Welcome to Friday 411, issue #137. In 4 minutes, with 1 insight and 1 action, you’ll know what to do when leadership feels isolating.
1 Insight
When a leader carries doubt and isolation long enough, it always spills over—into decisions, relationships, and the people depending on them.
I (Garland) experienced an uncomfortable feeling that I haven’t shared until now—a secret that I kept hidden for over a year.
If you’ll give me a few minutes, I’d like to show you how my confession can help you.
First, a little background.
My work is all about people. I spend my days with people who I respect, enjoy, and care about. Dorothy and I get to walk alongside leaders who want to grow and help their companies succeed. That part of the work is a gift I wouldn’t trade for anything.
At the same time, we don’t actually work inside any of those companies.
We teach leaders how to lead better, but we’re not one of “them.” We’re vendors. Outsiders. This gives us some advantages:
- People often trust us with information they don’t feel comfortable sharing internally, and
- We can challenge their assumptions, decisions, and practices without instilling fear of job loss or demotion.
But our status as “outsiders” also comes with a disadvantage. We live in an unusual space: building our own business while serving leaders inside much larger ones.
Over time last year, that reality started to weigh on me.
What I Started Feeling
I began to feel like no one really understood the challenges I was carrying. The pressure. The nuance. The responsibility of helping other leaders succeed while trying to build and sustain our own business. Other than Dorothy, there wasn’t anyone I could talk to who truly “got it.” I wasn’t just tired. I felt unseen. Alone.
That loneliness didn’t hit all at once. It crept in over the year.
I started feeling like Tom Hanks in Castaway. Like I was the only person dealing with these problems. When challenges came up, I had no safe place to talk them through. No one to help me sort out what mattered and what didn’t. I even tried talking to a volleyball. That didn’t help.
How All This Affected Me
I didn’t know what to do when I was alone with my thoughts. I had a few good ones and a plethora of bad ones. Sadly, the bad ones tended to over.
Over time, it started to cost me.
I didn’t lose my ability to think. I lost my confidence in my thinking. Ideas that once felt clear started to feel shaky. I reread emails before sending them. I second-guessed decisions I used to make quickly.
Doubt didn’t just get louder—it got closer. It sat with me in quiet moments and whispered questions I didn’t know how to answer: Are you actually helping anyone? Does this really matter? Are you the right person for this work?
And I knew something else was at stake.
If I stayed in that place, it wouldn’t just affect me. It would affect the clients we care so deeply about. The leaders and teams we want to see win.
That’s when I realized something had to change. I didn’t need another tool or tactic. And I didn’t need to process this with anyone who couldn’t fully understand the weight of the role. I needed other people who could relate.
Why I’m Telling You This
Why am I telling you all of this? Because this isn’t just my story. In my conversations with leaders, I’ve heard a lot of the same thing. Dorothy and I have talked to many leaders who feel alone.
They spend all day with their teams. Have multiple meetings with their peers and supervisors. They even go to after-hour functions with coworkers. But at the end of the day, they still feel isolated. Like no one understands them.
When a leader carries doubt and isolation long enough, it always spills over—into decisions, relationships, and the people depending on them.
This loneliness creates a lot of shame and uncertainty—especially when you feel stuck—because you’re not sure who is safe to confide in. If you talk to your boss, will they question your ability to lead? If you talk to your team, will they lose confidence in you? If you talk to your peers, will they use it against you later?
Research backs this up as well. In 2018, the Center for Creative Leadership found that 76% of executives experienced feelings of loneliness. More than half said it negatively affected how they made decisions.
Here’s the crazy part. Most leaders believe that they are the only ones who feel this way.
You feel like you’re carrying the weight by yourself.
If any part of this feels familiar, pay attention. You’re not broken. You’re not weak.
And you’re definitely not alone.
Back to my story.
I started looking for people who lived in the same tension I did—entrepreneurs building their own businesses while helping other organizations succeed. I found a small group who fit the criteria, and we began meeting regularly. We talked about real work, not polished stories. We shared ideas, frustrations, goals, and questions we didn’t know how to ask anywhere else. We challenged each other. We helped each other think.
And slowly, something changed. Decisions felt lighter. Perspective came faster. I had more energy, not because the work got easier, but because I had more support. That community didn’t remove the pressure of leadership. It helped me carry it better.
That’s why next week, we’ll be sharing something new we’re launching called The Unleashed Community. It’s designed to give leaders a safe, practical place to connect, think clearly, and grow alongside others who understand the weight you carry. Keep an eye on your inbox. If leadership has ever felt lonely, this will matter to you.
You don’t have to be alone anymore.
Join a community that finally gets you.
1 Action
On a scale of 1-5, rate your own level of loneliness. (1 – Not lonely at all. 5 – Extremely lonely.) Write down how you see loneliness affecting your leadership and what you wish was different.