Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much nor suffer much, because they live in the gray twilight that knows not victory nor defeat.
- Theodore Roosevelt, Strenuous Life
1: I Can Not Redo
I held my breath.
After 5 hours of waiting between scans and consultations, the doctor says it’s conclusive. My shoulder is torn.
I stared at the X-ray, half listening to the doctor. Not knowing what to think of it. All I remembered was that he wrote me a note giving me 2 weeks off from work, and some prescriptions to help with the pain.
It wasn’t until I got home, I realized the severity of the situation. This is bad.
I was crippled. I can’t do much of anything. The plans and goals I’ve set for the year are tossed out.
Overwhelmed and exhausted, I crashed to sleep.
…
How did I get here?
I wanted to leave 2023 behind me. It was a year of stagnation. I hoped to forget it by moving ahead.
I planned to start 2024 strong, to renew my purpose and momentum. Any momentum I hoped to make now stopped cold.
This injury set me back. It threw off my plans. My ambitions were brought to a stop. What could have been a better me is now lost.
Physical activities are not just exercise—it’s self-expression. Because movement requires the mind and body to act in unison. When intent and action is aligned, the impact is amplified.
Since I can’t practice, I have no other outlets. No means of expressing myself. No way of blowing off steam.
This feeling is made worse by the arm sling and back brace I had to wear. Restraining the range of my movements. It felt like a straightjacket. Trapping my body. Two weeks off from work, but I was just confined to my bed.
The painkillers added to my misery. They induced a hazy feeling, making it difficult to do anything. Like a flame being smothered. Thinking became sluggish. In daylight, the pills knocked me cold. At night, I was just too tired to even watch a movie. I killed time by counting the spinning of the fan. This went on until the days bled into each other.
I was restless. My thoughts and emotions swirled.
…
When the painkillers ran out, I wanted to get a refill on the prescription.
For a moment, that thought lingered. That scared me—that would have been a trap I’d never escape from. It was a quiet desperation. Numbing myself from the pain was easier than facing it. That flicker of awareness was an anchor.
I was trapped, I cannot redo the past. I took a wrong turn and there’s no turning back. No reset button.
If I couldn’t go back, I had to find a way to move on.
Or, surrender to despair.
2: I Can Not Advance
By mid-February, I started physiotherapy.
Weekly sessions at the rehab center to restore my shoulder and fix my posture. Putting in the work to heal my body, but it was taxing to my state of mind. Each session with the physio was a reminder of how far I still had to go. To heal means to be made whole, but I lost time. I can never get them back.
Back at work, management approved a flexible arrangement to accommodate me—working from home most days with the occasional office visit. It should be a sign of relief, being able to contribute productively. Right?
Instead, I found myself dreading each day. The energy drained out of me as soon as I booted up the laptop. I caught myself zoning out, staring at the laptop screen. It was like looking into a black mirror—reflecting not just my work, but every failure I could not shake. Tasks I once found engaging were now a chore, and I felt the weight of time slipping away.
…
I told myself that it wasn't a burnout. Calling it a burnout was too dismissive of my genuine commitment. I cared about the work, at least when the work got going. Still, even in misery, I wanted to push on. But it was like wading through quicksand. The more I tried to push forward, the more stuck I felt.
But I tried to break free. I applied for department rotations. I wanted to try out different types of work and expand my skills. That lead nowhere.
I then tried a different approach: spoke with management, volunteered myself and even pitched projects. I made the effort to block in time for coffee chats to find out what is coming down the pipeline. It didn’t happen either.
In parallel, I sent out a number of job applications, leading to a handful of interviews. Some went well, or so I thought, others I blundered. Yet, I have nothing came out of this.
Nothing was going wrong, not really, but nothing is going right either. Things just weren’t happening for me. I wasn’t winning and I wasn’t losing. I was caught in that gray twilight. I was in stasis.
…
This dread persisted. Each day, it felt like a part of me was being chipped away. It’s like this slow internal erosion and I was hollowing out on the inside. Steve Schlafman, an executive coach, calls it a burning down.
Burndown happens when we’re out of alignment—our outer lives no longer align with our inner lives and who we are at our core. We’ve run out of innate passion for the journey we’ve been on despite pushing forward like an ultra marathoner on mile 45—you might feel like you want to “burn it all down.”
That fire within, gave out more heat than light.
…
One day, the truth hit me. My attempts to ‘break free’ were an act of desperation. I was not looking to move forward. I was looking for an escape. I wanted to jump out the first window I can find. I was escaping something deeper.
I was avoiding the fact that my life, as it was, wasn’t working. And maybe, that it hadn’t been so for a while. I was on a path that had run its course. It was a dead end.
The option I hadn’t thought about was to exit this road and start all over again.
But I didn’t want to quit. Not at first. Quitting meant admitting to mistakes, to missteps. It meant that I failed in no small way.
But I can not advance. Not unless I let go of this life I was clinging on to so desperately.
I had to quit.
3: Exit Strategy
The thought of quitting wasn’t easy. It was scary. Writing the resignation letter felt like stepping away from familiarity. Choosing to stay offered comfort, despite the mounting frustrations. If I stayed, I know for certain I’ll always be miserable.
I was afraid of facing uncertainty. Sure, there might be an upside, but also much greater risks of failure.
