Leaving Corporate For a Creative Career

A Practical Guide to Following Your Dreams by Vinamrata Singal

I know many people who read my essays are interested in learning more about how to take the leap from a corporate job to a creative career. That’s why I’m excited to share a guest post from Vinamrata Singal, former tech product manager turned writer and director, who has taken this leap and is reporting back to us.

In this piece, Vinamrata shares how she finally summoned the courage to take a bet on herself and quit the corporate path to explore her creative passions, which led her to writing and directing. She’ll share how she’s gotten to the point of making her film After Moonrise, including writing the script, built out her team, cast her actors, secured her location, and is shooting in less than eight weeks!

If you want to learn more about Vinamrata, you can follow After Moonrise on Instagram for updates and subscribe to her Substack, The Next Chapter, to get a more in depth look at her journey.

Vinamrata’s piece is below, enjoy!

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Leaving Corporate For A Creative Career

Two and a half years ago, I quit my job as a Lead Product Manager at Match Group to do…something.

I had some vague ideas about things I wanted to try (YouTube! Coaching! Novel writing!), but no concrete direction.

Before that, I had built an 8-year career in product management, steadily climbing the ladder from a Stanford Computer Science degree to Google APM, to startup product leader, and finally to Lead PM at Match Group. But I still didn’t feel fulfilled.

When I share this with people, the most common question I get is How do you decide to give up something stable for something uncertain?

The truth is: It was a long time coming. Deep down, I had always known I wanted to do something different from a product someday. But timing isn’t a straightforward thing to figure out, especially as we get older. There are always more responsibilities and factors to take into consideration, not to mention the fear.

What if this new thing isn’t as successful as my current thing?

What if I go broke?

What if I look like an idiot in front of others?

I don’t know if I ever overcame this fear. Instead, I accepted it wholly—until it became a no-brainer to do the thing, anyway.

Conquering my fear, one step at a time

Finding My Way Back to Writing

Before I discovered computers or product management, I had a first love: writing.

I’ve always been drawn to words, and stories have helped me feel a sense of belonging and connection during a chaotic and lonely childhood.

But despite my love for words, I never thought of writing as a career. Maybe it was because there were no creatives in my family, or because I was too scared to bet on myself, but I threw myself into math and science instead.

Almost a decade later, on a boat ride in Cartagena, Colombia, I remember having this nearly spiritual experience where I felt like the water was telling me to start writing again.

Taking a little break from writing

At the time, I was working at Thumbtack, a pre-IPO startup, with some of the strongest product leaders from Meta and Google, which was a deliberately calculated career move so I could start a startup or grow into product leadership. Despite the progress and accolades, it just didn’t feel…enough. Whenever feelings about dissatisfaction came up, I’d push them away.

The boat ride felt like a sign.

Maybe my path exists outside of product.

But believing that meant giving up a big chunk of my identity, something that felt so foreign and unsafe and bad that I couldn’t accept it.

So, I did the next best thing: I signed up for a short story writing class.

During the class, I felt like a part of my brain that had been dead had finally woken up. I loved my writing assignments, even though I still didn’t feel entirely comfortable with the process. When I moved to New York a few months later, I built on this by building a regular writing routine, even hiring a writing coach and going to writing conferences and workshops to improve my writing chops.

Falling Out of Love With Product

Over time, as my interest in writing increased, it became increasingly complex to manage both my product and creative career—especially as my dissatisfaction with product increased. While I had been excited about using my product skills to become a social entrepreneur, I became increasingly jaded about whether venture-backed startups could truly maximize impact. If startups weren’t going to be my thing… then where was I headed? I thought about product leadership, but successfully navigating company politics and making my vision “come to life” felt like I had sold out, betrayed my values for the sake of corporate performative culture.

I needed a new purpose, a new mountain to climb.

My Failed Attempt (And Why it Didn’t Work)

I had realized some version of this truth in 2021, but at the time, it was too hard to accept fully. If I wasn’t a PM or chasing something that felt big, then I wasn’t special; if I wasn’t special…then who was I? This is why when a startup reached out to me with a head of product role, I caved. “It’s what I’ve always wanted,” I convinced myself.

Instead of taking the uncertain path and finding myself, I took a “mini-sabbatical”: two months where I checked off every single item on my backlog: tennis lessons, writing classes, and my NYC bucket list.

A few weeks into the role, I quickly realized I had made the wrong choice. The company was not ready for a head of product, and I was not prepared for the ensuing level of chaos and dysfunction.

Looking back, I realized that this was partially because I hadn’t taken the opportunity to give myself a break and actually clarify what I wanted next! Instead, I jumped into something because I was too scared of the uncertainty required to find clarity.

Visiting Tulum During My Mini-Sabbatical

Making The Bet to Chase The Uncertain Path

Eventually, I left that startup job for Match Group, which was, in many ways, my dream role: I had an incredibly supportive boss, significant scope, and decent work-life balance. Yet I didn’t feel great. Ultimately, it got to a point where taking a break didn’t feel like an option, but rather the only option.

So, I started saving up for it, and six months later, I handed in my notice. It was one of the scariest yet proudest moments of my life. But I couldn’t help but wonder, had I taken too long to make this decision? I already knew something wasn’t right in 2021, but it wasn’t until the end of 2023 that I made the move and took the plunge.

For a while, I felt shame about my “failed” mini-sabbatical. Maybe if I were braver, I would have taken this plunge sooner. But I realized that this is an impossible ask. I had to work through so many scripts—about self-worth, ambition, impact, money—while making sense of my desires that there’s no way that I could have dove in so quickly. Instead, it’s a process, something that I cultivated by taking intentional actions and smaller breaks to prepare for the bigger step.

I’m so grateful I stepped away when I did, because I was finally ready to give myself the space to really explore and figure things out.

Now, I’m pursuing writing and directing by making my first short film: After Moonrise. It’s a mother-daughter story inspired by my relationship with my mother and grandmother. It’s been an absolute labor of love getting this film into production: from interviewing tens of producers, cinematographers, and production designers to countless revisions of the script to fundraising to casting, I’m still in shock that I’m actually making a movie. I am so incredibly excited to finally bring this story to life when we shoot in October.

Vinamrata the Filmmaker

Take Your Time Making The Bet

So if you’re someone trying to follow your dreams but too scared to take the plunge, here’s my advice: take your time.

Let it come to you. These decisions are never easy, and there are so many different forces: family, identity, money, just to name a few. At some point, leaving will feel like the inevitable choice, which will make it easier to pursue—even if it feels like it’s too late.

Leaving is never a linear path.

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Thank You for Reading!

I’m so thrilled that Vinamrata was open to sharing more about her experience leaving tech to create her short film. If you’re excited by her film and want to support her, you can do so in a few ways. I’ve personally given to her crowdfunding campaign for After Moonrise, which closes in a few weeks. While they’ve reached their goal, any additional support is always appreciated and helpful in the film making process.

Keep tabs on After Moonrise through the film’s Instagram below.

For more peeks behind-the-scenes, you can subscribe to Vinamrata’s Substack below and continue following her filmmaking journey.