Leaving corporate job after twenty-two years is not what the clean version of the story suggests.
I have told the story of leaving corporate many times now.
The version I tell most often is the clean one. I left deliberately. Not fired. Not broken down. I had seen what the machine was doing to people, including me. I made a decision. I moved to Dehradun. I built something that mattered. The painting came true.
That version is true. But it is also incomplete.
This story is the version I don’t tell as often. Not because it contradicts the other one. No, it doesn’t, but because it is harder to tell and harder to hear, most people who are thinking about leaving want the clean version. They want proof that it works.
It works. But the first year looked nothing like the proof.
The first thing that happened was the silence.
Not metaphorical silence. Actual, ambient, sustained quiet. After twenty-two years of an inbox that never emptied, a calendar with no blank slots, and a phone that was the last thing I looked at before sleeping and the first thing I reached for when I woke—silence.
I did not know what to do with it.
This is the thing nobody tells you and that I did not find in any book about leaving corporate: the silence is not immediately pleasant. It is disorienting. Your nervous system has been calibrated to urgency for two decades. It does not simply recalibrate because you decided to leave.
For the first three weeks, I kept picking up my phone to check something that wasn’t there. I kept mentally scheduling things. I kept waking up at 5 am with the low-grade anxiety of a person who has somewhere to be, then remembering I didn’t, and lying there in the particular discomfort of a body that has forgotten how to rest.
My wife, watching this, said something I have not forgotten.
“You left the job,” she said. “The job hasn’t left you yet.”
She was right. It took longer than I expected.
What Leaving Corporate Job Actually Does to Your Identity
The identity question arrived about two months in.
Not as a crisis. More as a slow, creeping realization that surfaces when you are introduced to someone at a dinner party and they ask what you do, and for the first time in twenty-two years you do not have an easy answer.
I had been a head of HR. Then a CHRO. Those words had done a lot of work in introductions. They explained me to strangers, placed me in a hierarchy, and communicated something about the kind of person I was. Without them, I found myself giving longer, more uncertain answers that trailed off in a way that felt, to me, like an admission of something I wasn’t ready to admit.
The discomfort surprised me. I had thought I was above it.
I was not above it.
I had underestimated how much of my sense of myself had been built on a foundation of institutional affiliation. William Bridges, whose work on transitions remains the most honest account of what the identity shift actually feels like, described this as the ‘neutral zone,’ the disorienting space between the old identity and the new one.
The organization had given me not just a salary but a context—a reason to be in the world that required no justification. Without it, I had to build a new reason. That process took longer than the painting on my bedroom wall had suggested it would.
The income took longer than I expected too.
I want to be honest about this because most accounts of leaving corporate elide it or treat it as a minor inconvenience, and it is not.
I had savings. I had planned. I was not in financial difficulty. But there is a particular psychological experience of watching your bank account move in one direction when you have spent twenty years watching it move in the other, and that experience does not care how carefully you planned.
The first few coaching clients came slowly. Synergist, my consulting practice, existed but needed to be rebuilt outside the structures that corporate affiliation had provided. The first speaking engagement as an independent practitioner paid a fraction of what I had earned as a CHRO.
None of this was catastrophic. But I am being honest: there were months in 2023 where the gap between the life I had drawn on the canvas and the life I was actually living felt significant. Not because the direction was wrong. Because the timing between decision and arrival is longer than the story usually admits.
Here is what actually helped.
Not the books about building a second act. Not the podcasts about entrepreneurial mindset. Not even the strategy.
The thing that helped most was a very small discipline I had developed years earlier: writing down, every day, the three things I was doing that were pointing me toward the right side of the canvas. Not achievements. Not milestones. Small, directional things.
Had a good conversation with a potential client. Wrote 400 words of the new book. Woke up and walked in the hills for an hour without checking the phone.
The function of this was not motivational. It was calibrating. On the days when the income gap felt large and the identity question felt unresolved and the silence felt like judgment rather than a gift, those three things were evidence that the direction was right even when the arrival felt distant.
Direction before destination. That is the principle. The mistake most people make in transition is measuring only whether they have arrived, when what matters more, especially in the early months, is whether each day is pointing the right way.
The second year was different.
Not because everything resolved, but because something settled. The nervous system did recalibrate, eventually. The identity question did not disappear but became less acute—I found, slowly, that I had built a new one, assembled not from a title but from a body of work and a way of living that felt chosen rather than inherited.
The first speaking engagement that paid well. The first retreat cohort. The first client who told me that a conversation had changed something fundamental for them. These did not arrive on a schedule. They arrived when the foundations were ready for them.
In May 2025, I moved to Dehradun. The painting came true. Not on the exact day I had imagined, but a little before that. Two months before my 45th birthday, precisely enough to count.
I am telling you this because I work with a lot of people who are thinking about leaving, or who have left, or who are in the middle of the transition and wondering if they have made a mistake.
Here is what I know.
The first year is not the proof. The first year serves as the raw material. It is supposed to be uncomfortable. The discomfort is not a sign that the decision was wrong. It is the system recalibrating—the nervous system, identity, income, and sense of self—and recalibration is not pleasant while it is happening.
What matters is not that the first year feels good. What matters is that each month, each week, each day, the direction is right.
If it is, keep going. The arrival takes longer than the painting suggests.
But it arrives.
If you are in that gap right now—between the decision and the arrival—the Clarity Call is a good place to start. Thirty minutes, free. I know what that year feels like.