
I read stories and articles on Substack to make me feel better but at times, I come out feeling worse. Everyone seems to be a Substack Sage. Almost everything that is published is about someone who has already made it. Stories of struggles that end with success. About someone who has come out of the abyss, someone who has found a more peaceful way of living, someone who has quit their job and is now dispensing advice on how to navigate this journey, to become a calmer, more present you.
I am merely scratching the surface and have nothing much to show for. Everyday, since the day of my quitting my job to building my own thing, I am wrestling a voice that tells me I am not good enough. That building my own business or career without the backing of a corporation is too lofty a goal. Almost absurd. That abundant-mindset is only for the rich and successful, or materially privileged. That I have absolutely no place and time for such delusional aspirations.
Iām not quite anywhere yet. I have good days, then bad, anxiety-paralysis days. But in this new journey, Iām learning valuable things about myself and the world. I recount some of them here.
21 Year-Old Lilly Would Not Have Guessed That Her Career Trajectory Will Look Like This
For context: I recently left a stable, high-paying (some say coveted) job at a management consulting firm. Against my initial reflex of moral judgements (Lilly? At at MNC?! Who are you?), I took the job because I was curious. Through a truly random series of events, I was presented a chance: To experience whatās it like to be in the company of consultants. So much of what I heard about it was badā tech bros jerking off one another as they glorify the impact and value their work has made in the world. How they are disrupting the now, revolutionising the future.
I also wanted a higher benchmark salary, which I offset this uneasy feeling with a personal mission: To be, what David Graeber says, on the edge of the inside. I wanted to go in with a journalistic mindset. And it was uncanny that when I signed the offer letter, I was in the closing chapters of Graeberās Bullshit Jobs. Perhaps that fuelled my curiosity further.
So, I told myself I will try. And that I could always leave when it got absurd.
Thereās much to say about my experience there. But in this post, at least, Iāll say one thing. You just canāt be on the edge of the inside (or at least I couldnāt). A company culture and its ostentatious posturing, blatant display of wealth, opinions, power, and bad management will get to you. You end up sleepless and anxious over not being good enough, about feeling ridiculously small unless you play the game. You become the very person the company sets you up to beā vying, fighting for attention, propping yourself up on a pile of half-assed jobs done by everybody including yourself. I felt crushed, demotivated, uninspired, and emotionally burnt out.
On my last day of employment, I whispered a major fuck you to the company. Said thank you for all the unexpected lessons I have learned (and they are honestly good lessons, which maybe for another post?). Said thank you to the handful of people (actually just one person) that genuinely made my experience a less lonely one. Took one last cup of free Nespresso coffee from the foyer and left.
I Knew The Time Is Now. It Was A Culmination of Clarity, Confidence, Courage, and Buffer Money
In the years since the pandemic, Iāve been talking about starting my own company. Never had the courage. Never had the confidence. But the idea always found its way into conversations with my partner. Even found its way into my extensive career mapping endeavour (thanks, Tim Urban).
When I left my last job, it was with a sharper sense of clarity.
I was going to build on my freelancing endeavour. Formalise it into a business. I wanted to do this not because I love writing. I wanted to do this because I want to do more of what I liked and less of what I donāt like. I wanted to shape my work environment and have it align with my values. And I figured the best way to do that is to be my own boss and hopefully somewhere down the line, be a good boss to others.
As a side noteā I wouldnāt have done this with at least a fair amount of confidence. And I ascribe this to my ex-boss (from a company before the management consultant one). Perhaps another post for that, about mentors and mentorship? She was one hell of an amazing mentor and friend. Iām doing what Iām doing now because Iām sustained by her words of encouragement and her belief in me. Her willingness to guide me and make space for me to grow. Of course, the confidence also comes with time and practice. I spent so much time thinking, charting, writing, structuring, talking, visioning in the past two to three years alongside a good amount of skill-and experience building even if via the management consultancy firm, that it has finally come to some fruition ā clarity.
Anyway, building my company. Iām really just at the beginning of it all. Just two months through this thing. I told myself during my first day of unemployment that I will take a break for at least one month before doing anything about the company. To rest, to explore writing the things I want to write. To walk the routes Iāve always wanted to walk, but hell no.
The relief of quitting a job quickly metastasised into an anxiety of not having a job.
So, I put a bit of structure into my days to quell unrest. Some days for working, other days for anything at all. Built a website, came up with a company name while I was mid-pee at 2AM, registered the company, reached out to some friends, acquaintances, and networks, etc. And yet, amid the progress, I was and sometimes am, discouraged and anxious. I had to constantly take long, deep breaths, usually had sub-optimal sleep, and in my half-awake moments, questioned if what Iām doing is even the right thing.
