do I know where I draw those lines?

And I think it can be especially challenging for people in design because I think that there’s often this mindset that is this kind of service orientation. Like we do what we do in the service to users. We do what we do in service to the business. We’re always in the service in some way. And we forget that, you know, to your earlier point, sometimes the best way to be in service to others is to make sure that we’re taking care of ourselves, so we can show up in our full capacity. And part of that means not getting into situations where we’re so constrained by our organizational context, that we can’t be our best selves as leaders.

And then, you know, that just is a cascade effect across the organization.

Abby: Yeah. So that whole, like saying about how you have to put on your mask before you can help other people put on their mask. Like that’s, that’s what it comes down to. Like if you’re, if you’re not meeting your own intentions and your own self in terms of your needs, you’re not really going to be able to do that for other people.

You might be able to pretend for a really long time, yeah. And also, I mean, for me, the older I got, the less I could hold on to that, you know, like I felt like in my twenties I really could burn it at both ends and pack the hours on and not sleep and skip all the stuff. And as I got older, I couldn’t do that anymore.

It’s a, it’s a natural forcing function of like, oh crap. I have to choose. I have to choose turns out. I’m not invincible. We’re all gonna die one day. God dang it. So yeah, you got to choose. And I chose me. That’s just that…

Peter: We’ll just keep hitting that chord every, every 10 to 15 minutes. We’ll we’ll…

Abby: …like a politician. That’s my, that’s my line. That’s my [garbled].

Jesse: But this wasn’t your first time going independent, right? You’d been an independent consultant before, hadn’t you?

Abby: Yeah, no, this was, I had been independent for years. Etsy was my last client. Well, it was a kind of like a, a typical, a woman meets company story. You know, she goes in as a consultant and there’s so many messes that they hire her full time. And it was, it was exactly that. I mean, I, I made sense of some of the most amazing messes of my career at Etsy, and I really enjoyed my time there.

Things just got weird at the end, you know, I became the edge case, so that’s never good, yeah.

Peter: I’m going to go… I’m here we go. We’re going in. We’re going into your time…

Abby: …do it.

Peter: So you were brought in as an information architect kind of explicitly,

Abby: Yes.

Peter: You were the only person with that title, with that role, kind of set, set, some set the stage for what it means for Abby Covert, the, the a traveling Troubadour of IA to land within an organization and, and plant your roots., And do I in this one place, what, what was that experience?

Abby: Yeah. So so like back then a big part of my business was going in and doing overall IA assessments of organizations of all shapes and sizes. And so I went in to do that for Etsy. There was 10 large-scale recommendations that came out of that. And one of them was that they had such a large information architecture problem set that they really needed somebody to own that space in house.

And that was a proposal that was for in-house without it kind of being attached to me. But once it started to be discussed that this was really going to be a job, they were really gonna hire somebody to do it. That kind of coincided with my own life choices of sort of wanting to slow down and go somewhere and really focus on collaboration with a team.

And so, yeah, kind of like all the forces came together. Once I was there the big decision was like, what level do I exist at when there are no other people that do what I do. There was no manager who did what I did, although I was brought in by Alex Wright, who is an information architect of his past, so there was a lot of, you know, understanding of that skillset. So when I got there, I was brought in at a staff level. I was basically like a, like an IA ninja for hire within the organization. So instead of doing consulting projects with clients externally, I just did them from my seat in Melbourne, full-time for Etsy. Teams from all over the organization that were coming to me and asking me for help on discreet projects. And that’s sort of how the whole thing started. After that, I got the attention of the executive team for some of my work, and I was invited to pitch a larger project, which was figuring out how Etsy could look at the voice of the customer that was coming from a whole lot of different channels.

And so I was put it into a seat of sort of like project leading that because it was a really large initiative. It was like take all of these different customer service and research and social media, all these channels from all over the world, and put them into a single list of issues that the business faced and then create a rubric that would allow us to organize that list by something meaningful for the business. So…

Peter: So that’s something internally focused. That’s that’s a tool for, for executives on a dashboard…

Abby: Yeah. Yeah, it was actually a really big Google spreadsheet. That’s the big fanciness of it. But that was a, that was really like a, a banner project for me because it, it took the idea of information architecture outside of just the interface layer internally. And so more and more, I was asked to consult on things that were about the information architecture of the business.

So I was brought onto the team that renovated the help center which “we now have one” was kind of like the, the headline there. Also like the, the tool set for sellers was something that I had quite a hand in. So yeah, it was just sort of like collecting projects that were on the end-user side for both buyers and sellers, but also trying to focus that same effort internally to kind of raise the information architecture competency, but also to use the tools to get real work done which the voice of the customer program, I think ended up being pretty cool.

Peter: should I just keep going Jesse? ‘Cause I…

Jesse: Well, I mean, so the next question is, so that all of that sounds great, but what happened next?

Abby: Well, I mean, next I, I went and got myself pregnant and was really excited about that. Went through the whole pregnancy, doing my thing. And then I went out for six months, which is a blessing. I was very fortunate to work for one of the companies in the US that does that. One of the few companies, I would say, in the US that gives that kind of benefit.

