I think day-to-day experiences are always a tough question to answer because it drastically depends on the type of project, the people you’re working with, and the phase of the project. Lately, I’ve been working on some projects that are much more collaborative and systems thinking than I had before, which has been a cool opportunity. I get to work with people from all kinds of teams that I haven’t interfaced with before, and people who are very good at what they do.

And typically what I’ve noticed with them is that they have a lot of strong opinions and they come in with a lot of confidence. To help me be more prepared, I had to be much more intentional in the early phases of a design and really think through how I approach the collaboration, how to approach this problem, and really understanding the type of work I’m dealing with.

So I spend more time talking to people, summarizing different points of view, writing docs and making tables, or finding a breakthrough point for the problem we should tackle first and laying a good foundation for future designs.

All of this is really trying to get to an alignment of the problem we want to tackle, and the way we want to tackle it, before working with more designers on the actual design exploration. Sometimes that involves making designs for provocation purposes, or illustration purposes, to align the goal...but it’s more about doing work ahead of the “design exploration phase.”

Yeah, provocation work. The work is meant to very clearly, in a few screens and key moments, explain what the tension points are. It’s for alignment purposes and making the discussion more concrete. It’s less for something that’s shippable, or that’s ever going to be user-facing .

It always ends up in some sort of spectrum. Some work is similar to what exists today, what people are used to, and some is very far out and something we may never do. But it’s used to paint the edge a little bit. And then having a couple of notches in between those ends really helps bound the conversation. Everyone is having a visceral reaction to see what’s too far in the extreme, and we can dial back. Then the conversation really becomes where in the spectrum you want to dial in.

I’ve been very unstructured in the way that I do retros for my own work. I felt I went through my entire career so far just going on intuition, and somehow I haven’t failed too hard. The path definitely came with a lot of falling and tumbling, but I think part of it is that I’m lucky to be in situations with very awesome team members who help to course correct along the way, and to have good managers and mentors who also guide me towards the right direction.

But now with the speed some projects are moving, I’m finding it really difficult at each stage to feel confident about what the next step should be purely based on my intuition and relying on others’ timely course correction. As I’m constantly finding myself in situations that I’ve never been in before, it’s triggering something in me to just be a little bit more structured about knowing what are the one or two soft skills that I’m trying to develop that might be blocking me from getting to the next level of effectiveness. I’m starting to jot down little notes here and there of things I’ve learned from other people, or seeing how other people handle the situation in an area that I don’t feel confident in. This gets me to think about things like “what could I have done in that meeting?” Or “if someone else were doing it, what would have yielded better results?”

Yeah. In recent months, the thing that’s been on my mind is “how do I get out of my head?” I think that’s something that I see myself do. For example, when I’m in a new situation – which happens often these days – with really confident people surrounding me, I tend to hole up a little bit. I’m unwilling to share things, or ask questions, until I feel confident.

So that’s one thing I’m working on: how do I get out of my head earlier on in the process? I have to constantly remind myself when working on projects with a lot of different stakeholders that I can never truly 100% know the right solution, because often there’s no right solution. So I have to look for different ways to build conviction or feel conviction, where I’m communicating an idea to help move the project forward at a more reasonable pace.

In some ways I’ve come to embrace the feeling of not feeling confident in situations, because that typically comes when I’m in a new situation. So I know I’m learning.

One thing that helps me get up in the morning is knowing that I’m going to get out on the other end stronger than I am now. I know this because I’ve gotten out of this feeling before, and I’m stronger than I was before. That’s the overarching thing that I’ve learned through all these years: I’m going to get into these situations where I feel extremely bad about everything I do, but if I power through and try to learn as much as I can through the process, I am going to improve.

More tactically, I think that something that has really helped me is building a safe group of people that I can be vulnerable with, that I can bounce ideas off, and knowing that they can tell me the truth. It’s a way to kind of gut check certain things before I share it in a wider group. For example, I would ask really silly things before I have to send a message to a larger group, like “does this sound reasonable?” Or I can try out some weird designs that I don’t know if they’re good or not any more because I’ve been looking at them for too long. It’s helpful to have a fresh eye on it.

I only have two or three people in that camp now, it’s a very small group, but I hope to grow it over time.

I am a good listener, an active listener, where if there are a lot of disparate ideas, if I follow my intuition, I can organize different opinions and ideas into something that can help people find common ground and move forward. So I typically like to work on projects that have that nature. But I think what that leads to is a perpetual feeling that I don’t have a strong conviction because I can see multiple sides.

That’s definitely something that I strive to improve. You need to have both sides: knowing where everyone stands, but also having your own strong opinion. Because I’m so eager to find out everybody else’s side, sometimes I lose myself a little bit.

