Kevin Cheng is a Direct of Product, Product Manager, and author, although he is not a ninja, rockstar, or guru. Currently Director of Product at Indeed. Also currently a storyteller, VR maker, and DJ. He previously worked at Product or UX at Twitter and Yahoo, and was Founder/CEO at Incredible Labs.
IA Summit 2015 Main Conference Talk
Topic(s): career development and personal development
A decade ago, my very first talk at a professional conference was at IA Summit. Just 6 months prior to that, I was deciding between job offers for Interaction Designer, User Researcher, or Information Architect. I remember thinking at the time, “This is a major crossroad. What I specialize in will determine my career for many years to come.” The process was agonizing.
The versatility and skills we develop as user experience practitioners allows for many paths in our career. Today, I sit at another crossroad and questions still seem to remain. Product or design? Management, founder, or contributor? Large or small company?
This talk is for those who have been in the industry for a few years and have started wondering, “What’s next for me?”
It’s a vulnerable and personal sharing of experience. It’s also be a look at the questions I asked along the way to help make difficult choices. Sharing these questions and this experience is an an opportunity to give back to the community that helped me start on a path. We’re all sharing part of this path; where yours leads will likely differ from mine, but the questions may help your answers.
Kevin Cheng: Thanks to Johanna Kollman over here, I got the idea to give you all index cards which Tiffany is handing out if you don’t have one already. The index cards are feedback cards.
What I’d like you to do is draw a line down the center. On the left side, put a plus and you can put down the things that you learned from or took away from this. On the right, put a triangle and that’s the deltas, the things you would’ve liked to have learned, things to add or that you think could improve. At the end, you can feel free to just please drop them off with me.
As I was saying, this is an extremely personal and vulnerable talk for me. I have not really done one like this before. A lot has happened from the time I submitted this talk to today.
This year, I turn 40.
Kevin: This year also marks the 10th year I have lived in San Francisco, the city I call home. I have actually never lived in a city more than 10 years, consecutively. When I pass this year, it will be a record.
This year also would mark the fifth year anniversary of my marriage. Unfortunately, between the time, I submitted and now, we’ve decided to separate.
Also 10 years ago or rather 10 IA summits ago, I was not here. I was in Vancouver in my hometown and I gave my very first presentation to IA Summit. That little kid is me at IA Summit 2006. That was not only my first IA Summit presentation but my first professional conference presentation. It’s very meaningful to be back here.
When I submitted this talk, I thought I’ve been working the industry for so long. I’ve done all these different things. I’ve got lots of answers for people. Today, I actually find myself in a place where I have a lot of questions instead. I feel I should be in the audience because I could really use a talk like this.
A little background on me, just to give you a little context of what my path has been and where I’m coming from. I started with a computer engineering degree and I was an engineer for all of two months of my professional career before I discovered HCI and this company Trilogy in Austin.
Then I went to do a master’s in HCI. I went to San Francisco and worked at Yahoo as a designer. Then joined a startup as its first designer. Eventually, also ran product for them at the same time.
I went to Twitter, ran product for the websites. Then started my own startup,as a founder and CEO. Then got apart and went back into Yahoo which is where I’m working now as a director of product. There a lot of full circles in more ways than one when I was at IA Summit that first time 2006. I was also at Yahoo.
The decisions that I made through this had always seemed pretty straightforward. What had been coming to me when I was an engineer, I discovered HCI and I was like, “Well, I like designing things on the side, so this seems like the perfect meld of my interest.”
Then I had imposter syndrome that I did the master’s. That was not helpful, by the way.
Kevin: Because I’ve been doing it for four years already. Then I met people in South by Southwest and it was clear that my people were in San Francisco that I moved there.
Then I was like I want to try a small company that I did Raptr. Then I discovered product management and went to Twitter. By then, I have been there long enough and been thinking long enough about I definitely want to start a company at some point.
Then Twitter threw management changes, let me go and I was on that day, in the shower, I was like, “It’s time to start a company.” Then the company started running out of money and the acquisition market was hot that it was clear that getting apart was the way to go.
