Why I Left (And What I Gained)
Self-Reflection on My Career Journey (2019–2024)
This isn't about technical insights—it’s a personal reflection on the career decisions I’ve made and the lessons I’ve learned. Writing this is a way to capture my thoughts as I navigate this ongoing journey.
2019: The Beginning
Before defending my PhD in May 2019, I had two full-time job offers: Microsoft and JP Morgan Chase. Content with my options, I canceled other interviews and joined Microsoft in July.
Why Microsoft?
Higher pay.
Seattle felt more appealing than Delaware or NYC.
My Mindset Then
I didn’t fully grasp what a "good career start" meant.
I underestimated the significance of securing an H1B visa right away.
I was eager to "make an impact" without knowing what that really entailed.
Promotions motivated me—I wanted to prove myself.
2021: Changing Gears
I switched teams within Microsoft.
Why I Left My Old Team
The work centered on analytics and Power BI, which didn’t align with my technical growth goals.
Being part of a product management org made me feel undervalued.
The slow pace and lack of learning frustrated me.
I missed out on the promotion I wanted.
Lessons Learned (2019–2021)
Soft skills endure. Company-wide trainings and teammates taught me interpersonal skills I still use today.
"Rest and vest" isn’t for me. I need challenges and opportunities to grow.
Fit is personal. What doesn’t work for me might be perfect for someone else.
I chose my new team because the people seemed nicer—and I was right.
2023: A Bigger Leap
I left Microsoft for Workday.
Why I Left Microsoft
The work lacked excitement and challenge.
I wanted to work on customer-facing projects, not internal tools.
The tech stack felt outdated; I wasn’t growing technically.
Lessons Learned (2021–2023)
Stop coasting. From 2019–2021, I coasted—not out of laziness, but because the environment was too relaxed.
Storytelling matters. I improved my ability to communicate impact, thanks to teammates and a supportive manager.
Different paths suit different people. Former teammates thrived after I left.
I chose Workday for better pay and the chance to build something new.
2024: Rediscovering Excitement
I decided to leave Workday and join Reddit.
Why I Left Workday
Leadership lacked empathy, and I often felt undue pressure.
Collaboration between teams and engineers was minimal, stifling learning opportunities.
The work felt repetitive, with little room for innovation.
Lessons Learned (2023–2024)
Technical growth. I gained firsthand experience with LLMs and generative AI in a B2B SaaS setting.
Demystifying HR. I learned how to proactively engage with HR for support.
I chose Reddit because:
Compensation was compelling.
The ads domain at a social media company excited me.
The role offered remote flexibility with quarterly offsites—a perfect balance.
So far, I couldn’t be happier with my team at Reddit. It’s everything I need and more.
Reflections: Patterns in My Career
A few themes emerge when I look back:
Reactive decisions. Most of my job changes stemmed from dissatisfaction rather than finding something better. Fortunately, they all worked out.
Action over inertia. I’ve been good at recognizing unhappiness and taking steps to avoid being stuck.
Risk-averse but growth-focused. I want to grow quickly, but I also value stability.
Culture matters. Team and company culture have always been critical to my happiness.
I’ve yet to face a choice between more money and less happiness vs. less money and more happiness.
This reflection isn’t just a chronicle of my career moves. It’s a reminder of my growth, what matters most to me, and the principles that guide me. Here’s to the next chapter.
Closing Thought
The only person responsible for your happiness at work is you.
The holiday season is here—a perfect time to reconnect with old friends and build new connections! If you'd like to chat with me, check this out: 2024 Year-End Connect!
— Dec 10, 2024. At Home in the East Bay.