I finish two years at The Whole Truth today. Which is also two years of leaving behind my life in the mountains of Mussoorie, my freelance no-office life, days and weeks devoted to the life of the mind. The texture of my days has wildly turned around. What didn't change was my sense of self.

I have learnt to live with the existential tension: life is meaningless, and yet I choose to construct meaning through my choices and actions—through love, care and commitment. That was a phase, this is another, and there will be another.

This morning, I wanted to capture the questions around the idea of ambition that I have sat with in these two years. I have conflicted feelings, most of it is captured in my diary, and I am sharing glimpses of my dilemmas. I think I know where I lean, and yet, my work at TWT keeps rewarding me with experiences and situations which then re-shape my leanings, so I am entering the year with equal levels of excitement and curiosity.

Staggered notes follow.

First, before I talk about ambition, I want to share how I mostly feel. I wrote this on 12th of May.

I wake up. I make good coffee. I exercise. I eat good food. I do work I like, with people I like, and get paid more-than-enough to be comfortable in a city where being comfortable is a great luxury. I read, watch films, think about things I care about, write about them. I speak to my friends (though not as much as I want to). I try to do whatever best I can do for my family while living in a different city. I don’t go around the world as a mute spectator. I speak up. I try to live with kindness as a governing principle. I want my freedom to be, and honour freedom of others. Then when I am done with the day, I go sleep. And mostly sleep well.

This is my life. And this is it. I don’t understand why we make it more complicated than this.

This is my baseline state. Fully at ease with my sense of being. Santulan.

Everything else that follows is held on this foundation.

I remain deeply conflicted about the idea of ambition and my relationship with it. Am I an ambitious person? If so, what does that mean? What does it look like really? Do I really want it? Or do I just like the idea of it? Is lack of ambition for someone with my privileges an immoral act? Shouldn't I always be driven by the desire to change the world for the better?

There are times I am moved by it, and there are times when it feels like a giant act of self-deception—it's greed, it's insecurity, it's the lust of power and control, all that.

I wonder if the want of ambition is really a want of a story we can tell ourselves. A delicious story with an "inspiring" character arc with elements of growth and transformation—that “working at The Whole Truth will teach me X, which I can use for Y, which will then lead to Z, and that's how I will leave my mark on the world.”

No. That is not how I think. This doesn't move me. I have no personal need of a grand narrative about myself. Because stories are a trap—and I want to be free.

I am thinking this through.

What I do know is figuring that out doesn't affect how I choose to organise my present. Everything I do is the downstream result of a single question: What does a good day in a good life look like? This, I know. And so, my life design at the moment is not ambition-backwards. It's a-good-day a-good-week forward.

I don't know whether my shape of life—which is anchored around enoughness, presence and attention—is in sync with the demands of ambition. And honestly, if it doesn't, at this moment, I don't care.

My question remains open. And I am curious where it takes me. My two years at TWT have taught me that this openness can take you to the unknown—towards things you can't fully grasp at the moment, where the understanding really comes through when you get there. And how amazing is that.

I found this year-old diary entry from my digital notes where I was thinking on page about the question I raised above. Sharing it as is:

How does ambition look from a micro lens. For me, the push comes from thinking about the world at large—our big, magnificent world.

Nothing was supposed to be the way things are. We made it happen. We. Humans. We did small things and big things. In our individual capacity and as coordinated actions.

We sometimes feel things are progressing, and sometimes as if things are regressing. The former makes you feel our work does matter in the larger scheme of things. The latter makes you feel that our existence and our work is doing no good. I stay firmly in the former camp. So much of the world remains broken, yes. But much of it has gone better. And it could be a lot better. And we can play our bit.

So my push for ambition comes from the desire to participate in this giant sphere of human civilisation. I have lived the slow disengaged life in Landour, and it fed my inner soul like nothing else. But when I got out of it to play with others, it is a totally different experience.

If the mountains called me to stay in peace with my core being—and made me realise that contentment just comes from being—I entered the world of ambition with full acceptance of its illusion and fascination. And then play. At max. Of my ability.

I still feel like I am relearning the rules and behaviour of deep engagement and doing things together. I have come a long way—I know it, and even with that awareness, I have given myself a hard time. That is now gone because I know how hard this was, and how much I had to work on myself to make myself accustomed to demands of the Big World. I have had to confront questions around identity and self of being—but then it is through this discomfort that I moved ahead. And I am happy about that. Now as things settle, my ambition needed a container that screams no limits. I am in it. That is TWT. And it is now time to play. For infinity.

Another related thought, again from my diary.

At modern workplaces, where do we get time to think about the fundamental existential questions: what kind of life do I want and what kind of work and ambition supports it? Why is it that folks in their 30s and 40s say "now I am getting serious about XYZ"? Why are we not taking more sabbaticals? Why not learn to brew fucking amazing coffee? Do we have to believe that our choices lock us in? Why don't we imagine life into phases? That you can do X today, Y tomorrow, and then something you can't think today a decade from now? Are folks even thinking or we remain fully consumed to not wonder? Is this thinking a trap or a source of meaning?

