Deliberate Discomfort –

Cute kid credit: Brielle Gundersen

Adapted from a talk I gave at Forge Conference on September 26, 2016

You know that eager-to-mess-with-you someone (cousin, sibling, friend, etc.) that pushed you off the diving board before you were ready to jump? Discomfort is like that someone. You’re angry at first because the experience was scary and mildly traumatizing, but in the end, you’re actually glad the person did it. And from that day forward, you can face that diving board over and over again.

This discomfort has guided me for many years, where seeking out the unfamiliar kept me ready for the turbulence of startup hustle and product design life. I’ve learned many lessons from the uncomfortable turns, and through a handful of personal stories, I’ll describe what deliberate discomfort means to me and how it’s affected my career.

A fish out of water

I always had the tendency to be risk averse. I’d choose certainty over anything unknown, and that led to a reliance on status quo and the stability that came with it. While this approach sustained me through college, what it didn’t do was provide a clear picture of what might lie ahead. Here I was, a Berkeley grad, with a ton of student debt, no job, and no idea what I was going to do.

I was reflecting on this time with a wise friend of mine, Jenn, who neatly summarized my situation like this: When you’re frustrated or anxious, your body is just telling you to grow. Back then, I think I was following that very impulse, and I’d eventually learn that in order to grow I’d need to get used to taking more risks. Wrestle with discomfort a bit and try to emerge from it. So, as I was preparing to leave Berkeley, I decided that’s how I’d proceed. Get uncomfortable and learn to struggle.

My buddy, Davis, and the moving truck, somewhere in South Dakota

Having never lived outside California, I thought a good forcing function for change would be to move far away. Go to a place where I had zero history and hit the reset button. So, I switched coasts and drove across the country to Providence, Rhode Island. Upon arrival I got a job waiting tables … at a restaurant that was kind of known for it’s mafia ties. The truth is, there wasn’t a hot job market for confused new grads with environmental science degrees, and I needed a way to subsist. The restaurant was classy, the people were friendly and not at all gangster-y, and even though I once slipped and threw the dessert tray all over a dining room full of paying customers, no one made me disappear. It was a reliable pay check, but it was clear that I wasn’t cut out for the restaurant business.

Seeing that I was struggling, a fellow waiter referred me to a temp agency; “Save yourself,” he advised. I landed a job as an editor’s apprentice at a lottery technology company where I’d spend my subsequent working hours redlining business proposals. Not exactly the career path salvation I was after, but the opportunity did lead me to occasional run-ins with the design team. They actually had a design team doing all the page layout and graphic design for these printed proposals. Out of genuine curiosity in their work, I’d pick their brains about their tools and their craft, and inspired by those interactions, I came to realize that this was what I wanted to do. I wanted to design. Even if it was going to be business proposals, I wanted to play a creative part and make things. Soon thereafter, the company was paying for foundation art and design classes, and eventually, the team made room for me on the squad.

This was the opportunity that introduced me to design, and while this job wasn’t precisely my calling, it cracked the door open just enough for me to catch a glimpse and get excited about design as a possible career. I had to be there in Providence, to work at the mafia restaurant, where I’d meet the guy, that would refer me to the temp job, that revealed design to me. It was the butterfly effect manifest.

Embracing my inner imposter

After Providence and a subsequent move to Ann Arbor, MI, I decided it was time to head west again. The web was blowing up, and I had to give Silicon Valley a closer look. Yet, like a freaking masochist, I again moved cities without securing a damn job. Nevertheless, my previous experiences gave me some confidence that I’d land on my feet. I had already been pushed off the diving board, and I was determined to be in SF and exist.

Somehow, I scored a design gig at Yahoo!. A proper visual design role on a proper User Experience Design team. I knew what I knew from earlier toe-dips into design and UX, but in the grand scheme of things–here at the epicenter of all things technology–I was relatively green. This was a world-class design team at one of the biggest internet companies on the planet. But I was there, and I had to get comfortable with feeling like a bit of a fraud.