All through these 15 years, it seemed my path was very clear. It was obvious what I was going to do next. I always had an idea that at least what I wanted in the next two years, if not five. Now, for the first time, I’m really not sure.
I’m sitting at Yahoo and this how I’m feeling. Like this is Jon Stewart and why he left The Daily Show. He goes, “It’s not like I thought the show wasn’t working anymore or that I didn’t know how to do it. It was more, ‘Yup. It’s working, but I’m not getting the same satisfaction.'”
These things are cyclical. You have moments of dissatisfaction. Then you come out of it and it’s OK, but the cycles become longer and more entrenched. That’s when you realize, “OK, I’m on the back side of it now.”
That’s how I’m feeling right now at Yahoo is that my cycles are longer. Please, don’t tweet that. I haven’t told anyone that.
Kevin: Steve Jobs has another way of saying it where he’s like, “I’ve looked in the mirror every morning and asked myself, ‘If today was the last day of my life, would I want to do what I am about to do today? If the answer is no too many days in a row, it’s time to change something.'”
It was time to change something and I wasn’t sure what. At the same time, all these job offers were starting to come in. Not job offers. Job opportunities, I should say. Head of product, head of design. Places at really well-known funded startups. Places that were exciting. Places with that social impact.
Also places that are small where the entire team are people I’ve worked with before and know to be smart and working on cool hardware things that are super interesting to me. I just had no idea how to decide on these things.
How do I go about it? One way could be to write your own obituary. You’re familiar with Amazon’s method of writing. The press release for a product, before they start any product development. This is Brad Meltzer. He’s an author. He has a TED Talk on how to write your own obituary.
That’s maybe one way to do it. Setting goals is a pretty common way to do it. I’ve not been big on setting goals explicitly. I don’t why. I’ve tended to do theme words. Instead New Year’s resolutions, I do one word a year. I’ve done this for the last seven years. That word is the thing that carries me through that year and is a reminder for me.
Some of the words I’ve used were, realize, listen, nurture, persist, now is one of them, that’s not my tattoo, oneness, and this year’s is focus. Focus on fewer endeavors. Focus on closer relationships, fewer but deeper relationships, and focus on myself.
All of these are great in terms of looking forward, but I’m not sure how helpful they are for me right now either. For those of you that might have gone to interaction, Bill Derusha was doing a talk on don’t have a UX career. He pointed out how long your career is and how really unknown the future is.
We’ve gone through a bunch of cycles already through web, through mobile and who knows what’s next. I realized that although it’s been 15 years, I have more career ahead of me than behind me, still. My career goes through probably to at least 20 to 35.
Also the problems are unknown. What problems will be encountered? What world will be it? If not that, then how do I decide? I could ask myself, “Maybe I can go bottom up? Maybe instead of what do I want to do, I start asking what do I like?”
One of the things I used to talk about when I taught the workshop actually here about moving to product management is do you like perfection or do you like good enough? If you’re perfection, you’re more likely to lean towards design. If you’re good enough, then you’re more likely to lean towards product because somebody needs to ship the product.
That was a thing that I learned at Raptr was I had to pick between those things. Do I like a big company or do I like a small company? When I was at Yahoo the first time, after a year, I moved into the small innovation office called Brickhouse. That was sort of removed from the large company.
I find myself moving in faster cycles this time. I went into Yahoo and within three months I was often at my own little team up in San Francisco outside from the main campus. Maybe big companies not it.
Do I like to work for the leader or the underdog? When I joined Yahoo the first time, I remember my mom talking to me I was like, “I got a job at Yahoo,” this is 2005. She’s like, “Oh, why you not work for Google instead?”
I’m like, “Well, that’s because they’ve already one and there’s more lap side with Yahoo.” I’m not sure about that anymore. I then worked at Twitter later and that’s a leader. That feels really good. It felt good to work in something that I was clearly making a difference.
Then I also did startups and that’s sort of an underdog. I wasn’t sure what I wanted to do there. Am I people person? Do I want to be in hole and work on things? Do I like organizational things as problems? Do I like systems as problems?
