To help you understand me better, I'd like to share with you bits and pieces of my story - who I was, what I struggled with, and how I got to where I am now.
Say hello to high school me — daughter of two Chinese immigrants, older sister, born and raised just outside of Boston.
Hello!
I may have seemed humble and modest, but on the inside, I believed I was the shit.
Why shouldn't I? That's what I'd been told all my life.
Getting into college? No problem.
Getting into a top tier program? Yeah, no sweat.
I’ll admit— high school me was cocky, but I do believe that my heart was in the right place. Because at the end of the day, all I wanted to do was help people. I wanted to help people believe in themselves and fulfill their dreams, and I was ready to unleash 10000% of my potential to do that.
Off to college to achieve great things!!
College was fun, but it was also very sobering.
Suddenly, I was surrounded by the best of the best. Everyone was good at something.
So I did what I knew best. I raced. We all raced to the top.
I did everything. Clubs. Sports. Greek life. Computer Science. But unlike in high school, people in college didn’t tell you that you were great. Everyone was great. And for someone like me who got so much of my worth from others' praise, I didn't know how to feel when that praise disappeared.
They're all so smart.
I don't get this.
I'm not good enough.
How come I always need help?
Why don't they ever need help?
How did they get that internship?
How can they accomplish so much?
I wanted to run. But I also needed to prove that I was worth something. How else would I be able to help the world in a way that matters, in a way that was big?
I didn't naturally like coding. I preferred to put my time into stuff like figuring out how to make my student clubs impactful and rewarding. But I needed to prove to myself that I could be a software engineer. I needed to know that I was just as good as everyone else.
After graduating college in 2016, I moved to San Francisco to work as a software engineer at a tech start-up. I had done it. I was going to be working on an app that helps students find and work with math tutors. It seemed like a worthy cause.
New grad Kelly - eager and ready to prove her worth
And so I climbed the ladder.
For two years, I lived the Bay Area techie life. I worked. I ate snacks at the office. I hung out almost exclusively with other techies. I went bouldering after work.
It was on the weekends that I truly felt alive. Every weekend, I'd head straight for the mountains so that I could immerse myself in the trees, the lakes, the stars. I'd be exhausted on Monday before standup, but it was worth it because for two days, I got to get away.
But it wasn't enough. The great big world was calling to me, beckoning. I wanted to see more, do more, get outside my tech world life.
In November 2018, I packed my bags and decided to work remotely...from New Zealand.
Wellington, here I come!!
Going to New Zealand was, in many ways, a baby step off the beaten path. I was still playing it safe — keeping my current job, going to an English speaking country (that my mom had researched and suggested), choosing a city where I could make friends through frisbee. But, it was the first time in my life that I had decided something on my own and was putting in the legwork to get there (well some of it — my mom was the real star here).
I discovered a lot in those six months. Living across the ocean and in a new time zone meant that the life I thought I should live and the people whose approval I wanted were all so far away. I finally had space to think my own thoughts and make my own decisions.
I'm ready to get engaged to my partner.
Spending a weekend at home with no plans is okay.
Being alone doesn't mean you have to feel lonely.
I don't like coding and that's okay.
I want to work more closely with the people I'm trying to help.
Maybe I want to be a product manager.
When I returned to the US, I was ready to pursue something new: Product Management. This was going to be my calling.
Ta-da! It's Product Manager Kelly!
And for a long time, it was. I talked to students and learned about what they needed to navigate the college application process. I analyzed the results of our newest ideas. I thought of future improvements. I made decisions. I believed that I was making an impact.
Until I didn't.
It's hard to explain what suddenly made me feel so differently about my work. The pandemic? The explosion of awareness around racial injustice? Hitting that '2 year mark' at my company? All I knew was that my day to day work felt unimportant.
My work never felt like it was for the students. Instead, we kept building things that catered to the whims of our investors, chasing each new shiny thing.
I was unhappy, yet, I still couldn't get myself to leave. I felt completely stuck.
It was at this time that I bumped into the world of coaching. I heard it was a tool that could help me move forward. I decided to give it a shot.
Coaching unstuck me in a way that I couldn’t do on my own. For the first time, I had dedicated space and support to talk through my thoughts. I encountered questions that cut straight through the noise and made me confront my deepest feelings.
It was through coaching that I realized why I was struggling to leave. Because to me, my job was more than just a job.
It represented prestige. Status. Wealth.
It represented my worth.
Through these conversations, I saw all the pieces of myself that were entangled in my job - my need to prove myself, my financial fears, my fear of rocking the boat, and my inability to acknowledge my strengths.
There was something powerful about naming my fears. The future no longer felt so unknown. By understanding why I was scared to leave, I could finally do something about it.
In July 2021, I found the courage to leave my job. I had no interviews lined up and no concrete career plans. I decided to enter a new phase of my life: exploration mode!
For seven months, I took time to be curious, explore new interests, and better understand myself. The biggest thing I realized during this time was how much I cared about people, relationships, and community. Although I had gone to a tech school, I had never been motivated by technology itself - and I was finally realizing that that was okay.
I wish I could say that post-sabbatical, I immediately left tech and pursued something else, but life doesn’t always work that way. I wasn’t ready. I still felt scared - my bank account was running low, and I doubted my abilities to land a job somewhere else.
I ended up staying in tech. In my head, the role still sort of made sense - we were building tech for communities and my teammates were phenomenal. Besides, I thought it’d be a good opportunity to be less attached to my work and to treat is as just a job instead.
It wasn’t until I got laid off one year later that I realized how unhappy I had been. It had gotten so bad that I had fully detached myself from my work - leaving it out of conversation, and feeling so shitty if a day passed without me doing anything outside of the work day. With the support of individual therapy, couples therapy, peer coaching, and time, I realized that it was time to be honest with myself. I could no longer do any old PM job. I needed to choose work that mattered to me.
And the work that matters to me is supporting others towards their dreams. Cheerleading has forever been a part of what I do — from building a product design club in college so students could realize the impact they could make, to supporting individual and team growth in my ultimate frisbee teams, to running storytelling classes so people could gain confidence in their voices. What if I could that sort of work full-time?
This time around, I feel ready. I have the tools, the self-awareness, the support. I’m ready to do work that excites me, that aligns with my identity. So for the meantime, I’ve decided to pursue 1-1 career coaching. I’m excited to see how I can continue to develop a healthier, more fulfilling relationship with my work (even if it may be a work in progress forever 😛), and how I can help others to the same.
<aside> 📅 Interested in a getting career coaching? Sign up for a free 45 min coaching session to see if we’re a fit
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28 Days on the Pacific Crest Trail
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