It was 5:15 am. That was my regular running wake-up time, but not here, at this lovely resort in Bali. The AC was comfortable, but I woke up to a familiar feeling, my head weighing many kgs, a churning stomach, and an uneasy feeling which left me tossing & turning all night. I drank too much at a friend’s son’s wedding in Bali, and like I do very often, I vowed never to drink again. But the good life calls again, very soon, I am sure! And I don’t want to leave the good things in life undone!
That got me thinking about why I don’t want good things to end, though I know that they come with a best-before date. What is it about not wanting to end pleasure, even when one experiences the pain, like I did with that queasy, rumbling stomach and heavy head after that mad bout of drinking?
To end something, one needs courage to imagine a possible new you. What allowed us to flourish in one environment may actually be the millstone around your neck in the next. I learnt audacity of thought at HDFC Bank, with those aggressive Monday morning reviews; it served me well in early entrepreneurship, but soon became a liability. Almost like a rocket that takes off & changes complexion at each stage of its journey.
Intuitively, we think of growth as accumulation: learning new skills, becoming better by listening more, and learning how to handle stress. But what about subtraction? Often, endings are about that! It is said that rockets can’t keep going to the next stage without dropping mass. Are we like rockets, and is each ending in our life like the stuff we leave behind, allowing us to propel ourselves to the next stage?
Konstantin Tsiolkovsky was a self-taught, nearly deaf Russian schoolteacher who lived in isolation. At age nine or ten, scarlet fever destroyed his hearing, forcing him inward. He survived on black bread in Moscow, teaching himself physics and mathematics. In 1903, using only equations and imagination, he proved that single-stage rockets could never reach orbit; staging was essential. Rockets must shed mass sequentially to gain velocity. He never built a single rocket, was never petrified by the sound of one, yet he laid the mathematical foundation for all spaceflight. His insight was purely theoretical: the physics of letting go must be understood in the mind before it is proven in the sky or in your life.
Act 1: Ignition
Every meaningful pursuit starts with faith in something that’s not visible yet, just a hazy outline that invites you. You don’t have the stamina, the capital, the skill; all you have is just the crazy belief that says go anyway. Those early days are high-energy, loud & noisy, just like the first stage of a rocket. Everything burns at once, all parts of you are firing, you are excited & you are scared. But that combustion is the price of lift-off. You don’t build altitude on any formula; you build it on belief.
Endings are sudden and yet not so sudden. My exit from Cequity was accompanied by my belief that I would not compete with my old company. I never wanted to set up anything that would compete with Cequity. And yet my strength lay in data, analytics, and the customer aspect of business. But the dream that I should create something had not died. I still wanted more.
But I still had the energy of external validation even now. I still wanted to prove to the people around me that I could succeed in my next venture. I had begun learning Leadership coaching at the same time, & so what emerged was a confused mishmash of styles: my directive, pushy, aggressive, let’s-get-things-done style mashed up with a reflective coaching orientation that was trying to be born but wasn’t yet there. You can’t hasten a baby, it takes 9 months & I wanted it immediately.
Clevered was an ed-tech company I co-founded with someone I knew before, whose vision was to scale mentorship. It was meant to be nimble, digital, and purposeful. In retrospect, I stood on the cusp between entrepreneur, leader, and coach, and leaned too far into the coach role. I listened more than I led. I paused when momentum was needed. This was my confused ignition, all engines firing but in different directions, burning fuel without achieving clean lift-off.
T.E Lawrence said it amazingly: “All men dream, but not equally. Those who dream by night in the dusty recesses of their minds, wake in the day to find that it was vanity: but the dreamers of the day are dangerous men, for they may act on their dreams with open eyes, to make them possible.”
Act 2: Ascent
Then comes the middle: the long ascent. You’re no longer just dreaming; you’re inside the monotony of it. The startup finds its rhythm. Or in my case, with Clevered, it doesn’t. This is where most of life happens, the dream guiding you, but the discipline sustaining you. Except when you’re carrying contradictory versions of yourself.
I oscillated between coaching and commanding, confusing everyone, including myself. The business shifted shape. Models. Cities. Directions. Nothing stuck. You’re carrying every version of yourself that got you here. And somewhere along the climb, you start to feel the weight. We mistake what got us here for what will take us further.
The irony of not being able to coach my co-founders while trying to create a company that wanted to scale mentorship was not lost on me. The point hit me rather rudely in the co-working space from where I operated in Mumbai, with the other founders at Noida. I often used a telephone booth at the co-working space, a name they gave to a tiny, enclosed space people used for calls so others would not be disturbed in the open office. Most times when I used that phone booth, within 10 minutes someone would pop around to ask me to speak at a lower decibel. I never realised how intense I got in those calls. I would sheepishly, in panic, move from a shout to a whimper within seconds. I looked like a stand-up comic in decay.