I would say the downside of such a benefit is that it was an, an organization that literally reinvents itself every three months. So I missed two cycles, is basically what happened. And when you come back into an organization with a title that no one has, a track record that proves that you need promotion, but no one has any kind of understanding of what that might mean or where to put you, it starts to create some really uncomfortable conversations.

So when I first got back, I had sort of like the greatest experience you could possibly have, which is not having a boss and being told you could work on anything you want. It turns out that’s terrible because nobody’s actually responsible for you. No one is actually green-lighting what you’re doing with your time. And so you’re just sort of like floating out there, hoping that you’re creating enough value, that you’re not going to get attention in a negative way, which is not a way to go to work day after day. So I attached myself really quickly to a project that I saw a lot of value in from an IA standpoint.

And I was able to function as an IA on that project for the first six months. And then there was a position opened up through my work on that project for a product manager. And knowing that the jobs title conversation was getting very fraught, um, I decided to take a rotation as a product manager and use my IA skills to help stand up a team.

And so I stood up a team of 10 engineers. I think it was by the time I left and we were doing a pretty high value project. But it also was like the moment that I realized that while I was a really good PM because of my IA skills, it was absolutely not the job I wanted to have. I didn’t get to actually do the work in a deep way.

I could only do it at a very high level kind of like hand-wavy way. And that wasn’t ultimately going to be fulfilling for me. So as the cycles were like kind of the, the driver of all things, there was an end of a cycle coming up with a quarter ending. And I just decided to do my team the service of saying, Hey, you should plan the next quarter without me, because I don’t think I’m going to make it.

And yeah, that was, that’s what happened.

Peter: I want to, I want to rewind,

Abby: Sure.

Peter: Something I’m trying to better understand, which is, why does it matter that the job title thing was a problem? Right? Like, like you are a capable practitioner, you know the value you were bringing. It sounded like a lot of the other people within the organization understood the value that you could deliver them.

It had gotten a little confused during your maternity leave when, when some of the sands shifted, but who gives a shit what your title is…

Abby: oh

Peter: …as long as you’re doing good work and getting well paid?

Abby: Yeah. You know, I really wanted that to be the case. And I think that for like four years, I was cool with that. I was sorta like, all right, every meeting that I go into, I’m going to have to explain what an information architect is, why I’m the only one, what it is that I do and how I’m going to be able to help you.

And I need to be able to do that in the first three and a half minutes, because look, we only got half an hour meeting and we actually have to do work in that. What I found though, Peter, is that after a few years of doing that two things happened. One, I got fucking jaded. I was just, like, so sick of explaining what I do to every single person I encounter, sometimes the same person again, that I’d have to explain it to because like cycles have changed.

They have a new boss, we’re on a new project, whatever it is. I just got, I got sick of it. I just got really, really jaded. And then two, I got really down on myself. Like I started to believe that maybe information architecture is not a real thing. Like maybe the job I do, isn’t a real thing that’s necessary.

And I’m gonna tell you right now, that’s not the case. And it especially was not the case on the teams that I was at at Etsy, but it is what my self-esteem started to tell me, because you can only go so long, fighting that hard, to be recognized for the value that you have, before you get burnt out.

And so it was just like the culmination of those two things, the jaded and the self-esteem crash. It just put me into like a, I went from being a, A-player to an, A-player that was like not wanting to get out of bed. And that’s not cool. That’s, that’s not the way that good work gets done. That’s not the way that information architecture has a chance in that organization.

So, yeah, it was, it was time for a change. So you’re you’re right though. I mean like, why does it matter that nobody knows what your job title is and that you make money. That’s cool. Like, why not just do that? And I think that works for some time, but there’s a limit,

Peter: yeah, it feels…

Abby: limit.

Peter: …it feels to me, or if I were to diagnose this, like there, there, there, there was a, failure might be too strong of a word, but the one that comes to mind, a failure, a failure of leadership, right? Your leadership didn’t quite make the, like, they made enough of a space to bring you in and they recognized the value that you could deliver, but then they didn’t continue that work to maintain that space, to inform others to weave you into their practices.

Like one of the questions I had ahead of time is like, because. And I’m sure you talk to people about this with some frequency, like what is the relationship between good IA practice and standard issue product design as as practiced in most of these companies, right?

And as I was thinking about your time there, I found myself wondering, like, how did you integrate with whatever the existing practices and processes were? But it sounds like that would have it, it sounds like it kept being one-off one-off one-off one-off it never got systematized. And, and that strikes me as like a failure. There’s some failure of recognizing that kind of ongoing sustainable value. And that, that to me is a failure of leadership to encourage it. If it’s, if it is delivering value…

Abby: right…

Peter: …to the business, which it sounds like it was.