That’s the other reason I hesitated—failure. Quitting was an admission of failure. I was not ready to admit that I’ve made mistakes. I was not ready to admit that I’ve hit a limit of my abilities. I was not ready to accept that I failed in some personal, existential way.
Looking back, I think I might have subordinated my life to material but meaningless pursuits: financial security, career progress. All that time and effort, and with very little to show for it? To quit then felt like a condemnation of myself. I was afraid that I would have to live with this black mark for life.
…
I understood where my fears were coming from. But I didn’t know how to overcome them. A recovering injury and a career in stasis, I was far from my best self. It was daunting.
Then, I thought about reframing my fears. Annie Duke’s book “Quit” was informative. She reframed quitting as less about giving up, but more about a reallocation of resources: time, energy, attention and our self. It’s about accepting that mistakes were made and the price was paid, and we will never recoup it. But what we do with what we have now, matters far more for our future.
Yet we fail to see the upside in quitting, because of the sunk cost fallacy, we fail to consider the opportunity costs of staying even longer. We double down, pour more money on a losing gamble. We lose even more, setting ourselves back. We subjugate ourselves to prolonged and often needless misery.
Life is far too short for that. The world is also too vast to pour all of ourselves into one narrow lane.
In that light, quitting becomes an investment decision. A decision that can be analyzed rationally. The exit becomes a strategy: guaranteed stagnation OR the possibility of growth.
…
Understanding where my fear came from didn’t make the next step any less uncertain. I was quitting with nothing in the pipeline. No next project or work lined up. Just the world of possibilities, and chaos.
That’s where I needed a model—not a step-by-step plan, but a torch to light my way forward. Models help make sense of the unknown, not by eliminating the fear but by framing it.
As I thought about it, instead of waiting for yet another job. I thought about taking a sabbatical. There were others before me who quit the path they were on and went on a break. Stories abound.
Matthew McConaughey rejected rom-coms, risking obscurity, income, and even his career. Two years of rejections later, he emerged as a more authentic actor, with roles like True Detective and Dallas Buyers Club. His McConaissance paid off
David Maisel walked away from BCG to chase his passion for entertainment. It was a risk, though he entertained job offers, he stuck to his course. Eventually he landed a job at the Creative Arts Agency (CAA), marking the beginning of a career that culminated with the birth of the Marvel Cinematic Universe.
Paul Millerd left a successful corporate career as a strategy consultant. He quit what he called the default path. He then went off to experiment, write, and create a life on his terms. He found a way to live more authentically, documenting this in his book the Pathless path.
A friend of mine revealed to me that he too went on a sabbatical. Partly frustrated by work, partly looking for more challenging things to do. He spent a year teaching himself to code and Machine Learning.
These weren’t just examples of people quitting; they were stories of reinvention. Exiting the comfortable path to tread their own journey.
As Joseph Campbell wrote:
We have not even to risk the adventure alone. For the heroes of all time have gone before us. …Where you had thought to stand alone, you will be with all the world.
I felt that much more assured. I am not alone.
…
Still, fear lingered in me. Survivorship bias tells that for every McConaughey or Maisel, there are countless others, who quit and floundered. Their stories are untold and remain unheard.
I reasoned that I had to have a backup. A contingency in case my decision ends up in failure.
I confided with a senior colleague about my plan. Someone who, at this point of her career and life, has perhaps seen it all. She found my decision to quit admirable ( to my surprise) and my plan was reasonable. But then she gave a counterintuitive piece of advice: “The most reasonable decision is not to have a Plan B.”
That was a revelation.
…
Life is never about guarantees. Without consequence, without an element of risk, is it really a choice? To remain in that gray twilight would be to deny life of its richness. To quit, with no alternative, was to dare mighty things. There’s no promise of great triumphs, but I’ll know that I’m living a meaningful life.
Quitting becomes a declaration of intent. By stepping away, I created space for something greater, something truer to myself.
I don’t know what lies ahead, but for the first time in a long while, I’m stepping forward with purpose. And that is enough.
Inspirations
Quit by Annie Duke
Annie Duke examines the often-stigmatized act of quitting and argues that knowing when to walk away is a crucial skill for success in life. Duke provides a compelling framework for reevaluating our goals, recognizing when to persist and when to pivot, and making more informed choices about where to invest our time and energy.
The Pathless Path by Paul Millerd
Partly a memoir about Paul Millerd’s life, and partly a call to action: to be brave in making your choices, be comfortable with sitting in uncertainty, and tread a path of self-discovery
Greenlights by Matthew McConaughey
Persist, pivot or concede. It's up to us, our choice every time.
A fun and insightful look at Matthew McConaughey’s life as written by him in his signature folksy but insightful way. I previously wrote about the key lessons I learned from the book.
I quit my job by Matt Yao
Taking a sabbatical as someone still early in their career felt like a blunder. Typically, you’d expect people in their mid-to-late stage of their lives to take a break. But it was re-assuring that I was not the only one. Matt Yao’s piece helped in that regard, and his blog also contained stories from others who left the default path early.
Balancing these, to be able to survive for the long term yet be daunting in the short term, is something I think about a lot. I wonder now that you've taken this sabbatical have there been any changes in your thoughts about balancing this out?