My career journey, part four

The final conclusion to the series

Hi everyone- I’m back! I had a wonderful few weeks off traveling all over Europe and I’m excited to come back to this blog more energized now than ever. This is the last (and final) part of the series, and I’m excited to move onto new content.

For new folks, refer to parts one, two, and three (including more details on the motivation for this series) of this series before diving into this post. 

My job search kicked off in April 2022, when the job market was hot and the opportunities plentiful. However, I had a feeling the days of a hot market were limited given whispers of layoffs and interest rate hikes, which added pressure to land a job as soon as possible. I started my search by conducting 30+ informational interviews at companies that seemed interesting before formally starting the interview process. I really wanted to make sure I found the perfect fit to ensure space for my creative dreams. 

Soon, my weeks were filled with interviewing, networking calls, or preparing for interviews or networking class. I turned down weekend plans to squeeze in prep for interviews, prepare case studies, or strategize about my job search. My calendar became a sea of back to back meetings, and multiple days when I forgot to eat lunch. The job search started bleeding into my personal life as well. When I met my partner’s family for the first time (an occasion that my parents had flown down to NYC for), I had a hard time staying present in the conversation. Despite the significance of the moment, I had a hard time remaining present in the big moments of my life because I was too wrapped up in the job hunt. 

Once I was done interviewing and had to pull the trigger on an offer, all my doubts and anxieties multiplied in the face of making the perfect decision. There were so many ways each prospective job could fall apart: maybe the boss that I thought was supportive might not turn out to be supportive. Maybe the team and I wouldn’t gel as much as I thought it would. Maybe the job would be more intense than I realized and I’d burn out, again. Maybe I’d get bored of working on this product: what would I do then? I was so scared of making the wrong choice and forever feeling unhappy in my career that my brain spiraled every time I thought about the decision. It didn’t help that everyone had differing opinions of what I should do. 

In the end, I ended up choosing to work at Match Group because: 

• Dating is fascinating problem space, especially as a consumer PM

• I really respected the manager and thought I could learn a lot from him

• The work life balance seemed really great, especially in the way I was treated throughout the entire process. 

And I felt the most wanted by Match. I am not proud of how much it impacted my decision to take the offer… but after my experience at my previous startups, all I wanted was to feel wanted again. Looking back, I realized this was my trauma speaking, and I wish I had been more self aware about this. 

Me roaming the NY Botanical Gardens post accepting my Match offer.

I’ve now been at Match for ~9 months (coming on a year soon!) and the experience has been a whirlwind. The role has matched a lot of my expectations, which makes me really happy. But, there’s a lot that changed after I joined, and I’ve had to reset my expectations at various points of the journey. While the experience wasn’t 100% what I expected, that forced me to think about what I could learn from this experience to better inform what I want next for myself. Some of that vision is consistent with when I initially started this journey: 

• I still want a multi-hyphenate career. 

• I still want to build products.

• I still want to find ways to flex my creativity, especially through writing. 

But some new aspirations have entered into the picture. 

• I want to live a flexible lifestyle that’s centered around my energy rather than timelines and requests placed on me by others. 

• I want to take my creative career beyond short stories, exploring screenwriting for television and tackling my first longform project (TBD whether novel or memoir or somewhere in the middle). 

• I want to take more entrepreneurial risks with product. Specifically, I wanted to build and launch products that are a mix of software and non-software components (think community, content, etc.) that enable expression for myself and others. 

I’ve taken some steps towards the above goals. I spent a month in Europe in April where I focused on living a lifestyle that catered more to my energy levels rather than my to do list. I am about to sign up for my first TV screenwriting class and have attended a few writing workshops to grow as a fiction writer (reflection on the experience forthcoming). And I launched my first few product “bets,” the biggest one being my coaching practice, with more software- driven bets in the pipeline. 

But there’s more I want to do. I’m excited for the things I have cooking and I hope to share with you all soon. In the meanwhile, I feel grateful to have this community to share my thoughts, reflections, and lessons with along the way, and I hope the context of my life journey helps put the next few posts in perspective. 

Things of Note

Recap: This section is my way of bringing attention to a thing, person, or idea that’s meaningful/related to the mission of this newsletter. This week, I want to highlight Min Jin Lee’s book Free Food for Millionaires. 

I recently came across Min Jin Lee after nursing a writing rejection, where I took to Google to understand how other writers had navigated rejections in the past. Lee had written an article on LitHub about how it took her eleven years to write her first book, Free Food for Millionaires, after facing years of rejection. I had read Lee’s Pachinko (which had taken her another decade to write), an intergenerational tale of a Korean family across a century of history. Intrigued, I read the synopsis of her first book and decided to read it, since I had loved Pachinko so much. 

I absolutely loved Free Food for Millionaires. The voice, tone, and setting are the opposite of Pachinko, but many of the themes- class, love, and family- rings true across both books. As a writer, I loved geeking out over all the ways in which she employs POV and character development to really get at the heart of the themes. Plus, I loved how Lee shows how the search for belonging can make people act in self destructive ways. It is also the first accurate fictional depiction of what it’s like to be in debt and feel poor (even if you aren’t financially poor), and how this desire to feel rich can often lead to counterproductive decisions that lead to even more debt, locking folks into a deadly cycle.

It’s also a coming of age story not just for the main character, but for almost all of the characters in the book. They’re all looking for something- love, status, money, acceptance- but by the end of the book, almost all of the characters realize they’re actually looking for something else. In a lot of ways, it reminded me of my own personal journey that I’ve articulated in the last few parts of this series. I thought I was looking to become a social impact entrepreneur, chasing impact and “success”, and only recently have I realized that what I’m really looking for is freedom.