The Time I Quit My Job After a Cycling Weekend

The second major break I took in my twenties was somehow even more ridiculous than the first one.

At least the Everest Base Camp plan had some buildup to it. There was preparation, overconfidence, emotional commitment, physical training, and Himalayan suffering involved. This one, on the other hand, started with a completely harmless cycling weekend with colleagues, mentors, and friends from work.

We went cycling, had a genuinely good time, came back home, and I woke up the next morning and casually wrote a resignation email as though this was a perfectly reasonable follow-up activity after recreational cycling.

Till today, my boss tells people this story because even I had absolutely no clue what the plan was after that point. There was no dramatic workplace issue, no toxic environment, no life-changing argument, and no deep existential crisis. I was just restless again, which honestly became a recurring pattern throughout my twenties.

I packed my bag, informed my then-boyfriend and now-husband that I was going to Andamans to “figure things out,” which in hindsight sounds completely insane because I had absolutely no idea what exactly I was planning to figure out there.

While writing all of this now, I genuinely cannot decide whether my twenties were brave, stupid, chaotic, or some dangerous combination of all three.

And once again, I landed there with almost no plan.

I spent about two weeks wandering around the islands, navigating creepy men, strange situations, beautiful beaches, random conversations, and eventually meeting one of my closest friends for life. At one point, we even took an overnight cargo ship to one of the remotest islands and woke up in the middle of the sea just in time to watch the sunrise from the deck. Most days involved renting a scooty, getting lost inside forest roads, sitting near beaches for hours, watching beautiful sunsets and waking up every morning without any larger life strategy beyond deciding where I wanted to go that day.

And I think that is what I miss most about that phase of life now. The ability to exist without constantly converting every moment into productivity, optimization, or future planning.

There was something deeply freeing about not treating every decision as a five-year career strategy.

When I eventually came back to Chennai, I still did not feel like returning home yet, so I randomly decided I would “quickly explore Tamil Nadu” for maybe a week before going back.

That one week became an entire month.

I backpacked across Tamil Nadu with absolutely no structure because I kept getting distracted by places I had never planned to visit. Sometimes I literally got off buses because I saw a beautiful temple from the window or because some random bird in a tiny village looked interesting enough for me to stop and explore the place.

I still remember getting down at completely unplanned towns just because something about them felt curious enough in that moment.

At Kanchipuram, a sweet old pandit at one of the temples became deeply concerned about the fact that I was traveling alone and wrote down an entire list of places I should visit nearby, including wonderfully obscure recommendations that no travel blog would have ever given me. I think he found me mildly foolish but also low-key admired the commitment.

And honestly, some of my best travel memories came from these completely unstructured detours that no itinerary could have planned properly.

During this phase, I eventually traveled through Kerala too, which also unexpectedly reconnected me to one of the friends from my Leh trip years earlier. I had mentioned wanting to experience Theyyam and he immediately told me to stay with his family because that was the only way I would really understand it.

And this is where I genuinely feel my twenties rewarded me far more than they punished me for trusting people.

His family hosted me with ridiculous warmth, his mother fed me endlessly, and they helped me experience parts of Kerala I would never have discovered by myself because Theyyam is not some staged cultural performance designed for tourists. It exists within temples, timings, communities, rituals, and local rhythms that outsiders rarely get to witness closely unless somebody local decides to open that world for you.

Somewhere in the middle of all this wandering, I made wonderful friends, backpacked parts of Kerala with them, and somehow the entire story eventually concluded with me partying in Goa with the exact same friends from work whom I had essentially abandoned after one innocent cycling weekend.

The funniest part is that none of this felt extraordinary while I was living it.

I was not trying to “find myself,” heal spiritually, optimize my mental health, reject corporate culture, or become a solo travel inspiration for anyone. Honestly, most of us were not even speaking in those frameworks back then. I was simply following curiosity wherever it seemed to lead me next and trusting that life would somehow figure itself out along the way.

Everything I have done sounds slightly brainless in retrospect, and objectively speaking, many of these decisions probably were, but I also do not think I would have wanted to experience my twenties any other way because so much of what shaped me came from saying yes before fear, over-planning, adulthood, and endless caution slowly started replacing curiosity.

I think that is also why I find the internet discourse around “micro-retirement” so funny now because none of these breaks were carefully calculated lifestyle experiments. I was not trying to retire from work or escape responsibility forever. If anything, I was trying to participate in life more fully before I got sucked into routines, deadlines, optimized calendars, and postponed dreams.

And strangely enough, those temporary breaks slowly ended up shaping my life far more deeply than many of the carefully planned phases ever did.