Experience has taught me that being a solid imposter goes hand-in-hand with developing a keen sense of self-awareness. You know what you know, but as Confucius posited, “true wisdom is knowing what you don’t know.” With time I came to realize that imposter syndrome can be leveraged as an indicator. It shines a bright light on the areas you should probably improve; the subjects you want to better understand.

At Yahoo! I began developing an understanding of the product design process, but in execution I was too deliberate. I worked tirelessly to improve efficiency, but I wasn’t as prolific as the other designers around me. Frustrated, I reached out to my buddy, Sam, for some advice. Sam was a colleague and fellow designer that had it dialed. Work-wise he made things look easy, and was regarded as one of the best designers at the company. While I’m struggling just to deliver my features, never mind feeling good about the quality of the work, Sam’s over here playing kickball on weeknights, juggling multiple side projects, and generally kicking-ass at life. This did not compute.

Arial, our Boston Terrier as incredulous of this Ugly Doll, as I was with using Illustrator for UI design

We started talking about his process a bit, and he showed me how he used Adobe Illustrator for UI design (back then, everyone including myself was using Photoshop; Sketch and Figma did not exist). So, I’m watching him work one day, and his hands are ablur with keyboard shortcuts, right-click-spawned contextual menus and strange drawing tools, and the output was incredible; precise, too. Exchanging notes, I then showed him a feature I had spent weeks designing in Photoshop, and he says, “let me see that … I’ll recreate it in full vector by end-of-day tomorrow.” I was like bull-shit, $10 bucks says you won’t. And you know what? He nailed it, easily. A perfect, pixel-for-pixel remake, and he didn’t even collect his money. Plus, I could edit every attribute of every element down to every corner radius. Mind blown.

Up to this moment, I thought I had my hard skills on lock. However, once I observed someone with real chops, it became clear that I didn’t know my tools so well after all. This simple examination of my technique ended up changing the trajectory of my design career, and exposed the one thing I needed to improve to get out of my own way. From that point on, I made myself struggle with Illustrator for every new project. Then something started to happen. By forcing myself to practice, forcing myself to master my tools, my chops started to improve. This facility then gave way to production speed. Production speed gave way to creative output. I could finally focus on actual solutions, and eventually, my managers noticed. My assignments became less tactical and more strategic, and I was given more runway to explore. I learned to embrace and jiujitsu that inner imposter to highlight and attack areas in need of improvement. This was another fundamental shift for me, and the experience gave me the confidence to push a few more boundaries and grow creatively.

In Julie Zhuo’s reflection on imposter syndrome, she offers some additional perspective on the subject: “Experience makes anything look easy, but insecurities never fully disappear. … Here’s the thing though: it gets easier. You start trusting yourself. You’re an imposter less and less, and you’re yourself more and more.” #truth.

Professional puberty

I’ve been at Lyft now for 4 years and 10 months; where–like dog years–one year at Lyft equals four years at the mafia restaurant. So, I’m on a long run, and it’s been one of the most rewarding, and at times, most uncomfortable journeys in my career. Throughout this time I’ve experienced multiple inflection points. The roles, the priorities, and the people all changed many times over; but again, it’s good to experience that change. Like going through growth spurts, your clothes never fit; you’re always growing out of something too small, or growing into something too big. So for me, what this has all amounted to is a professional puberty that I experience now every year or so. Certainly uncomfortable, but a necessary coming of age.

Lyft’s first billboard on Brannan Street in San Francisco, CA

Product Management

When I started at the company, I knew nothing about transportation. I had never worked at a small startup, and I had never worked as a product manager (the role I took on soon after joining). I took the risk to learn something new, and I got the nod to be the Product Manager of the mobile team. While I knew mobile and UX and how product managers worked with designers, I did not know–in detail–the full scope of the product management role, where the more technically fluent, organizationally disciplined specialists tend to succeed. I would learn soon enough, however, and would take my lumps along the way.

