Interview #2: How To Let Go of the "Perfect" Career, With Karen Chi

Karen Chi had the perfect resume, on paper. She was a Berkeley alum, longtime director at LinkedIn, then part of the executive team at Cameo, the wildly popular website during the pandemic where you could request personalized videos from celebrities. But sometime last summer, she found herself re-evaluating her career, unsure that she wanted to continue the same trajectory, yet lost on what she should do next. 

I knew I wanted to interview her when she bravely posted on LinkedIn about how she used to let others’ “imagined opinions” guide her career choices. Today, she’s the founder of Karen Chi Consulting, which helps early stage companies unlock their next phase of revenue growth — but the path there wasn’t an obvious one. Today, we talk all about letting go of our ideals for the “perfect” career, how to listen to our gut when it feels impossible, and how to finally find clarity on what lights us up in our work. 

First, I love your point about being scared of other people’s “imagined” opinions during your career searching. Can you talk more about that? What kinds of opinions were you taking in? 

Yeah. I'll share the internal stuff first. I’ve had an amazing career to date. I had an incredible experience at LinkedIn. I spent almost a decade there. I had so many people who knew me, knew my reputation. I felt I was fairly well respected. And then I left LinkedIn and I got to go to Cameo, which at the time when I joined, was deep in the cultural zeitgeist. It was a newly minted unicorn startup. 

When I left Cameo and took a much-needed career break, I felt like the next job had to be just as amazing and cool. If not better than the opportunities I had at LinkedIn and at Cameo. Like, when I put my LinkedIn update announcing my new role, I wanted it to feel like it was in line with the trajectory that I was on until then. 

As a result, I kind of put blinders on. I felt like, I need to be at a company that is exhibiting incredible growth. It needs to be hot. People need to know about it. I need to stay on my trajectory. I kind of closed my eyes to any opportunities that came my way that didn't necessarily fit. 

What was the job search process like at first? 

Like many of us who were looking for work last year or continue to look for work, I wasn't necessarily getting the feedback from the market that I wanted. It was difficult to begin with, finding the opportunities that fit that mold that I had.  And then even when I was having conversations with companies that fit that mold, I wasn't necessarily feeling inspired or excited. 

When I was having those conversations, I felt like, I already know what that job is going to be like.

That’s very interesting. You’re saying you were only looking for jobs within a certain set of criteria. And then when they came up, it sounds like you actually didn’t want to do them anymore. 

Yeah. I hadn't thought about that before. I was having conversations that fit the profile and still I would come out of them feeling like: there must be more. And so I'll get to the part that's kind of the external feedback and opinions. 

When I was commiserating with friends and mentors and people in the ecosystem, I heard a lot of: what you are feeling is normal because we're in a weird time and the economy is in a bad time. All true. But I think I heard that often enough that I started to feel like, That's probably what it is. It’s probably not me, it’s the market. 

It’s difficult when you're on a journey where you're trying to get to some outcome that you're not necessarily clear about. It's difficult to know if you're taking the right steps towards it. Looking back, it probably was a mix of me and the market. But sometime last summer, I took a minute to really think about why I was feeling these things. 

What did you do? 

I actually took the time to finally do a thought exercise that had been on my radar for years. It's taught by Debbie Millman. She teaches an exercise to her design students called “Your 10 Year Plan for a Remarkable Life.” 

I did it for a five year timeline. You are supposed to write a day in your life, five years from today, from morning till night, from the moment you wake up to the minute you go to sleep, and in really vivid detail. There are many versions of these sorts of visioning exercises, but it's supposed to get at: who are you hanging out with? Perhaps: who are you waking up next to? Where are you waking up? What are you doing for work during the day? How do you fill your days? And I think a couple of things I realized was that, one, I really want the next half of my career and what I considered to be work, to feel much more diverse than what the first half felt like. 

And the first half for me was: full time job, focused on working my ass off, getting good results, growing in my career. But that's kind of it. So diversity, meaning the way that I spend my time during the days and maybe nights are different, was in my plan. And then the second thing that came out in my five year plan was that I really want to get deeper into the world of startups. 

You're supposed to write this exercise without fear of failure. It’s so hard to do because by the time you're my age, 45, I'm scared of everything (laughs). I want to do things I'm really good at. But it was really helpful for me to think about, okay, I want things to look really different than what they were before. 

Had you ever done exercises like that before? I'm curious as to why it sounds like that exercise in particular was really effective for you. 

