They had IITs, ISB and high-paying jobs. Then all four walked away, choosing uncertainty over predictable careers. Was it a ‘huge mistake’?

A prestigious degree, a high-paying job and a predictable career are often seen as markers of success. But for four professionals, that conventional definition of achievement was not enough. IIT-Kanpur graduate Kanak Agrawal recently reflected on how she and three others walked away from high-paying jobs to build lives on their own terms. After spending four weeks living and working together in Sri Lanka, Agrawal shared why choosing uncertainty can feel difficult yet deeply meaningful.

Four people who had ‘made it’ on paper

Kanak Agrawal took to social media to reflect on an unusual chapter in his journey, describing the four people as individuals who had seemingly achieved conventional success. “IITs. ISB. Mithibai. Four high-paying jobs between us, all left behind,” Agrawal wrote. She explained that all four had reached a point where, at least on paper, they appeared to have made it. Yet each eventually chose to step away from the conventional career path and pursue something more personal. The decision, however, was far from effortless.

Leaving a predictable career

Agrawal acknowledged that choosing a different path comes with its own doubts. When most people around you continue following familiar career trajectories, stepping away can make even a confident decision feel uncertain. “At some point, each of us decided we wanted something different from the life we were building. And that choice is difficult,” she wrote.


She added that people who choose unconventional paths can begin questioning themselves, particularly when their decisions contrast sharply with what society considers safe or successful. “You start wondering if you're making a huge mistake, especially when everyone around you seems to be following a more familiar path,” Agrawal said.

Four weeks of living and working together

Against this backdrop, their recent time together in Sri Lanka became particularly meaningful for Agrawal. The four spent four weeks living and working under the same roof while building their respective businesses. Rather than simply being a getaway, the experience gave them an environment where their career choices did not need to be explained or defended. She said they worked from the same house and built their businesses together, creating a sense of reassurance that the unconventional lives they had chosen were both real and possible.

Agrawal’s ‘freedom-first’ approach to life

For Agrawal, the idea of freedom has been a deliberate choice rather than a passing phase. She revealed that she has spent the past five years designing what she calls a “freedom-first life”. But pursuing that kind of independence can sometimes come with an unexpected downside: loneliness. “I've spent 5 years designing a freedom-first life, and I've learnt that freedom can get lonely when nobody around you understands why you chose it,” she wrote.

Her time in Sri Lanka, however, reminded her of the importance of having people who understand the choices behind that lifestyle.

Why having the right people matters

Agrawal’s biggest takeaway from the experience was not necessarily about entrepreneurship or career success, but about companionship. She believes being surrounded by people who have made similarly unconventional choices can make the journey feel considerably less isolating. “The right people make a huge difference,” she wrote.

According to Agrawal, such people can make unconventional choices feel less strange, provide support when doubts creep in and serve as a reminder that there are multiple ways to build a fulfilling life. “They make your choices feel less strange. They give you someone to call when you're questioning things. They remind you that there are other ways to build a good life,” Kanak Agrawal shared. As the month in Sri Lanka came to an end, Agrawal said she was returning home with a renewed sense of reassurance about the path she had chosen. For Agrawal, that sense of belonging was the most valuable thing she was taking back from Sri Lanka.

Netizens react

Netizens praised Kanak Agrawal’s decision to pursue an unconventional path, saying the right community can make such choices feel less lonely and meaningful. One commenter admired his courage but noted that pursuing passion can be harder for people with families and financial responsibilities. Another found his experience relatable, saying reconnecting with one’s purpose helps during periods of doubt. They also highlighted how supportive co-founders and the right people can strengthen an entrepreneurial journey.