The milestone that stopped exciting me
A few years ago, if you had asked me what came next, the answer would have been obvious. Like many people in corporate life, I had a clear mental model of progression. More responsibility. Bigger teams. Greater influence. The next title. Then the one after that.
What surprised me was not that I eventually reached a senior leadership position. What surprised me was discovering that the role above me no longer felt particularly compelling. The closer I got to it, the less certain I became that it was what I wanted. It was not a crisis. It was simply an observation. The milestone that had motivated me for years had quietly lost some of its appeal.
The benchmark we rarely examine
Behavioural scientists call this Hedonic Adaptation. Human beings have a remarkable ability to get used to things. The promotion we longed for becomes normal. The achievement we celebrated becomes expected. The future we imagined becomes the present we barely notice.
We often assume that dissatisfaction means we have chosen the wrong path. Sometimes it means something else entirely. Sometimes it means we have outgrown the reward that once motivated us. The challenge is that we rarely stop to ask whether our goals have evolved. We continue pursuing them because they made sense once, not because they still do.
What I’m noticing
Leadership
Many accomplished leaders are discovering that the next rung on the ladder is not always the most interesting one. Increasingly, the conversations I hear are less about advancement and more about meaning, contribution, flexibility, and impact.
Life
I know many people around my age who have stepped away from successful corporate careers to teach, coach, consult, create, travel, or simply spend more time on things they care about. What strikes me is that these decisions are rarely driven by failure. More often, they reflect a change in what feels meaningful and a recognition that the goals which once motivated them no longer do.
Culture
One of the reasons The Devil Wears Prada continues to resonate is that Andy achieves the opportunity she spent the entire film pursuing, only to realise it is not the life she wants. The film captures a truth many professionals eventually encounter: sometimes reaching the goal is what helps us see that we have outgrown it.
Reader question of the week
One of the themes that keeps appearing in coaching conversations is not uncertainty about what people can do. It is uncertainty about whether they still want what they have been working towards.
So this week’s question is simple. What is a goal, milestone, or definition of success that once mattered deeply to you but feels different today? Not because you failed to achieve it, but because you are no longer sure it is what you want.
The question leaders rarely ask
Most leaders spend time reviewing goals, plans, and performance. Few spend time reviewing the assumptions behind those goals. We often assume that because a milestone mattered to us in the past, it should continue to matter in the future.
Yet some of the most important transitions begin when we realise that the goal has not changed, but we have. The destination is the same. The person travelling towards it is not.
Which goal am I still pursuing because it matters to me today, and which one am I pursuing because it mattered to a previous version of me?