250: LIVE at Combine (feat. May-Li Khoe, Katie Dill & Soleio Cuervo)

Welcome to episode 250 of the Design Details podcast. I'm Bryn Jackson.

And I'm Brian Levin. Today is the day that we don't.

Usually ship podcasts, don't ship podcasts, but we did a special episode on Wednesday live from our friends Combine's office. And we got to talk to three of our favorite guests ever again in front of a group of some of our best friends.

Yeah, 250. We've been doing this for, give or take, three and a half years. So thank you to everyone who has been listening. If you've listened to all of them, my God, thank you. I guess if this is your first.

Episode, maybe a weird jumping on point.

Interesting place to start, but probably a good one. We had a really, really fun panel with Melee Khu, Katy Dill and Soleil Cuervo.

And we talked about, like, getting hired, planning your career, building teams, which are questions we've gotten constantly over the past three and a half years. Just like, how do I get hired? When should I build a team as a junior designer, where do I start?

All those sorts of things.

And we got to ask some of our favorite team builders about that process.

So if you tuned in live, I hope you enjoyed it. If you were there, thank you for coming. Otherwise, thank you so much to Combine for hosting this live event. It was a beautiful space and a very fun evening.

Yeah, we streamed it live on Twitch.

I'll probably put that video up on.

YouTube somewhere, but we don't really have a Spec FM channel.

I would, I would just listen to this, not watch an old stream video, but that's just me.

Brian's preference. Before we get into the episode this week, we want to thank our sponsor, and that is Abstract.

Abstract is a secure version controlled hub for your design files. It's a source of truth to make you build better things together with your team. Better, better, faster, smarter, wiser, stronger, faster.

All of those things really, at least as many times as he said them. It makes it way easier to collaborate as a team and actually, like, work closely with engineers, other designers, other product people, because you can have a source of truth and know that, like, if someone changes something, you can always go back. You can iterate really quickly and move forward as a product team in a bunch of different directions all at once. It's pretty cool.

Everything is managed and versioned in one place, which has profound consequences on the stability and security of your files and also the ease of collaboration. It means that your teammates, your engineers, your PMs, they don't need to have Sketch installed on their computer to review your design file. They can just go into abstract, leave comments, and you can have conversations in real time straight from that tool. It changes the way that you work together while simultaneously affording a ton of security that version control provides. You can scrub back through history, revert mistakes. You don't have to worry about conflicting files with other designers on your team. Everybody can be working on the same file without worrying about corrupting some file.

Yeah, it takes all the risk out of actually like iterating and modifying files because if it's really comes down to it, you can always go back to last version and they'll build it from scratch for you.

And if you haven't had a chance to work with version control, this is an awesome jumping point to get in because they've made it super accessible. And also version control is going to change your life and the way that you work for Forever. Abstract is giving a free month trial on their website@goabstract.com if you just go to goabstract.com you can sign up, start that free month, give it a try, invite your team. We are confident that you're going to enjoy the way that it helps you build stuff together. So go do that. Goabstract.com thanks so much to Abstract.

Thanks, Abstract. With that, let's get into episode 250 live from combine with Mele Koo, Katie Dill and Saleo Cuervo. All right, Adam's telling us we need to start so we can get out of his building. Guess it's about that time.

Okay. Hey, J.P. that got everyone. There we go. Yeah, I'll call you out. If you're talking, he's your Spanish teeth friend.

And we can do classroom style. If you can hear me clap once, you can hear me clap twice, you can hear me clap three times.

You work at an education company. This makes a lot of sense.

Clearly.

It works no matter, like, if it's students or not, it's great.

Yeah, if it works with middle schoolers.

It'Ll work with Brian specifically. Thank you all for coming tonight. We're also streaming this, which is not something we've done before. I don't think so.

Just keep that in mind before you do anything dumb. Matt.

Thank you for playing.

Wait, are we streaming this visually or audio?

There is a camera.

So there's a camera back there.

Hi, Internet people.

I just checked the numbers.

You're spinaching your teeth.

2 million streamers.

We're actually breaking 2 million streamers that are unrelated to us.

We're breaking Twitch's records.

There are 2 million people.

Oh, my God. Drake's tuning in.

We broke the Internet in that.

This is amazing.

It no longer works in this building. I'm the joke boy. You have to do the actual question asking. That's how this has always worked.

All right, you all know the drill. We're going to ask for a brief introduction. So the last time we've had you on the show, things might have been a little bit different than today. So it'd be good to do a quick refresher. What are you up to now? And then we'll go from there.

Soleo pointed to his start With Soleo, I think that means you start.

I will take the lead here. Hey, folks, my name's Soleo. Welcome to Combine. This is our office space here that we're very happy to be hosting design details for our first design community event. So I'm absolutely thrilled to be inaugurating this space with y'.

All.

I am a founder and partner here at Combine, along with Adam and our dear friends Josh Puckett, who I think is online somewhere, probably tweeting at us.

He's laid up, right?

And Beck Stone, who's somewhere in the crowd. Hey, Beck. Before Combine, I was a angel investor for a couple years. Was very fortunate to partner with teams ahead of becoming a full time vc. And before that I led design at Dropbox and was an early designer at Facebook.

Hello, everybody. My name is Katie Dill and I, that's my team. I lead the design.

They're contractually obligated to do that at every event.

I just met her. I cheered.

Anyway, performance reviews are coming up.

So.

Yes, I lead the design team at Lyft and yes, we have a strong contingency here. I've been there for just about seven months. And before that I was over at Airbnb, also helping to lead the UX design team there. And I live in San Francisco and I'm a mother of a dog named Snacks and he's adorable.

I love the word snacks. My favorite words. My name is Mei Li. I lead design at Khan Academy, which is an educational nonprofit. Yeah, I've been there. It'll be four years in September with lots of scope. Creep. I started out with less scope. Now I lead design user research. Also co founded some of the early product development efforts there, which were kind of more researchy on the long term side, which is more my background. So before that I was at Apple for seven and a half years, worked on HID prototyping. So we did stuff that were like new ways of poking at machines. So that they did interesting new UX things alongside Linda, who's in the audience. Hi, Linda. And bounced around a bunch before then I guess other things of note. Dj and I'm also a dancer, co founded La Pelanga, which is the DJ coalition in the Bay Area. And I dance at every chance I.

Get, including right now.

Oh God.

Brian and Mamie, I'm sorry this is.

A chance, but your music needs to be better. And then I'll dance.

Okay.

That was a diss to the no music that is playing right now.

That can change real fast.

So we've been thinking about this episode.

For a long time.

Really want it to be something special and really focus on the really important questions around building a team. But there's one question that's been the most frequently asked question from all of our listeners and that's should designers code? I actually don't want to.

Where's that for that?

I have a. I am pretty passionate about this.

You have a serious answer, please.

Oh, we weren't actually going to ask you that.

I actually, I mean I actually feel like, you know, there's a lot of conversation around learning all kinds of things in life that are like, you should do this because it will get you the next job. And I understand that that's really important and people need to have a path forward. However, coding is also really cool and fun. It's this really empowering thing that lets you make interfaces do things. And I feel like, you know, kind of when we talk about industrial design and we talk about the kind of innovations with like injection molded plastic and the way that that made entirely different chair designs possible. Understanding software and understanding the way that it behaves at a deeper level allows you to work better in your medium.

It's a lot of heres about two times as many as people that said it.

But do it because it's fun. Figure out how it's fun.

It is fun.

Brian does that all day, every day.

And simultaneously Frustrating, but fun. It's only frustrating if you're bad at it. Like me.

Can't confirm bad at it like Brian.

I mean like, I think it also depends on like how friendly of an environment you found to learn how to code in.

Yes.

So I think that sometimes people go and they find a course somewhere where they have to spend like a whole day setting up their environment. And of course that's not fun.

So wait, where can you not do that? I do that for side projects.

I mean also don't be afraid to use kids stuff to learn how to do it. Like, there's, there's a. People are making cooler and cooler apps and even online games and apps to learn how to code. So you could go on to, for example, Khan Academy.

