I shut down a tech marketing business and destroyed my pathway to working in venture capital.
Why?
Over the past 5 years, I’ve found myself increasingly depressed. Post-COVID, the reality of my life — hustling for hours every day to build a tech business — was uncomfortable. I had set out to work for myself, yet I still dreaded the work week every Sunday night. I didn’t want to get out of bed to attend client meetings or market products I didn’t care about.
But my unhappiness goes deeper than just work dissatisfaction. It’s a creeping malaise that has slowly set in as I convinced myself I was forging my own path while becoming a carbon copy of everyone else’s path over and over again. It’s harmful.
As I drifted further from my passion for writing, I found new goals that aligned with the accepted pathways of those around me — starting a business, exiting a business, and becoming an investor. That path made the most sense.
Looking back, the signs were there all along that I had veered off course. As a child, I was imaginative and expressive. Given a blank page, I would fill it with made-up stories and drawings. In school, English and art were my favourite subjects. My curiosity led me to read voraciously outside of class. I filled notebook after notebook with poems, lyrics, and reflections. Writing helped me process emotions and make sense of the world.
After studying journalism and media college, I started down the “practical” path of business and marketing, believing it would lead to financial stability. I told myself I could always return to creative pursuits later. But years after graduating, after giving up my creativity to work at a series of technology companies, even winning awards for my work, I felt unmoored. Marketing jobs held no appeal. I wondered — is this really what I want to dedicate my life to?
So I took a risk. I left my CMO role and invested my savings into a small content studio. My plan was to pay the bills with client work while using my free time to develop my own writing.
At first, it was a juggling act, but I was determined. I built the business steadily through connections and word of mouth. Within a few years, it was profitable enough that I knew I could hire a team and mostly step back from client work. Finally, I thought, I could get back to writing.
But it didn’t happen. The business became an all-consuming distraction. Instead of writing, I focused on growth — taking on more clients, hiring more strategists, and angling for an acquisition. My identity became fused with the company’s success. Letting it thrive made me feel important and valued.
Meanwhile, my blog gathered dust, filled only occasionally when emotions boiled over, demanding an outlet. I told myself I would start writing again once the business was stable. But it was constantly growing, requiring my constant attention. There was always some new fire to put out or a goal to meet. I had pages full of ideas, but once they were written down, I never looked at them again.
Years slipped by in a blur of media plans, analytics reports, team meetings, conferences, and networking events. Somewhere along the way, I stopped being a writer who also ran a business and became a founder who used to write sometimes. My work was increasingly unfulfilling. But it paid well and earned me prestige, so I repressed my growing discontent.
The pandemic finally forced me to confront that suppressed anguish. With travel halted and clients pulling back budgets, I suddenly found myself alone with my thoughts for the first time in ages. The business’s fragile facade crumbled. My fancy office, roster of high-profile clients, and six-figure income now felt insubstantial.
Joining a VC fund’s investor accelerator program should have been the highlight of my career. I was selected as one of a handful of promising investors to receive support and access to the firm’s partners and resources. It validated all my hard work building “hot” startups poised for rapid growth and positioning myself as a tech leader and an “angel” investor. This was my golden ticket into the venture ecosystem I had long envied from the outside.
But within a few months of joining, cracks began forming in the shiny facade. I witnessed how many VC decisions hinged on buzzwords, egos, personalities and tribal loyalties rather than business fundamentals. I realized much of this world was built on bullshit — entrepreneurs pitching grand visions they knew were flawed and investors funding them to get in on the next big thing. Everyone was trapped in a collective fiction, playing their part to keep valuations rising.
The startups I had worked on played that game well. We made sweeping claims about the future of our industry. We shared impressive metrics that obscured underlying problems. We talked in the language VCs wanted to hear — world-changing technology, rapid growth, huge exits.
For a while, I believed the hype. But over time, the cognitive dissonance grew. My fictional startup narratives felt increasingly disconnected from the day-to-day reality. I began questioning what we were working so hard to build and why.
I had lost my sense of purpose. In chasing arbitrary markers of worldly success, I abandoned activities that fulfilled me. I replaced creative expression with commercial ambition. My goals became society’s goals, not my own.
I began listening to the voice I had ignored since college — the one reminding me I was meant for something more than churning out content and chasing deals. I missed developing ideas that set my imagination alight. I yearned to write not for metrics or money but for the sheer joy of creation.
I considered passing the business off to a team so I could return to writing and taking a quiet step back from the VC world. But deep down, I knew half-measures wouldn’t suffice. As long as this comfortable but unfulfilling path remained open, the temptation to retreat to it would remain. I needed a clean break.
So, I made the difficult choice to shut it all down. To my network, it seemed reckless to abandon my hard-won success. And to be fair, leaving my path behind felt like throwing everything away. I ignored the concerned messages. I knew it was time to stop building someone else’s dream, of building someone else’s dreams, so I could finally pursue my own.
