Why the “Five People” Rule Fails in Men’s Work
The catchy line is a staple of entrepreneurial culture: “You are the average of the five people you spend the most time with.” It has a kernel of truth because we are social creatures. If everyone around you normalizes overworking, you may, too. But the notion fails in men’s work.
The “five people” idea assumes that growth happens through ranking: higher performers pull others upward. But men’s work depends on flattening hierarchy. In a men’s circle, status is irrelevant. A man’s value is not derived from his résumé, net worth, company revenue or ambition. It comes from his willingness to show up honestly, hold space for other men and take responsibility for his inner life.
When men enter a circle scanning for who is “above” or “below” them, the work stalls. Vulnerability becomes performative, like a man who “shared” by boasting about advice from his 7-, 8-, and even 9-figure friends. Men’s work functions well when status temporarily dissolves.
Wisdom is not distributed by income brackets
Research shows that wisdom is associated with intellectual humility, emotional regulation and tolerance for uncertainty. These qualities are shaped more by lived experience and reflection than by entrepreneurial drive, wealth or prestige.
When I complained to a cab driver in New York City that my relationship lacked intellectual conversations, the driver wisely replied, “You’re not going to get everything from your romantic partner.”
My father, a dockworker, was far from an entrepreneur. Yet, when I was about to fight a trademark battle for my company’s brand name, he asked, “Would it be cheaper to rename the company?” In the end, the threat disappeared, but my father’s wisdom stuck with me.
Average of what?
The “average of five people” oversimplifies us. Average of what? Income? Emotional maturity? Integrity? Courage? Parenting skill?
We are not linear variables; we are complex beings shaped by upbringing, trauma, temperament, culture, relationships and choice. One person may influence how you think about money. Another may teach you how to grieve. Another may show you how to listen. Another may challenge how you handle anger. Men’s work respects this complexity rather than flattening it into a simple quote.
What actually matters in a men’s circle
Healthy men’s circles operate on a different principle: not who you surround yourself with, but how you relate to the people in front of you. What matters is the ability to listen without performing, to tolerate uncertainty without rushing to authority, to receive feedback regardless of status and to speak from lived experience rather than borrowed frameworks.
This requires epistemic humility: the recognition that insight is not conferred by success, credentials or hierarchy, but emerges through honest engagement with reality.
When men treat relationships as a way to raise their “average,” they subtly instrumentalize others. People become inputs. Conversations become transactions. Worth becomes conditional. That orientation is corrosive to men’s work.
Men’s circles thrive when men stop asking, “Who will elevate me?” and start asking, “Can I be present, honest and accountable here?”
A different invitation
At Conscious Colombia, men’s work isn’t about who you know; it’s about who you become: a man grounded in emotional intelligence, self-awareness and trustworthy connection.
You don’t need five optimized peers. You need the capacity to learn from whoever is in front of you.
Sometimes it’s a man building a company.
Sometimes it’s a man whose life just fell apart.
Sometimes it’s someone trading stocks.
Sometimes it’s someone driving for Uber to pay the bills.
And sometimes, it’s the man sitting across from you in the circle, saying something simple, unpolished and exactly right.
By Richy Dalton
Founder, ConsciousColombia.com
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