My hot take on this is that there’s no company I’m aware of that has this all figured out, that has the incentives to support a straightforward path for senior design ICs.

Even the senior engineering path seems to be pretty case by case, or company by company. Anecdotally, I’ve seen a pretty variable outcome for individual engineers. It feels there’s not necessarily a repeatable model.

Maybe the incentives are different with design. It does seem in engineering-driven companies that design is drafting behind engineering culture. Similar to tooling, it feels like there are a lot of things where we’re kind of like, “Oh, well, engineering has this figured out.” Often, there was a forcing function for them to figure it out because they’re the bulk of the company.

So I guess my cynical, and very personal, take on this is that in those kinds of environments it became my individual responsibility to articulate what my path was supposed to be. I did the organizational work to make sure that that I fit in and that I could be effective — and then did the work to maintain that over management changes, teams restructuring, those kind of things.

In the beginning, you sort of say, “Oh, well, you’re more senior now. It’s your responsibility, it’s your blessing and your curse. You get to write your own job description.”

But in multiple cases now for me, that just eventually became exhausting. Eventually the amount of energy and effort that I needed to put in to just maintain my own role outstripped the energy that I had to actually be effective in my role.

Rdio was one time when I did take the path straight to manager. I grew with the company. At the beginning I was a contractor because that was what they needed. And then I was the first product designer. At that point there’s no reason to be a manager when there’s nobody else doing any work.

Then we hired some people. We built a team and thought about how this is going to grow, so I focused on recruiting and those kinds of things. I formally took on the role of “Head of Design.” But that was very much because the company’s needs were growing.

At the beginning it’s like, “Well, I’ll do some management and some recruiting, but I still need to be doing some design because we don’t have the resources yet.” My responsibilities grew, and more and more of my time was spent on people management and team health.

Eventually I got to a point where there was no more room for any hands-on design work. I couldn’t responsibly spend my time on design work. There was too much of the management stuff that needed to be done. I had a hard time looking down that path and staying motivated and engaged.

Even though the management work and growing the team was very satisfying on its own, when that was all I was responsible for, it became clear to me that wasn’t sustainable. I couldn’t get up every day just for that.

That was when I made the decision to leave. And since that point, it has been an exercise in having a principle and a value that I don’t want to be a manager. It’s not that the work isn’t valuable. But what I want to do is stay here, in the role of actually doing hands-on work.

As a senior IC, the work looks very different than it did when you’re more junior. Maybe it is a lot of meetings or conversations or work that happens through guidance. A lot of the work is happening through other people. But the boundary for me was that I don’t want to accept the responsibility of people management; of team health and growth.

When that’s your responsibility, that eats everything else. Teams grow and there’s always areas understaffed.

I’ve had that conversation dozens of times. “Wouldn’t it be easier if you just became a manager?” So far I’ve stuck to it, but I’ve also left roles because of it.

That’s a great point and one that I can speak to less, because I actually think that my natural fit is somewhere in the middle, where it’s really about working with and through others.

But it’s still about the work itself. It’s not about career goals. And it’s not about recruiting. It’s not about team structure and team health. It’s more what I used to understand as “creative direction,” which is now a loaded term with lots of different meanings.

But what I mean by it is someone who is taking responsibility for the quality and the direction of the work of a team of multiple people. It’s sort of about coordination and cohesion, and it’s also about steering and direction. You want someone with more experience in that role because they’re drawing from their own experience to be able to make quick decisions, to say “Yes, we’re going to commit to this, or we’re going to bring these things together that otherwise would have been disconnected.” And that role benefits from more experience.

The thing that you’re talking about though, which I’ve never seen a mature company really have a sustainable space for, is the “senior craftsperson.” They’re not pivoting at some point in their career to saying “I’m going to take what I know and leverage it through other people.” They’re saying “I want to get better infinitely at the thing that I do.” I believe that that’s possible.

You see it more in pure-art kind of careers. Like “I’m an illustrator” or “I’m a concept artist” or something, and there’s a need for that person being really fucking good at that one thing, and continuing to do that one thing. I think a lot of people can intuitively understand why that would be really satisfying for someone as a career path.

To say, “Look, I’ve found my corner of the world, and I just want to get better at it and have an environment and a context that sees the value in that. One that wants me to be better, and that can make something out of me being better, and that can help me be better.” Rather than saying “Well, you know, aren’t you really good enough? And we just need scale, so can you take the plateau that you’re at and productize that for us so that we can have like a hundred diluted versions of you?”

That’s the cynical version of what happens. Again, it’s this trap where you got so good at the thing that you really loved doing, and now you can’t do it anymore. I’ve seen and worked with a lot of people in the industry who’ve really gotten stuck on that and have to carve out their own space.

