We are the company we keep

In my previous life as a traveling keynote speaker and corporate trainer, I got to meet a lot of interesting people. Often, I would find myself going out to dinner with the people who hired me, along with their top sales teams. It always provided a nice opportunity to speak a little more candidly with the people I’d been working with.

Usually, about halfway through dinner, I’d ask something along the lines of: “So, how are things really going?” That’s when the real stories would come out – the stuff they felt they couldn’t really talk to anybody else about.

Time and time again, I would hear some variation of the same thing: at this stage in their careers, and in their lives, they felt they should have more. They had the house, they had the car, they had the vacations. And yet, that little voice in their heads was always telling them it wasn’t enough; that they weren’t enough.

They were constantly beating themselves up, and they didn’t feel they had anyone to talk to about it. Worse still, some of them felt bad for even wanting to talk about it. They had the attitude that “this is just how it is when you’re at the top of the mountain” and that was that.

I couldn’t help thinking there had to be a better way. I’d tell them that I worked with a lot of business leaders in a lot of different industries, and what they were describing was very common. And without fail, after these dinners, I would go back to my hotel room and think, “How can we better serve these business leaders, so they know they’re not alone?”

It took me a long time to come up with an answer. However, I strongly believe that when you keep asking questions, it leads you to the answers. And I was right.

The idea came to me in a business meeting in Toronto, as I was listening to a fellow coach talk about a mastermind group they were running. Now, a mastermind group isn’t a new idea. It was coined by Napoleon Hill in his book, The Law of Success, in 1925. The basic idea is a peer-to-peer mentoring group in which members help each other with their problems.

So, it wasn’t like I was hearing about this idea for the first time. It just so happened to be the exact right time I needed to hear it. My ears heard “mastermind group” and my brain whispered: “what if I put them all in the same room?”

As soon as I got home that day, I sat at my desk and wrote down all the names of the people I’d want to invite to this very special meeting of the minds. I came up with 14 names.

Next, of course, I had to think of a venue. At the time, I was doing a lot of work for LinkedIn in Toronto and New York. I texted a friend of mine at the Toronto headquarters – one of those super-sexy offices of the future with people going around on scooters and hitting up the staff room pool table on their lunch hours – and asked if they’d be willing to host us. He said sure.

And so, within a matter of minutes, I had the idea, the people, and the venue. Now all I had to do was get the word out – and explain what exactly I had in mind, which turned out to be a slightly taller order than anticipated.

My prospective guests were all from vastly different industries. The only things they had in common were:

  1. I thought they were ridiculously smart – and ridiculously cool
  2. Every single one of them had expressed a need, either directly or indirectly, for some kind of community

As I went around and made my pitch – a three-hour group coaching experience at the LinkedIn office in Toronto – I got asked the same question by pretty much everyone I approached: “Who else is going to be there?”

They weren’t asking this question for social climbing purposes. They were asking it because that little voice in their heads was telling them they didn’t belong. I know this because I asked, and time and time again, they responded with some variation of the same answer: “what if I’m not at everyone else’s level?”

I did my best to assuage their concerns. In the end, 13 out of 14 agreed to come.

The night before the big event, I hardly slept. I was trying something for the very first time. I knew all these people individually, of course, but now I was putting them into the same room – and they were all feeling varying degrees of imposter syndrome. What if it didn’t work?

The next day, as I looked out at the nervous sea of faces in front of me, I remembered that honesty is always the best policy – and went with it.

“Welcome, and thank you so much for being here and for trusting me to host this event,” I said. “I want to start by saying that most of you reached out to me ahead of today and said you were nervous because you thought you’d be hitting out of your weight class. I’ll say again what I probably said to you then: ‘Fuck you – what about me?! I have to lead this whole group!’”

Everyone threw back their heads and laughed. In that moment, the anxious energy in the room was disarmed.

It was the perfect foundation from which to kick off some introductions. I asked everyone to tell the group a little bit about themselves – and then to state how they knew me. As we went around the room, and everyone told stories about our respective relationships, the atmosphere got more and more relaxed. Within an hour and a half, everyone was sharing things they didn’t share with anybody else.

I sat there, dazzled and delighted by how quickly this group of people – who had been total strangers before today – came together. As they each shared their stories and their struggles, they learned that they weren’t, in fact, alone. The transformation in their faces, and in their body language, was incredible. Simply put, they were in a room with people who got it.

Of course, the real test came at the end of the session. We had arranged to have snacks and cocktails at the restaurant downstairs for anyone who wanted to continue the connections. To my amazement, everyone showed up, and the party went on into the night.

For the next three months, I continued working with this same group. I’ll never forget this one moment with a friend of mine, who works for a big ad agency. Her name is Stephanie, and she just so happened to be the youngest person in the group by far. During one of our sessions, after listening to everyone else share what they were going through, Stephanie stood up and said: “It’s intimidating being the youngest person in the room. But – and I say this with love – it’s also extremely liberating knowing that you guys don’t have your shit together, either.”

The room erupted with laughter.

The truth is that so many of us have that little voice in our heads, the one that insists on telling us we aren’t enough in one way or another. The only way to address that little voice – or at least, the only way I’ve found that works – is by having real, honest conversations. In finding and fostering community, we learn how to start embracing all the parts of ourselves – including the parts we usually try so hard to hide.

Takeaway Tip:

Do you have a group of people you can have open, honest conversations with on a regular basis? If not, consider exploring some different coaching programs. There are so many out there – from my monthly membership program, which brings together leaders around the world via Zoom, to groups like Strategic Coach or Entrepreneur’s Organization.

The path you choose is up to you, but it starts with a question. Ask yourself: who is my support team? If you don’t have one, ask yourself: How can I start my own, or find my community, today?