Reflection #2: On Not Having the "Perfect" Career, With Karen Chi

Last time, I chatted with Karen Chi (link to interview here), who talked to us about the winding journey of leaving her leadership roles at LinkedIn and Cameo to take time off and figure out what she really wanted to do. Curating this interview was much more complex than I realized — I naively assumed that she probably hated what she was doing before, but that was not at all the case. In fact, I realized that she was mostly happy on her prior path, but that still didn’t stop her from having to truly soul search and ask herself some tough questions about what she wanted to do with her life. Today, I’m sharing 5 reflections from this wide-ranging, unexpected conversation. 

#1: What we actually like doing might surprise us. 

Fear can cloud our interests, a lot. Karen felt groggy and unexcited for a while, looking for her next role, before she tried out an important self-reflection exercise (Debbie Millman’s 10 Year Plan for a Remarkable Life). In it, she realized that she wanted to do something completely different than before — to not just have one job anymore, as opposed to climbing the corporate ladder and leading big teams like she always thought. But the key thing Karen mentioned is that “you’re supposed to do this exercise without fear of failure.” Only by diving into the exercise whole-heartedly, and even taking an hour to imagine a different life, did she get true clarity on what she really wanted. 

#2: It can take time to understand our gut feelings. 

I wish making the right choice were as easy as listening to our gut and calling it a day. While I do believe intuition is very important, Karen’s story reminded me that answers are not always so black and white in real life — they take time to develop. Sometimes, as Karen talked about, it is legitimately difficult to tell the difference between healthy discomfort versus something that’s maybe just not a great fit. It’s not always obvious early into an experience, especially if you’re someone who works hard and tends to view problems as things in your own control to change. 

This learning was especially valuable to me because I’ve often judged myself when I felt like I couldn’t make the right decision “fast” enough, and therefore wasted my time. Seeing an accomplished person struggling with this problem too helped me feel less self-critical about not “getting it right” immediately. 

#3: Once again, community really matters. 

One of the things I’m most excited to do in this newsletter is to connect learnings between different people I interview. The theme that emerged between the last speaker (Joel Hoekstra) and this one is that community is really important, particularly for niche topics. Karen specifically mentioned that some of her fear to try something new was rooted in the fact that most of her network was not doing anything similar. By spending time with people who shared her same interests, she gained enough confidence to continue her new path. 

#4: Clarity involves both internal and external questioning. 

I love Karen’s phrase of “collecting more dots to connect the dots.” While the thought exercise she did was very enlightening, she also had over 100 conversations with people to figure out what she wanted to do next. I’m sure the number differs per person, but for me even having a handful of conversations has helped me feel less confused during transitional times. It’s amazing what getting out of our own heads and collecting real-world information can do for our sense of direction. 

#5: Even a happy career can lead to doubt. 

Whenever I question myself in my career, I tend to wonder if it’s because I’ve made some wrong choice. But Karen’s story helped me realize that even great careers can lead to doubt or dissatisfaction — because our priorities naturally shift over time. A career that might have been an amazing fit five years ago might not serve us anymore — and not because we weren’t cut out for it, or that it was a “mistake” to pursue it in the first place. 

In fact, if we do something too long that we enjoy, without changing it up, it can actually make us unhappy — because then we’re not learning and growing anymore. 

Thank you for reading! I hope you’ve enjoyed today’s reflections — what did you take away from this conversation? Comment below, and reach out at anna.raskind@substack.com if there’s anyone you’d like to recommend for this series!