There’s not a lot of examples you can point to. You can’t talk to someone who’s at the beginning of their career and say, “this is a possible end point for your career. This is a possible future for your career.” Most of the time, yeah, you’re going to get talked into being a manager, or you’re going to get talked into being this sort of like mid-level hand-waver.

Oh God, that’s such a triggering phrase for me because every time I hear that in a design or tech context I think of the job description where they ask for 10 years of experience in 10 different unrealistic things. To me it just says you want to extract value from me unsustainably.

It says you want two conflicting things from me and you don’t want to acknowledge that they are in tension with each other. You just want both. You want more work. It just triggers a sense of “you’re not going to protect space for me to do one or the other of these things.”

And that’s the thing that I’ve been looking for. And that was what I’ve been looking for when I’ve decided to change roles: to find a place that will protect space for other people who are way beyond my level of experience, and continue to be valuable contributors doing what it is that they’re good at.

We can be kind of cynical about that, but I think it is an economic decision. There’s a reasonable level at which to value design. There’s a diminishing return on investment at some fuzzy point. That’s different for every company and every situation.

It’s very personal and very subjective. Everybody likes to use the Craigslist example, but you can’t generalize any one of those things and say, “Well, see that proves that design doesn’t matter.” Or “Apple proves that design is the end all be all.”

It comes down to: what are you going to do with design? What is it going to do for your company, for your reputation, for your customers, for your long-term growth? And essentially what it becomes is: if you’re going to value design beyond that point, that becomes a values choice. That’s an intentional moment where someone says, “Look, I’ve seen the numbers. I know this doesn’t make any sense on paper. But this is something that I’m going to stake out at a leadership level and at a culture level. That we are going to care about design, and then we’re going to stick to it.”

To varying degrees we’ll see different companies in this startup ecosystem assert some level of value there. Stripe for example. You can look at Stripe and say, “Wow, from the beginning they invested in design more than they had to.”

You can imagine a version of Stripe that invested in design and quality a lot less, and was still very successful. So at some point that was a value for them.

But it’s still not like it’s not the same combination with Apple. Privacy is another example of where Apple looks at the trade-offs of privacy versus everything else and makes a choice. A company has to say, “We really care about this because we know that there’s constantly going to be decisions that are made harder by us caring about this thing, that are made more expensive, where the incentive is going to be for us to drift from this value. So we need some mechanism to hold it up.”

I think that comes into play with senior employees of any kind: engineers, designers, HR people, and so on, where there are diminishing returns on paying to keep more senior people around. That company could get more out of five junior people with a manager than they could out of that one person who’s been there for eight years, who has all this stored up knowledge that’s now no longer relevant because the company has doubled every 18 months for the last three years.

I think most companies with some kind of reasonably mature leveling system have incorporated this idea of having parallel tracks. But as you said, that system will move away from craft in a lot of places.

I think that if you want to stay doing the things at one level, and you don’t want anything to do with the things in the level above, it should be feasible and a reasonable choice for you to say, “I’m going to hold here.” This is true outside of the earlier levels, which should be designed to move you up.

I think the idea of a Staff role is that you’ve crossed this threshold where there’s a floor, and you can kind of hold there. I think the problem is that we’ve created this ladder system and there’s only one way to go but up, and there’s more up there. And we sort of have this social incentive system, you know, an anchoring kind of thing, to go up.

But I think that’s a problem of the system. It’s not a problem with that choice.

I do think that option should be supported and that staying on a level makes sense. That’s where I have found myself feeling stuck. I saw nothing above me in this leveling matrix that I was interested in, or that I thought I would get more out of, or the company would get more out of me.

I found my spot and I feel like I should be able to stay there to the extent that I’m incentivized to continue doing the work, or to the extent that I’m not incentivized to feel bad about staying there. That’s maybe a problem with compensation structures or performance culture.

I don’t know. I do think that there’s a fairly well understood way to structure a system where you’re still getting incentivized based on your performance at a particular level. It’s not about constantly exceeding expectations, it’s about “Oh, you’re doing a great job at this thing so we’re going to compensate you for that. And we’re not going to force you out of that band.”

I think a well-designed leveling system should incentivize that. It should incentivize you to find your balance and stay there. And if you feel artificially incentivized to grow for the sake of it, then maybe you’re just a highly ambitious person and you should factor that in. Or maybe there’s something about the incentive system that is driving you to do that.

And companies should question anytime the incentives don’t align with desirable outcomes. You need to question: “Is this the outcome that we’re looking for? Do we want people to level-seek constantly? How does that benefit our company? Maybe that’s a flow that we want: We want people to come and stay for three to five years and then cycle out and go do great things.”

You have a midlife crisis, Just like every everybody else?

It’s a very personal question and it’s a very personal journey for everyone. At what point do you recognize, and then internalize, that these external markers of progression and success have been artificial all along? That they’re scaffolding at best. They’re scaffolding to help you find your own path by creating the illusion that you’re following a pre-set path.

