She Said, She Said

You Just Have To Do It

Hi there Stories by Shiv community,

It's been a while. I've missed you all, and I've missed writing in this format!! This year has been...textured...to say the least; more on that in a future post. Maybe. For now, I'd like to share a conversation I had with a friend a couple months ago that felt resonant.

Given there's only a couple weeks left in the year (and also of my 20's — I'm turning THIRTY on January 3rd… 3-0 — eeeeep!), I've been reflecting a lot lately. I'm sharing this transcript from our chat in case you've been finding yourself in a contemplative headspace as well.

Some context before we jump in:

My friend

Vinamrata Singal

left her job in Tech a couple years ago to explore creative interests. We actually met through this newsletter when she reached out to me in 2023 to chat as our paths are similar. We immediately connected over our love for Thai food and desire for getting the most out of life. Since then, we’ve kept in touch and she's become one of my first pals in NYC.

Vinamrata is thoughtful, introspective, and more of an empath than she gives herself credit for. We often help each other think through our creative journeys, what role productivity plays in our lives, and the ambivalence that comes with leaving a traditional career to pursue a new path.

Here's an example of one such conversation…

She Said

Vinamrata:

Okay so. I’ve been thinking a bunch about whether I want writing and/or directing to be my full time thing or not. Because I’m really worried about doing it in a way that might burn me out. I had a conversation with this comedy writer who I guess has “broken in”, and he kept encouraging me to go-down-the-mail-room-at-a-talent-agency path…and I don’t know if that’s something I really want especially given my background and how much I can bring to the table.

^ She’s being modest. She’s a Stanford graduate who’s been a PM at several leading tech companies, large and small, and she now has her own coaching company where she helps others navigate their careers in Product.

I’m wondering if I don’t take any opportunity to break in and never do, but keep making art by writing scripts or shooting films, is that enough? Or have I wasted my career? I feel like this need that some form of external validation or ladder is necessary for it to be a career. But I don’t know.

I want to say that doing it is enough, in whatever form, but I have a hard time accepting that as a “career”. Especially given that "breaking in" is so out of my control. Like, I don’t want to beat myself up over it or feel like a failure if it doesn’t happen.

I think there are two questions I have:

1) Do I want to go into TV or film (especially independent film)? I got really inspired by the short film we worked on the other day and the process so far of making the short, though I need to see it through to know.

2) If I never “make it” would it be worth it to pursue either? I feel like the answer is yes, but for some reason I have a hard time accepting it.

She Said

To which I respond:

Okay I can understand where you’re coming from. And I have definitely had these existential thoughts about what a “career” in this industry looks like as well.

I agree that the idea of going the mail-room-route-yada-yada is probably not something you should do. And honestly, it’s not even because I think you’re “better than that” so to speak, but more so because that route feels extremely distant from the path you’re on.

As in, maybe it’s something you might consider later when you feel like all you need to “break in” is a little extra push, so you might try unconventional ways to get a project over the finish line. But right now, it's such early days, which kind of bring me to my next point…and that’s something you mentioned yourself:

You just have to do it.

You just have to make the thing — or make the 10 things — to find out if you’re on the “right” path. There isn’t really a way to A/B test this thing, the same there isn’t a way to A/B test life. It does require some level of committing to a path, I believe. And that doesn’t mean you have to commit to it forever, but commit enough that you actually give it a shot.

Try, learn, and then make your next move.

I genuinely think life is like that. It’s very hard to grasp for me too, by the way, even though I know it’s true. But there’s no other way to answer the questions. Or at least not one that I’ve found.

The other way to look at it could be — you’ve already made the decision to try.

You already quit your job, you already have been writing scripts, you already have been seeking out mentorship and programs, etc. All that’s left to do is just make something and see how it feels.

I’ve tried this strategy for the last two years and discovered that theater and writing are two things I will try to stay close to forever. They call to me in a way that very few other things have in my life. Filmmaking — I don’t know. Maybe I stick with it, maybe I don’t. I will need more reps to decide.

I’ve also come to realize that pursuing only one of these things, i.e., acting, wouldn’t be enough for me. It’s not intellectually stimulating enough. Does that mean I don’t “make it” because I’m not as gung-ho about it as the actors I’m competing with for roles? Maybe! But wanting to pursue it anyways is a telling sign that there is something still here for me to explore. I don’t know if the supplement to pursuing acting will come from corporate work, or maybe volunteer work, or something else entirely, but that’s how much I’ve come to learn so far.

I imagine that as you go down this path of your own, you’ll have some similar takeaways. I like this, I don’t like this. I’ll tolerate this shitty thing about this industry, I won’t tolerate this other shitty thing, etc. etc.

I hope this is helpful. But also, I just want to reiterate that your feelings of existentialism make complete sense. I get it. I’m there with you.

Answering these questions feels difficult, I think, because it’s actually not about writing or directing or filmmaking — we’re essentially trying to answer: what do I want out of this life? And I think wrestling with that question time and time again is kind of life’s work.

It’s not surprising to me that you would struggle to find the answer to that; it’s such a big question!!! What I’m often more shocked by is how few people ask themselves the question at all, and fewer still who allow themselves the chance to explore it.

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I share this excerpt from our conversation because it represents the cyclical nature of triumph and self-doubt; the push and pull of taking a bet on yourself. I think Shiv from 2022 thought that quitting my job and pursuing my dreams would be a solution to the existential uncertainty I’d been accumulating for so long. However, I know now that it's just another path. It might pose fewer existential questions, but the uncertainty is alive and well.

I don't think that's a bad thing. Not at all. It just means there's more work to be done; work that is directionally sound, but still executionally ambiguous.

Shiv

P.S. Thoughts on me starting an advice column here?! I feel like I’m pretty good at this thing. 😏

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