Abby: Yeah. No. And I think that, like, if you had asked me if we’d had this conversation right after I wrote that piece, I think I would agree with you that this was like a big failure of leadership. But there’s actually, I think reflecting on it more recently, I think the part that I wrote in there about the Ship of Theseus is actually really important in this.

So the Ship of Theseus is like, if you replace all of the pieces of a ship over time, is it the same ship? Like, can you still call it the same ship? Etsy was very much like that from a leadership perspective. So like, when you say that it was a failure of leadership, who exactly is the leader that was failing because the people who were leading me at every discreet moment were part of a chain.

And the handoffs between those people were not handled great, but when are they, you know, it’s like individual people, leaving roles is almost always messy, especially if they’re leaving the organization. So I see it less as a failure of leadership and more a failure of being able to see real people in organizations as people, and understand that their resilience as people in those organizations actually do demand attention long-term that doesn’t tie to just one person staying the same in the org.

Like, I mean, we all need like a fairy godmother who is going to shepherd us through the organization. And none of us seem to get that, you know, if you’re lucky you’re going to get a manager that you’re gonna have for some time, but in my experience, not just at Etsy, but also with clients that I worked with before, that management in this industry changes over very quickly.

And so it’s really difficult, especially when you throw something like a six-month leave in the middle of it for that chain to not break. So, yeah, I don’t, I don’t have any, I don’t have any blame for any specific leaders and it’s hard for me to sort of like call it a failure of leadership since that’s like an individual person skill, as opposed to like the skill of the org.

So I think, I think it’s something else. It’s something it’s a failure of the organization, for sure. And like, in your specialty at org design, a big old failure, they just, I was like a hot potato on the org charts. Like throw her over there. She will make value, throw her over there. She makes bullion fries.

Like it was just, you know, I, and I was, I was very valuable in every position that I found myself in, but it was, I think in the piece I described it as one of my last managers there said that it was all invisible work. It’s all work that is very valued by the people that you’re doing the work for in the org, but when it gets to the, like, who gets promoted, who gets the understanding of like value in the org at that like larger place that all comes down to a totally different set of criteria that I was not properly hooked into. Simply because I did not have a job title that I shared with other people.

So, and, and like, to your point about product design, product designers were facing similar challenges to the challenges that I was facing, in that there was level issues. There was, you know, career path issues that needed to be ironed out, but there was more than one of them to consider. And so it was easier for patterns to be deduced. It was easier for reuse to be a thing in preparing those folks. You couldn’t do that with a single person.

So yeah, I, I just, I became the sore thumb in the taxonomy.

Jesse: I think that your position as an outlier in the organization is really important and it’s, and especially in smaller organizations, there are a lot of people in design roles who are the only person who does what they do and are constantly having to explain it to people and so forth. I don’t want to diminish that aspect of it, but there’s another thing here that I think is also really important, which is you’re right: it may not be a failure on any individual leader’s part, but every organization has a leadership. It has expectations of how a leader is going to show up no matter who you are. It doesn’t matter how new you are to the organization. Those expectations are going to be present. How effectively the organization and culture rates its leaders with its values of leadership is a sort of a systemic failure of leadership, I think.

And one of those breakdown points, and I have heard this from women over and over again, who did not even take six months off, was that you are, you go on family leave. You are out of sight, out of mind. And importantly, no effort is made on the other end to reintegrate you to bring you back into the organization.

And for women leaders, especially if you’ve had your leadership responsibilities sort of doled out to other people, it can be very difficult to step back in and sort of reassert the value that you bring. And again, I think that does come back to the, to the culture of leadership and the willingness of leadership to take responsibility and take active steps to reintegrate people back into the organization when they’d been on leave like that.

But I’m curious about something else because you, you, you said you had stepped into a product management role for a little while, and I’m curious about how that changed your perspective on, or maybe your relationships with product managers after that.

Abby: Oh yeah, yeah, no, I actually, when I wrote the proposal to do a, we call it a rotation because I wasn’t ready to let go of my job title fully. I just, I wanted to do another job for a little while and see what that was like. So we wrote this rotation and one of the points in the proposal was that I wanted to have more empathy for product managers in my own practice, but also as a senior leader on the design team, I wanted to bring that product manager empathy and perspective into the design community at Etsy, because there was definitely, you know, an, an us versus them thing, a-brewin’ between product and design, as is quite common.

And yeah, that was actually a really great experience for me. I mean, I mostly learned that your incentives change really quickly. Your incentive changes from as an IA, my incentive is very much clarity. Like increasing clarity is the sort of highest level metric. However you want to measure that.

But as a PM, it was much different. It wasn’t about clarity. It was definitely about like serving a lot of different needs and doing it in a certain timeframe, which is a completely different of yeah. Then when I had been working with and I think I, I thought that I could shield myself from that switch or at least kind of like maintain both incentives in mind at the same time.

But that doesn’t happen because you have the same number of hours in the day as every other PM in that org, and there’s a lot of work to actually get done. And so yeah, very quickly I started to notice like, oh wow, I’m making decisions on a completely different set of criteria now. And that was really great.