What I really wanted was to build something meaningful, not just fundable. I wanted to answer fundamental questions, not manufacture desires and then pretend to satisfy them. I wanted to create again.
Our society pays lip service to creativity, but it does not actually value creators. It values a creator economy, where shrewd entrepreneurs build platforms to extract profit from artists’ work. The founders of Substack, Patreon, YouTube and the like are lauded as visionaries. Meanwhile, the writers, musicians, and filmmakers producing the actual content are dismissed as impractical for pursuing unstable creative careers.
We claim to celebrate innovation, but we steer young people toward conventional professions that fill corporate coffers. We talk about the importance of self-expression, but we measure worth by paychecks and credit ratings. We pretend the ideal life involves equal parts freedom and stability while shovelling citizens into office cubicles devoid of either.
Beneath the platitudes and social media quote tiles praising follow-your-dreams individualism, our culture remains deeply risk-averse, sceptical of those who step off the worn career path. We are told to admire billionaire tech moguls but pity the starving artist. Message received: dream creatively; don’t actually try to live creatively.
So, we valorize the shrewd managers who extract profits from creators’ toil. The venture capitalist, not the author, is the bold risk-taker. The record label CEO deserves the mansion, not the band. The streaming executive warrants adulation for building the platform, while the filmmakers using it to share their art are deemed impractical.
When profit depends on the relentless output of creative work, why do we continue downplaying the value of those generating it? Perhaps because a culture that genuinely prized innovations of the soul would be hard to co-opt for profit. It is easier to keep dreamers anxiously chasing stability, allowing their creativity to be monetized by others. A system thrives best when its dreamers believe their dreams don’t matter. And my own dreams had slowly drifted into the commercial.
Rediscovering my unique purpose required introspection. I asked myself — beyond status and wealth, what matters most to me? The answer was creativity, self-expression, and nurturing human connection through writing. When I realigned my life around those passions, fulfilment returned.
The path society deems “sensible” is not always right for the individual soul. By examining my values and reclaiming my agency, I gained clarity. My choices are mine again. There is hard work ahead, but aligned with purpose, it feels lighter.
The transition back to writing has been messy. I am filled with uncertainty and self-doubt. My skills are rusty from disuse. I have no name recognition or ready audience. Money is tight without my past income. Rebuilding a career around my passion requires tremendous patience, persistence, and trust in the process. I’ve picked out a handful of clients whose products and work I believe in with all my heart, and I’m working with them as a freelancer. They’re the folks who ignite a spark of passion and excitement in me.
But with each passing day, I grow more confident that writing is the right path. Because unlike before, my work feels genuinely meaningful, even when progress seems slow. Instead of optimizing campaigns to maximize clicks and conversions, I pore over sentences until each precisely captures my thoughts and feelings. It’s patient, painstaking work, but I savour it.
Sure, I still have nagging fears about the future. Publishing is a notoriously tricky business, and freelance writing income is unstable. My marketing business provided comfortable stability that writing may not. I can’t guarantee this new path will lead to financial success.
In my heart, this work matters because it matters to me. Each story I write is a small gift to myself, to the person I used to be, and to the person I want to be again, born of my unique experiences and perspective. I am comforted by the knowledge that creative work connects us more profoundly than any marketing campaign. If even one piece resonates with someone, touching or transporting them briefly will be enough.
This is the work I was meant for. Not everyone will understand leaving a lucrative career to pursue a creative passion with no guarantee of reward. But I owe it to myself to discover what is possible when my outer life finally aligns with my inner truth.
As Ralph Waldo Emerson wrote, “What lies behind us and what lies before us are tiny matters compared to what lies within us.” For too long, I oriented my life around external markers of achievement I thought would finally make me feel fulfilled. But fulfilment doesn’t come from acclaim or fortune. It comes from fearlessly creating work only you can give shape to.
My path from here won’t ever be smooth or clearly marked. There will be twists, turns, and bullshit ahead. But that’s okay. My inner compass is pointing true north again. Each small step towards living my purpose feeds my spirit and lights the way forward. Financial success may come, or it may not. I may reach many readers or only a few. But I will keep writing because it brings me home to myself.
I don’t regret the past because it brought me here. Everything I experienced was part of the journey, teaching me about the world and myself. I am ready to write the next chapter on my own terms.
To anyone feeling trapped on an unfulfilling path, take heart. It is never too late to change course and reclaim your dreams. But don’t wait as long as I did. Listen to your inner wisdom now. Then, take the first step.
I am still taking those first steps. I do not have all the answers. My journey is just beginning. All I know is that when I write from the heart, I feel whole. There is power and purpose in giving voice to your truth. Let that purpose guide you home.
