Crafting my life’s work: a progress report
thoughts about the past and what comes next
I’ve spent the last few months focusing on a deceptively simple question: how do I craft meaningful work? My thoughts remain a work in progress, so I won’t be able to offer neatly wrapped advice. But I wanted to document my process while it’s still live and messy, instead of waiting for a retrospective through (hopefully) more solid and success-tinted frames.
The last time I was in this position was two years ago, miserable at an investment fund and desperate to work on something more creative and raw. After lots of cold emails and exploration, I created my dream job at a startup called Highlighter (and wrote a somewhat viral essay about it.) I gained a breadth of Silicon Valley experiences: I helped build a consumer social app for 100k users, hosted interviews with well-known founders and investors, and made my first six angel investments alongside firms like a16z and Founders Fund. This fall, when we shut down Highlighter, I returned to the drawing board.
This time has felt harder because the canvas is more blank than ever. My dreams vary widely: writing a book of diaspora essays, investing in world-shaping founders, creating products for a kinder, greener world, and regardless, earning financial independence. If I create something, it could be a book, show, microfund, community, company, or something else. So where should I start, and how will it pay?
Thinking about this has made me feel empowered, grateful, and stressed at once. I know the dots will connect in retrospect, but the present moment means squinting through chaos. This is a recap of some observations from the last few months, as I’ve faced a blank canvas and decided where to start. If this resonates, I’d love to hear from you.
Going gut first
After we shut down Highlighter, I sat down in front of a blank page of options and felt a paralysis similar to writer’s block. My first urge—a bad false start—was to ask as many friends and mentors as possible for advice. I got a barrage of strongly-held and often-conflicting opinions that resulted in stress and confusion.
It was much more effective to ground my explorations in a few core truths about who I am and what I like doing. My most distilled current statement is: I like to connect people and ideas—through writing, discussion, or organizing groups—in ways that spark surprise, empathy, and invention.
Rewinding to remember who I am
Thinking about my core truths meant unwinding years of social pressure and status cues. (Do I really like X, I often wondered, or do I just know my friends / parents / the market rewards it?) I spent many hours completing various life reviews, from sources that ranged from Designing Your Life to a template making the rounds on Twitter by founder-turned-farmer Anthony Gustin. The most helpful gut-first approach was to ask: what did I love as a child that has endured over time? I came up with some ideas and then asked close friends if they agreed.
These are my answers so far:
Writing and the arts: I grew up around piles of books. At eight, I’d bound my own novella about American voyagers to India, written for magazines, and scribbled notebooks of embarrassing Victorian poetry. I came to love ancient languages and philosophy. Nothing gives me the same awe as reading words written thousands of years ago—and adding my own.
Connecting across tribes and disciplines: I moved to the US from India when I was two. I spoke Hindi at home, English in school, broken Spanish at the grocery store, and studied Latin in high school. In college, I was often the only brown person (or woman) in my philosophy seminars, and perhaps the only philosophy major studying linear algebra, hieroglyphics, or neural networks for fun. By living between lines, I enjoy prompting people to reconsider their assumptions about me and others.
Organizing people to make things happen: In fifth grade class, I rallied my class to publish a weekly newspaper. At college, I helped revive Princeton’s Sanskrit program. I convinced my leftist co-op to throw a surprise appreciation party for the campus police, which made national news and earned both sides new friends. I’ve hosted fifty-person potlucks and run book clubs on race & social issues with my conservative neighbors and college friends. I’ve always found joy in getting people together to do or create things.
Before getting to this seemingly crisp list, I spent time rejecting other ideas. As a friend told me, it’s easy to shortcut this process by re-hashing phrases we’ve been coached to say for interviews, without really challenging if they’re true. My best examples of these were lines from years of fellowship applications, like: I’m interested in the intersection between technology and policy. I’m interested in developing tools to help partisans better process complex arguments. I want to combine education and technology to build an informed citizenry. I’m still interested in many of those things on an abstract level, but they aren’t core.
The things that are core, above, have been true regardless of my job, social circle, or income, and run-through the themes of my writing. (See other essays in this newsletter for example reflections on everything from Hinduism to the ethics of curiosity to rural America.) Reflecting on them has been the first step to dreaming bigger.
Too much advice, taken too seriously
Starting off with too many perspectives from people I loved—and taking them as personal obligations—was worse than getting none at all. Some people thought it was high time to be a “real” product manager at a big tech company; others thought I should join a venture firm. Some thought I should get a PhD; others thought I should build a freelance marketing consultancy. As soon as I imagined living up to someone’s vision, I imagined disappointing someone else.
Next time, I’d keep two things in mind. First, people’s advice comes in reference to the ladders they’ve climbed and the risks they’ve taken. Mentors who entered the workforce decades ago have a very different sense of the risks of creating a non-corporate path than I do. Second, no one actually cares what I do. They want me to thrive and have their own lives to worry about.
Sketching out a few big projects
Finding the right people or organizations to work with takes a long time. Instead of outbounding and waiting around, I’m defining projects I can start working on immediately—without anyone’s money or attention.
To brainstorm, I am considering three things:
-what do I want to learn about? what’s underexplored?
-how do I want to learn? (reading, discussions)
-how do I want to document it? (writing, video)
Each learning and documentation process can help a future company idea, investment area, community, or publication take shape. I’ve tried not to self-censor too much based on “uniqueness” and instead trust that an edge will emerge as I try things. The bigger and more playful I let myself be in scope, the better my ideas have flowed. Here are some examples
My ideas felt hard to nurture in a vacuum, so I made a list of inspiring people and organizations to turn to when I feel stuck. The list includes friends, friend-crushes, and even icons of their respective fields. I don’t endorse each person, project, or methodology here, but find each inspiring for divergent reasons. There’s something that makes the summation of their voices a pool where I feel I belong. Here’s an excerpt:
Every person I’ve met who has independently defined their career has taken the leap of faith that if they think and create enough in public, the market finds them. That is what happened with my last role, though it doesn’t make it less scary the second time around.
