I'm still insecure

Despite years of therapy and self-work, I'm right back where I started.

I recently went through old texts from 2019—what I consider my “golden era.” I was a PM at Thumbtack, working with some of the strongest product leaders in tech and growing rapidly, living a great life in San Francisco with a thriving friend group. I felt like my life was on track.

Or so I thought when I came across this:

A raw moment of clarity.

This text hit me hard. At first, I thought it was a fluke, but as I kept scrolling, I realized there were a LOT of texts that had a similar vibe. Detailed, paragraph-long sagas venting to my friends about something or asking them about their thoughts on a specific work or romantic situation. I needed other people to tell me what I felt was okay or what I should do (even though I already knew what I needed to do).

Honestly, I can’t even remember what this was about.

Looking at it now, it just makes me feel… sad. I feel compassionate towards this younger version of myself, just trying to figure out her place in the corporate and dating world, looking for answers from everyone else rather than trusting herself. But also, in many ways, this feeling of “not feeling enough” hasn’t gone away.

One step forward, one step back.

I’ve been feeling increasingly insecure over the past few weeks. It’s strange, because in some ways, this is the most stable I’ve felt in years: I’m working part-time at a technical writing agency, which, while not the same as my tech salary, still gives me enough to pay my bills with the flexibility to work on my writing/directing. And for the first time, instead of doing a thousand different creative projects, I’m laser-focused on one: making After Moonrise, my short film directorial debut.

I should feel excited. Instead, my ego feels like there’s a step down.

I feel this the most acutely when introducing myself to new people. When they ask me what I do and I say “technical writer” (even if it’s followed by writer/director), I can tell their eyes glaze over. When I was a product manager, I was treated differently, almost like people respected me more.

This struggle also extends to the creative world. I’m not quite in the creative world yet, but I have enough of a foot in there that I feel I should be more confident about being there. Instead, I constantly battle self-doubt and question my instincts. I find myself shrinking, which others have also noticed. For instance, when my mom asked our family priest about my creative career, his most significant piece of feedback was that my self-doubt would hinder my success.

Damned if you do, damned if you don’t.

It maddens me that, despite years of executive coaching and therapy, I’ve regressed and become the insecure person I’ve worked so hard to overcome.

Some days, I convince myself it’s a sign that I should quit and go back to 2018 me. But I know that this, too, won’t really solve the problem. It will satisfy my ego—temporarily. One strange comment, bad presentation, failed project—and the doubt will come creeping back in. Why did I come back? What if I’m not good at this? Did I make a mistake leaving my creative career behind?

In facing these insecurities, I recently reprocessed a memory in therapy about my first creative writing seminar at Stanford, which featured a prominent writer. On our first day, he told us that not everyone has what it takes to be a writer. I still remember the fear: Will I have what it takes? By the end of the quarter, it was clear that despite my effort, I didn’t, given his response to my work and contributions. This narrative is still stuck in my brain, and every time I have a creative setback or imperfection, I’m convinced it’s a sign that he was right all along.

These texts have also reminded me that I have similar memories as a product manager. Difficult engineer collaborators, tough stakeholders, challenging scope. During those moments, a voice in the back of my head said, "Maybe I don’t have what it takes to be a real product leader." These texts were my way of trying to silence those voices, even though I wish I had the strength to look inward first.

Finding peace.

The one thing that gives me hope in the face of these insecurities is that, despite them, I’m still moving forward.

My movie is still happening (more on that in next post). I’m still pitching myself to people in the entertainment industry. And I have no plans of stopping anytime soon.

Perhaps I’m the kind of person who, no matter what I do, there will always be a voice in my head that doubts myself. Maybe acceptance isn’t about eliminating the doubt, but staying the course in spite of the doubt.

Thanks for reading!

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