#22: How Two Years of Freelancing Rewired My Understanding of Work
what it's like to find your way when there's no ladder to climb
Welcome to Homebody Stories! A newsletter offering reflections from an ex-productivity enthucutlet trying to live a more meaningful life, one step at a time.
When I was about 14, my mother would take me and my brother to Crossword. It was our weekend ritual. There was only one Crossword store in my hometown back then.
Once there, my mother would simply say, "Pick whichever book you like." That was it. No limitations. We'd scatter like explorers, fingertips grazing spines of different colors and textures, hunting for treasure. Those Sunday afternoons were magical.
When we eventually outgrew this tradition, my mother got me a library membership. This new sanctuary of books, lovingly maintained by a father-son duo, was just a stone's throw from my home. I could walk there whenever I wanted. The library smelled of wooden shelves and well-loved pages. It became my weekend haven.
Till date, these moments remain my most precious childhood memories. I return to them often.
Years later, I noticed something striking about my professional life.
In my most fulfilling work moments, I experience that same transcendent feeling. I lose myself completely in research rabbit holes. Hours vanish as I map out strategies and jot down possibilities. The thrill of crafting visual narratives that connect with audiences echoes that same childhood joy. It's familiar. It's home.
What connects these chapters of my life?
Immersion.
In both realms, I become part of something larger than myself: a sacred exchange where stories matter and imagination transforms everything it touches. Some passions never leave us. They simply grow alongside us, waiting to be recognized.
So, how did I go about uncovering this thread?
It was thanks to the genius Simon Sinek.
When helping people discover their WHY: that deep purpose driving them through life and work, Sinek asks just two questions:
"Tell me about a specific, strong, happy memory from your career that really sticks with you."
"Tell me the same again, but from your childhood."
He then identifies the theme connecting these seemingly disparate memories.
The exercise revealed what I might have otherwise missed: my lifelong love affair with immersion, discovery, and the transformative power of stories.
On that note, let's dive into today's newsletter which is essentially me celebrating my two-year freelancing anniversary (why is it still so hard for me to believe this?!). This journey, with all its exhilarating highs and lows, has taught me lessons. Doing these five things will change your life - these are NOT those kind of lessons.
Whether you're standing at the edge wondering if you should jump, have just taken your first tentative steps toward building your independent career, or are miles down this winding path, what follows is my roadmap of the territories I've explored, the treasures I've found, and the traps I've fallen into (so you don't have to). So, let's get started :)
First Things First
Us, millennials, have been sold a beautiful lie: "Find that one thing, love what you do and you'll never work a day in your life," they said.
What toxic, destructive BS.
I spent a very long time trying to become someone else. Someone whose work filled every corner of their identity. Someone who felt like she had to choose that one path forward. In Sylvia Plath's The Bell Jar, she writes about seeing her life branching out before her like a fig tree.
"I saw my life branching out before me like the green fig tree in the story. From the tip of every branch, like a fat purple fig, a wonderful future beckoned and winked. One fig was a husband and a happy home and children, and another fig was a famous poet and another fig was a brilliant professor, and another fig was Ee Gee, the amazing editor, and another fig was Europe and Africa and South America, and another fig was Constantin and Socrates and Attila and a pack of other lovers with queer names and offbeat professions, and another fig was an Olympic lady crew champion, and beyond and above these figs were many more figs I couldn't quite make out. I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn't make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet."
For years, I was that figure beneath the tree, paralyzed by possibility, terrified of choosing wrong.
I came across this somewhere: "Are you living a life that connects to things you value, or a life that's in opposition to them?"
I had become so adept at morphing myself into whatever shape the world demanded that my own contours had disappeared.
But then, I discovered a powerful antidote to career anxiety: curiosity.
Leaning Into Curiosity
No, I am not talking about the anxious, frantic curiosity of "What should I do? Where is my life going?" But the gentle, childlike wonder that asks, "What interests me about this?"