But at some point you reach either the top, or the point of diminishing returns for you personally, and you realize “Oh wait, there’s no structure here. This was all just an artificial way to get me here.”

“And now I have this new problem that I haven’t been preparing for all this time, which is ‘What are my values and what do I care about? And what am I going to do personally to measure whether I’m moving in the direction of my values or away from them?’”

And that’s a challenge, or at least a difficult transition for a lot of people. Because what you did before hasn’t prepared you for that at all.

There’ve been a few times where I’ve sort of reached that point, not of crisis necessarily, but where I had an opportunity to reassess and say, “Yeah, all things being equal, I’d rather be doing more of this, less of this.”

It’s hard. We don’t have infinite opportunities. Sometimes somebody offers you the promotion. You’re lucky, or maybe you’re not. When you’re lucky, you get excited about it, and maybe you take it. Sometimes it requires a change of scenery. It’s refreshing and can kind of keep you going for a while. But eventually I needed to actually sit down and think about what is it that I want more of, and what I would rather not be my responsibility any more.

I don’t know, we’re all just lucky to have jobs. At this point it feels like a very privileged conversation.

But also something that I don’t think we talk about enough, or don’t talk about openly enough, is that we realized in the modern age that HR is not your friend. You can’t depend on a company to have your best interest in mind. You can’t outsource what’s in your best interest to a company. You can’t outsource the trajectory or your career path to a level system or to any one company.

You’re going to either carve out some things for yourself within the environment that you’re in, or decide when it’s time to find a different context.

This isn’t quite the answer, but, maybe it gets me there:

I talked about this a little bit earlier, but I think one of the skills that you sort of accrue over time is that you’ve seen a lot of problems and contexts. And through that you’ve made a lot of choices. You see a problem, you make a choice, you see the outcome. And as you do that over and over and over again, you start to build up a kind of training data. Now, when you see a problem, you can pattern match it against a similar class of problem that you’ve seen before.

You can seek across all the solutions that you have, and all of their outcomes. And you can start to, if not predict the outcome, articulate the trade-offs. Instead of just looking at two options and saying, “Hmm, that one, I like that one better,” you can start to render an assessment of what you’re trading off between these two things. “If you go in this direction, you’re going to be able to do this, this, and this, and you’re not going to be able to do this.”

That’s the thing that every designer does to some extent, but as you do it longer, you’re able to do it faster, more accurately. And more...I don’t know, particularly.

There’s a point at which you sort of work on instinct, where your instinct is honed, but you can’t really explain it and you get a little disgruntled when people are constantly asking you to justify it or explain it. But then you reach a point where you’re able to explain it more. That comes from nothing but putting yourself in a position where you’re constantly encountering new problems and contexts and being put in a position to make an informed choice, and stay in a position to see the outcome.

I think one of the downsides of agency work, for instance, is that sometimes you see the problem, and you are in a position to make a decision, but you don’t see the outcome. Or if you see the outcome, you see it slightly removed, through some sort of rose-colored glasses.

You can put it in a case study, but you don’t reap the consequences of all the choices that you made. So you don’t quite value the trade-offs of those decisions accurately. You might think you made great choices and now you’re going to go make the same bad choices again and again.

Yeah. Well, really nothing is bad. But I think a truism of design is that everything is a trade-off. There’s no pure solution. And sometimes we get in that trap, you know, when you’re going in circles around a concept or an idea or something, thinking that there’s a pure solution that has no trade-offs somehow. If we just keep working on this, we’ll be able to solve for these three things that everybody’s asking us for, instead of making a strong design choice that includes a strong defense or rationale of what it doesn’t do and what the trade-offs are.

And usually that’s disappointing to some people. But you have to calibrate or change the variables of your decision so that the thing that you’re losing, or the thing that you’re trading off against, is the thing that you’re happiest to trade off. You’re not trading off something that’s a core value to your product or your company.

You end up saying, “Okay, we’re going to lose this, but it’s okay because X, Y, and Z.”

Yeah, totally. Or you’re doing this sort of Frankenstein thing where you’re actually trying to solve three different and deeply conflicting things, because three different executives are important. Stakeholders want those three things and you’re not willing to go back to any of them or all of them and say, “Actually, we’re not going to satisfy these requirements exactly as they were required. And here’s why...”

That’s a difficult conversation to have, and can often be disincentivized by how those types of conversations have gone in the past with that person.

It depends on a lot of factors that are personal, and cultural, and organizational – even culture at a societal level. What titles are a proxy for is credibility. And that’s what you’re talking about here is how credible is this person’s point of view to this other person. Credibility itself is a proxy for trust.