There was one project in particular that really tested me as a PM. It was just before Thanksgiving 2013, Lyft was about a year and a half. The mobile team was hustling to ship a complex set of features before the notorious December-AppStore-freeze-armageddon (if you’ve ever shipped an iOS app around the holidays, you know exactly what I’m talking about). But, we kept hitting set-backs. We go to exec review to share our current status, and the questions start flying: “Why hasn’t this shipped? What are the technical hurdles? Why was this taking so long?” Well, feature creep, for one. The priorities kept shifting. We couldn’t decide on some implementation specifics … I had a bunch of excuses. The problem is, no one in that room wants to hear that shit.

Early version of the Lyft iOS app

As we’re closing the meeting, my manager asked me to hang back for minute, and I was like, damn, I’m toast. The questions continued: “What was the ship date we last agreed to? That puts us how many weeks behind? What are the current blockers, exactly? And you haven’t stomped them out because …?” And the kicker, “If you’re having so much trouble getting this done, do you need me to handle it for you?” It was that last one that really snapped me to attention. The real-time translation going through my head went something like this: “I’m about to give you an opportunity to fix this. Succeed and survive, or fail and walk.” I had it coming to be honest. I wasn’t steering the ship, and the team was thrashing because of it. That was unacceptable. So I blurted out, “No need to step in, we’ll ship in three weeks.”

Now, I had to ask the team to dig deeper still, to come into work the next two weekends, and do everything possible to get this built, tested, and across the finish line in three weeks. And they would’ve been perfectly justified in telling me to take a hike, but to my surprise, there was not a single detractor. Everyone rallied and helped execute the plan to get this done, and we did. We shipped the feature set and it helped streamline our driver-side operations to get more drivers on the road. It was a humbling experience to say the least, as well as an important lesson in leadership. Yet the more dominant feeling washing over me was this realization that I was reaching my limits in this role. My self-aware voice was telling me, maybe this wasn’t the best thing for you; maybe carve out a role that you’ll really love, a role where you can add meaningful value. So I minded that signal. I decided I’d go back to my roots and shift my focus back onto design impact and scaling the design team. A new role, a fresh challenge, another inflection point. Bring it on.

Design Management

So, I’m a Bear Grylls fan. If you’re not familiar with the guy, Bear Grylls is a British survival expert and reality TV star. Also a veteran in discomfort–more of the physical kind–though he’s probably most famous for drinking his own piss.

Bear Grylls “Loneliness” meme

While I don’t share his enthusiasm for pee, his approach to survival and his methods for staying motivated do resonate with me, particularly in my role as a people manager and design director. When you’re lost, you get to higher ground and gain a vantage point and plot a course. If you hit an impasse, don’t panic. Stay positive, stay active, and adapt. Improvise or collect a good set of tools that will help you negotiate the elements. Do these things, and more often than not, you’ll come out the other end. It’s good stuff.

Gain a vantage point

During the early days at Lyft, a nice perk that came along with being a people manager was getting our own coach. One of the first conversations I had with mine was about feeling overwhelmed in the new role. I was spreading myself really thin, and running around like crazy just to maintain order and cover the gaps. Hearing this, the advice he offered was simple: “Focus, man.” Learn to empower your team and delegate, and do fewer things well. But one of the biggest hurdles for me as a new manager was that I wasn’t sure how not to lead by example. If I wasn’t producing design artifacts or building product, what would be my perceived value? Worse than an imposter, what if I’m just a vestige. After some discussion, we concluded that design execution was not really my primary role anymore. How could that be? Well, my output was really the team’s output, and more importantly, that’s what I’d be measured by. So, my managers already knew that, which was a revelation.