Sick Plug, Torque.

Sorry, We. I mean, we do have a code learning thing. There's also code.org, there's. Let's see, was it called the Human Resource Machine? They had a little game that they came out with that sounds monstrous. It is kind of monstrous.

That's Gusta's new product.

Hopscotch is really cute and fun. Scratch. There's lots of things to just get started with and play with. Just make something fun and share it with your friends.

Thank you for taking our joke and making it useful.

This is why we invited you on the show because we are going to need a lot more of that. One thing that's been on our minds, and especially since y' all have been doing this for quite a while, is thinking about career progression.

Brian's looking for his next phase after he leaves the company we work at together.

I'm on the fence about my next move. No. So we ask most people that come on the show what keeps them up at night, and the very, very consistent answer is, am I on a good path? Am I on the right path? Am I doing the right kind of work? So I'd love to know how you thought about your career, whether it's been intentional or accidental or if that changed at some point and why. Katie, we'll start with you.

It's a good question. I feel like in some ways, I don't know if I've ever had, like a perfectly clear path. I've always had assumptions. I'm kind of one of those folks that loves to know where the North Star is, whether it's in the work or whether it's in your life. And I have.

It's in the sky.

Yeah.

Thank you.

Super helpful. Like, out there somewhere. But in terms of, like, what is the actual trajectory to that and like, the step that I'm going to step here and then I'm going to step there. I guess I learned early on that I was not going to be very good at making that path because things ended up always taking me down to a different direction. I graduated college, had no idea that industrial design or design even existed other than interior design, and I ended up kind of falling into it. A friend saw the 60 minute special making the Shopping Cart with Ideo. Have you guys ever heard of that one? I know there's others that have come into design because of that, so thank you, ideo. But my friend saw that and then recommended I get into design. I learned about it. Lo and behold, now I'm a designer.

When I think about shopping carts, yeah.

That'S what you think about. But, like, the whole idea was, like, the process of solving problems. That's what design is. At least, that's what it is to me. And that was why I was referred to it. And I got excited about it, but, like I said, would never have planned it. And so I think there's definitely some risk of, like, I'm gonna do this and then I'm gonna do that. I'm gonna do that, because then you don't open your eyes to those. The knocks on the door of that opportunity. And I think that's kind of happened for me again and again in terms of, like, my career path and where I've ended up and what I've done and not done. But I guess two things that I would say that I hope could give as recommendations would be one, to listen to the door knocks, and two, say yes. And, you know, I think in terms of the door knocks, right, it's just a matter of, like, you know, you hear about something and it tickles and you're curious about it. It doesn't mean you have to stop everything and jump into it, but, like, explore it. Explore it on your side time and explore it through friends and talk to people and then saying yes. And I'll try to cut this short because I'm rambling, but it's like, it really had a lot to do with my career. I was once invited to speak at a design event, and I was going to say no, because that inner voice was going to tell me. It was telling me, like, you're not good enough. You're going to screw it up. Everybody else on the thing is much better than you. And so I wasn't gonna do it. And then there was this, like, voice inside of me, like, well, if I say no, then I'm, like, never putting myself out there, and opportunity's not gonna go. And so, at any rate, I said yes. And it just so happened that Joe Gabia, one of the founders of Airbnb, was in the room that time, saw me speak, liked what I was speaking about, called me in, had the interviews, et cetera. And the next thing you know, I got my dream job. So I'm a big fan of the, like, saying yes and putting yourself out there and. And letting to see where it goes.

Could we actually, as Meilee and slay, as you answer, could we add in the context. I'm really curious how you increase the volume of those knocks or. I think a lot of people get the right knocks. Get the right knocks or identify the right knocks. I think one frustration I've heard from people, especially younger or from outside of this area, is how do I even get that first knock in the first place? They're frustrated that this is a very networking, heavy industry. So if you could speak to that as well.

Yeah, I think for me, with respect to hiring folks, the thing that has consistently stood out over time has been people who are able to channel energy around projects that they spearhead. I think we even talked about this when we had our design details podcast. But side projects?

That was 200 episodes ago, my dude. I don't remember.

We for sure did.

Maybe everybody has side projects now, but to be frank, this whole firm started off as a side project. I never imagined that angel investing would be an area of focus. For me, it was something that was a way to help out friends and to stumble into a specific niche that I didn't imagine would somehow turn into, like, a thing that I would be known for. And that would then bring me to a zany company called Dropbox that had a really phenomenal business and a really interesting way for design to operate in a business model that was very different from Facebook. And for me to answer your question as far as, like, how to, like, find the knocks, I think a lot of it does come through experimentation and doing things that you have no business doing. Honestly, if somebody told me 24 months ago that I would be managing a fund, I'd be like, come on, are you serious? And I would hate to know that One of our LPs is live streaming this right now.

But.

The fact of the matter is, it's only through doing that you actually learn whether or not you're actually good at something. But more importantly, there's a hidden reward center that you may not have been able to service. And I think that, to me, is like, what's really fundamental to both really exceptional design work, but also just trajectory in one's career. It's like finding those hidden reward centers.

Do you want to add anything, Milli?

Yeah. Your first question was like, was this? How do I know I'm on the path? And was this the path that I set out to be on? And the answer, do you plan your career? Yeah. Absolutely not. It sounds like none of us did. So if I were to assume There's a talk that Nikki Case give at xoxo. I think it was like maybe two, two or three years ago, which I absolutely love. Look it up. Even hadn't had a chance to look at it. He does this wonderful visualization of the possibilities in your life as this organic branching pattern that starts at today and branches out all the possible choices you can make and how you could just never know. It's like a, you know, it's a combinatorial problem. You don't know what's going to wind up happening. You're making lots of little choices along the way. You're going to wind up somewhere and there's just no way of predicting that. There's something else that I remember super loving that Steve Jobs told us the day before we announced the iPhone. So we had a town hall sick name drop. Sorry. No, this has been on my mind because he said this thing, he said, people ask me what the five or ten year plan is for Apple all the time, but the world could completely. Oh God, too soon. But the world could completely change in a year. So how would you actually know five or 10 years what you're going to be doing? Because I mean think of all the things that have changed. So yeah, no, so that, so that first question. Absolutely not a plan. And how do I. How do you know you're on the path? I mean, I don't. Quick poll. Did you know, do you have this concept in your mind of like the path and that you were on?

I think so. I mean I'm a little bit selfish and I keep sort of revisiting my selfishness with my two kids. I've got a five year old and a seven year old boy. Two boys. And it's amazing to sort of see what they find rewarding. And you don't know what's weird about yourself until you see it in your children. But it's amazing to sort of see these like old reward centers, these things that I just like. Oh yeah, I used to love doing X or Y. I used to love organizing like stupid games for us to play. That was like a thing that I did. I would just create games. And now my son's like creating games for me to like participate in and now we're like wrestling over who's like the game creator, how do I hire him? Get in line, buddy. And you know, the reason why this is relevant is because I think that there's like these, like these deep reward centers that really inform the things that we are not just like passionate about, but we're actually well equipped to do. And sometimes those get resurfaced in, like, entirely new applications. And so for me, like, one of the things that I always have enjoyed doing is talent spotting. I just really like finding people and seeing a future version of someone that nobody else can see. That was like, the bit in my head that I flipped at Facebook when it came to design hiring. It was like, can I create career paths for people that are going to be far better at this job than I am? They're going to be able to take this company much further than I ever could myself as a. As an ic and then realizing that actually, maybe VC is actually an interesting way for me to apply myself. Because as it turns out, what do venture investors do? They look for hidden talent. They're in the business of talent spotting. And so that's kind of given me some confidence in this particular career path and more importantly, in regenerating this old reward center in a new application.

Could you.

One thing that's. Sorry, I was going to say one thing that's so powerful about that and so rewarding about that is that I think about that in everybody's life and I wonder if you all have a moment when somebody looked at you and saw potential in you that you didn't see in yourself and how much that gave you the power to go further than you had imagined. Doing that for people is so huge.

