I Never Aimed at Meaningful Work. I Aimed at Fun and New.

A few weeks ago I sat down with a chatbot for an interview that was supposed to surface my thesis, and I told it the most honest thing I had said out loud in a year.

The chatbot had asked me whether I'd ever felt like I was running toward something. Money. Status. Some specific destination. I tried to answer the question and realized I could not. The closest I got was this: "I don't know if I ever ran towards great meaning or wanting to change the world. I have always been running away from one thing or the other."

A few weeks after that initial conversation, in a different session with the same chatbot, I said this: "This is the first time in 15 or 16 years of me being a working professional that I feel fulfilled and happy. I think what I'm doing is meaningful."

Both of these are true. Neither is the same person speaking. The first is the person who is honest about not having aimed at anything. The second is the person who is honest about the fact that something landed anyway.

This is my attempt to write down what I think connects the two, because I think a lot of operators are quietly running the same protocol and not saying so.

What I actually aimed at

I aimed at fun. I aimed at new. I aimed at people I thought were smart and good. I aimed at not letting down anyone who took a bet on me.

That is the full list. None of those four things involves meaning, mission, or impact. None of them maps cleanly to find your why. None of them would survive a strategy offsite. The closest the list gets to ambition is not letting down the people who bet on me, which is the opposite of running toward something. It is running away from a specific failure mode, the one where someone who took a chance on you regrets it.

I have run that protocol for fifteen years. I went to a small private liberal arts university in Oregon on a full scholarship because my Dad did not want to bet on a mediocre student and I had to earn the bet myself. I joined hCentive in 2011 because Tarun and Manoj seemed smart and the work seemed new. I joined OneDigital in late 2024 because Vinay seemed like someone I could learn from and the work was new again. Each transition was an escape from dressed up, briefly, as a move toward.

If you had asked me at any of those moments to articulate my mission, I would have failed the question. The honest answer was always the same. I do not know exactly what I am running toward. I know what I am running from. I will report back when I see what I have arrived at.

What landed anyway

The funny thing is that the answer the chatbot extracted from me about the first time in fifteen years I feel fulfilled is not the first time fulfillment has actually happened to me.

It is the second.

In 2010 I graduated into one of the worst job markets in modern American history. The Affordable Care Act had just passed. The federal government needed someone to build the insurance exchanges that would let people who had been priced out of health insurance for years finally buy a plan. Tarun and Manoj's team at hCentive built those exchanges for Colorado, Kentucky, and a few other states. I spent the first three years of my career inside the engine of one of the largest pieces of public infrastructure that had been built in my adult lifetime.

I did not know, at the time, that I was doing meaningful work. I did not aim at it. What I aimed at was closer to: Tarun and Manoj are some of the smartest people I know and they took a bet on me. So let's not let them down. I would have told you, at the time, that I was working hard, learning a lot, and being paid reasonably well to do something interesting. I would not have told you I was changing anyone's life. I am pretty sure several million Americans got insurance because of the systems we built. That fact landed on me retroactively, in pieces, over the next decade.

I am living through the same pattern now at OneDigital. I am running the AI program at a 6,000-person consulting firm, eighteen months in. I think we have figured out something genuine about how AI actually deploys in a large workforce, distinct from the keynote version that most enterprise software vendors are selling. Harvard published a case study on it. My boss has a book coming out this summer that quotes me in five places. A joint research project with Harvard, MIT, and UCLA is in motion that has invited me as a co-author.

I did not aim at any of this. I aimed at Vinay seems sharp, the work seems new, I am tired of the existing thing. The rest landed. It is landing right now, in real time, in a way that has the same retroactive quality the hCentive years did, except this time I am old enough and rested enough to notice it while it is happening.

Why I think this is the actual pattern

There is a whole orthodoxy in the operator world about finding your why and starting with mission and aligning to meaning. Most of it traces back, in one form or another, to a TED talk most of you have seen.

I would not say this in a public talk because it would be needlessly mean and I might be wrong, but I will say it here: I have watched almost no one I respect, who has actually shipped something that mattered, frame their work that way at the start. Most of them ran the same protocol I ran. They aimed at new + smart-and-good people + don't-let-the-people-who-bet-on-me-down + this will make me some money. They then worked hard as hell. Something landed. They were as surprised as anyone, even if they don't tell that story to the VC they pitch when they raise money.

The people in my life who have started with meaning, who have chosen their cause early, who have aligned prospectively, have largely either gotten lucky or burned out. I am not arguing they are wrong. I am arguing the pattern is rarer than the genre of business book pretends it is.

There is a quieter alternative posture that I think is actually true to how operators who ship meaningful work get there. It looks like this:

Pay attention to who you want to be in the room with. Pay attention to whether the work is new in a way that makes you walk to your laptop instead of away from it. Pay attention to who has bet on you and pay your debt to them by doing good work. Look at the spread of what you have built after a decade and notice what the spread is telling you.

The pattern that emerges from doing that, if you do it long enough, is what meaning actually looks like. Not from the front. From the back.

What I owe the people who bet on me

The bet-debt is real. It is a quieter motor in my work than I usually let on. I am writing it down here once because it deserves to be in the record.

I owe Tarun and Manoj for picking me out of the 2010 graduate market when nobody else was hiring. I owe my Dad for the bet he made that I would take his rejection as a challenge and score well enough on the SATs to make the scholarship cover the gap, and not take the L and continue being mediocre. I owe my brother for running the family business for the years I was not in the country, and even after I was, for letting me figure my own way (mind you, he is six years younger than me, but mature beyond his years). I owe my wife for picking up the relationship costs of my work hours, the constant ups-and-downs from our move back to India, and the absolute tough, tough phase through SmartCue. I owe Vinay for picking me, in late 2024, for a job I do not think I could have gotten based on my credentials.

None of that is the engine of my work. It is the floor of my work. It is the version of seriousness that operates beneath whatever surface fun-and-new framing I am wearing on any given Tuesday. I do not chase it. I do not optimize against it. But I notice when I am about to violate it, and I do not violate it.

What I would tell someone trying to figure out their "why"

Stop trying.

Pay attention to who you want in the room. Pay attention to what makes the new tab open at six in the morning instead of feeling like a chore. Pay attention to who has paid for you to be where you are and what you owe them. Then go do work that does not make any of those three people regret the math.

If a meaning shows up, you can write it down ten years later. Until it does, the meaning is doing what it always does, which is hiding inside the texture of the days.

Closing

I never aimed at meaning. I aimed at fun and new. I aimed at not letting Vinay down the way Tarun and Manoj before him bet on me and I owe them. Twice in sixteen years that has accidentally produced something I think was worth doing.

I really hope it stays that way.