I am a big believer that things come to you, or you find things, when you need them. I had learned about this exercise years ago, and I think up until last summer, I had always felt like, I have a plan for life. I'm a big planner — I think about annual goals. But I think what I really needed last summer and why this exercise, why I finally felt like I should do it, was because I was seeking something bigger, more meta around life, not necessarily concrete goals anymore. 

Were there any other kind of internal signals that you had, or just feelings that you had that helped you realize, I need to do something different? 

I wish I had a great answer for that. It's hard. I think my own sense of energy was a big indicator for me. I felt dull, a bit robotic, really. Nothing necessarily sparked real, deep curiosity in me, but if I look back, it makes sense. I went back to what I was familiar with — and so if you're familiar with it, you’re probably going to be less curious because you’ve already been down that path before. 

Wow, you feel physically different, doing something more aligned?

Yeah. Now, even though what I'm doing is way less comfortable for me, I'm excited about doing it almost all the time. 

How else can you tell when you're doing something that is uncomfortable because you're growing — versus plain uncomfortable? 

Well, maybe a relevant example is when I left Cameo. I really had to think hard about that.

What was difficult about that experience? While I worked with the most incredible, smart, funny, driven, creative people, and we were working on interesting challenges, the business itself was incredibly hard. 

The marketplace drivers that drove such strong results for Cameo during the pandemic went different directions once the world started to open again. I and the rest of the executives who joined Cameo around the same time, our mission was to scale this wildly successful startup. The reality was that we needed to rebuild a business that could sustain the astronomical growth it had seen during the pandemic. I have never worked so hard for such little satisfaction in business – and with such a capable team too. 

What that left me with was this constant wondering, am I not working hard enough? Am I not working smart enough? Or is this discomfort I'm feeling? I grappled with that for a long time. At some point, I realized the discomfort meant that it was no longer the right fit for me. I wish I had a better compass for recognizing it sooner, and I hope I do going forward based on that experience. 

What was it like to launch Karen Chi consulting? 

Thank you for asking about that! I have called it consulting, but really in my head, though, I'm using it as an umbrella to plant seeds in a number of different places to see what takes root and might set me up for the next chapter of my career. 

I am really interested and committed to spending my time with underestimated founders. I'm really thrilled that at the end of my first two-ish months of having launched this venture, I have my hands in a bunch of different things I would absolutely not have had on my “Karen Chi Consulting” vision board. 

When you first decided to kind of go out on your own, were you nervous? Did you also have other people's imagined opinions in that, too? 

Oh God, I probably doubt myself at least once or twice a day, if not once or twice an hour. I've also been so pleasantly surprised by how generous complete strangers are with their time in wanting to help me. It's given me enough to buoy me, I guess, through the doubt. 

Most of my network are folks who aren't doing what I'm doing. I felt fear wanting to do something different. And then I quickly found so many others doing it. Like, when you look for it, you find it, right? And so I think that's given me a lot more confidence in my decision as well. There's a tribe of weirdos out there who want to do this thing, too. 

Yeah, that's what I'm learning, too. Pretty much anything you want to do, no matter how niche you think it is, somebody else is doing it, too. 

I think that's important. Exactly your point. It's unlikely that I'm trying something that other people haven't ventured to do before. And so I think not only is it important to find those people so you can learn from them, but also to have a community around it and to normalize it, even just in your own mind. 

What advice would you give to people who are going through a tough time in their career — or are confused about their next steps? 

I was just talking with one of my dear friends about that this morning. I'm a big believer in collecting dots to connect dots. That sounds like a slogan or something. 

When you're not sure about what you're working with currently, go out and get more to work with. So if you're exploring what to do next in your career, go have conversations with people in other areas, things that you might have some fledgling interest in. Being able to bring all that information back and then sort through it can help you start to find your way. I was doing a lot of that last year. I just kept having these conversations and then reflecting on my energy and how it fit with what I thought was the right thing for me. 

How many conversations did you have?

Oh my God. Prior to me having the epiphany around wanting to do this consulting umbrella of work, I don't know. Maybe 100 conversations. 

Thank you so much for sharing your story. Oftentimes, real life is so much messier than the neat stories we see in the movies or in social media. 

I feel like LinkedIn profiles don't really tell a good story —they are the “after”, right? They're the narrative that I have come up with to connect the dots around what my journey has been to date. And I think that it misses a lot of the peaks and the valleys. All it shows is what the end result was. And yeah, often what's most useful is: what kind of shit did you have to go through in between those peaks?

Thank you so much for reading today’s post — what are your takeaways from today’s conversation? Comment below, and please reach out if there’s anyone you’d like to recommend for this interview series!