Yeah. And then they follow through and then they become badasses. And you're like, yeah, of course you're gonna be a badass. I knew that years ago.

You're like, yeah, I knew that.

But do you have anything concrete? Like, I think we have a lot of managers in the room or new managers, and Bren and I are trying to figure out.

Yeah, can you tell us how to.

Hire our own hiring thing? No. Like, is there anything concrete here about identifying a somebody that's going to do great in the future or has great potential that isn't hand wavy, like, gut feeling, or they were really passionate, like, how can we be better or more systematic about identifying?

And how do you choose? Not great now?

Yeah. I mean, I like talking about error correcting systems, and I look for that in people. Like, do they have error correcting, like, error correcting systems built in, which is like, do you take feedback well? Do you incorporate feedback well? Are you looking for feedback? Are you constantly looking to get better at what you do? Because then even if you do something that's not that great, you're going to ask people around you, like, how Can I make this better? Cool. Here's like the five ways that I tried, given what you said, and here's how your feedback's reflected back. Is this better or not? Yes.

No.

And you keep doing that, you do that rapidly, you're just going to get better.

Totally. I agree completely because I think a lot of times people think about it like it's like a shiny portfolio or like they've only worked on products that have shipped or that they've had some massive impact, but reality is like, great, that's wonderful. But they were probably also like one of many people that worked on it and you don't really know which part they did. And then secondly, just because they were successful, successful or lucky in the past doesn't mean they're going to be again. So honestly, it's all about getting into understanding their rational thought and like, how they came to the decisions and how they learned and how they reacted and, and when they failed, how did they change the way they're going forward? And so like, I think about like, interviews and that whole thing all about just trying to understand that. And frankly, like, you know, there's just like, I've seen tons of shitty portfolios that like, perhaps there's a lot of other things that are going on behind the scenes, like, oh, okay, they've got some things that they have to coach on. And I think, you know, as to your question about like, you know, tactical way of looking at this, I think the other thing is that like, you have to think about like, what can we support, what can we coach? What are the things we know we need and we like, you know, can't wait for. And you know, where are the ways that we're going to be able to help someone? Because I think a lot of times people just like, they start to go right for that like, cookie cutter thing that maybe they used at the last company they were at or that they've like hired before and they're just looking for that stuff, same thing every time. And you know, we're all in different bites and sizes and that's like the, the benefit of it. But you just need to know, like, what do you hold dear first that like, must be a part of the next person that you hire. And then think about these other things as either coachable areas or even value ads on top of that.

Is there a first thing you look for in any hire? Is there like a must have this quality you mentioned? Error correcting is. Is one of them. I wonder if there's like a, if I see this we're good kind of thing.

I wouldn't say it's the only thing, but, like, I will stop the conversation if there's a lack of humility.

Sure.

I think so much comes from that.

I'm okay taking this in the opposite direction, too.

Yeah. Because if there's a lack of humility, then there's no input, there's no coaching, there's no evolution.

Like, I don't know. I believe in great design comes from collaboration. And, like, if you're just going to be like the one woman show, then you know that there's going to be some challenges there. I definitely, of course, look for people with, like, exceptional skill and, like, they should have confidence in their skill. But, like, what's the saying? It's like, it's courage, not confidence or something like that. There's a different way to slice it where you're still a good team player and that you're still able to learn from others and, you know, bring your skills to the table in a more shared approach.

I look for initiative. I love folks who don't wait for somebody to give them permission to do something that's often like, there's just an internal impetus to exert themselves on the world. And that, for me, is probably the higher order bit. Certainly humility is important, and I think humility does come to folks, especially with experience and with setbacks.

Experience is the greatest humility creator I find.

Totally. Totally.

Yeah. This is fun. I get to poke at what you said. So the initiative thing, I find that with some people, it takes a little bit of extending a hand before they feel the entitlement to have the initiative, where people don't realize that it is their place to have that initiative. Even though I've seen super talented designers who just have this attitude of like, well, how can I help? Tell me what to.

And I'm like, is that the ask for forgiveness, not permission thing?

It's. I think it's related in a way to the initiative thing, but it's. It's just that if. If somebody maybe comes from a background where they don't realize it's their place to start things, or it's their place to, you know, elbow out some space in the world and say, like, I'm gonna do this thing. Sometimes they need a little bit of coaxing first. So it's also fun to figure out who's going coachable with that. And as soon as you open up that space for them, they fly. And that's also amazing because you've lit some sort of spark in somebody that might not have realized that was their place in the world. Especially because if you look at traditional labor patterns, like historically, there are some people that may come from a background where their idea of labor is very one directional. And so you're also trying to course correct for history where there was a boss and they are the person that's like punching in, punching out. And so if that's all they've ever seen, they're never going to know that they're the person who should start the business, for example. Right. They've maybe never seen themselves that way. And so if you can ignite that in people, then that's pretty magical.

Is there like a first thing that you try and get new hires to do or a thing that can kick off that process? Is it like a task? Or here's a project that nobody's wanted to touch. Does this look interesting?

Here, take this.

This thing sucks. No one else.

Something no one else has solved.

I would love to watch you onboard a new employee.

We could make that like the next hit podcast if we just draw the paper, recorded the trials and tribulations and draw the paperclip. Eventual failures. Redesign the paperclip. Yes, that's a good idea.

It's a good. I mean, you do have to be thoughtful about it because oftentimes, like, if you're hiring, it's because you have a need. And so as soon as they get there, you're like, oh my God, thank God you're here. You should have been here like two months ago. But the reality is like, I mean, these early days are like when a lot starts to like, take hold. And so there's just a big place where a lot can go wrong. I 100% agree. Like, it would be great to like one set them up with like the support structures, should you. They know that they can run and also give them opportunity to run. But there's probably a way. Some of the things that we've talked about, like Matt here basically organized our onboarding. Thank you very much for doing that.

Thanks, Matt. Thanks, Matt.

We look at what's a mini project to give them, maybe it's a week and it's during the time where they're doing other stuff. But they can start getting their hands dirty a little bit and give them an early win. Because I do think that once they start to know people, they know where the stuff. Stuff is, then they can start taking on bigger things with like a little bit more vigor and a little bit more like comfort. Because you throw them into, like, a massive problem that, like, we hadn't been able to crack for, like, six months. It's like, it's tough. It's really tough, even for, you know, someone with a lot of initiative.

I oftentimes try and give people one of those internal projects because I think every design team has a bunch of stuff that they've been wanting to get to for a while. And so if the person starts out with a small win. Tech debt. Well, yeah, with, like, a small win that gets the rest of the design team excited about something they've done to empower everyone, then it sets them up to have a good relationship with everybody.

Where does that. Where does this fit into giving designers their first job? Hiring juniors is like, first of all, do you even do that? Are you hiring juniors today?

When do you hire juniors?

And then if you are, when did you decide? And the reason you said, you know, the business obviously has objectives and, like, the business wants people that can hit the ground running. And it becomes increasingly hard to hire someone in their first job. And, like, you know, there's a lot of education there. There's getting them those first wins, and then you're looking at, like, months to ramp up. And how do you start hiring for juniors? Like, when. When did that happen for you? Or if you're not doing it today at all? Why?

It's. I don't know why. I just started talking. Sorry.

I think it's good.