When I joined TWT, I did so with wanting to also build a journalistic magazine. The Plank. My attempt at building the publication of my dreams. In a blog post at the time of joining, I had called this out:

This experiment might confirm what I’ve been thinking about: we need new ways to sustain meaningful creative work in a world of rapid technological change. The future of work, food, journalism—it’s all uncertain. And adapting to changing times demands more. Those of us with the privilege—who also end up getting even luckier—get the chance to try things most people can’t and help shape what the future could look like.

...

I don’t know how this story will turn out. Wherever it will go, I will come and write the whole truth. Because that’s how we do things here.

I know how this story turned out. I couldn't do two things together. I had to choose. I paused my magazine dream, and chose TWT. And I did so with no resentment and full commitment. (How I arrived at that decision is a story for later!)

But I am so glad—and so proud of myself—that I tried this. This poem Failing And Flying by Jack Gilbert captures it best. Sharing a few lines:

Everyone forgets that Icarus also flew. […] But anything worth doing is worth doing badly. […] I believe Icarus was not failing as he fell, but just coming to the end of his triumph.

I have a conflicted relationship with "doing more". At what point do you know you have done enough? Is ambition compatible with enough? If not, then fuck ambition. Or is it that we have really got the idea wrong here? What if there is no real tension?

I have had phases where I stretch and stretch and stretch and go way way beyond. But I now know this is not for me.

I am learning to identify enoughness, which is basically rejecting the idea of limitlessness. I am okay to not be limitless. Because I am not chasing that either. I hate the self-righteous internal heroic narrative that I have experienced in the mad phases. It's a self-enforcing loop. There is something so seductive about it.

It is hard to know what is the reason when things don't move fast enough.

Did I just grossly underestimate the needs of a big project? Or am I just slow and not as good (skill issue) or I am just procrastinating (behaviour issue)? Am I just giving something the time it deserves? Or am I not pushing hard enough? I sometimes struggle to identify what is a failure of execution or what was so improbable that failure was what the setup was designed for?

I do feel that the startup world is cursed with a misguided romanticisation of suffering. Where signs of pain are treated as signals of doing it right. When it might just mean exactly the opposite.

As a big proponent of active rest, ruthless prioritisation, and constantly saying NO—however bad the optics may be—my primary analogy for why this is the right way to do things comes from fitness.

Anyone who has got any sustainable results in fitness knows this: there is good pain and bad pain.

Good pain is what you feel on an insane leg day when two days later you are feeling DOMS and you wonder “is this what I want to feel after putting so much effort?!”

And then you learn this is how muscle grows: fiber breaks down, recovers and comes back stronger. There is no other way. So you have to make peace with the discomfort and endure through it. You have to stay focused, do the boring things repeatedly over a long period of time. It really boils down to that.

Bad pain is when you've either not designed your workouts well or you are not careful about the form and loading too heavy. Which, sooner or later, brings the avoidable injury, which takes you off track for weeks. There is no glory here. Just stupidity or ignorance.

The part that gets missed out often in the startup discourse is the primacy of rest to get where you want to be. That even when you are in good pain, you must rest. And focus on recovery. Overloading a system without rest doesn't make you stronger. It overloads you. And you fail. It's almost sacred in the strength community—it's not even a debate.

Exactly the same applies to work. Get the macro (program design) right by ruthless prioritisation. Then get the micro right (form) by obsessing over craft. And then rest brilliantly. And then wait for the magic of the system that will deliver.

But no. We will keep adding stuff. We will continue to be dissatisfied. We will continue telling ourselves stories of limitlessness. The short-term delusion driven by low rest makes you feel virtuous. Where suffering is seen as the proof of purpose.

What a delusion. Because the cost will show up. It always does. The colleague who's often down with illness. The absent father or partner whose family life is incrementally eroding. The one who's always on but always missing details—and those small errors then compound into problems you pay for months later.

The system is designed to be blind to this and it gets away because it is so hard to attribute. And good people—and especially if you still don't feel secure in your own self—often blame themselves. So you carry on.

I've felt all of this. And I wonder: isn't learning to step out of this its own kind of ambition?

Another question I have been interested in since my late twenties is around privilege: what is it that privilege actually enables that is harder for those who don’t have as much as me? Is it more success? More opportunities? More money?

Umm, no. Because that’s what privilege is. It’s the definition. Not what it does. So what does it enable?

My current answer—all such thorny questions are a work-in-progress—is that privilege lowers the cost of doing the right thing.

I remember what Clayton M. Christensen said:

It's easier to hold your principles 100 percent of the time than it is to hold them 98 percent of the time

And this, amid everything else, is the one anchor that keeps me honest-to-self as I navigate the unknown.

Year three, let's go!