#166 - Learning from my younger selves

Talk to your past selves to unlock a better future self

My eyes are shut. I’m wide awake in my head. I know it. I also know that at this moment before day break, as the darkness bleeds under my eyelids, on this already warm summer morning, I’m dead and buried. Before I’ve wrapped my fingers around my phone on the bedside table, I know. It’s another night of broken sleep, another one of those broken R90 sleep cycles as all those podcasts say. I open my eyes to check why. 

Wife beside me. Daughter in her crib. I sit up and crane my neck to look beyond the edge of our bed. Dog on her mat, check. The nightmare is within, I confirm.

The reason for my disquiet returns to me. I’ve written an ebook, yet another, and the world has remained just the same. People aren’t queuing up for it; those who have it haven’t read it, pushing the act of reading it further and further away like a visit to an acquaintance they can afford to avoid. My nightmare, it comes to me, is about distribution. Content is king, but my nightmare is about distribution! Hahaha…even at this ungodly hour, despite the knot in my belly, this has all the ingredients of a funny joke. I slide my tongue over my parched mouth. It tastes un-funny. The timing of this nightmare in my life sucks. I’ve just quit my cushy job to be a solopreneur. 

It’s the day after I have turned sixteen. The mood at home is funereal. It’s the end of my first life, my first real failure. I don’t know what to do with it. I step out for a game of cricket to escape the fact that I have not only not topped my school but also missed scoring the high water mark of ninety percent in my tenth boards. My teammates, friends from the neighborhood, shout at me from the boundary line. They couldn’t care less about my less-than-stellar grades. They want me to step up the scoring. The nightmare is within, I realize.

The next two years I’m a small fish in a big pond that keeps getting bigger every time I turn my tail. I swim as fast as my little fins and gills can take me toward the fertile banks of IIT, but others are faster. Many others are way faster. All this while I’m still figuring: Am I supposed to be a fish? 

I have no strategy. I know no hacks. I’m supposed to just give it my all. I do, I try to. I lose my first girlfriend. She outswims me. She’s in a hurry to be something, anything. Everyone is, it seems. Except me. I go for tuitions, I take mock exams, I get caught up in eddies.

I take a full year longer than the rest. It is my year of being left behind. I’m now the runt of the litter. And it’s not IIT I get to. At nineteen, I manage the country’s tenth-best undergrad college at the time. By the time I’m there I’m dead tired. Away from family for the first time in life, I’m lost. Away from the everyday reminder of their expectations, I love the open air. I strut for the next four years. 

At twenty-two, I have something to show—two jobs and a choice. I have a ton to hide—what does making a living mean? What doe sbeing happy mean? I’m too afraid to ask it out loud.

I want a labor of love. I’ve read about it in books written by those with lives more sublime than mine. They all say it is worth aspiring toward. But where there’s no love, there’s only labor. At twenty-three, I have made up my mind. The thought of an MBA feels like labor.

Robin Williams with Robin Williams by Ard Gelinck

At twenty-six, I’ve made enough money to quit my job and start writing. At twenty-nine, I’ve been arrogant enough to not show my manuscript to a soul until it is done and dusted. And by then it is too late. I drain the dredges from my bank account before going down on my knees to my girlfriend.

I spend my thirties losing myself in the game of being useful in a way that makes the world pay me back. Until I find myself playing the money game. And here on this bed, in this house I own, in the car that is mine, I wonder these days.

I want to go back to that twenty-nine-year-old, that twenty-six-year-old, that nineteen-year-old, to that sixteen-year-old. I want to go back to the accordion of my past selves and ask, How did you make music?

Most of all, the forty-one-year-old me wants to go back to the sixteen-year-old and I ask him, How did you do it? If you had given up, I wouldn’t be here. Why did you do it? 

Satyajit Rout at forty-one is a much easier project than Satyajit Rout at sixteen. I’ll take all of you, or some, or a little, but never nothing, I say to that teenager. 

The first light is sneaking in from between the curtains. I’m sitting on my bed, wondering. Distribution? Being jobless? Being a solopreneur?

Just get up and get out of your own way. 

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👋Hi, I’m Satyajit and welcome to my newsletter. I learn from the best with the goal of unpacking lessons that help make decisions for a better career and a better life.