I was just. I wanted to jump in because I think it's a very difficult situation because I think it's like, yes, we need to hire juniors. Like, absolutely. Like, if. Do we want to, like, make this a, you know, a thing that is permeating into more parts of different businesses? We have to empower and educate more designers. We have to give them opportunities. And. And you can't expect that everybody's going to, like, have that wealth of experience. But like you said, it also does require a lot of support, and you have to be prepared to do so. Like, for example, I was at Airbnb for about four years, and I would say that maybe, like, in the last, like, little bit, did we say, like, we're going to hire juniors now? Because for that whole time we were growing the team from, you know, while I was there, from. From 10 to 100, and it was all about getting in people that are going to be able to, like, you know, operate, hit the ground running, huge ambiguity, and not have to be able to, like, also look after somebody else. But I think there's Some massive issues with that. Because, one, being a mentor is an amazing learning opportunity. And so, like, you're going to help people be better designers on your team when they're providing that support to others. And of course, like, that opportunity of bringing people in and helping them learn, and then, like, next thing you know, they turn into, you know, the future rock stars. So I'm a big fan of it. And, you know, for example, we on our team, although we're small and mighty, you know, we have interns coming this summer. And, you know, we definitely do have folks on the team today that, you know, we're making sure are getting the support and growing. But it's an effort for sure. And I think one of the missing pieces in design education today is leadership of in education.

Yeah. I'd say the other thing that you have to watch out for is the balance of your team, because if there are not enough people to mentor the junior folks on your team, then they're also not getting the mentorship you need, and you're also not getting the vice versa, which you were talking about, like, people that are getting the benefit of mentoring other people. So it's kind of like a composition thing. Yeah.

Is there like a ratio you aim for? I don't know if that's too specific.

I feel like it really does start with finding motivated and competent mentors, folks who are going to really bear the responsibility of somebody else's success. Where I have seen this fail miserably is when you don't sort of have somebody in the building who's like, hyper motivated to take that responsibility and really own it and sort of sees it as a way to be a force multiplier, not just for the company, but for this individual that's essentially entrusting somebody with more experience to kind of show them the way. When those pairings work, it's amazing. It ends up being these very fruitful and rewarding relationships that you help form. And I think that that's extremely motivating, extremely rewarding to see. When it flops, it flops poorly. And looking back on my own experience, one of the first designers I mentored at Facebook was Joey Flynn. Great guy. I think he's at Instagram now. Terrific designer. I did a horrible job, but it was an excellent exercise for me in appreciating and learning, like, the empathy required to be an effective mentor.

Did you know that at the time or did you learn that later?

We both learned. Was a humbling experience.

I'm so curious about what it is that made you Feel like you didn't do a great job.

I think it was easy to just sort of take the perspective of, like, this is where you need to be, versus taking the perspective of recognizing where he was and also recognizing that there were, like, specific blind spots that he had. Like, he was a new grad, he was joining a company that he really had to prove himself. Because at the time, Facebook was very cynical about hiring junior folks, and I was very confident that he was going to be an exceptional designer. But that confidence didn't translate through to where he was in the day and in moment around, hey, you are now joining your first tech company and, like, one of the mother of all tech companies at a period where, like, the growth was extraordinary, and so the earth is literally moving underneath you. And so it's a very unstable environment. So it's difficult to kind of intuit what one should be doing in an environment like that. And for me, it was an extreme learning experience because I realized I'm not fit to manage here, or at least not as fit as the folks that have been selected to do so, because clearly I didn't think through what was necessary to set him up for rapid success. And I think that part of it was. It was never imparted on me, like, the importance of really taking the time to structure his first few months and taking the time to make sure that I was filling in and identifying all those blind spots for him because he didn't know what he didn't know. And so I think that when thinking about the exercise of hiring junior people, it really starts with finding the folks who are going to be responsible directly for empowering those individuals and who are, like, super motivated to take that on. And if it's something that you're interested in doing and if. And management's a thing that you want to pursue, there's probably ample opportunity to do that, but that's really what it requires.

Yeah. I also think it's worth if depending on your organization and what's appropriate for your organization. I also think it's worth considering how you incentivize that. How do you incentivize that force multiplying? Is that something that you're expecting people to just do on their own time, on magic time? Or is that something that you're really rewarding, you know, in your career rubrics or your incentives or anything like that?

Yes, my career rubric.

If someone can generate magic time, we hire them immediately.

Is there a time in the process of growth or. Cool.

Hey, Juan, you want a microphone? Is there a time during the process of growth or a specific point in a company's lifetime to say, all right, cool, now we're ready to hire, like, you know, junior designers or whatnot. Or is this something that you, like, embed as you kind of grow that company? Right. So is that like a. Is there a time? Or is it like a we believe in our DNA, you know, like Juan.

Araguin, everyone, Juan generates magic time and shows initiative, asks forgiveness, not permission. Hire Juan.

Are you looking for a job, Juan?

It's a good question. I think Soleil called it, though, in terms of. I don't know if there's like, a time in a company's life form that it should be okay to have juniors or not. It really comes down to, like, are the people there that are going to make that work? And I think, you know, for example, when a company is really young and you only have a few people on the payroll, you know, it might be hard to bring on that additional, additional help. However, it also could be fantastic, like staff augmentation in addition to what you're getting done. And so there's an argument to be made either way. But it really comes down to, like, are you going to have that person that can help? Because it is. It's an art and a science to be a good mentor and make sure that you're giving that person, you know, what they need in order to be successful to make good use of that work. So, yeah, I don't know. I wouldn't say there's a timeline.

I think it also depends on what you're building. So if you were building something that was, like a highly complex professional tool, then that's pretty different from if you're building products for middle schoolers, for example, where it's going to be a huge advantage to have somebody who was recently in middle school. Yeah, it just depends.

Closer to middle school than I am.

Don't hire Soleo. Cool.

Incentive structures are very interesting to me right now.

Are you making a rubric?

He is now my incentive rubric. Maybe let's dig into something that's relevant to everyone here. And this is going to be really hard to talk honestly about, but I want to know how you approach negotiating salary and thinking about equity as you've gone through your career. And maybe we can do it from the person can we do it from.

You can negotiate equity right now, Like.

I'm not asking your salary. I'm asking, like, how you think about it, because. But.

I want to clarify equity, like money, though, right? Not like, equity. Like, let's all equity, like, level the playing field equity, like money.

Okay, but I want to clarify. Can we do it from the personal perspective?

Because can you tell us your personal information?

Cool, thank you. As as opposed to the, like, company perspective, you know, like, for the mission. And, like, doesn't matter what my salary is. Like, can we be real? And if that's you, then let's hear. But like, how have you thought about that?

Learnings. Brian does not believe in the mission. He's only in it for the equity and the pay.

I feel like I'm butchering this question, but, like, okay, so for startups, like, that's what you need is someone who's cool, like, not earning probably as much money. Because they're really invested in the thing that's getting built, they're willing to take that risk.

If you're a nonprofit, you also don't have equity.

There you go.

I mean, you have a lot of equity that you're building by leveling the playing field, but that's different from the cash.

Word play.

Love it.

All right, I'm not going to give you the company's jargon, but I will tell you, like, if your question is, like, how much does money matter to you? I don't know how much I make right now. You just made me realize I'm, like, going in my head, like, what is that number again? And literally, I forget that's how bad I am at this. What'd you say?

So back to career planning?

Yeah, exactly. Well, I'm not in it for the money. I mean, I need a certain amount of money to actually maintain a lifestyle and live in San Francisco, but certainly I am not in it for the money. I actually would not ask anybody to do this the way I do, though. I definitely look at others with inspiration. Taking the time to talk to people at jobs similar to that one, or trying to understand, like, other people coming from that industry. I talked to my VC buddies, for example, when I went to a startup. Like, you got to ask around, you got to have those conversations. It's a difficult conversation for sure, but, like, it definitely is something that you probably need to get ahead of. The thing that ends up being, I think, to me, the most bothersome is when, like, we see inequalities within it. And I think a lot of times, you know, there are plenty of people that aren't asking those questions. A lot of time they happen to be female, or a lot of times they're coming from, you know, a different part of the world or in different demographics. And, you know, that's got to stop. We all just got to start asking these questions. It sucks to have to go through it. I don't like doing it either, but I do think that we have to, like, look out for ourselves and prepare for the long term. And so equity is of course, a big piece. How you value that, you know, you have to dig into, you know, the company and the success of the company and how are they thinking about, you know, what their plans are for the future and how have they divvied out shares thus far and try to learn as much as you can as to that company. And one, you know, kind of in the same space at the same size. What is protocol, what is typical? And then, you know, you still got to make your own decision. But getting an understanding of, like, what is generally happening can help you inform your own decision because frankly, like, do not let it slide of like, it's just what you made last time. Plus, a little bit more like that. That should not be the conversation that you're having.