That was, I mean, I knew for years working with product people that, that they were doing that, but I had never had to do it myself. And once I had to do it myself, I had a whole new understanding of sort of the, the emotional baggage that comes along with owning something like that in an org is different than the emotional baggage of helping people make sense of the thing they own.

So yeah, I, I learned that I don’t want to be a product manager and that product manager should be better at IA ’cause, it’s a neat skill set to, to knit into an already very valuable space.

Jesse: How is the emotional baggage different for product managers? How’s their relationship to the problem different?

Abby: There’s a lot of times, at least in my experience, there’s a lot of times where the data and the kind of wants of the organization, like the data outside of the org and the data inside the org are not necessarily in alignment. And your gut really is the way that you have to go forward and taking those chances and making those bets, it’s something that I was really comfortable advising other people on doing, but having to do it yourself, like having to decide, oh, I’m going to ship that feature to these millions of users and have this thing happen potentially as a result.

Like that was just a different scale of responsibility than I’ve ever had in any of my roles. Because like I said, the person I’m usually working for is the one making those calls. I’m just an input. As we think of you take it on the RACI ind– index, I was never responsible. You know, I was always just the, an informant.

And yeah, I didn’t, I did not like it in that capital R place. No, not at all.

Jesse: Yeah. You know, it’s interesting because I’ve heard people from both sides, from both the design side and the product management side, advocate for product management coming from more of a, of a, of a user-oriented user-centered lens. And I wonder, given your experiences, what advice would you have for product managers who want to, like, juice up their practice with a little bit more user-centeredness.

Abby: I mean, I hate to be self-serving with this question, but I kind of would tell them to make more diagrams. Like I found in my time at Etsy as a product manager, that like, that was the thing that made people be like, oh my gosh, she knows what she’s talking about. She has a picture of the thing and a designer didn’t have to make it for her.

Like that was very valuable. And I think a lot of product managers shy away from those kinds of methods because they belong to design or they belong to research. But I’ve, I’ve actually found a lot of value in using diagrammatic technique to, to get strategy across. And to really like anchor people on where we’re going with this whole thing.

I mean, honestly, make more Gantt charts and who, who, who are running these projects with no project plans? Like this is, this is just a thing that needs to be taken care of. It’s like, we have tools for this and they’re not just useful for making interfaces for users. They’re also useful for making projects that move people through complex challenges.

So yeah. Use ’em.

Peter: Well, I mean, it, it, that resonates…

Abby: To like the people on your team are your users as a product manager. And I don’t, I don’t think enough people kind of make that leap. You know, you have so many different users that you have to keep in mind. You have to keep the end-users in mind, obviously, but you also have to keep your, your team as your users, ’cause you’re, you’re leading them to make the thing. You’re not actually making the thing yourself. And that’s, that’s shared with IA, that, that part I was very comfortable with. But yeah, I think, I think that would be my biggest advice is like, know that your team members are your users and make them more pictures, yeah.

Peter: Well, I gave a talk a few years ago, at the last time we could all be together, IA conference about how I couldn’t have written, or the way I wrote Org Design for Design Orgs was it, was very much rested on a foundation of information architecture. And in my org design work, my ability to diagram these things gets me farther along than others, just because I can, like, I’m not afraid of sketching out kind of how it might, how it might operate in a, in a visual way.

And that that’s like this power we have that others could probably have, and this is probably what you’ve been writing about. But, but which for some reason many others are kind of hesitant to use. I had a question I wanted to go back to. I found myself, I’m trying to think just how idiosyncratic you are and it might be highly, right?

But, but the way…

Abby: high. Yeah.

Peter: Right, right. The, ’cause…

Jesse: poor Abby.

Peter: Well…

Abby: I prefer for, for the record, I prefer persnickety.

Peter: Well, no, I mean, by idiosyncratic, not persnickety, not like curmudgeonly or anything like that, what I mean is “a case of one,” right? And as I started applying my org brain to this stuff, you know, w- w- what you realize is that organizations are made of people and people are all cases of one. And that however separate or unique you felt within that structure at Etsy, there, there was probably a lens you could take where it’s like, oh, you’re just part of this team, but no one quite knew how to, how to approach it from that angle.

They were approaching it with whatever their assumption was. And then there was this thing that we’ve added to it, as opposed to, oh, if we incorporate the kinds of things that Abby is doing into this larger stew there’s another way of thinking about it, that you feel that you’re just part of the team and it just flows.

But my thought, I found myself wondering if you. So, engineering also has an architecture function and probably has some weirdos over there who, who find themselves doing the kind of work that not everyone else in engineering is doing, but is valuable and systemic in ways that you are doing work that is valuable and systemic.

And I’m wondering if you had connections with anybody like that at Etsy and what you saw about them as professionals that you either were like, why like, couldn’t I, couldn’t I be set up in my org or in my context, more like they’re set up in theirs. Was there a model there that, that you could learn from, or did you try, or just kind of curious what you saw with that?

