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Dear reader,
There is a particular kind of conversation that only happens at a certain level.
It doesn't happen in the first decade. People in their first decade are still too busy climbing to ask about the mountain. They are learning the craft of the ascent, getting faster, getting stronger, getting better at the particular kind of effort the organisation rewards.
By the second decade, some of them start to notice something. They can't quite name it. It feels like friction of a different kind.
Not the friction of not being good enough. The opposite. The friction of being very good at something and still finding yourself wondering, in the quieter moments, whether this is the summit you would have chosen if you had understood what you were choosing.
I have sat across from enough people in their third decade to know that this question almost never gets asked out loud.
The reason is simple. By then, the climb has cost something real.
Most of us do not choose our ambition. We inherit it.
Not deliberately. The people around us didn't sit down with a map and say: here is the mountain, here is the route, here is what success looks like from the top. But we absorbed it anyway. From the organisations we entered. From the peers we measured ourselves against. From the culture of whatever field we happened to enter when we were twenty-five and still forming.
And for a long time, that inherited definition of success is enough. It gives you direction. It gives you fuel. The borrowed compass points somewhere specific, and specific is useful when you are learning to climb.
The problem is that borrowed compasses don't recalibrate.
The mountain you are climbing in your third decade may not be the mountain you would have chosen at forty, if you had stopped to choose. But the question of whether it is the right mountain is much harder to ask at forty than it was at twenty-five, because by forty you have built a great deal on the premise that this is the right direction.
Your title is built on it. Your reputation is built on it. To question the mountain at that point does not feel like intellectual curiosity. It feels like dismantling something.
I was talking to someone recently. I won't say who, or in what context. Senior enough that the question had some weight to it. Successful enough that from the outside there was nothing to question.
They said something I have been carrying since.
"I think I've been very good at the wrong thing for a very long time."
Not said with despair. Said with the particular calm of someone who has finally stopped arguing with themselves and arrived at something true.
I asked what made them say it now, rather than five years ago.
"Five years ago I still had somewhere to put the doubt. I was busy enough that it couldn't find me."
The altitude, they meant. The pace of the ascent. The calendar full of things that require your full attention and are very good at consuming it. Genuine high performance, not laziness, not distraction. And precisely because it is genuine, it becomes the most effective way of avoiding the question that most needs asking.
Here is the part I didn't put in the LinkedIn version of this letter.
What I remember most about that conversation was not the moment they said it.
It was what came before it.
There was a long silence first. The kind of silence that has a question in it. I have learned not to fill those silences. Most people, in most conversations, fill them immediately. A reframe, a softer version, a question that gives the other person an exit. We are trained to rescue people from discomfort.
But that silence was not discomfort. It was someone giving themselves permission.
The thing I have noticed is that the question, am I climbing the right mountain, almost never arrives fully formed. It arrives as a feeling that something doesn't quite fit anymore. A mild restlessness that is hard to justify, because everything is going well. The sense that a version of you that existed before all this would not entirely recognise what you are optimising for now.
And it cannot become a clear question until someone gives it space. Until the silence is held long enough that what is in it can surface.
That is not something you can do for yourself. When you are inside the question, you are also inside the answer you have built around it. The justifications, the sunk costs, the identity that has formed around the climb. You cannot step outside your own altitude.
What another person can do, if they are paying the right kind of attention, is hold the silence. And then ask the one question that lets what is already true become sayable.
Not a coaching framework. Not a structured intervention. A human question, asked by someone who has been at altitude long enough to know what it costs.
That is the work I find most important now.
So the question I want to leave you with is not dramatic.
Whose definition of success are you climbing toward?
Before the industry named it. Before the organisation gave it a job title and a salary band. Before the comparison with peers turned it from a direction into a destination.
What did you think a good life looked like, when you were honest about it with yourself?
That answer may not be different from where you are currently heading. For many people, it won't be. The borrowed compass turned out to point somewhere true.
But it is worth knowing.
The difference between climbing someone else's mountain very well and climbing your own mountain with everything you have is not visible from the outside. It is only visible from the inside, in the private accounting that no one else sees.
You are the only one who knows which it is.
With gratitude and the honest imperfection of still being mid-climb,
Avinash
P.S. If you are at a point where the silence has something in it and you want someone to sit with it alongside you, my details are on my LinkedIn profile (linkedin.com/in/avikaul). I work with a small number of founders and senior professionals at any given time.