Yeah. One thing I've heard as a tip as well is if you have a lot of discomfort with negotiating for yourself, the advice that I heard that I really liked was imagine that you're doing it on behalf of someone else. Yeah. So I that really $1 million.

What I would say.

But I, you know, I'm glad we're having this conversation because frankly, when I started my career, nobody was talking about how everybody should negotiate. And I'm never going to see that money. Like, I feel like I started multiple 10k, at least below where I should have been because nobody told me to negotiate. And I'm glad that we're having more of that dialogue.

There's the negotiation piece, but there's also the transparency piece. And I feel like I could be way off base here. So please correct me if I'm wrong, but it seems to me that one trend that's happening is companies are just saying salaries are banned so that they can just make this really, really predictable thing in public.

We won't negotiate.

Right. BuzzFeed does this, but the equity is, is where people make their money. Assuming the company is. Has some liquidity to that stock and the company can get away with it saying, like, oh, we pay everyone at this level between this amount and this amount, but behind the scenes, people are either getting screwed or not. And that's the part that nobody talks about. It's not really a question, but am I wrong? Is that something that you've seen or experienced.

I think there's a couple of factors. I think maybe the thing that's most critical in my opinion is that candidates are fairly evaluated on a consistent benchmark that's agreed upon by the team. Right. So that you're accurately leveling someone. Otherwise the comp conversation is like super arbitrary. It's like you're a level X. It's like, well, I think I'm a level X plus 2.

I got a real L6 vibe.

Yeah. And so there's a very clear rubric internally on understanding how leveling works. Because that leveling exercise isn't just going to magically go away. It persists into employment. It's like part of that first conversation around, like, so what do I need to do to level up? Okay, well, here's the game plan to get you to the next benchmark. If you don't have an evaluation process that is consistent and well defined, you should not be surprised that you're having like clumsy, arbitrary, like compensation conversations. And I think that's really important work that needs to be done by the early management team. As a constituent of it at Facebook, it was extremely frustrating to know that the first version of it. I'm going to throw my former employer right under the bus right now. It's happening. Right?

Sorry, Mark.

Yeah, mute the mic there.

People were really apparent upset because the rubric was not super clearly defined. It was using like adverbs to disambiguate, you know, different levels. And this is like significant not just from a compensation standpoint, but really from a personal identity standpoint from like knowing like how you stack up relative to your peers. And any ambiguity there just only creates resentment, creates like distress, unfairness, creates unfair fairness. It makes things feel like really arbitrary. And so I think that that's where like, you know, I was a couple years ago, someone asked me like, okay, well you're not designing anymore, so what would you like interview with? You know, if you were interviewing for a job? I'm like, well, that's not true head production. I felt as though like the exercise of designing like career levels and career tracks at Dropbox was like, I really enjoyed that process because it really felt like a load bearing, structural thing. It was a cross functional effort. It required a lot of hard conversations around like where people were and more importantly, creating some parity across these different functions that were adjacent to one another to make sure that, you know, if you are level X in design, you are having comparable impact as somebody who's level X in product or in marketing. Right. And making sure that we're also being really equitable across these different, different functions and weren't skewing things in the wrong direction. And I think that that really provides a foundation for having, like, a sane and rational conversation around, like, what you're going to get paid. Because if you don't have that rubric, if you aren't able to sort of level somebody when they're coming in, how are you going to level them as they progress in their career as an employer?

Yeah, completely. Agreed. I think it's. That's the moment when you're creating those rubrics and when you're doing them equitably across the entire company. Also when you make sure that there aren't sort of invisible expectations of people where you might promote or, like, level people up based on some sort of invisible thing that isn't expressed explicitly. And that is, that can lead to a lot of, like, bias or, you know, other issues of unfairness. The other wonderful thing about doing is it really makes you think about, like, what is this job? Like, what are my actual expectations? And what actually does it take to sit there, succeed in this organization, and.

To have comparable impact relative to a very different role. Right. How do you sort of have a sane, rational conversation around that?

This is really helpful for those of us who are negotiating our own careers or in a position where we're helping other people to discover their own paths, but for the benefit of the people not in the room or those of us who are actually very early in our careers and don't have connections with VCs or friends who work at startups. What do you regret about decisions you made at the start of your careers or in this industry that you wish you could tell yourself or a brand new person now.

Junior designer Dan Eden.

Do you need a. You need a first job? Dan, we're hiring.

You're working on a rubric?

We're working on a rubric.

Last name Eden. That's first metric on our rubric.

Those are gonna be the names of the rubric. I would say what mistake I made is I tried to be the boss too fast. And so it was early on in design school, I was asking my teachers, cool, how do I get ahead? How do I get to be the leader? How do I get to, to be the boss? And I wouldn't use those exact words, but more or less it's what I was asking for. I wanted to know what the fast track was. And they told me at the time that the saying that they gave me was that it's all about mileage, essentially, experience. And I just didn't really want to hear that. And so I, as quickly as possible went into my design career. And also while I was in the work, I would very quickly start evolving into, you know, more of a leader. I have some natural leadership abilities and so I was able to do that. It wasn't until maybe my next job that I started to realize why that was an error. Like, I was able to do it, but was it the right thing to do? And so my, the first job I was talking about was at Frog Design. I was a designer there and I left as a creative director. Then I went to a company called greenstart. It's not too dissimilar from the, the model of Combine. And essentially we were a VC that invested in startups with design services and received equity in return. And when we were doing that, we were helping these really early stage companies with all of the things that they had to work through. And sometimes that meant we were getting our hands dirty and doing design work. Sometimes it was more consulting. It was the whole gamut. And so all of a sudden I was designing websites again and getting my hands really dirty. And it was that wide awakening of like, I tried so quickly to rush past the doing of the work and the pixels of the work that, you know, I found myself kind of flailing. And then I also realized once I started to build that back up and like, get more comfortable with the tools and know what was happening and, you know, get back into the thick of it, I was a far better leader than I ever was. I was so interested in getting past that that I forgot that, like, those, those craft skills become the foundation of the work that you do and make you a better leader, a better manager. You know, nobody's going to be motivated or inspired by somebody who just doesn't get it. And, you know, it really helped me to kind of change a corner in terms of, like, the way I could be, you know, a help to a team and to do my job better. So if I could go back in time, I probably would have chosen, you know, not necessarily slow down, but to augment my, my gusto for being the boss.

I mean, craft builds credibility with like team members, right? Like, it's, it's very clear when craft exists.

I would say if I were to go back in time, there's two things. One, like I mentioned earlier, nobody told me that I was supposed to negotiate. That would have been a nice thing to know. The other thing is that I feel Like, I really undervalued myself, actually. I think I also graduated at a time where the economy tanked and it was just like, the only things that were hiring were, like, porn, spam, and Oracle, basically around that time.

That's the whole Internet.

Cool.

The Dark ages.

Yeah.

Thank you for that.

But, yeah, I mean, I. I do feel like I spent a little. I did spend a little too long not really valuing where I was. And so I think one of the things that I try and be really conscious of now, and I wonder whether or not we have a better answer to this question for the people out there, is how do you figure out where you are? I wish that I had figured out a way to calibrate better where I was in the scheme of things. I think I was just kind of in my own. Yeah, I didn't have a rubric, and it was kind of in my own nebula.

I actually struggle with that quite a lot just because of the nature of social media, honestly. Like, everyone's doing dope stuff online and posting about it. I'm like, shit, where am I? So how have you figured out how.

To calibrate that Twitter celebrity, Brian Lovin?

Well, kind of to come back to something that Soleil said earlier, which is also like, these are. And Katie, also both of you, when we were talking about mentorship and what you get out of mentorship, it's that, I think is when you realize what you know. Like, you just don't know what you know until you start mentoring someone and you're like, oh, that's a thing that I know that I didn't realize was a thing that one could know.