Abby: Yeah, no, there was a lot of learning coming from the engineering org. So when I, when I got to Etsy the level that I had and the title that I had was not seen in design yet. So having staff in design had not happened. And so all of the specification about that level actually started from engineering and engineering is like the sort of like backbone of that culture.

So they have a really, really detailed way of looking at career paths and leveling. And that was something that through my entire time at Etsy, there was sort of like this want to have a similar version in design. But to be honest, it always started to fall down in that specialist versus generalist conversation of like, if you are a product designer at Etsy, but you don’t have full stack skills, what is your position?

Like, are you a specialist? Do you get traded only on to teams that have that particular need? Like how is that all kind of going to come together? And so the team that I found myself on by the time I left was the structured data team. Ripe with engineers. And you know, we didn’t even have a designer until a month before I left that project.

So it was very much kind of like finding people that were very close to my own kind. I wouldn’t call them weirdos. I call them very cool people that care about data. But it was a really messy environment where like I could, I could give them a perspective that was an additional layer on top of the perspective they already had about a pretty big move they wanted to make from a data standpoint, from traditional taxonomies to more of an ontology type of system for, for product understanding. And so there was a lot of opportunities for me to see, like, how do architects work when it is on the engineering side? And what I found was the difference really was about people understanding what they do.

People understand what a data architect does. They understand because they literally own these tables full of data that other people need to do their jobs. ‘ cause, I didn’t have that concretized thing that I own, that became like, well, what do you do if you can’t own words. That’s not a job. You can’t just own all structures. That’s not a job.

So in a culture that is very much about ownership, engineers had very clear ownership and I didn’t. Where product design actually has pretty clear ownership. They own the interface. Sometimes they even build it depending on who the product designer is. So, yeah, I think there’s a lot to learn from engineers about how to support specialty through education of the rest of the company, but also about like making it tangible, like taking the thing that somebody does and, and making it clear in a tangible way.

So people see it as something they can apply to their project or their thinking, which I was doing just like one person at a time over and over again. As opposed to like something taken from the organization. And I don’t know if it’s necessary, you know, like I think that another part of the problem space is that a lot of IA work is done by people of different functions.

So what is the challenge that comes along that is too big for an IA that is also playing product designer or product manager? That, that became a real question because it’s not like the product projects don’t have me on it don’t have IA, they all have IA. It’s just whether or not they have a need for a specialist to segment that function away from product design or partner with product design to get it done.

And I did projects in both of those camps where it’s sort of like more of a handoff because of resourcing or more of a collaboration. And, you know, both of them worked for what they were supposed to. But it’s still confusing.

Peter: I mean, think we have a model for that, pretty robust model for that, with UX research. And I dunno how it was practiced at Etsy, right? But I, I, I operate under the assumption that product designers should be doing research. But that you have, and so, so then that leads to the question, well, What do UX researchers do? And they’re doing meatier, heavier, broader, deeper research pro- programs that you– a designer, wouldn’t make sense for them to do. And those researchers are also enabling designers and others in doing better research.

Abby: Yeah, very similar..

Jesse: I think the difference is that research, researchers don’t touch shipping product. You know, you can set up huge elaborate research programs and they can go off on their own and be their own thing. Whereas an IA, if they’re going to have any impact at all, they need to be in the weeds. They need to be in your data structures, which means that they need to be more integrated with your delivery.

Abby: Yeah. Yeah. And I ended up doing a lot of my own research at Etsy but also helping to upskill the user research team on IA methods within research. I mean, card sorts, treejack, that kind of thing was just very foreign. At that point they hadn’t used that, that sort of thing.

Peter: Was there ever a thought– so I’m getting into problem solving, and you can tell me that that’s not a constructive place to be– but was there a thought that instead of Abby, the staff information architect, it’s Abby, the staff designer with an information architecture specialty where Abby, as I’m assuming staff designers, like when I, when I help companies figure out this role in other organizations, a staff or, or principal designer is still leading a design initiative, often has other designers who don’t report to them, but kind of that they direct, right? And so that it feels like you were this kind of, this, this isotope kind of bouncing around, but could you not have been a team lead on an IA heavy project?

Abby: yeah, no, absolutely. I could have been. Yeah, no, if I, I…

Peter: But that, that that didn’t come up…

Abby: The, the actual structuring of that was talked…. It was talked about in terms of like, you know, at some point or in the next year or so. And meanwhile, you know, my professional identity and self-esteem was hanging in the balance, so yeah.

That, that could have happened. But there’s also reasons I didn’t stick around to see if it would happen. A lot, a lot of like, yeah, great idea. We’ll get to that. But also knowing that like, yeah, I was like this hot potato, but I was a very small potato in the potato farm. Do you know what I mean?

There’s a lot of big, bigger things to figure out. So, so…

Jesse: A small, very hot potato.

Peter: And the ship of Theseus. I mean, I. I need to, I now need to write a blog post about the Ship of Theseus in, in, in this context because it’s, it’s, it’s real. And it means that people get lost in the cracks, right? You there’s, the people fall through. And if there’s not a good structure in place to kind of buoy them along while all that swirl is happening, you get a lot of, I’m sure you were not the only person who fell through the cracks in, in this instance.