A dude on a rock enjoying a nice view at Joshua Tree

That small mental shift made my priorities as a design director suddenly clear. Simply do everything necessary to help the team do their best work. Create space for the team to operate; get them the resources they need; remove any speed bumps; and be the umbrella when the shit hits the fan. So, now that I understood my role and how I could add value, I was free to focus on team health and output.

Positivity and culture

I’m going to brag about my team just a little bit. Internally, the product design team is known for our incredible culture, and it’s by no accident. Early on, we decided that we would build the team around genuinely good people (in the human being sense) above all. Of course, skill, craft, and a passion for Lyft were also table stakes. In maintaining that bar, we might have passed on some really amazing people, and some really amazing people passed on us; but the team that we brought together truly became something special.

The Lyft Product Design team in 2015

Skill wise, when you’re small, you’re typically looking for multi-stack designers. The idea being you can give them any project, and they’ll be able to take ownership, execute from snout to tail, and assume full accountability for the outcome. Inevitably, though, we fall short here or there. The thing is, we’d always be at the ready to bolster any weakness, and support any failure without judgement. It was critical that we not allow anyone to fall too far.

Tactically, we’ve always kept the product engine humming. In the early days, this was, in fact, our charter. Honestly, there was little room for flourish back then. We had to be about nailing the basics with less focus on the shiny, which is a hard pill to swallow for us creatively-driven people. Yet the team was steadfast and united in that regard. Everyone selflessly rallied behind this shared focus, and we took care of each other when we were stretched to our limits. As a team, we’ve grown up a lot, and we’ve brought in many new people and points-of-view. Still today, our culture is very important to us, and we’ve worked hard to maintain and evolve it as our team has grown.

Develop a tool

As a design org, we’ve also had to evolve and adapt with time. Just in terms of size and scale, you operate much differently as a team of 2 designers vs a team of 5, or 50. For example, at 2, we didn’t have a ton of process. In fact, we had almost none, and that was appropriate at the time. Less overhead helped us move quickly and keep pace with product and engineering. We didn’t emphasize optimized communication either because the flow of information was naturally good when the team was small. But at some point, you need some structure and process to remove blind spots, create efficiencies of scale, and improve quality as the team grows. One such tool we developed was a set of design principles.

Our design principles are based on Maslow’s hierarchy of human needs (I realize this is the new Venn diagram, but I swear our principles have been around over a year), where you start with sound fundamentals and a solid foundation, and build each subsequent step upon the previous.

  • Principle 1: Nail the Basics. We have to be sure we’re asking the right questions, solving actual user needs, and understanding our customers’ priorities as deeply as our business priorities.
  • Principle 2: Build Confidence. Here we focus on consistency and a systems-based approach to design. If we do that successfully, we build more trust in the product. That trust builds confidence in our experiences and our company, which then improves customer loyalty and brand affinity.
  • Principle 3: Be Unique to Lyft. Having addressed the first two principles, the ambition here is to make our solutions ownable. Do things in way that only Lyft can do well.

What we don’t do, is jump straight to the 3’s without addressing the 1’s & 2’s because we’ll only frustrate our passengers and drivers if we can’t deliver on the basics.

So, adopting simple frameworks like the Bear Grylls-inspired method above helped me develop as a design manager by compartmentalizing my responsibilities and slowing the game down a bit. But I had to first jump into the uncomfortable void to engage these new experiences and identify opportunities to earn my stripes.

Wrapping it up

In summary, consider how you might get comfortable with discomfort. I’d encourage some purposeful changes to your routine to help develop resilience–especially if you’re at a fast-paced startup–because change will be incessant and unpredictable.

  • Try a new environment, work with new people, you don’t necessarily have to go very far.
  • Be an imposter, but be self aware and confront your weaknesses.
  • Look forward to regular and constant change. Maybe it’s professional puberty telling you it’s time to grow.

And continue to evolve and seek out challenges that will stretch you out. The discomfort is temporary, you’ll eventually outrun the inflection points … and you probably won’t have to drink your own pee.

Author: Frank Yoo

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