But I also don't know what I don't know.

You don't know what you don't know.

It's a lot.

So in reality, it's pretty extra. I don't know anything.

Your word's not mine.

For me, I think the two things that I wish I had understood a little bit more deeply when I first got started in my career, the first is the importance of teamwork. And I think a lot of that was instigated by just, like, who I am as a person. I just had done a lot of things growing up on my own and was very independent. And so teamwork just didn't come naturally to me. And I think that impacted me. It created more headwind for me than I would have guessed, especially in a world where back in my day when we made software, we were just building stuff for desktop, web, and so you can just go solo and get stuff out the door and ship. And in today's environment, design as a team sport is now the status quo. And that transition was a bit choppy for me professionally. I didn't realize or fully appreciate how motivated I was to be the best, be the best, be the best and not realize like how much more impact that could have had had I been just more effective. Like teammates.

Did that exhibit as competitiveness or just.

Like.

Devoid of every other context?

It's low motivation and like instigating and pursuing teamwork. I think a lot of it just boils down to motivation. Are you more motivated to go on your own and try to get something done or are you more motivated to try to stir up a team to embark on something? The second is this concept of leverage that I still think every child much like coding. I wish there was a way to teach kids and fully internally understand the idea of leverage. I think that most people early in their careers don't have the perspective or the understanding of what does it mean to be highly leveraged? What does it mean to pick problems that are highly leveraged? And I just can think of all this clowny stuff that I did early in my career that was extremely low leverage. And I wasn't really fully appreciating how being an effective teammate is extremely leveraged. Being an exceptional hire is extremely leveraged. Knowing how to pick problems effectively or framing the things you can find the point of leverage in a given problem space. I wish that I can go back in time. I would just grab myself for like an off site, like a two week off site and try to like instill that and try to teach that to folks who are earlier on in their career. Because I don't think that once you sort of see the power of that and understanding how to choose highly leveraged problems, you then start to exert extraordinary agency in the world. And I think that that's. People kind of like learn this on their own. But that was maybe the most important concept that I encountered in tech.

For the sake of illustration, can you provide an example and a counter example of like something that is high leverage and something that's definitely not.

Like working on? You know, we would work on.

All.

Of these like nitpicky edge cases for Facebook news feed. What do we do when like this person is in this state and like they have this privacy setting and blah blah blah blah and what icon should we select, blah blah blah. And I was thinking, well, I'm just sweating the details. I'm like, I'm sweating my work I'm like, chasing down all the corner cases and whatnot. As it turns out, if you don't have 10 friends on Facebook, Newsfeed is worth shit to you. Solving that for people who sign up for the service in their first day is far more leveraged. It may not be as sexy as working on a newsfeed, but guess what? Who's moving the business forward? The person chasing down these edge cases for, like, a hypothetical scenario, or the person who's actually ensuring deterministically that Facebook's absorbing new users, engaging them with the people that they know, and making Newsfeed a relevant product for them, you know, days or weeks after they sign up. That would be like an example of leverage. Is that an okay example?

Yes. Accepted.

Sorry, Mark.

I figured it out.

Let's do one more question, then we'll take a couple more and then we'll wrap up. We can pass on this if you want. When do you think?

Good start.

The thing about the thing is, he's.

Staring at me as he's saying this.

I honestly think it applies to everyone in this room. And just because you talked about Facebook, it's very relevant. But how do you determine or start. When do you start thinking about when those decisions have the potential for negative impact 10 years from now? Is that even a conversation that happens? And if it wasn't, like, how do you think about that today?

Fourth dimensional edge cases, where.

Where do those conversations start for you today, now that you're all doing, like, highly diverse things at high levels?

I, I kind of, I'm like, if we don't talk about that now, when are we going to talk about it? You know, I think you have to be thinking about it.

So is that a conversation that came up a lot in the Apple days, or was it like, we have this problem to be solved, let's solve it and then hope for the best that nobody abuses it?

I don't think. I mean, I don't think it was at the top of people's minds the way it is now. Yeah, like, when I think about the time well spent movement and all of that stuff. Yeah, that's something we're talking about now. I don't think we were talking about it nearly as much 10 years ago.

So there are a bunch of excuses that I can make. Right. One excuse is that software did not reach as many people back then as it does today. People joining Facebook were not thinking, this will someday be relevant to 2 billion people. Right. 2 billion people didn't have access to software, period. Right. Or Any sort of device, like the smartphone, had not yet been invented. And so I think that there's like, the scope of impact of software today is extraordinary. It's much higher, and therefore the stakes are much higher. Decisions that are made at the team level, at the individual level, do cascade out into the world in very profound ways. That's a tidy excuse. But I think that one mechanism to prevent for irresponsible decisions, or at least to be a bit more socially responsible, I think the one potential hack is just investing a bit more upfront around culture and how companies make hard decisions. How do you sort of trade off? Because before any software is written, there's an existing culture around hard questions, sometimes ethical questions, and how those conversations are conducted, and then how decisions then come or arise from those conversations will dictate what software gets written or what designs will get implemented, or even what opportunity paths will be explored. And I do think that that is a reckoning that the tech industry must fully internalize. That is now a new cost of doing business in order for us to be able to build, like, more ethical companies and ones that can be a little bit better about anticipating some of the ways in which, like, the software that we build can be abused or that can create, like, structural inequalities in society today.

Yeah, I would love to see more people questioning things more deeply now, like, starting now, going forward, now that we have the access to data that we have now that we didn't have back then and have seen the way that things have played out, especially in the last 10 years. I think to some extent, we were thinking about it as much as we could back then. But, yeah, the tools are totally different now. The way that we process our information is totally different now. Especially when I think about design as a discipline and the fact that we have this power to envision things and have other people see those visions alongside us, I feel like we're uniquely positioned to paint what that picture could be and so feel like we need to use our tools for that, which is part of the reason why I'm part of this weird experiment that's a nonprofit that ships software in education.

So, yeah, I feel like there's some risk in the fact that what designers do is fun and, you know, a lot of times that we can let a lot of joy out about what we're making and we're creating and we're innovating and we're trying new things. And I hope we're all striving to be empathetic for the people that are using it. But a lot of times I feel like we tend to lean on the positive experiences, right? Like, the edge cases are one place where we start to, like, dive into, like, oh, how could this go wrong? But one of the other things that we have to ask ourselves that's really hard and sometimes, like, scary is like, well, what are the bad things that can happen and what could the bad people do because they are out there and they can use the product and they're going to use the same product. And sometimes, you know, good things with good intentions do go the wrong way. And, you know, we, I mean, obviously Lyft and Airbnb, like, these are, you know, sharing economy companies where, you know, the world, strangers are coming together. And it's a lot of hard work to ask yourself, like, what. What could go wrong? Because the answer is quite a bit. And, you know, we have a lot of work to do in order to put people in the right position. And some of the, you know, random, like, safety precautions we put in place, like, we'd never have to do for ourselves because we're good people. But, you know, we're not the only ones using it.

Stranger data, I think. Chiakeezi and I. I'm nodding at Chiquizi, who's in the audience. We were talking about it just before this session, and he was saying how he's come up with the idea of, like, what is the bad, quote, unquote, bad user. I'm not a believer in dichotomies, by the way, as far as categorizing people, so I just need to caveat that. But we called it the troll.

I'm always a bad person.

We called it the troll flow because we've been talking about main user flows. Like, what's the main troll flow? And I believe really strongly in the curb cut effect, which is, like, when you create something that may be considered to be something to support a small case of people that might have a special need, as in the people that might be on the butt end of what a troll flow might be, then you wind up making things better for everybody. The curb cut effect, if people are familiar, has to do with the way that we've cut sidewalks in cities so that wheelchairs can make it up and down. But everybody benefits. Anybody who's ever had a roller suitcase or, you know, a stroller or grocery, you know, all of those things. And it was originally fought for by people in wheelchairs, but everybody's benefited. So, yeah, I take a lot from the curb cut effect, and I feel like, we need to design software that way.

