A few weeks ago I wrote about how lonely it can be as an entrepreneur. I had a surprisingly large number of people reach out and share their own stories, and the theme was pretty consistent… “I just don’t have anyone to talk to”.

It confirmed my story and what I was talking about, but then it helped think through what helped me get past feeling so alone.

In the peak of my time running Appletree Answers, we had 650 employees and 24 offices throughout the U.S., an amazing leadership team and phenomenal culture, great performance across the board…and I was spending over 40 days a year in some form of learning event, personal development, or mastermind group.

At least 10 of those days were time spent at events in mastermind groups I belonged to. I’ve written previously that when asked why so many days, and so much expense, just on development. I have always answered it was because of pattern recognition (see previous email!) and it was, but the point that I missed until I really reflected on it was this.

It was my chance to be around my tribe, crew, squad, peers (however you refer to your community). Entrepreneurs sharing the same challenges I was facing.

I will never forget the first industry event I attended, based on the call center space, and hearing that EVERYONE had employee issues!! I was about 27 years old and had never been around other entrepreneurs. Here I was gutting it out and making it up as I went along, thinking I was a moron for not being able to solve all the problems.

The sense of relief I felt by just learning I WAS NOT ALONE was staggering. And that led me to open up in other groups about depression, family issues, and a full range of things that I couldn’t discuss anywhere else.

Masterminds have been around forever… I will tell the story of Ben Franklin and the Junto in a future email… so the idea is hardly new.

But I really believe it is more important now than ever. In the age of social media, isolation, work from anywhere, and just a general reduction in face to face contact it is critical to be IN PERSON, in a meaningful way, to connect and talk. Whatever it is that is nagging you, the rock in your shoe, talk time really matters. I am incredibly grateful that for the last 20+ years I have found many of those tribes to help me tremendously!


Founder of the align5 Companies,  CEO of Scaling Up Coaches, and Serial Entrepreneur

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