I started being curious about myself, versus curious about how particular paths/jobs might make me feel content. This subtle shift freed me from the crushing pressure of making the right decision. Instead of forcing myself to choose a perfect destination, I began exploring what naturally drew my attention. The thing is curiosity operates differently than anxiety. Anxiety narrows your vision, forcing you to focus on threats and catastrophic outcomes. Curiosity expands it. It invites possibility rather than limitation. It transforms mundane tasks into opportunities for discovery.
Now when I approach work with genuine curiosity: asking questions, following interesting threads, making unexpected connections, the quality of my experience transforms. Time moves differently. Energy flows more freely. Problems become puzzles rather than obstacles.
Curiosity is not just a mindset. It's a practice. It requires intention. It means resisting the urge to categorize experiences as good or bad (there are no neat binaries) before fully exploring them. It means asking questions without knowing where they'll lead. It means embracing the possibility that what you discover might surprise you.
But, it took me a long time to get here.
Collaborating With Uncertainty
The truth is brutal when it finally arrives. Mine came like this: A job is not a soul. A career is not a self. It's a means to support the things in your life you do love.
Let me repeat that, because I needed to hear it a thousand times before it sank in:
A job is not a soul. A career is not a self.
The modern Indian workplace demands everything: our time, our energy, our creativity, our health. It rebrands exploitation as hustle culture and sells burnout as a badge of honour. We've been conditioned to believe our worth is measured by productivity, by titles. The greatest trick capitalism and our glorifying-the-grind society ever played was convincing us that work should be the primary source of our fulfillment, purpose, and identity. That time is of utmost essence, hence the five-minute delivery (!)
I started recovering when I wrote down my actual values. The truths that mattered to me.
Connection. Creativity. Growth. Nature. Joy. Sukoon (Tranquility).
Rilke wrote: “Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answers.”
This became my mantra. Repeated on morning runs. Whispered during moments of doubt.
Love the questions themselves.
When I stopped demanding the next project to be the thing - the perfect fit, the dream position, the answer to all my existential quandaries, something unexpected happened. The pressure valve released. I could breathe again. I could see each opportunity for what it actually was: just one small part of a complicated, beautiful life.
As Paul Millerd wrote: "Conventional wisdom says to grow fast, to take advantage of every launch. However, that increases the odds that you end up doing something you don’t want to do. My approach has been to take a slower path."
Clarity for taking that slower path arrived not in the form of certainty, but in values. Now when faced with decisions, I ask myself "Does this project align with what matters to me?"
I discovered something both terrifying and liberating: the questions never stop coming. They just change form, approach from different angles. The eternal return of doubt is the human condition itself. Today, I understand that living with the end of the story in mind, knowing exactly where I'll end up and how I'll get there inhibits me from experiencing life in all its messy expansiveness. Martin Luther King Jr. once brilliantly said: "Faith is taking the first step even when you don't see the whole staircase."
Working with uncertainty is exactly the same. You just need to see far enough to take the next meaningful step in your freelancing journey.
Finding Your People
Perhaps, the single most underrated factor in work fulfillment? The people you surround yourself with. I've had technically dream jobs I had manifested that became nightmares because of toxic colleagues or absent mentors.
We absorb the energy, perspectives, and values of those around us. Their influence shapes not just how we work, but how we think about work itself.
I remember my boss Bhumika, who took me under her wing. She approached challenges with a calm curiosity that I found magnetic. She asked questions rather than making declarations. She maintained strong boundaries between work and life without apology. Her mentorship wasn't about career advancement strategies or networking tactics. It was about modeling a healthier relationship with work itself. I've been equally fortunate to learn from mentors like Indrajeet and Mahema, each sharing wisdom that shaped my professional journey in profound ways.
Initially when I switched to freelancing, it was all about taking all sorts of projects to cash those first few invoices. But when considering opportunities now, I evaluate the people as carefully as the project. I deliberately sought out people who embody qualities I want to cultivate: perspective, wisdom, balance, generosity.
And these individual mentors changed my approach to work, but finding my communities has been huge.
A few months into freelancing, the isolation hit me hard. I missed the casual collisions of workplace conversation, the shared language of an in-house team, even the eye-roll exchanges during tedious meetings. My apartment walls started closing in. My confidence wavered. My creativity stagnated without the friction of other minds against my own.