Maybe there's an element to scale, but it seems really hard to think about the troll flow at early stages when those troll flows will not get hit, at least in the foreseeable future.

Is it high leverage?

That's something that Bryn and I are working on today, is how do we think about spam and moderation and banning people and reputations within a platform when today we're just not big enough to have those problems. They don't exist. So we build a lot of code for problems that don't exist yet, and we just hope that we're being proactive.

How do you do that?

You know, you're going to be big and huge and amazing.

It's going to be a lot of hard work.

Thanks for the faith, Katie.

How do you. How do you justify that? Like, it makes sense in Airbnb, at a Google, at a Lyft, like, you got millions of users. There's some bad ones. Let's figure out how to deal with this kind of stuff. But how do you think about it at earlier stages when, like, you can see that these problems are going to come, but you also have to make this business successful financially and live long enough to see that day?

I mean, those big companies, it's really hard to change it then, right? When you realize that, like, you know, you haven't been taking care of, like, people's private data in the right way, and then you've got a billion users or more like, that is going to be a much harder problem to solve than, you know, in the early stages. But I get you, like, in the very early stages, when you're basically, you know, you're just trying to keep the lights on and you barely have any users. Of course, like, don't spend all your time trying to, like, make that system airtight. I don't know when the moment is, but definitely, you know, before you, like, you know, get caught having done it wrong. And I don't mean caught like the police are after you, but, like, you know, you. You backed yourself in what happened then.

Though.

You gotta get ahead of it. And I think, you know, like, and there's probably also a classification of, like, how bad is the stuff, right? Like, people's personal data is a big freaking deal. And especially when you're a young company and, you know, if you've got credit card information or user data, like, those things you just, you just don't mess around with. So you probably. And I would highly recommend if you have questions, reach out to experts that have been through this before and learn from what they would recommend. But it definitely is going to require different things for the severity of the issue.

For the sake of time, we can let y' all ask a couple questions and then we'll wrap up. Do we have a mic somewhere out there?

It's this one.

It's that one. Cool.

It reaches most people.

You can just get up and come up to the mic too.

Or that. Yeah. Hi. Maybe we can form a line behind.

John, you have to stand up, right.

And can you introduce yourself? Hi, I'm John Gold. I'm a junior design technologist at Airbnb.

Thanks, Ben.

How do you.

I guess this goes back to the.

Kind of career paths conversation and slayer you were talking about. High leverage opportunities. I think this is kind of related.

How do you weigh up the having.

The follow through or the grit or.

The kind of perseverance to deal with things versus the.

Opportunity cost or the sunk cost of kind of not going after other things?

I think there's always a tension there.

Of do I keep slogging through this.

Thing or is it time for something.

New, or am I being too flighty?

Sorry, Brian.

Chesky, can I repeat the question back to you to make sure that we've all understood it? So you're asking how do you navigate the tension between following through with something versus trying a bunch of other new things that I'm not sure if I understood?

Yes, hard questions are hard.

So this could be with regards to a career move, or it could be with regards to, for example, a project of yours that you're fighting for at work.

I think there's always a time when it's time to move on to something else. This is all asking for a friend.

There's a.

You know, when I was growing up, I used to read 37signals, had this great blog, Signal vs Noise, and they had this really great post about paying attention to when the code pushes back at you, which I thought was a really novel observation. What I've observed myself personally is that sometimes the code is hard to write when you're not doing the right thing. It's kind of. It's counterintuitive, but sometimes it's like maybe the code is pushing back at me.

Or like the copy explaining the feature to a user is hard to write because you just shouldn't have that feature at all.

And so I've kind of generalized this. It's just like the universe is giving me a lot of friction right now. I've sort of generalized the it like the Matrix is telling me, this is not the path I should be taking. I find that sometimes it helps to lean on people who know you well, who you trust, to sort of give you perspective on where you are at. And sometimes they can offer like some pretty interesting suggestions as to paths you have not yet considered because they're just familiar with who you are, but have just a different pathway. So they can often surface ways to get around an obstacle that you hadn't even considered. And that more importantly, the people who know you best know you're well equipped to execute upon right where you're like, well, you can jump really high. Did you think about just vaulting over it? Oh, yeah. I don't know why I was trying to climb over that dumb rock. I stubbed my toe a bunch of times. I should have just vaulted over it. Maybe it's a terrible analogy, but I do think that if you don't have those friends who can tell you if you've got ups or don't, then you need to go find those people. I think that those conversations have been some of the most influential for me. When feeling those friction points, sometimes they are your manager. Those conversations need to be had with your manager. But I do think sometimes it helps to have your contemporaries give you some perspective on it, give you a sense of whether or not you should be leaning into the opportunity or if they're like, I don't know if you're going to be good at this and I'm going to be straight with you and tell you that, like, this doesn't seem like you're set up for success or that you're going to be fruitful in this endeavor. You had expressed this phrase like, listen for the knocks. I think part of it's that too. It's like listening, like, is this resonating with me? Do I feel like I'm creating energy or am I creating headwind for myself?

It's an interesting thing coming from a vc, however, because historically startups, if it's a good idea, you're going to have to beat people's head over with it. And there's a lot of very successful companies that we hear their stories about 55 no's or whatever, or 5,000 no's, whatever it was before, that they could see it through. So what do you tell somebody who's also dealing with that? The universe is telling me to stop, but then they might not see their startup through.

Yeah, I think that in the case of Robinhood getting, I'm guessing you're invoking Robinhood. I would have put money in Robinhood. I think that again, in this case, maybe it's people who lack deep familiarity with you that's saying no. Or maybe it's just an angle of attack that you had not yet considered. And sometimes breaking out of your current context can help you get that perspective. Sometimes you're just not ready for it either, I think. And it's sometimes okay for you to just say like, I don't have it in me to do this right now. And that's okay. I think that sometimes we can be a bit unforgiving of ourselves when we're not well equipped to do great work. The important thing is to put yourself in a position to do great work and be aware of the fact that, yeah, you can sink a lot of time and energy and hopes into a path that may be fruitless, but it's hard. I wish I had a formula. I'd put it in a book and sell it to y'.

All.

It's not. It's not quite as formulaic as that. But the thing that has been helpful to me has been leaning on people who I deeply respect, who I feel like have known me over time. My best relationships are very long standing ones. And I think that having those long arcs gives people a lot of perspective on who you are. They sort of see the through line and because they're not neck deep in the weeds, they can often be the best person to have like an intuition for how you'll excel or what pathways you might want to consider.

Yeah, I think there's some advice that I give, especially students to like early.

Career.

In a way, to kind of think about their path forward. Different people have different ways of splitting this up, but I kind of think of these three things when it comes to work. There's how fascinated you are with the problem that you're actually solving, and whether that be technical or from a design standpoint or whatever. Then there's like all the stuff on paper, which is like your position, your title, your equity, all of that stuff. And then there's like, what's your daily experience? Are you around people who support you? Are you working with friends, et cetera. And I've noticed that people tend to have their priorities in one way or another. Most people aren't exactly balanced on those three. So, for example, I think a lot of people that work, for example, in research academia are super fascinated by their problems. They're not necessarily getting paid very much. Some people will work someplace where they get paid a whole lot of Money on a problem that doesn't really matter to them, but they're just fine. They're coasting. Some people will work with friends that they love coming in to see every day, but the problem is just like a fun little, like, doodle, like, you know, little itch that they're scratching, and they're doing it for almost no money because they're starting a company with friends or whatever. So depending on where you are in life and who you are as a person, that balance will be different for you. And I find that using that as a way to kind of think about what's important to you now and here and what you're going to get in your current spot versus another spot, it can be helpful to split things up that way. The other thing I'll add to what you were talking about as far as having, like, a little. Some group of people that know you really well, is to. To try and find people that are going to take different angles. Because I had a really difficult time deciding to take the position I have now. And one thing that was really interesting when I asked friends around me what they thought was that there were patterns and it was completely controversial. There were some people that were like, absolutely, do not do that. That's the worst thing for you. And some people are like, wow, that's amazing. You should absolutely do that. And that was really fascinating because they were all people that knew me really well. But I really appreciated having totally different perspectives. And then that forced me to do, like, a deeper analysis on, like, why is it that these people have such different perspectives? And all of them know me really well, so.