Act 3: Separation
Here’s the part we don’t talk about enough ,the part where the rocket starts to break up, leaving parts of itself behind. To continue its journey, the rocket has to eject something to keep rising. Not because it failed, but because it achieved its purpose. It’s done its work. So is the nature of endings: they are not errors, they are not bugs, but rather the design itself.
These endings may not be gentle. Sometimes the endings are violent. It may not be a gentle uncoupling but a controlled explosion. The rocket shudders, leaving debris falling in its wake. Life’s endings often feel this way.
But how do you describe the flavour of endings, the subtle aftertaste they leave in us? We’re trained to associate endings with decline or irrelevance, but endings are often the most charged, alive, emotionally intelligent moments in our journey. They’re reminders that you’re ready for the next stage in your orbit. The dream that preceded your capacity has done its work; now the ending must complete the cycle.
Sometimes we forget first principles. The basics of any venture are a common purpose and values. At Cequity, Swamy & I had aligned core values of integrity, honesty & ambition. With Clevered’s co-founders, I could see the values didn’t match, but I let it be. I tried to start a new venture without the necessary raw materials. It couldn’t hold.
And then I stopped trying. With Covid, I found myself in a Goa café, laptop closed, watching the rain. No manic Monday, with high adrenaline, just the Goa rain & steaming hot cup of coffee. After a few years of sputtered starts, just before Covid, and after putting substantial money into the venture, I called it off & exited. This separation was brutal, not because it failed, but because I had to jettison the part of me that still needed external validation, that still wanted to prove something to people around me.
The leaders I coach today often stand at this precipice, where a dream that once empowered them now wants release. They confuse the end of the dream with failure. A rocket needs to keep shedding parts of itself as it gains altitude, becoming lighter for the next stage. What in you is wanting to be released to become lighter for the next stage?
A few days back, a friend, Ravi, came over to my place in Goa & he was an Ironman. While chatting with him about his training & the next Ironman he was participating in at Goa in a few weeks, I realised how quietly a part of my journey had ended. I ran marathons and cycled long distances, yet today, at 61, I realised I no longer want to chase those accolades. Ravi was describing his training regimen & my first reaction was, I just cannot imagine myself doing any of this now. I still did everything, I continued to run and ride, but I no longer wanted a sub-2-hour half-marathon. A DNF (did not finish) no longer scared me.
I still have friends who are training for big events like these, but in that moment, I realised I could finally admit to myself that a phase had ended. There is a contradictory bunch of emotions I can feel: longing for something that seems attractive & fear, a new parameter that seems to have slunk in quietly, making me question. Did a part of my identity go with that ending? Did something in me die for the new me to be born?
Just as I was thinking about it, the vision of two tough treks in the Himalayas that I had always wanted to do but hadn’t done till now came up. I still dream about them. Auden’s Col & Kalindi Khal in the Gangotri region, both above 5,500 meters, have called me for years. Maybe I might still do some of them, or maybe I wouldn’t if I take the ending seriously & listen to what it is saying. Fear is ok. There is nothing to conquer.
The difficulty of this closure, like all closures, is the relationship you continue to feel with what lies in your past. I could still play pretend and go sign up for another marathon, join my friends in their training. But that belief has now shifted, and I am playing with different resources; that one shift means I am not that athlete right now. To recognise and accept that is, again, an ending I have struggled with and finally reconciled to. It just means that my dreams have changed. Some don’t even need the same kind of physical conquest. That long walk with Annapurna peak by your side for over a week requires you to be time-rich, and maybe that’s the one resource I have more of now! But this phase takes time; it took me 2 years to adjust to the shift in Goa’s pace, and I am still a work in progress in that area.
Act 4: The Return
Endings are never final, or they should not be. They are emotional containers in which something has been frozen. If the right conditions are present, unfreezing can happen. What are the right conditions? A sense of revisiting everything from first principles. Maybe I will attempt Auden’s Col, or maybe the dream itself will transform into something else entirely.
After re-entry, the leader realizes the destination was never Mars; it was maturity. The success isn’t in how far you traveled, but in what you left in motion. The Clevered failure taught me that external validation was excess weight. The quiet ending of my athletic identity, witnessed in conversation with Ravi, showed me that some stages separate so gently you don’t even hear the explosive rocket thrust.
As poet Wendell Berry said, “It may be that when we no longer know what to do, we have come to our real work and when we no longer know which way to go, we have begun our real journey.”
Tomorrow morning at 5:15, I’ll wake for my run. Or maybe I won’t. Even that ending is negotiable now.