Then I found multiple communities that helped serve different purposes in my life: work+writing+creativity+reading. There's a place to share resources and find collaborators. Other communities blur the lines between personal and professional: spaces where we discuss everything from AI and writing challenges to creativity and book reccos.
I'm sharing those here in case you find them useful:
The 6% Club by
and- and
What they all have in common: they've transformed my curiosities into a collective adventure.
I've found that surrounding myself with the right kind of people provides a powerful counterweight to the achievement-obsessed narratives that dominate our culture.
Sustainable Success: Health+Mindful Productivity
I learned about boundaries the hard way. Through their absence.
During my 9-to-5, my body staged a revolt. Tension headaches that lasted for days. Insomnia despite bone-deep exhaustion. No amount of caffeine fix was enough. My body was screaming what my mind refused to acknowledge: this pace will break you.
We glorify the physical sacrifice of work in our culture. We celebrate the all-nighter, the working lunch, the vacation interrupted by urgent emails. We treat our bodies as inconvenient obstacles to productivity rather than the very vessels that make work possible. I had to learn painfully, reluctantly that health isn't something you attend to after everything else is handled. It's the foundation that makes everything else possible.
Now, I guard my sleep. The seven hours that make the other seventeen possible. I move my body daily, not to optimize performance but because it's what keeps me human. I step outside midday to soak in the sun. I've stopped treating food as fuel to be consumed at my desk between calls. I go for my runs. I go for boxing twice weekly. My trainer has helped me a build a whole new relationship with my body. He did the unthinkable: made me fall in love with resistance training. These aren't indulgences. They're necessities. They're the difference between a sustainable career and a spectacular burnout.
The greatest revelation? Taking care of my health hasn't made me less productive. It's made my work better. My mind is clearer. My creativity flows more easily. My resilience in the face of setbacks has deepened. One big thing that has helped me make freelancing sustainable is that I began tracking my energy patterns religiously. I'd left my 9-to-5 partly for more control over my hours. I protect my peak creative hours like sacred ground. I schedule meetings and admin tasks during my natural lulls.
Anne-Laure Le Cunff's Tiny Experiments (highly recommend this book) introduced me to a reflection tool so deceptively simple yet profoundly effective that it's transformed how I navigate my weeks and these energy patterns: Plus Minus Next
Plus (+): What energized me? What flowed effortlessly? Which interactions left me feeling more alive?
Minus (-): Where did I feel resistance? What drained my energy? Which commitments left me feeling hollow?
Next (→): What adjustments will I make? Which experiments are worth trying? How might I amplify what's working?
What elevates this tool beyond a typical framework is its embrace of the whole person. And as the book suggests, I don't maintain separate trackers for work, home, creative pursuits, and relationships. Life doesn't operate in such neat categories, why should my reflection?
Most radically, I embraced the power of NO.
No to projects that don't align with my values, even when the money is tempting. No to unreasonable timelines. No to the constant availability that clients sometimes expect from freelancers.
I've found quiet contentment in removing feeling settled from my goals. I've found fulfillment through variety: through love, family, friendships, fitness, hobbies, nature, art, my cats (Roo & Idli).
I am in my early 30s. And it took me all this time to learn how much writing and drawing mean to me. I like using my skillset to help others, because I absolutely enjoy doing it. I'm currently in a contented phase of life, and a big part of arriving here was learning that an attitude adjustment will work wonders for your life.
So, that's all I have for now. One last thing: the freelance path isn't about arriving somewhere. It's about developing the capacity to be fully present for each step of an unmarked journey. To find joy not in certainty. But in continual becoming.
I make mistakes all the time. I can't sit still with my thoughts (!) But now, I show up with curiosity rather than anxiety. And I no longer show up alone I bring with me the wisdom and support of those who help me see more clearly.
If there's anything I can do to help you in your freelancing journey, I'd be more than happy. It is different for each of us, but no one should have to walk it entirely alone.
P.S. Here’s what I was listening to while writing this piece (it perfectly captures my mood).
Brilliant piece ❤️🤗🥰
Great to know the journey and the experience shared Kanchan. Would definitely help people like me who are trying to make the career shift. More love and success to you. Thank you.