I hate going back to San Francisco.
It’s the place where I really became an adult, after spending four years at Stanford and four years across Palo Alto/San Francisco. It’s my closest proxy to a “home.” But none of that makes me want to go back.
My outward reason: too much tech. The reality? It’s because I am not sure if I belong there. It wasn’t always like this. Initially, I fell in love with the laidback, tech-oriented culture of SF. Until I didn’t. At some point, I realized I was no longer interested in total comp chasing or founder networking present at most social events. That, plus my burgeoning interest in the arts, led me to decide that perhaps I was ready for a new chapter.
But I have roots in SF, which means I am often pulled back. In this case, it was the wedding of one of my good friends. After much deliberation, I decided that my love for my friend was greater than my disdain for tech talk, so I booked my flights. But I made myself a promise: I would respond to the “What do you do” question with my new identity as a writer and coach. At prior weddings, I’d either avoid or dance around the question, avoiding the discomfort.
But I decided that now, I was ready to do the damn thing.
The Wedding
The first event of the wedding was a small dinner for folks who had flown from out of town. The groom (my friend), whom I met working at Google, introduced me to a “ML engineer working at X startup.” I felt my chest constrict. Here we go again. I smiled and shook his hand.
We talked about travel and San Francisco. So far so good. Then, during a lull in the conversation, he asked me if I was still at Google. I shook my head. He took turns to guess which tech company I worked at. Apple? Netflix? Perhaps I’m an Amazon girlie now? I told him that plot twist, I was actually a writer and coach.
He turned to my fiance, and discussed something about Meta’s Llama model.
I thought that I would feel humiliated. That I would cry, excuse myself and have to leave the event early. Instead, I was calm. I found the whole thing really… validating? Like, what I had expected to happen actually did happen. And I was fine. In fact, I was great because I didn’t spiral or blame myself for his reaction.
Was this growth?
The next day, we ran into each other at the cocktail hour at the wedding. After making some small talk about the ceremony, I was about to excuse myself to make a beeline for the (incredible) goat cheese, but he stopped me to ask about why I took a sabbatical. After sharing my story, he told me that he had done something similar after his time at DeepMind. It was the dream job as an ML researcher, but he found it extremely dissatisfying. He wondered if he should have taken a longer sabbatical instead of diving back so quickly into full-time work.
At that moment, I felt more connected to him than anyone else I had met at the wedding so far.
Facing My Mentors
After the wedding, I spent a few days in Palo Alto, meeting up with college mentors. The first was a professor and the second was an industry person I’d met through a class. I was a nervous wreck. Both were people who had last seen me as a go-getter, ambitious PM with potential to become a future founder. I was anxious that I had disappointed them, let them down by not having achieved enough in my tech career.
My therapist asked me what I wanted to get out of these meetings. I don’t know if I needed any advice or “tactical” help. Perhaps I wanted closure from my former self, and this was a step in that direction. Does this mean that I was grieving? If so, who was I grieving?
The meeting with my first mentor started a little awkward. There were moments where I chided myself for not remembering more about his personal life. We talked a bit about tech, brainstorming potential roles that might make me happy. When I shared with him about my burgeoning interest in storytelling, he encouraged me to take small steps rather than big leaps. I was surprised. I thought he would try to talk me out of it.
Then, as I got ready to leave, he said: “Vinamrata, I hope that you realize that you have nothing left to prove. Not with your wedding, your career, or anything. You’re awesome just as you are.”
I was shocked. How had he seen me so clearly in forty minutes when I had struggled to pinpoint this exact issue my whole life?
When I left his office, I felt light and relieved. For the first time that day, I was enjoying my surroundings, drinking in each detail of the beautiful campus and warm sunshine. He understands me! He supports me! I don’t have to prove anything to anyone! Funny how it’s so much easier to accept this fact when someone tells you this versus you telling yourself.
This theme continued with my meeting with the second mentor, at the Four Seasons in Palo Alto. The upscale location retriggered my anxiety, and whether my outfit was “cool” enough for a venue like this. But emboldened with the confidence from my earlier meeting, I told her about my newfound realizations about storytelling. Similarly, she was excited. She told me that this shift in my ambition from external to an internal place is a sign of maturation from the achievement oriented culture at Stanford.
I didn’t realize how much I needed to hear that until she said it. There was a part of me that felt that I didn’t deserve this level of kindness. But a bigger part of me felt grateful and relieved that this meeting had happened, perhaps a sign from the Universe to keep doing what I was doing.
Shifting from closure to peace
Both these experiences have me thinking a lot about fear. Why am I so scared to share who I am? Why am I so afraid of judgment by others, especially peers and mentors? Why do I struggle to feel confident in my new self?
I think it's because for most of my life, I felt like an outsider. Hindu kid in Muslim Saudi Arabia. Brown kid in white New Zealand. Kid who skipped a grade in the inner-city middle school. When I got into Stanford, former classmates posted on my (now defunct) Tumblr blog with comments like “You only got in because your brother went there” or “You didn’t deserve to get in.” I ignored them, but there was a part of me that wondered: what if they are right?
Stanford was the first place I felt accepted, if not rewarded, for my intelligence. Yet there was also this fear that I couldn’t keep up, especially when I met folks that were way more accomplished than me. I felt like I needed to do something to prove that I did, indeed, belong here. Otherwise, where else would I belong?
This was amplified in the product role, where other people’s perception of your work is a big factor in your success. It’s a big reason why my anxiety went into overdrive, as the desire to belong led to taking on outsized responsibility over things that were way beyond my control. Admitting that I’m a coach and writer means exposing the “real” me. But will I be accepted for it?
Thankfully, the answer seems to be yes. Leading from a place of my true, authentic self, even if it means saying things that feel uncomfortable in the moment, has mostly brought me closer to the people from my past. With both my mentors, I had chats at a deeper, more personal level that I struggled to have when I worked full-time in product. With the guy at the wedding, I was able to explore a different side of an individual that I would have normally written off. And more than anything, I feel more peace with my choice.
Back to SF?
Weirdly, I’m looking forward to coming back to San Francisco. There is beauty in the city, especially with the waterfront and weather. I miss my friends out here, even if our paths are diverging. The produce is a million times better than New York, and I have such nostalgia for Philz and Oren’s (iykyk).
Maybe I am an outsider by San Francisco standards. But SF has a history of attracting outsiders. Perhaps, we are all outsiders in our own special way.
True healing happens when we make our peace with that.
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!
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You did such a good job capturing something I've felt, the dissolving of one identity for another and then having to tell people. I love how supportive and curious the people in your life were. You're doing such awesome things that seem to bring you alive, so happy for you!
this article speaks to a phenomenon I've been grappling with deeply! I think the key to moving through life fully aligned to my values and needs will be related to how well I can let go of others' judgement, ingrained 'high achiever' expectations, and 'elite' pursuits/organizations