So I don’t know you that well, but you come to me with credentials, so I will proxy actual trust for trust in those credentials. Then I can appropriately calibrate what I’m saying.

A lot of the people who I see arguing that titles don’t matter are arguing from a very privileged position where it hasn’t mattered to them in their career for reasons that have to do not necessarily with their skills or their credibility.

So I think in that way they are necessary, because they are a proxy for trust and it’s not safe or equitable to allow how you look or what your background is or what your gender is to be the proxy for that trust.

If titles, or those proxies for credibility, are only important to the people who aren’t part of that in-group, then it’ll never be equitable. Everyone has to participate. Everyone has to give up some of their inherent credibility in this social economy and put that into these proxies like titles or brands.

And it’s not just important for the person who’s the executive or on the receiving end of these things. Everyone who is participating in that conversation in that group has to defer correctly to these tokens.

We have to maintain the delusion of that system. It’s like money: if we pretend like it works, it works.

I think there really is a currency here. Titles don’t have any value if you don’t act like they have any value. Acting like they have value inherently benefits underrepresented and marginalized communities more than it benefits people who already have power in those situations.

This is kind of rough and may not actually land, but something that I’ve experimented with over the years is: through seniority and experience, I’m accruing a surplus of credibility that I don’t want to spend.

People are saying “you should be a leader, you should be a manager, you should be making these decisions.” But I don’t want to have those responsibilities. So now I’ve got this surplus of credibility that’s accruing to me.

I could be spending that, but I don’t want to. It’s like if I could afford a bigger house, but I don’t want to live in it or clean it. So something that I’ve experimented with over the years is redistributing that surplus, finding ways to redistribute that credibility. If I have more credibility in an organization or in a context or in this industry, then I can redirect that credibility to someone who could actually benefit.

A concrete example is saying “I don’t want to be the manager. Everyone is telling me that I should be the manager of this team. But I don’t want to be the manager.” So who should be the manager? And who is being overlooked for any of the reasons that someone might be overlooked?

Maybe they’re more junior. Maybe they don’t have the right profile or experience. Maybe they don’t look like the people who, in this organization, are promoted by default. But picking someone is not random. It’s not charity. If there’s someone who you also have the awareness and the visibility and the understanding to say “Yeah, I think this person wants to do it, and they can do it, and with some support they could be successful,” that works.

Often where companies don’t do right by people in that situation is they will elevate a person’s responsibility, but they aren’t willing to support them in a way that helps the person to be successful. It’s sort of a self-fulfilling prophecy.

A position that I found myself in is being able to say “this person should be the manager of my team. And I am going to take responsibility for helping them to get the support that they need to be a successful manager.”

Haven’t we given up on making any predictions about the future at this point?

Um, I’ve been very close to burnout at various times, but usually those have lined up with the points where I realized that I had walked into a trap. Or it was a point where I had walked down a path that was not sustainable for me.

We get stuck in these toxic relationships of careers. It’s like, “well, what am I going to do for health insurance?” Or “I’m getting paid well to do this thing, and I’ll just get through this and come out the other side.” And we continue to perpetuate that burnout cycle.

And that’s real. And sometimes you don’t have a choice, or it feels like you don’t.

I would like to just keep doing what I’m doing. And I would like to find ways to put myself in situations and make choices where I can keep doing what I’m doing without burning myself out. Or at least protecting myself from the incentives or the dynamics that want to burn me out.

One of the things that I’ve had to realize over the years that helps with that is taking less responsibility. Or less personal responsibility for things. Which sounds counterintuitive, and like a thousand self-help books. But especially in a large organization, there are things that are not your responsibility and there are things that can’t be your responsibility.

It’s egotistical of you to think that something’s not getting solved right over here, or something’s going in a direction over here, and you need to step in and take on the anxiety of whether that’s gonna work or not, to propose a solution and get in there and figure it out.

Over my career, there are more and more things that I’m willing to look at and say “yeah, that’ll go one way or the other, but there’s nothing that I can really do that’s going to change it.” Maybe that sounds defeatist, but I don’t really mean it that way. It’s sort of a freeing kind of thing to say.

It’s a trust thing. You’re trusting in other people in an organization and you’re trusting in the immune system of the organization to avoid bad ideas or train wrecks or collisions. At some point, in order to not burn out, I think you have to be able to trust.

In some places you can’t, and those are inherently unsustainable environments where you’re like “if I don’t literally step in and do something about this, no one will, and something disastrous or something counter to my values will happen.”

You have responsibility over problems that no one knew were problems until 30 seconds ago. And if someone doesn’t figure it out, the whole thing is going to fall apart.

I think that’s why people later in their careers drift towards larger organizations. It’s more plausible to do that in a more mature, stable organization. The whole thing is not going to fall apart because you didn’t step in and go into firefighter mode over every little thing.

No, Facebook messes up you.