Another thing I’ve learned recently from someone I really trust is the different ways to have conviction in a conversation. I think typically I find myself to have the most conviction on something when I feel very informed about something. But that takes a lot of time and energy, and we often don’t have that luxury to have all that understanding. Sometimes I can also feel conviction when there’s consensus, like when a lot of people I trust already feel this way. The third way I feel conviction is just a provocation: Putting something out there and feeling really confident that it’s going to invite other people’s strong opinions. And that ultimately shapes a better product. It’s not really the sense of conviction in the sense that you know you’re right, but that you’re just trying to invite other strong opinions into the party.

And I feel that is something I hadn’t really considered before because I always felt I had to have conviction in whatever I say. It’s just a different angle of approaching it.

I think now I’m much more comfortable with saying “yes” to opportunities because I know I’m going to struggle, and I know I’m going to improve, but it wasn’t so obvious in the early days of my career. For example, when I worked at Airbnb, I took on that role simply because I just had this personal dream of working in China and getting to know that new environment. And shortly after I started there as the first designer on the China team, I was asked to be a manager and to help build the Beijing office.

And I didn’t really consider that I would manage so early on, because there’s so much to learn on the individual contributor side, but that just felt it was aligned with what I wanted to grow. So I said yes to the opportunity, not really knowing what was going to come out of it. And I feel like every six months I was asked to have a big step change in my responsibility.

And saying yes to all of those led me to learn so much, or just have a different impact. But they often lead to responsibilities that make me question my decisions in the moment. At Airbnb it was such a new environment for me, both the management and the China design industry. I had to force myself to host a lot of design events, and try to meet designers in the industry. And that’s so far out of my comfort zone...I love just holing up in my apartment, tinkering on things.

So I forced myself to have to have dinner with a designer from a different company every week. That was just a regiment I set for myself. We also hosted a design talk every quarter, where we invited designers from the industry to come. And I’ve talked at big design conferences in China, which was all very painful. But I felt I signed up to learn about being a design manager and to try to build a team, so those are the tasks that came with that responsibility. So even though I felt in the moment I hated those responsibilities, they were things I had to do to truly get the most out of that opportunity.

If anything, just seeing how the management side works has been helpful for understanding how the people side of the equation, like org design and recruiting, really works. And I just started to have a little bit more empathy for design leadership.

Maybe more tactically, one thing I took away from that experience is that it’s time management. As an IC, on my best days I don’t have many meetings. I just dive really deep into something. And for days I can focus on trying to solve one thing. As a manager, that doesn’t come very often. My days were chunked up in 30 minute problems that I have to solve for. It’s a lot of context switching.

And that sometimes happens as an IC, too. So I think one thing I took away is how to be really regimented about the things that I need to get done on a certain day, and finding small chunks of time to work towards a bigger problem.

As a manager it was intuitive to do some small tasks, like repling to emails, during those small chunks of time. But as an IC, I had to develop this new way of working where I’d have that 20 minutes and have to use it to work towards something that would take hours. Context switching really effectively, just compartmentalizing the things I’m working on, has helped with my productivity a ton.

I don’t know if I have anything too insightful to say about calibrations. But it’s important to have participated or helped out on multiple projects, or worked with multiple teams. It’s so helpful when there are multiple people who can speak on your behalf. That paints a more holistic picture, rather than just having one person, like your manager, trying to tell the whole story.

I feel switching around jobs just to be promoted really quickly is not something that I had really considered for myself. And I feel it’s not a healthy path if you want to be in the industry for a long time. If your goal is to become a great designer, and make an impact in the world, that doesn’t seem to be the right path.

It just takes time to really know an environment well in order to have an impact. A lot of the work that we do takes so much iteration, and seeing how people respond to it in the real world. It just takes time to make any change. It takes years for a behavior to form or for your work to have a bigger impact. That’s just hard to do when you’re always thinking about what’s next.

I think once you find an environment that you are learning a lot from, and the problem excites you, it’s worthwhile to stay longer. With each job I’ve had, it’s like, “do I still feel I’m learning a ton from the people around me, and from the problem space?” And knowing what is the next thing I want to learn can guide my next steps. Maybe every year or two, I kind of reevaluate that.

I think it’s more about the learning and the skills, and less so about trying to get the next title.

I definitely think there are times where, especially when you meet someone for the first time or have more surface level discussions, I get scared off when I’m talking to a VP or director or something. I sort of have this innate feeling that I need to listen to them because they’re more experienced than me, or their title indicates or they’re more experienced than me.

I think a lot of that fades away for me after any sort of in-depth working together. Because of that, I also try to check myself in the first couple of meetings to have an open mind and not blindly follow titles. So I think in some ways, I don’t know how much titles matter in longer term product development. Especially at places like Airbnb or Facebook, if you have something good to say, and you’re able to frame it in a way that makes sense, you will garner respect and will have a meaningful influence on the product.