Like I said, maybe I am delusional for thinking I can do this.
Here Is Where I Recount The Lessons, The Good Things
1. You would do well to update your mental model of how the world works
- The one and only time I went to a spiritual reader was last year. She told me one thing: You need to reframe your relationship with money. This was one of those profound, perception-altering moment. I always known myself to be money-adverse ala Gordon Comstock of Orwellās Keep the Aspidistra Flying. I always thought there was some virtue in being anti-money (oh, so much to say here). But Iāve come to realise how this made me risk-adverse, fearful, and sometimes bitter. My first instinct is scarcity. I donāt do something because I fear I have not enough money. I feel guilty when Iām not saving up as I should. Knee-jerk reactions like that. So, Iām in the process of dismantling this archaic voice and listen to a deeper one, guided by a gentler, kinder, universe.
- This archaic mental model extends to placing too much of my self-worth in the work I do. A lot of guilt arises from not working. Rest becomes a well-deserved reward, no longer just time to day dream and lull unconditionally. The systemic nine to five had found its way into my body clock, wiring my values so that it is tied to a feeling of enoughness. This too, I found is something I want to change by choosing to work on my own. Itās not just about building a business. It also is about re-aligning my life and all its sinewy bits so that it fits a healthier, calmer version of a person I want to be.
- Through it all, I often find solace in my most trusted friends. Friends who share the same values, friends who make space. In conversation, we draw from the well that is our collective courage.
2. You have a bunch of people that truly supports you
- And this is that one thing that really keeps me going.
- During a farewell party, my mentor handed me a note and a small gift. The gift: A Maneki Neko Lucky Cat that has mega-muscles. The note: Fikir. Tapi jangan fikir lama lama ya. Just go for it. You got this.
- One day, I gave WB a call to ask him for advice. I have been collaborating with him for almost seven years. Iāve always looked at him as the kind of business owner I wanted to be: Generous, kind, authentic. Without hesitation, he shared his spreadsheets with me, on how to navigate clients, on how we can both collaborate further now that I have my own company.
- These are instances that remind me that Iām never alone in anything I choose to do. There is kindness and support if you just extend the courage to ask for it.
- Though, this also works best both ways.

3. Time is how you make it to be. And thatās wonderful.
- Quieter, non-work days like these are days where I can think. Write. Read. Get into rabbit holes. And it has been delightful. Iām grateful to even have days like these. No 9-5. Just time as youād like it to be.
- So, these is what Iāve been doing: Go for hikes at any time of the day. Have conversations with people as I please. Take a few hours to marinate in thought. Rabbit-hole the internet for ideas and inspiration. Build maps. Daydream. Let ideas shape-shift and bloom, let all of these be small pebbles and kitsch material for sense-making and world-building.
- In this time, Iām an independent anything. An independent researcher, creator, observer, documenter. Itās liberating to do something outside of institutions. When you do something that is purely guided by what you like ā you find yourself navigating fresh frontiers, opening gates into new gardens. You find yourself tending to different plants and animals, observing new life grow, decay and change. You find yourself in a new world with new language. Something in you changes.
4. Youāre leaving space for surprises
- You donāt need to look too hard but you could if you want to. But you canāt force the universe into a container.
- Random: I recently was asked to do a voice-over for DE&I Guideline so that it is accessible for the visually-impaired.
- Sometimes when you hold space for your life, the universe fills it with interesting things. You just got to define the space, but let all the interstitial spaces open for opportunity.
- The context is smarter than you. Collaborate with it. What do I mean by this? See Unfolding.
5. Iterate + Enjoy the process
- Henrik Karlsonās article on Unfolding has been instrumental in guiding my process and practice through this time. In a gist, you donāt start with a vision or a solution. You iterate towards calls out to youāpaying attention to the context, removing things that frustrated you, and expanding things that made you feel alive. Small step by small step, being a researcher of your own life.
- So, a reminder to be patient. A quote by David Whyte (beautiful voice) comes to mind: Ambition takes willpowerā a constant application of energy to stay on a perceived bearing.
- Almost all of the things Iāve done thus far building the business, I found myself thoroughly enjoying. I get into hyper-focused mode and time flies. Mostly, it has been fun. And I have never been able to say this ever about my previous job.
- So, just keep iterating towards what I like, and prune away the things I donāt.
- Itās a trust process and a long one.
- But I hope I take time to build the resilience to see me through.
Love,
Lilly

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