And that’s I mean, it, it, it unpacks a whole set of issues. I was on a a conversation recently on a Twitter space where we were talking about design levels. And I said that… there was a, I don’t know, it wasn’t an argument or a debate, but there’s kind of two perspectives when it comes to an employee’s professional development. To what degree is that the manager’s responsibility, because the manager really understands the lay of the land. They understand this, the, the opportunities. They’re more experienced, they’ve been in the industry longer, et cetera. So what role do they have in guiding a direct report in navigating that and to what, to, what degree is that the responsibility of the employee?

Like, because, as your experience was, managers change, people change, like w- we need to empower the individuals to be able to make their call and, and figure out how to make their, put their paths forward. The problem with that is if we do it in most companies, at this point, we would just be, we would have all these, you know, fairly novice designers, just struggling, because there’s not a clear understanding of what that possibility is.

And that’s why you need managers, but there’s this…

Abby: yeah…

Peter: …there’s a brokenness here that we need to address, I think, somewhat kind of systemically, institutionally across companies, in- industry-wide, figuring out, how do we help people get a sense of what it means to develop themselves professionally, absent of maybe you got lucky and you got a really good manager, but most people don’t have that.

And so how do we, how do we encourage that kind of growth or support that kind of growth?

Abby: I also find myself having to tell quite a number of mid-level people that there’s two different ladders, one for management, and one for individual contribution, and that they need to pick one at different points of their career, but that like those ladders are not stacked on top of each other. It’s not like you get all the way through the individual contributor ladder, and then you start on the manager ladder. Good managers are actually not made that way. They’re… bad managers are made that way, where you get so senior in a practitioner’s sense, you start managing other practitioners. I mean, I did that for several years and I mean, I’m… for anybody listening that, that reported to me, I’m so sorry, because it just was not my skillset. I was totally set up to fail. And I feel like a lot of managers in the design space, are in exactly that position, which makes sense, because you know, is a an industry that was inventing itself as it was also making huge staffing promises to global corporations.

So yeah, we got a whole lot of designers in seats that are really talented designers, but are kind of shitty managers. And then you got newer managers learning from those people. I mean, it’s, it is a systemic problem. It absolutely is. I think it was interesting, Peter, when you were listing off, you know, what managers have, you listed a whole bunch of stuff that I’ve never had a manager that had. More experience than me that, okay, cool, I want to have that. I really want to have that lead. Somebody who has more experience doing what I do hire me and be my manager, instead of telling me that I’m my own manager and to check in with you every two weeks. You know, I mean, this is getting me hot under the collar, but seriously, like I think the management lack in this industry, yeah, it destroys people. I’ve seen many junior designers leave our industry because they can’t find a manager that can treat them like a human being. So…

Jesse: Well, and it drives people out of

Abby: too.

I’d love to see that fixed. Yeah.

Jesse: Yeah. I mean, it burns out the managers too, because to your point, they are not prepared for what they’re getting into. They have not been supported by their organizations in growing skill sets other than design. And even those skillsets usually they’ve had to invest in developing on their own.


Abby: I think about imposter syndrome with, with people in those positions. ‘Cause it’s, it’s one of those unique positions where you’re like, oh no, no, no, that’s not a syndrome. You are in fact an imposter. You do not know how [garbled] that you, yeah. Oh, you’re not sleeping well at night? I completely understand that. We’ve ,we’ve all had friends in those positions, I’m sure. Over the years of just like, how the heck did I get myself in this position where I’m in charge of people instead of doing the thing I’m good at? I think that it can very easily happen.

Jesse: Yeah. So again, I think that it comes back to, for the, for the people that I coach, it comes back to like, can you change your circumstances, can you find new ones and in your case, you went out and you created new circumstances for yourself as an independent consultant once more. How is that different now for you? Different from how you were a consultant before? What, what, how has your practice evolved? Where are you now?

Abby: Well, I’m going to burst the bubble. Since I left Etsy I have done zero hours of consulting.

Jesse: Oh, wow. Okay. Nevermind then.

Abby: No, I am. I am not on the market as a consultant. If, if you were to reach out to me in my inbox and offered me a project, most likely I’m going to, I’m going to tell you, I got people I can send you to. No, I, I left, and remembered I was a writer and I started writing and I fell in love with what I was writing and I kept writing. And so, yeah, we’re, we’re 16 months into me deciding I’m a writer now…

Peter: How do you make money?

Abby: How do I make money? I make money off of the book that I wrote because of royalties, I make money from giving talks for people that want to hear what I have to say about information architecture, or more recently diagrams.

I have an Etsy shop where I sell templates of deliverables that I’ve found to be useful and thought leadership pieces that I find of value.

Peter: How does your income compare as an independent to what it was?

Abby: Oh my gosh. Yeah. Nothing.

Peter: Okay. so you are much happier, I take it, but far… Poor, far less well compensated.

