By 
I spent most of my twenties doing everything right by conventional standards, and feeling, underneath all of it, that something was significantly wrong.
I had a psychology degree from a good university. I was moving through a corporate career in Melbourne that looked, from the outside, like exactly the kind of trajectory a young man was supposed to want. I was hitting the markers. And I was, in the gaps between the hitting of markers, quietly miserable in a way I did not have the vocabulary or the courage to examine properly.
The conversation I was avoiding was not complicated. It was simply this: is this actually what I want, or is this what I was handed and decided to call wanting?
That question sounds easy to ask. In practice, for most men in their twenties, it is one of the hardest things available. Not because the answer is necessarily dramatic, not because it always leads to leaving everything behind, but because asking it honestly requires sitting with a degree of uncertainty that the structure of a conventional career path is specifically designed to make unnecessary.
The path provides the next step. The next step provides the direction. The direction provides the identity. As long as you keep moving, you do not have to ask where you are going or whether you chose it.
What the avoidance actually looks like
It does not look like avoidance from the inside. That is the thing that makes it so effective and so costly. A man in his twenties who is not asking the important questions is not, in most cases, staring at a wall doing nothing.
He is extremely busy. He is building skills, making connections, earning money, hitting targets, optimising his performance in a game whose rules he inherited rather than chose. The busyness is real. The achievement is real. The avoidance is running underneath all of it, invisible precisely because the activity on the surface is so continuous.
I worked in corporate strategy for seven years. I was genuinely good at it. That is the part that nobody warns you about: being good at something is not the same as it being right for you, and the fact that you are good at it makes the question harder to ask, not easier.
Walking away from competence feels like waste. It attracts the judgment of people who equate ability with obligation. It requires you to sit with the uncomfortable possibility that you have been spending real years of your life on something that was never quite yours.
The warehouse job I took after leaving that career, shifting televisions in Melbourne, was the lowest point by any external measure. It was also, looking back, the first honest ground I had stood on in years. There was no performance required. There was no identity to maintain.
There was just the work, and the breaks, and the reading I was doing on those breaks, Buddhist philosophy and psychology and anything that helped me make sense of what I was actually looking for beneath the confusion of having done everything correctly and arrived somewhere that felt wrong.
Why the twenties are when this conversation matters most
There is a version of this realisation that arrives in the forties, and it tends to arrive much louder and with significantly higher costs attached. The man who gets to forty without having asked the question honestly is usually the man who finds the question arriving anyway, in the form of a restlessness he cannot locate, a distance from his own life that he cannot explain, a sense that the things he worked for do not feel the way he expected them to when he got them.
The twenties are not a more comfortable time to ask the question. They are an earlier one. The earlier you ask it, the less has been built around an answer that is not quite true, which means the adjustment, when it comes, costs less. Not nothing. The adjustment always costs something. But considerably less than the alternative.
What makes the question hard to ask in the twenties specifically is the combination of external pressure and internal uncertainty that defines that decade for most men. The pressure to be building something, to be moving in a recognisable direction, to be making progress that can be reported to parents and peers and the internal voice that measures worth against output.
And the uncertainty, which is genuine and not a weakness, about what you actually want from a life you have not yet had enough of to know clearly.
Buddhism has a concept that helped me understand this period differently when I encountered it during those warehouse break times. The idea that suffering comes largely from attachment to expectations, to the story of what your life is supposed to look like, and that the loosening of that attachment is not the same as giving up but is rather the beginning of seeing clearly what is actually in front of you. That loosening is what the avoided conversation makes possible, when you finally have it.
What the conversation actually requires
It requires honesty about the difference between what you want and what you have been rewarded for wanting. These are not always the same thing, and in the lives of men who grew up in environments that praised achievement, performance, and the appearance of having things together, the gap between them can be significant and largely invisible until you look directly at it.
It requires the willingness to sit with not knowing. The conversation does not produce a clean answer. It produces a direction, a set of questions that are more honest than the ones you were asking before, a slightly clearer sense of what matters and what was borrowed from someone else’s idea of a good life. That is enough to move from. It is not enough to plan around perfectly, and waiting until it is enough to plan around perfectly is another form of the avoidance.
It requires, in most cases, a period of real discomfort. I moved to Southeast Asia at thirty-one, which was the external form my particular conversation took. That is not the template. The template is different for every person. What they share is a willingness to be in a place of genuine uncertainty for long enough to hear what is underneath the noise of the conventional path.
What changes when you have it
I founded Hack Spirit at thirty-two, after the years of reading and uncertainty and the slow accumulation of a clearer sense of what I was actually trying to do. I am not presenting that as the model outcome. I am presenting it as evidence that the conversation, even when it arrives late and costs something to have, does eventually produce ground to stand on.
What changed was not that everything became easy or clear. What changed was that the direction was mine in a way it had not been before. The work I was doing was connected to something I had actually examined and chosen, rather than something I had drifted into because the drift was available and the alternative required more honesty than I had managed.
My daughter is young enough that she will not read this for many years. But I think about the kind of father I want to be for her, and the kind of example that means something beyond the conventional markers of success, and the answer always comes back to the same place: a man who asked the question honestly and built from that, rather than one who performed the answers he inherited and called it a life.
The conversation is not comfortable. It is also not optional, not really, not if the thirties are going to feel like something you chose rather than something that happened to you while you were busy being good at things that were not quite yours.
Ask it early. Sit with the discomfort. The ground on the other side is more solid than the path you were on.