I spent the weekend with a group of friends, some old and some new, all connected by shared career DNA at one point or another, and by a love of good food, good wine, and long walks that leave our legs aching and our mind strangely clear.

Over the course of 48 hours, we talked and laughed and shared. We told the truth about our work, we confessed fatigue, we challenged each other’s thinking, and we shared ambitions we were not yet ready to make public. There were moments of irreverence, and moments of raw vulnerability.

It’s not lost on me that this is rare. Most of the senior leaders I work with are time poor and responsibility rich. Calendars are tight, and decisions carry weight. We are the steady hand for shareholders, Boards, teams, and families. We are paid to be decisive, composed, and forward looking.

And yet, many are quietly lonely even though we’re not socially isolated. We attend events and sit in rooms full of people. But we can be truly known by very few, and trusted deeply by even fewer. When the stakes rise, the circle often shrinks.

There is a particular tension that arrives in midlife leadership. We are no longer proving ourselves in the obvious ways, and we carry scar tissue and wisdom. We understand risk differently now.  We know that the risks are not only financial or reputational, but relational, existential, and about legacy. It becomes so easy to default to responsibility over aliveness, to optimise for stability over stretch, and to protect what we have built rather than risk being reshaped by something new.

Community disrupts that drift. Real community is not networking. It is not another dinner with polite conversation. It is a space where we can lay down the armour. Where someone can look us in the eye and say, I see what you are not saying. Where we are allowed to experiment with half formed ideas before they are ready for the Board deck. In that space, risk feels different. It becomes shared and generative.

Leadership at this stage of life is not about going it alone. That story is outdated. The myth of the solitary hero CEO has always been fragile. The leaders who endure and evolve are those who cultivate a circle that sharpens them, steadies them, and occasionally calls them out.

If you are feeling stretched thin, ask yourself not only how to manage your time better, but who you are doing life and leadership with.

·      Who knows the truth of your ambitions?

·      Who challenges your blind spots?

·      Who reminds you who you are beyond your title?

Community is not a luxury for the second half of your career. It is a strategic asset and a human necessity. These weekends with friends remind me that laughter can unlock strategy, that a long walk can surface a decision we have been avoiding, and that shared history accelerates trust in ways no offsite ever could.

Perhaps the most courageous move we can make this year is not a market expansion or a bold acquisition, but an intentional investment in people who hold us accountable to our highest self.

Build the circle, guard it, and contribute to it. Your leadership will be stronger for it.