Leap of faith or foolish gamble?

With great clarity comes great spiraling

The last two months of my sabbatical have provided me with clarity on my next chapter. 

What’s clear: a new career identity, purpose-driven ambition, high-level goals, and a vision for a lifestyle that supports all of the above. 

What’s not clear: the exact path to achieve the goals, managing the anxieties of this new path (especially financial anxiety), and confidence in the new identity. 

In this post, I want to share with you what I’ve figured out so far, with some learnings and reflections on the how to help others on a similar path.

My Career “Experiment”: 

I decided that the best way to find my new career direction was to experiment my way into it, trying things and learning from it. I loved having the freedom to try new things, but it was challenging to balance doing with reflection. 

Most times, I was engrossed in the “doing.” Other days, drained from work, I took a break to recharge, or if I was feeling particularly anxious, I took a step back to reflect. 

Some of the activities I tried: 

• Wrote a TV pilot via a TV screenwriting bootcamp

• Worked as a Production Assistant on a short and feature film

• Launched a product and career coaching business

• Took a No-Code course

• Wrote 20K words of a novel

• Hosted events (like a meetup for Paul Millerd’s community and an event for writers)

• Read books about spirituality and mindfulness

• Published a few YouTube videos

• Met 10+ of subscribers of this newsletter over virtual coffee chats

The Learnings: 

Through this journey, I’ve learned that I want a career that centers creative expression, ownership, connection, and growth. Specifically, I’ve learned: 

• I was burnt out of corporate tech, and needed to do something different (for now). This was clearest through the No Code Course. While it was fun to build things again, I realized that building requires stamina and patience, which I no longer have after 7+ years in the industry. Same goes for pure product consulting gigs: it just hits too close to home. 

• Writing is my ultimate calling: writing, across all mediums, whether it’s this blog, my novel, or a TV script, is so healing and energizing. This isn’t a shocker, as I’ve been writing since I was five years old, and storytelling literally saved my life. There’s a different kind of energy I feel when I’m discussing books or television shows, as if there is a new life inside of me that’s pushing to express itself. I want to dedicate more time towards it, and ideally, make a career out of it. 

• Coaching is a secondary passion: Some of my happiest hours were spent coaching clients, helping them get out of a toxic job, navigate a layoff with ease, or improving specific skills. But there’s some coaching that doesn’t feel rewarding, like pure “career” coaching (aka review my resume, tell me how to network, etc.) versus coaching in which I’m shepherding a transformation or teaching a hard skill. I always want to be coaching and mentoring in some way, even if it’s not my primary calling. 

• Building a lifestyle business is invigorating: I love the skills that I have to flex on the business side of coaching: branding, positioning, resilience, and sales. My end goal with product was always rooted in entrepreneurship, so this is also not a surprising realization. However, I’ve discovered that I’m able to build a lifestyle business in a values-aligned way, especially in the sales and marketing strategy, unlike venture-backed startups. While I value having near-total control over my time, the financial anxiety of entrepreneurship is very real, especially in the early stages of the business. If I’m going to build a business to support myself, I need to find a way to do it that doesn’t leave me in a perpetual state of anxiety. 

• Production work was too similar to my product job, but I loved the energy of storytelling for the screen. Production work requires a LOT of project management to ensure that the project actually comes to life, from dealing with SAG to scouting locations to running payroll. All work that I am sure I could learn, but really lacks the creative spark I felt when writing. Plus, the hours are terrible. The production coordinator I worked for would start most days at 6 AM and end at 8 PM. Not my scene. 

New Direction. 

Taking all of this in, I’ve concluded that my new dream is to become a working writer across the page and screen, articulating emotional truths about what it means to come into yourself. Ultimately, I want to publish novels and write TV shows, telling coming of age stories across different life transitions. I want to show the messy quarter life crisis, the unhinged post-retirement crisis, or the incomplete transformation of marriage or parenthood. Someday, I’d love to become a showrunner, merging my business/leadership and creative skills to lead teams into creating art that touches people. 

But a creative dream this big takes grit, hard skills, and a whole lot of luck. You have to be ready when the right opportunity presents itself. This requires time: to hone your craft, build relationships, and build your confidence. There are lots of ways things might not work out. I might burn out, giving up too early. I might stick it out for too long, resilience transforming into resentment. I might peak too early, landing a big win and then never writing again. Ultimately, I think I’m the most scared of standing in my own way of achieving my goals. Therefore, I want to give myself as much time as possible to become “ready” when the right opportunity presents itself. That’s why I’m giving myself until I’m 40 (~11 years) to make it happen. 

This means I need to find a way to support myself until my writing career takes off. I’ve decided to do this by growing my product coaching business, and picking up a few freelance gigs here and there to make ends meet until the business is more stable. 

