What Community Actually Looks Like

I witnessed a conversation last week that ended with a series of mic drop moments…

A friend brought a very important decision he was struggling with to a group of business owners and entrepreneurs. He was essentially struggling with the choice between a significant increase in income or presence and time with his family.

He’s spent years building and leading teams, developing internal systems that made some of the world’s biggest companies more efficient and profitable. His ability to get people rowing in the same direction, especially in high-pressure situations, makes him highly sought after and perfect for this next opportunity.

The offer was from another market mover, a company with potential to be a sector leader for years to come. It’s a serious challenge: this company is growing at rates others can’t keep up with. The financial package is lucrative, and the perks keep getting better with each conversation.

Twenty years ago, he would’ve jumped at this without thinking twice.

Now things are different. He has a wife and four kids. Taking this role means moving in the opposite direction they’ve been planning for two years. It means significant time away from family. And he’s at the point where he’s wondering whether to keep working for someone else at all or finally launch his own consulting practice with all the knowledge and contacts he’s built.

His struggle boils down to this: financial security for his family that’s hard to find anywhere else versus being the present and engaged husband and father he’s been striving to be for a few years.

Normally, family time would be the deal breaker. But this offer makes it a real choice.

He came to the group detailing the situation and his current mindset. Then he did something that so many high performers have trouble doing: he asked for help.

He felt as if he had hashed this out as far as he could up until that point. A decision needed to be made soon and he was at the point where each day he flipped from one spot to the other.

He wasn’t looking for someone to tell him what to do, and no one would have done this. Ultimately, he has to make the final decision.

He just wanted to get the perspective of people he knew he could trust to keep his and his family’s best interests at heart without being envious of his options or judgemental when he ultimately decides which direction to go.

The ability for high performing businessmen to have these types of conversations, rooted in mutual trust and psychological safety, is unfortunately still very rare.

We all understand how fortunate we are to be a part of this group and be able to bring similar struggles forward there.

A great conversation ensued after my friend put his “ask” out there. Others were asking amazing questions, combining their understanding of the situation with a general curiosity for what might lie beneath the surface.

What is the one consequence from your decision you would regret 20 years from now? Is the juice worth the squeeze?

Imagine yourself at the end of your life. What choice made you happy? What choice fills you with regret? Go with the one that made you happy.

Are you being sold on someone else’s goals or dreams? Will this allow you to pursue your own goals or dreams? Pursue your dreams, not someone else’s.

BOOM!

Amazing stuff, right? And what is really awesome is the fact that those of us in the group have come to expect this level of interaction and feedback.

When someone is willing to be vulnerable and share what is really going on, the others in the community are lining up to be supportive in some way.

My friend is very lucky for a number of reasons. He has worked his tail off to be in a position where his services are in such high demand. He has a supportive family that is open to the possibilities this position might bring.

And he is part of a supportive community of like-minded men walking along the same path as him.

These questions helped him make the decision that, deep down, he knew was the right one.

These kinds of interactions happen frequently in the community. Each time they do, I am reminded of how rare this level of support actually is.

This is the type of community most business owners, high performers, and entrepreneurs need in their lives.

So many are silently struggling.

Maybe they’ve built something great, but they are the linchpin and without them operations would grind to a halt. They want the business to grow, but do not want to sacrifice more than they do already to make it happen.

Maybe they aren’t business owners but ultra high performers, the kind of person who a company would do anything to hold onto while other companies would do anything to get them to switch over to them.

Maybe they simply have a dream of building something of their own, breaking free of the W-2 world and putting all of their knowledge and experience to work for themselves rather than in pursuit of someone else’s plan.

These are just some of the people who would benefit from a strong, supportive community.

I would imagine there was a time when you had to face a hard decision, one that wasn’t just going to impact you but your family and others.

Did you have to review the possibilities by yourself? Or did you have a support system of people who really understood the situation available to help you get to your decision?

If you are a part of something like I’ve described, I’d love to hear from you.

What is the greatest gift you’ve ever received from being a part of that community?