I know that I like building culture as a problem. That’s why I started a company was because I wanted to define the company culture. At Twitter, Doug Bowman was creative director. We reached this point where it was very clear that design management was needed and Doug was absolutely not into that.
That’s not his thing. He’s a brilliant designer. He’s a brilliant creative director. We needed somebody else and currently it’s Mike Davidson and he’s doing an awesome job to oversee that part.
Peter Merholz who’s here and speaking in about an hour. He’s found that he loves organizations as a problem. In fact, he’s going to be talking about that and his experience at Groupon, experience at Jawbone. If you find that fascinating, then that’s something to move towards.
Then what industry do I want to work in? Do I want to work in hardware because that seems super interesting to me now? It harkens back to my electrical engineering roots. Do I want to work on something with more social impact which I do? I’m tired of working on something that’s for taking photos and sharing it with everyone.
I also have fun doing those things. It comes very naturally to me. That’s a challenge as well. Really, the list goes on. What about money? What about job title?
One of the things I was thinking about was like, “Well, I need a plan for like I’m not going to be able to learn skills as fast as I used to. So, do I need to build skills that have more longevity like management skills?” Because 20 years from now, probably management, is the way to go to keep up to where I’m going in terms of salary or whatever else.
Do I need to build those skills? Do I like taking on a lot of projects? Maybe I should advice for a bunch of places or do I want to be in one place and focus on one problem?
These are all helpful questions. As you can tell from what I’m saying, I don’t know the answers to a lot of them. You may not know the answers to yours. That’s sort of a problem.
This is Ruth Chang. She also has a TED Talk. She’s a philosopher, teaches at Rutgers University. She talks about making hard choices, this is obviously a hard choice, and why hard choices exist. They exist because they are not obviously better than the other. They are what she calls on the par.
If everything actually was objectively better than the other, then we would all be picking the same things. Hard choices, instead of this conundrum that she states in some of these conundrum, instead of this thing of like, “Oh my God, I don’t know what to do.”
If you think about it, there are small hard choices like apple or orange? They’re not better than the other. They might have similar nutritional content. You make those small hard choices all the time.
Hard choices are actually an opportunity. They are the part where we are ourselves, where we let everyone know who ourselves is. Hard choices are actually great things and you make up your own reasons. I’ve definitely found this to be true.
It’s sort of I think also a talent of maybe somebody in UX or product where you’re arguing a lot that you become really good at coming up with reasons. Even in the decision of whether to divorce, that’s a hard choice. I realize that I can actually come up with reasons.
No matter which way I go, I can talk to you and go, “This is what we decided,” and you’d nod your head and you would feel those are good reasons. I realized I can come up with any reasons I want and I just really need to figure out what’s in my heart and what I want.
I’ve come down to doing three things to figure out what I want to be when I grow up. The first is to do nothing, to give myself space. This is Stefan Sagmeister from Sagmeister & Walsh. He talks about also this career thing where you’re learning then you’re working then you retire. He’s like, “Well, what if I like separate out interest first a little bit of the retirement into work?”
Every seven years, his studio closes for an entire year for Sabbatical. There’s a TED Talk on power of time off. That’s his talk. During that year, for example, his studio went to Bali and just experimented on a lot of things.
They made this talkative chair is what they called it. They made a bunch of other interesting furniture, interesting art, just experiments with a lot of things. A lot of what they did then inspired a lot of the work they did in the next seven years.
Elle Luna who is a former designer from IDEO and friend of mine. She helped design mailbox, a consultant for Uber, and medium. Really, has a stellar design career. Then she actually also took a Sabbatical which has actually more become her life and not a Sabbatical anymore.
This is her in Bali in what she calls “The House without Walls”. It’s a house literally with only one wall. During that time, she painted tons portraits and self-portraits of the people that came through. She also started working on a book which just came out two weeks ago. If you’re interested in this topic, you’d be interested in her book. It’s called “The Crossroads of Should and Must”.