Abby: Yes, far less well compensated is a great way to put it. Yeah. I defined what enough is. And I realized that the enough I was getting from the six-figure income of a high level job in tech was destroying my creative spirit and not giving me the life I wanted. So yeah. I make a whole lot less money and I…

Peter: so you’re a shitty capitalist.

Abby: Yeah, yeah, yeah, no I, yeah.

Peter: I mean you’re

Abby: Am I a shitty capitalist?

Peter: not, that’s probably not right.

Abby: I’m a really good capitalist, Peter. Right? I’ve

Peter: mean, you all of your means of production. You are.

Abby: I’ve reduced my hours and, and you know, I can, I can pay my bills, but I don’t have to go to work every day. Like what, what is bad about this capitalist situation? Absolutely nothing. So.

Jesse: So you’ve been writing about diagrams.

Abby: Yeah, I’m writing a whole book about diagramming. It’s very exciting. It’s such a skillset that has gotten done a disservice. I feel like as industries have kind of piled on the use of it, but no one is sort of zooming out and going like, Hey guys, this is a thing that we all do. Maybe we should like, talk about that and have a way that we learn to do that thing.

So yeah, I’m writing a book that I hope, hope is that way.

Peter: There’s books, like Back of the Napkin and the work of Dan roam. There’s what Christina Wodtke did a, I forget what she calls her book…

Jesse: Pencil Me In.

Peter: Pencil Me In. Oh, that’s right. That’s right. There’s, you know, th- th- there’s been attempts at li– or Linda Barry, right, has about kind of, how do we, how do we get, yeah, I, I’m wondering kind of two questions that might be related.

Hopefully they are. Like, what is your angle, kind of distinct maybe from, from any of the ones we’ve said. And I’m curious how, if, if you’ve seen, context shift over the last couple of years, particularly as companies are starting to adopt things like these digital whiteboards, your Miros and Murals, and even Figmas as a Figjams or whatever, like, like, is it, and is that aligned with kind of what you’re like this, this breath of, of energy or no, that’s a mixed metaphor, but this, this burst of energy that you have with, with writing and, and, and your approach, is it tied to some context change that we are a part of? Anyway, yeah.

Abby: Yeah, so I mean, my specific bent on diagramming is that I want to teach people to diagram. I don’t want to talk about diagrams. I don’t want to point at pretty diagrams. I don’t want to make historical references to diagrams that have done specific jobs in the past. Although I have done that in examples here and there throughout the book as interesting fodder but I really want to focus on teaching people how to diagram.

Specifically when they’re not coming from a place of learning it somewhere else, along the way. So like all of us came through information architecture. I learned to diagram from something that Jesse wrote. And so I feel like that’s, that’s something that like, we all had that gift. And I don’t know if this happens to you all, but like diagramming is my superpower.

Like not just in my professional life, but like in my life life, like people who are my friends outside of design have been in awe of diagrammatic abilities. And it’s not like big fancy diagrams. This is like little like lowercase D diagram, you know, like a little, a little sketch that you make on a piece of paper to explain something or something you jump up on the whiteboard to do.

But when I think about my students, there is this kind of like, I’m not a designer, I’m not a visual person diagramming isn’t for me. And I think books like Christina’s gave them a vocabulary of like hand drawn elements that they can use to bust out of that kind of void of not thinking they have the creative ability.

But I think that the thing that we still lack is a process that you can give to a person that they can grok all of the different pieces of making a diagram and also know when the thing is good and when it’s done and understanding that that doesn’t mean it’s pretty. And that doesn’t mean that it’s fancy or that it’s like heavily visually designed, which I think is kind of like a mistake that a lot of people make.

So yeah, I’m, I’m hoping that this is a book that actually teaches people how to diagram. It’s, it’s very much a textbook. It has a lot of really good stories of how diagrams have helped real people, which I think is also really interesting. But I think the, the commonality to your second point about like the current tool set of diagramming is that we rely a lot on templates, but the templates are not the stories that are actually out there that are blowing people’s minds about what diagrams can do.

It’s when you take the journey map and you decide to use it in this other way, that it’s interesting. It’s not necessarily always like following the letter of the law for the diagram sake or the template sake, but that is what I see a lot of in terms of thought leadership of like, here is a template of a diagram or here’s a canvas.

Here’s how you fill out this canvas. And I think that that’s super useful. Like, I think that’s useful the way that like weeknight dinner recipes are super useful, but there are times where you’re trying to do something that is unique to your circumstance and finding the template is a lot less important than just like starting the diagram.

And so that’s the main point I’m trying to get across to folks, is like diagram your own way. And see all these templates as more, you know, a box of tools that you can go to if you have easy problems, but know that like the right way is often somewhere between those recipes. So, yeah, it takes like more of a, a rigor to the craft of it as like a thing, as opposed to like, I know how to make this one kind of diagram and I just make it over and over and over again, which I see a lot of people do, you know, people were like, I learned how to make a journey diagram at a conference talk and now I make them all the time.