Managing and growing people was one of the parts of my product career that I genuinely loved.  I love helping people succeed and thrive in different phases of their product career, navigating transitions with ease so they can lead a fulfilling, holistic life. It’s part giving back, part self-healing to help others avoid the mistakes that I’ve made. I also love the idea of building something of my own, utilizing everything I’ve learned in my product career to make something of myself. Additionally, I’m learning skills that will help me survive in the entertainment industry, like pitching, branding, and networking. It’s energizing, gives me control over my time, and if it goes well, might allow me to experiment with building other things that have always been interesting to me, like communities, conferences, or courses. 

Somedays, I ask myself why I’m taking the hard path, in chasing building a creative career and business. Maybe it would be easier if I just went back into tech, found a full time job, and received a steady paycheck. I often wonder if I’m taking a step backward in life, going from making peanuts in comparison to my steady, six-figure salary. Maybe taking that kind of risk was okay in my twenties, but is it okay as I approach my thirties? What if I can’t support myself through this path and need to go back to full time work? Does that mean I’m a failure?

But I have to remind myself: I’m trying to get better at navigating uncertainty. Regardless of what happens, I will learn through this journey by confronting the uncertain parts of life, rather than insulating myself from them. Also, even though I hate to admit it, failure can be a great teacher. Maybe this is the journey I need to go on to make friends with it. 

If I don’t do it now, then when? 

Staring at the road in front of me like….

Metamorphosis

After I figured all this out, I told my fiance, my parents, close friends, and my brother. They all asked a lot of questions, but had unwavering support in me. My father even told me that his dream before he dies is to see a book or a Netflix series with my name on it. I almost cried when he told me this, relief mixed with gratitude from acceptance.

But soon, things changed. I felt anxious, more than when I first left my job. The support has transformed into a weighted blanket of expectations, suffocating me. Even though it’s still early in the year, I feel like I’m already behind. 

I’ve spent the past few weeks trying to understand why. Maybe it’s my fear of disappointing my loved ones, who have given me consistent and unwavering support. Or maybe it’s coming to terms with the scope of my dream, which feels approachable and daunting at the same time. Or maybe it’s the fear of what happens if I don’t make it, and whether I’ll find real happiness or fulfillment in my life. 

Perhaps this is what it means to metamorphosize. Growth is painful, especially when you’re transforming into a completely different person. Similar to butterflies, we’re not born into who we are overnight, but go through different stages to get to where we are today. I’m feeling connected to the pupa stage of butterfly development, where the caterpillar transforms into a chrysalis to become a butterfly. The outside looks like a giant green blob, with little clarity on what kind of butterfly it will become. How big is its wingspan, or the distribution of colors? However, there are a lot of changes happening on the inside, as small decisions lead to larger changes. 

I feel firmly in the pupa stage: I have a (broad) vision of where I want to go, while slowly growing into the parts to make them happen. I don’t have clarity on how long this stage will take, or what the final end product will look like. But perhaps this is an opportunity to cultivate the patience, the letting go of control, and acceptance of whatever path the Universe has in store for me. 

Which brings me to my word of the year: metamorphosis. 2024 is the year that I manifest metamorphosis for myself, chasing my (new) dream of becoming a working writer, building a business to support myself, and if nothing else, learning a lot about myself and accepting the uncertainty of life along the way. 

Huge thanks to

Devin Faddoul

, Khe Hy, Liz Hernandez,

Tobi Ogunnaike

,

Michelle Elisabeth Varghese

,

Avi Das

for all the time that you have spent with me talking about my career direction. Special thanks to

Lachlan Green

and Annie Tsai for reading an earlier version of this article. Final thanks to

Andy Johns

for inspiring me to look to nature when encountering difficult times. Y’all are the real MVPs. 

My next two posts will cover what I’ve learned about crafting an energizing lifestyle and re-defining ambition for sustainability, featuring key insights from the 10+ books/podcasts I consumed on the subject. If you’re not subscribed already, subscribe to get it when it first comes out. 

Thing 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 Four Thousand Weeks by Oliver Burkeman. 

I have a mixed relationship with time management/productivity “hacks.” I feel like I’m the kind of person who would take these things too seriously, almost to the point of becoming too hyper optimized on doing things the perfect way rather than taking a look at the bigger picture. I was skeptical about Burkeman’s book, but was surprised at so many philosophical examinations about thinking about time. Some of the tactical tips were so-so, but I think the book forced me to ask deeper questions about how I think about time culturally, and how that has an impact on how I live and manage time across all areas of my life. I also appreciated the set of questions at the end of the book to force a deeper reflection about the way I manage my time and what I decide is “important” (or not “important”) to me. 

Thanks for Reading!

I’m on a journey to create a blended career across the creative arts, tech, and business. This newsletter is my way of sharing my reflections, thoughts, and advice along the way. Here are some ways to support or further collaborate together. 

• I would love feedback on this post. 

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  • Hearing from readers also gives me a ton of energy. Drop a comment if you had any reflections about your path, as well as if anything about my path or the way I’m living my life resonates with you. 

• If you’re figuring out your own career transition or looking for more support in your product career, consider working with me as a coach. Here’s my calendly if you want to get the ball rolling.