This is her painting, different versions of the book cover. She chose must. She figured out what her must was instead of should.
For me, an interesting thing happened where I was talking to somebody I was mentoring at Yahoo. His name is Bernard. This is one of this art pieces. When I first became his mentor, he was about to go Burning Man for the time and he was going to start on Wednesday.
I was like, “Why are you going Wednesday instead of like Monday?” He’s like, “Well, I don’t have enough vacation days and work needs me.”
I was like, “Look, this is your first time. You can go into negative vacation and just make it back like the system allows that. And the work incremental difference of you staying two days is negligible. Whereas your experience difference from taking those extra two days is immense.”
He did it. He said that was some of the best advice ever given. Recently, I was telling him about where my state of mind was and we were just catching up. He was like, “Do you remember that advice that you gave me?”
I was like, “Yeah.” He’s like, “Well, when’s the last time you took time off? When’s the last time you took like more than three months off?” I was like, “I don’t remember. I don’t think I have.”
In this time, I was meeting with these head of product and head of design companies. They’re, like I said, great opportunities and I realized I can’t do this. I told them I’m not interviewing anymore. As soon as I did that, I felt free. I felt knowing that now I was going to have space was remarkable.
I’m going to do a short version of that by taking two weeks in Amsterdam in just two weeks’ time. You can do this in much smaller increments, even just meditating in the day, giving yourself space.
Then after doing nothing, I’m going to do something. Stefan called his first Sabbatical a disaster until he put up a little schedule for himself. Christina Wodtke who’s around was talking about living lean. She did something in order to figure out what she liked to do.
She was like, “Do I like teaching?” Then she did a general assembly, a two-week class and was like, “That was fun. I do like that.” She took this OK, our approach, like objective key results then she was like, “Do I like teaching full-time?” She taught this intensive and I was like, “Oh, I don’t like that.”
You can do little almost an agile method to your life and trying out little things. There’s the 100-Day Project which is doing a small thing for 100 days in a row. For me, I used to do something a lot. I did a side project where I made an iPhone game. I drew OK/Cancel which was the webcomic on design.
After I do nothing and give myself space, I’m going to use that space to work on my music, work on drawing and writing. Basically, work on figuring out which of these things I like. I’m going to build some side projects. I’m going to see which of those things I like to do. Just as importantly, I’m going to see what I don’t like to do.
That’s Jan Chipchase who also took a year off from Frog Design. This is from his talk a year in reflection.
Finally, I’m going to do something that scares me. When I was deciding to leave Yahoo the first time and go to startup, this is my brother, Jaime. He apparently also likes hand warmers and I wear hand warmers a lot. He’s five years younger. He’s even more of a baby as you can see.
When I was struggling with this, he was like, “Which of these things will you learn more from?” I was like, “Oh, that made it so much clearer.” The thing is every year, I’ve gone into a new job title. Every two years, I’ve gone into a new company. It’s because my learning curve tapers off.
When something scares you, it means that you’re going to learn. When something scares you, it means that it’s worth caring about. If you’re indifferent, then you don’t learn from it.
That’s what I’m doing now as well is doing something that scares me is giving this talk. Those are the three things. This is Joseph Campbell. It’s hard to read that. It says, “If you can see a path laid out in front of you step by step, you know it’s not your path. Your own path, you make with every step you take.”
I can’t give you answers because it’s your path. We’re fortunate enough to work in a field where our skills are so diverse, we can work in many different things. Really, it doesn’t matter if the job title had a product, have design, whatever. It’s really what you’re going to be doing in that job that you need to figure out what you want to be doing and the job title comes after that.
Finally, just last night, I was reading about Bruce Jenner, the Olympian gold medalist who won a decathlon, stepfather of the Kardashians, and him coming out on being a woman. One of the quotes he said and he’s still referring to he until he transitions said, “I want to enjoy my life as who I am. It’s that simple.” That’s a very true statement and that’s what I want to do.
I found this talk helpful for me. I hope you found it helpful for you as well. Thank you.