Still, these starting points have started to become a beacon for people interested in brainstorming ideas or working together. I’ve spoken with startups that need product or growth support, venture firms that need help with content and community, studios looking for founders to incubate companies, nonprofits writing grants, and more. Hopefully, this process can both help me land a few part-time (or even the right full-time) clients/partners and accelerate my personal explorations.
Doubling down on what I’m good at
Historically, I’ve tended to focus more on filling in my weaknesses than pushing on my strengths. In college, for example, I took many engineering classes but only one creative writing seminar. The approach helped me to build out well-rounded and interdisciplinary perspective, but I’m being careful not to fill “experience gaps” any more at the expense of building upon what I can uniquely do.
Convincing myself that it’s okay to double down on what I’m good at is an ongoing process. I’ll always have experience gaps that feel like prerequisites for legitimacy in someone’s eyes. Some people, e.g., think that I’ll never be a credible founder or venture investor without having operational experience as a product manager at a large tech company—but having seen many routes to success in different fields, I’m skeptical. Before I decide to “fill a gap” for it’s own sake, I now ask: will this actually help me do more of what I love?
Letting go of the fear of being pigeonholed
I sometimes worry that emphasizing my strengths pigeonholes me into low-paying roles. If I highlight my writing ability, people sometimes assume my capacities end at being a great ghostwriter or copywriter, which often have the lowest rung of pay and agency in the startup world. Things look very different if I highlight my product knowledge. In reality, most people just aren’t creative about envisioning the ways they might work on things with me—I’ve had to do it for them. I’m focusing less on epithets and more on the actual work I can do.
Embracing illegible ambition and creating my own conviction
The most freewheeling learning periods of my life have happened with “cover,” whether a prestigious university degree or fellowship. One of my generative years was when I moved to India on a Fulbright fellowship after college. The award gave me an excuse to explore the country, write a lot, learn new things, and not overthink my time. Its prestige ensured that no one questioned me—including myself. The Thiel fellowship and certain grant programs carry similarly massive and liberating value. Unfortunately, chasing blue ribbons isn’t always possible or the best use of my time. In the absence of ladders, awards, and social sanctions, I’m working on finding my own conviction and working without external “cover.”
My process of facing a blank canvas of career options remains bumpy. To stay positive, I’m reminding myself of other situations where I’ve had periods of extreme discomfort before flashes of flow—whether learning to code, surf, or immersing myself in unfamiliar communities.
I’m trying to start this year with a kinder self-gaze and the motivation to try many things and develop many perspectives. I want to know where immigrant communities thrive, how politicians and founders think about nuclear energy, how people in unexpected places dream about or fear AI, and why a farmer in Kansas and a waitress in Berkeley sometimes assume the worst about each other. I want to try out different disciplines, social circles, and interpretations of work, to understand different codes and share my processes out loud.
I’m open to many flavors of work, but the most important thing is to seed a voice of my own and find brilliant people to push my thinking. I’m giving my personal projects attention and trust that rewarding work and opportunities to earn income will open up alongside or in parallel with them. And I’m beyond grateful I can give myself a chance.
One of my favorite (paraphrased) Tyler Cowen quotes is this:
Raising the aspirations of other people is one of the most beneficial things you can do with your time. At critical moments, you can do so simply by suggesting they do something more important and ambitious than what they have in mind. It costs you little, but the benefit to them and the broader world can be enormous. So often, talented people just don’t see that they could be doing something different and better than what they are currently engaged in. Barack Obama had no plans to run for president until he found himself surprised by the positive media reaction to a speech he delivered at the 2004 Democratic National Convention; only a few years later he won the presidential election.
This is a small step towards raising my own aspirations: to stop thinking about the sandbox and to step inside to play.
I have many people to thank for reading various drafts of these thoughts-in-progress over the course of weeks. A huge thank you to Benjamin Laufer, who pushed me harder on raising my own aspirations, changing my mindset and this piece entirely. Thank you also to my family and Ivan LaBianca, Lavanya Sunder, David King, Jen Yip, Matt Siu, Sari Azout, Nadia Asparouhova, Tom Critchlow, my family, and Ivan for your thoughts. A recap of insights from Sari, Nadia, and Tom coming shortly in a separate piece!
If you’d like to talk or collaborate, I’d love to meet. You can reach me at vidushi.mishti.sharma@gmail.com or @m1shti on Twitter.
Hi Vidushi!
This was so wonderful to read especially because I resonate so much with your core interests in life. I utterly loved the project ideas!! Projects that come out of interconnectedness and the interdisciplinary nature of things is of special interest to me, I can already see the impact DIY Thesis Lab could have in connecting ideas from frontline communities that are often under or misrepresented in social/cultural/economical macrocosms of a country as diverse and complex as India. Also the creative technologist wiki— relatable as I’m pursuing a multi-hyphenated career myself! I’m so glad you decided to put your thoughts out here, your inspirations, your way of thinking (i think i’ve developed a friend-crush on you), I admire you so much for doing this, your thoughts are so well put!
If you’re in India or thinking about pursuing a project in India, I would absolutely LOVE to collaborate with you, it would be an honour!
Can’t thank you enough,
Debanjana :))