Let me start this discussion by saying leadership is a massive privilege. And I am fortunate to be in a job that I love. I feel that gratitude every day and know many would do anything to have what I have. But I also believe in being vulnerable about what I feel, to normalize the emotions we all experience in business.
One of the oldest cliches about leadership is that “it’s lonely at the top.” While this applies to CEOs, I believe many leaders feel a regular sense of loneliness.
The Show Must Go On
On the one hand, as a leader, you are constantly “on stage” in front of your team, peers, and external stakeholders. You strive to project confidence and instill a vision. You want everyone around you to be as excited as you are to go to work every day. You want to be, as some people say, fired up!
I Find Your Lack of Faith Disturbing
But on the other hand, you are also human, and it is human to have doubts and worries. Sometimes, you are not sure it will all work out. You may not always be confident you are the right person for the job. And to top it off, you probably don’t feel like you can share these uncertainties openly, for concern of creating a self-fulfilling prophecy. Your bosses or board might judge you or might themselves start to have doubts. And your peers’ incentives may not be aligned with yours.
Do You Want to Build a Snowman?
I’ve run Gainsight for 8.5 years and am certainly used to the ebb and flow of these emotions. Indeed, as I’ve shared before, I was very lonely as a kid (I ate alone every day from kindergarten through twelfth grade – yes, very sad 🙂 ) and never felt like I fit in. To be honest, I’m still not sure that I fit in.
But over time, I’ve found that one other, more specific, form of loneliness emerges in leadership roles.
If you aspire to run a team or business for a long time, many people will come and go. At Gainsight, we have 800 employees today. Many of them have been here for much of the journey. But still, many others have moved on over the years to do other amazing things. And as we continue to grow, we have teammates that are brand new to the journey. While I firmly believe in The Alliance (if you haven’t read it, I highly recommend it) it doesn’t make it any easier to say goodbye to those leaving for their next adventure.
The Lonely Conductor
A few months ago, I had a daydream.
The image I had in my head was that our company is a train, bound to some unknown, but hopefully sunny, destination, with many stops along the way. New passengers–new hires—board the train. They are full of enthusiasm for the beginning of their journey. They haven’t been part of this ride before and can’t wait to see where it takes them. They’ve even heard verified rumors that the train’s conductor is a terrible rapper!
At each stop, some passengers on the train have reached their exit and decide to disembark. They’ve enjoyed the ride and it has given them comfort and joy for the past several years. But they have reached their destination—whether it’s in terms of the next step in their career, a promising startup they can found, or a non-work aspect of life they want to focus on. So they decide to get off of the train. And I appreciate them and miss them.
Each day, I say goodbye, with hugs and gratitude, to all of the dear passengers who are no longer going on the ride. And after I say farewell, I turn around and welcome the new passengers with all of the bells and whistles as if this was the beginning of the train’s journey—because, for them, it is.
All along the way, I do this knowing that the train is primarily a method of transportation for most. But for me and a few other longtime Gainsters, the train is a big part of our life. We’re not planning on deboarding ever. Now, one day, someone might come aboard the train and decide that a better conductor could guide the next phase of the journey. But as long as I have the choice, I’m taking the train to the promised land.
I’ll Be There For You
I remember telling my wife this story. She had the best response I could imagine, as she always does: “It’s easy to feel sad about people leaving the train. But what if instead, you felt incredible gratitude that they ever chose to get on your train in the first place.”
Fast forward to early July. We had our leadership team together in Salt Lake City, Utah, for our first offsite post-quarantine. We laughed and learned. We hiked up and hugged it out. We dined and drank. And of course, we sported our favorite customer swag together.
On the last night of the event, I fell asleep and had a vivid dream, perhaps induced by the high altitude and low oxygen (Rocky Mountain high, as they say.) Have you ever had a dream that’s so emotional that you wake up and you feel like crying because it felt so real? I immediately wrote it down to share with my team the next day:
“We were on a train traveling along the ocean. All of you were there. The night sky was dark beyond the fire of the stars. The air felt crisp and cool. And I wasn’t in the front of the car—I was with you all. And I never wanted to leave.”
This is the paradox. One of the greatest benefits of leadership is the togetherness you get when you’re with your team. And one of the biggest challenges is the loneliness you can feel when you’re on your own.
For me, I’m going to choose to relish those moments with the team more and more and be grateful these amazing people ever decided to board our train.