I guess in my experience, I’ve been less swayed by titles and maybe that’s why I’m also less concerned about chasing it. It’s just more about how you conduct yourself at work and what you are able to deliver. That’s the thing that people are going to use to judge your capabilities.

I think as designers, we’re all aware of empathy. Empathy is the core of what we do, understanding our users, and understanding their problems. But I think too, within an organization, it also takes a lot to have empathy for your cross-functional members and for stakeholders, and to really understand where they’re coming from.

The ultimate goal of your team is solving some real-world problem, but to get there everyone will need to get on the same page and work towards a common solution. It often takes some influence to get there, so I think some level of empathy for people you work with is really important for framing and storytelling.

In my early couple of years working at Facebook, I had a manager who was great at storytelling. One thing that we identified as a growth area was presenting my work. So it was really lucky to have him as a manager at that time. We spent some of our one-on-ones just going through how I might present something to other people.

One thing he really drilled in my head is to always have the three takeaways that you want the audience to walk away with. Then you can use those to structure the entire presentation and simplify everything else away. That really stuck with me.

Of course you should also tailor your presentation to the different audience. But I think that’s kind of an underlying principle. My process these days is to have a draft deck where I add everything I can think of under the sun, and then just strip away, strip away, strip away. Strip away to the essence of it.

I think it comes back to confidence again: how confident do you feel? How confident are you in delivering that proposal?

I read an article a couple years back by Mindy Kaling about how she approached confidence. She shared a story about how everywhere she goes, when she gives talks, people always ask her “how can you be so confident as a minority, female, producer in this very male dominant world?”

And in the beginning of her career, she would always give some hand-wavy answer about how she had really supportive parents and, you know, a really loving environment. And she realized that’s super not actionable for people. So then she reflected on it and she felt like one of the reasons why she built up her confidence is just by working really hard and living through all the challenges. In a way she just feels she knows what she’s talking about because she worked for it.

There’s this thing in our industry where we talk a lot about work-life balance and mental health, which are obviously very important. But there’s a stigma against being a workaholic. And I feel like, for me, a lot of times building up that confidence is just spending a lot of days and nights sweating through something. There’s something about just putting in the hours, and putting in the frustration.

I think there’s a group of people who feel confident innately. And there is a group of people who don’t. And you just have to figure out your way of getting there yourself.

I think it’s really important for designers, no matter what level, to keep sharpening your hard skills. And that’s actually one of the reasons why I felt I needed to return to the IC life after a couple of years managing. I felt I was losing it really quickly. The first year back from being a manager was extremely tough. The last time I designed before I became a manager I was in Photoshop, so coming back and everyone was in Figma...

One thing I did when I was coming back was find an environment where I was surrounded by really awesome IC designers to whip me back into shape, and a place that I was somewhat familiar with to feel “safer,” Instagram was the right environment for me.

I think hard skills, and being able to create compelling good designs, is our way for influence. It’s really the designer superpower to create a good product.

I don’t know if this is helpful, but I think I am a naturally optimistic person. I think that helps a lot, having that sense of optimism, knowing that no matter how dark of a place I’m in now I’m going to emerge from the other side. Just seeing that light at the end of the tunnel, no matter how far it may be, it’s just helpful day-to-day.

And I think also being able to find your own ways to interpret what work-life balance means is useful as well. I find it’s a little easier for me to not follow the textbook things, like “you should always take off the weekends.” Working on Sundays is great for my stress-level, because then I feel a little more prepared on Monday.

Another thing I find helpful is to identify one thing you cannot let go, no matter how busy or challenging work becomes. It can be exercise, eating breakfast/dinner with your family, crafts, anything hopefully somewhat healthy and productive. That’ll help to ground you and feel more in control.

Lastly, I also learned to not get stressed about being stressed. In the early days, I would get really stressed about how stressed I was, and that’s a really ugly cyclical cycle

Knowing that I might not be in a great spot, but I’m going to emerge from the other side, is all easier said than done obviously. Sometimes it’s a little hard to see the light at the end of the tunnel, but knowing that I’ve done this before, others have done this before, and finding little tactical things that make you a little bit less stressed throughout the week, has been helpful for me.

I have not posted on Twitter for... seven years, I don’t know how long. I don’t really like to talk about myself or share my opinions. It’s all connected to the fact that I live too much in my head.

I enjoy watching other designers talking about their work and themselves and enjoy chatting with designers in small groups about our experiences. I always take away a lot from those. I always felt my thoughts are not ready to provide any meaningful value for others in a broadcast format. I think it’s giving myself a break on things that I know are not natural to me and to do things my way a little bit.