There’s other diagrams that might be more helpful. There’s also other things they could do to the journey that would make it maybe more helpful that they don’t know because they’ve only done it to the letter of the template that they were taught. So, yeah, that’s, that’s the fun of my life right now that and Google document comments.

Peter: Yeah, I know I it’s, as you’re saying this, like I’m, like, the diagrams that we did have in the book or that I have on my blog posts and or that I use in my talks. And I am both sheepish about them, because I’m not a good drawer and I’m not a good illustrator,

Peter: graphic designer, but I consider kind of my diagramming, like my version of outsider art, like it’s just kind of from my own brain, as opposed to like any, any, any, any grounding in how to do this stuff, but it seems to connect and resonate with an audience.

People seem to appreciate it.

Abby: Well, there’s diagrams in all of our minds, you know, all day long, we have diagrams in our minds that we’re just not putting out there and people are drawing them all the time with their hands. When they’re talking about things too. I mean, Peter, you have drawn several diagrams in this conversation where you’re like, I’ve got this thing over here and I’ve got this thing over here and there.

And it’s like, that’s a diagram. It’s whether or not you choose to get it out of your head and share it with the rest of us that sort of the… so. In the, in the book, I had to define the word diagram and that was probably the most challenging part to kind of get it started. And what I came up with was that a diagram is “a visual representation that’s helpful to someone.” And sometimes that someone is you. And I think that, like, by that definition, there’s a lot of work in this world that’s done by diagrams. But is there a lot of sharing of insights across that? Not really. We’re pretty locked up on those templates and those process standards and such.

So yeah, I’m going to unlock a little bit of that, I hope.

Jesse: Very exciting. I love the idea of using your newfound freedom to empower others with new tools.

Abby: It’s it’s the most fun and hardest thing I’ve ever done, so, yeah.

Peter: What, is there timeline for when we’ll see the fruits of your labor?

Abby: So one of the, one of the like big creative decisions, I’ll call it, that I made, was to not define a release date for this book. Because I did that my first time around and I was off by a month and I really beat myself up about it. I don’t think anybody gave a crap really, but I did. And I’ve been thinking a lot about kind of what we’ve gone through as a world and what I’ve personally been through over the last couple of years.

And like, I don’t want to set up a situation where I’m pushing myself to get this thing out by a certain time. So yeah, I- I’ve given myself permission to not know when my book will be done. But man, that Gantt chart is getting smaller and smaller every day. Like holy cow, we’re.

Peter: Like the horizon line’s coming closer and…

Abby: Yeah. Yeah. I mean, it’s, it’s written, it’s sitting here on my desk, so I mean, it’s, it’s a book. It’s just… it needs to be, it needs to be line edited further.

It needs to be designed. It needs to be indexed, which is the most fun part. I cannot wait. I’m currently writing a lexicon for the back of the book. We’re working on the back matter. I hired a friend of mine, who’s a research librarian, Jenny Benevento, to write an academic paper for this book about the historical discourse on diagramming over time. And so we’re currently going through edits on that.

So yeah, this is a beefier book than the first book. And I’m excited about that part of it. I keep adding things to it because I’m my own publisher, so why not? So we’ll see, we’ll see, when it comes out, we’ll see how big it is. “I’ll let you know,” is the main marketing message.

You’re right. I’m a terrible capitalist. Peter. This is the worst marketing. So, when is this book we’re really excited about coming out? When can we give you our money? I have no idea. I’ll let you know.

Peter: But in the meantime, people should be following you at abbycovert.com and are there other means by which people that you encourage social media stalking?

Abby: I am fine with social media stalking, but I’m very boring on the social media. I just don’t, I don’t go there. I don’t post there. I have a mailing list that I’ve been sending out once a month about my process and what I’m thinking about and what I’m working on. So yeah, I would say that’s the number one thing if you want to stay in touch with my work and also support my my efforts, that’s the way to do it. That’s the metric that I’m paying the most attention to at the moment is…

Peter: …is a mailing list, subscribers.

Abby: And how many people care when I say something to my mailing list, once a month, is a really important number to me. Because I, I don’t know. I feel like there’s a, there’s a gap between what social media was able to provide to me as a content creator maybe five, seven years ago, and what it can provide now. And so I’m, I’m kind of grappling with what that, that gap is and how to fill it. So email, let’s go back to email everybody, but everybody likes more emails…

Peter: what’s your, what’s your ICQ?

Abby: It’s hardcore hybrid no it’s not…. That’s not true. You may…

Jesse: Thank you so much. This has been great.

Abby: This was awesome. Thank you for inviting me. This was really fun. I’m glad y’all are back to this. Cool.

Jesse: Thank you. We’re glad to.

Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s @peterme and I’m @jjg. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com.

You can also contact us on our show website, findingourway.design, where you’ll find audio and transcripts of every episode of Finding Our Way, which we also recommend you subscribe to on Apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find.

As always, thanks for everything you do for all of us. And thanks so much for listening.

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