And if you are considering a new design career, you should talk to me.

Same or me.

Hi, folks.

My name is ati. All of your experienced designers, design leaders, technologists.

So everyone here is here to hear advice from you.

I'm curious what you need help with in your own life, in your professional capacity. Like, what do you need help with?

Design details. Favorite intern, Addy.

No longer an intern.

I don't know. This is where you were going with that. I guess my first answer would be just shutting off. I go home at night and I maybe spend a couple of minutes with my husband and my dog. And then next thing you know, I'm opening my computer and I'm back in there again. And it's just a vicious thing. It always pulls you back in. And I guess part of the joy is like, well, I like my work, and so that's why I'm doing it. And I wouldn't be If I didn't. But of course, like, you know, the things that we're leaving behind by doing that are just like, you know, you don't notice it until too late. And I really want to get in a better habit and make time for my family, my life and things that are not behind a screen. So if you can help me with that, that would be awesome.

More snacks.

I'm gonna do it.

Such a good name. Everybody loves snacks.

Is that the type of question you wanted? Okay.

Soleo doesn't need help.

It's harder.

On the contrary. Yeah, well, I've got sipa. That helps quite a bit. No, I'm just running this like, sort function in my head. I'm like, how do I sort this massive list of things?

Is it a binary sort or a bubble?

Sort of.

I think so. Professionally we are in the business of like predicting and seeing the future before other people do. If you see any. I need help seeing around corners, especially around corners that we're not looking at. So yeah, if you know of entrepreneurs.

Or if you know of a hot.

New startup that sees around corners.

No, I think before companies there are people. Yeah, sometimes, you know, a lot of times, like when I, you know, we're very fortunate to have terrific mentors in the venture community. And a very consistent thread that I've observed is that these deals aren't won like in real time. These are like long standing relationships that are established years before the entrepreneur embarks. And so seeing around corners is meeting exceptional people before they step up to the plate and embark on something big and really hard. So that's. That to me is a.

That is rough when you're not here.

That is very rough. Yeah. But I think that, you know, again, if opportunity is network bound, then the most leveraged thing that I can do is expand my network, try to have a larger network. And that's through you, that's through the people tuning in at this hour. Yeah, it's just getting introductions to folks that are maybe just outside of that network. It's extremely helpful to us, especially if there's like the. Why the thing that you see that maybe nobody else sees in that person, what is that sharp edge that they're going to cut the world with? I think the other piece is. I wish I had a little bit more perspective on. This is going to sound kind of absurd, but on the design community today, I think that in starting this business we've become so like, heads down, neck deep in like the dark side, becoming venture capitalists and being good at it. You know, trying to be good at it. And so with that, like, we spend our times, you know, doing very different things than I did as a designer. And so it's often helpful to get perspective on how much the landscape has shifted. Things that I'm concerned about in the near term is here in the Bay Area. We are pricing people out of opportunities, right? People in tech, we're pricing them out of opportunities, and we're continuing on a path that does not seem sustainable for this ecosystem. And I would never have pictured, say, six years ago that there would be, like, such an existential threat to Silicon Valley, but it is very real. It is at our doorstep. And it's one of those things where once it starts, it's really hard to unwind. And so I think that, you know, tackling that problem, I want help with that, because it's a policy problem, but it's also a community problem. And it's something that I think that we, as an industry, we can either just, like, let it happen to us, or we can take, like, a more proactive stance on it.

Yeah, I'll add to that. Yeah, I feel super strongly about that and things along those lines. I feel like one way that one thing I need help with is that I often find myself in the position of being a bridge. I'm a bridge between different cultures. I'm a bridge between different economic levels. I'm a bridge between different fields of study. I wish that more people would get out of their bubble and go speak to people that are not in their bubble, because I feel like, especially in tech, especially in the Valley, people get super caught up in getting the next fancy. I don't know what it is. And don't talk to their neighbor on the street who is getting priced out of San Francisco, even though they've lived there for 25 years or whatever, whose rent's just gone from 1600 to, you know, 4500amonth, and now they're having to commute two hours from Richmond, you know, and, like, we keep talking about it like we care, but it feels like there's this, like, fog of blurry stuff between us and reality, or at least that seems to happen for so many people. And I just wish that we were all more proactive both ways, you know, in or in all directions of getting out of our bubbles and being those bridges and being super interested in things that are so far outside of what our comfort spheres are.

And history will not look kindly on us if we don't alter the course of how we're headed right now. It's a weird perspective to have, but I think it's an essential one. Because if the world is really starting to be reoriented recentered around technology, then these decisions really do add up to where we go as a society and a species at large. And the design industry in tech can either play a role in it or it won't. That choice is really up to us.

We're over time.

I saw you two exchanging looks and.

You should have seen the texts.

I think now's a great time to stop. We can go grab another drink, hang out while y' all are here. But let's. So let's. Let's take a break and end it there.

Thank you all so much.

Thank you.

Really appreciate you guys being here.

Brian and I feel very lucky to have made it to 250 episodes with pretty much the support of everyone here. Like, most of you have been on the show or support us in some way. Thank you all for doing that.

Yeah. Thank you all.

It's been a weird three and a half years, but the best ones, it's been real good.

Yeah. Thank you.

Thanks, Sarah, our producer, Sarah.

And who we would not.

Sarah doesn't like our show, but she produces it every week regardless.

And of course, huge thank you. To combine Soleil Adam for the space. It's amazing. Thank you very much.

Thank you. Combine. Thank you for having us.

Thank you for being on the show.

Thanks for having us.

We invited you like a week ago. I'm so sorry.

The real story behind this episode was we always try and record on the weekends, and then we release it the next Wednesday, which we try to record.

On the weekends because we remember we have to record on Friday.

Well, last week we were like, shit, it's Friday. Thursday maybe. We're like, well, we haven't planned anything. It's 2:50. I don't know. Let's just email everyone and see what we can pull together.

So I idealized a panel before 200. For 250, I wanted to do a panel. I want to do a live show. And then I never got around to it. Thank you for putting up with us.

Yeah. So thanks everyone for coming on such a short notice. Appreciate it.

Awesome.

Cool. Let's go grab a drink.

That was 250. Hope you enjoyed it. We certainly did. It was maybe the best way we could have celebrated such a milestone. I think we had a blast. It was fun to get to stream it and share it with a bunch of people, but also have, like, a room full of some of our closest friends.

Let us know what you thought of this 250 in our Spectrum community at Spectrum Chat SpecFM. And of course, before we go, huge thank you to Abstract for making this particular very special specific 250 milestone live panel wonderful extravaganza Extravaganza possible.

Abstract. Again, it's a design version control system that makes it really easy for you to work with your team and move faster, build momentum, iterate quickly and not have to worry about losing things in the process.

It's gonna make your life easier. Go try a month for free@goabstract.com Once again, that's goabstract.com thanks so much to Abstract. Thanks Abstract and thank you for listening and joining us on this, this 250 episode journey.

It's been a long one and also I'm going to be leaving the show at 256. So episode 256 will be my last episode. That is basically five years worth of episodes if you go weekly. It's also a multiple of eight, which we've been advocating for since the beginning. It's also exactly double the number of initial guests we reached out to. We made it that far.

Numbers. Pretty cool.

Remember those like two episodes where I tried to like name interesting facts about numbers? Yeah. Let's not do that ever.

I'm still figuring out what, what's going to happen with design details after Bryn steps away. We'll be posting more updates in Spectrum and on Twitter, esigndetails FM or Spectrum chat specFM.

Yeah.

See you next week.

SA.