Lonely at the Top

Published by Timothy Reed on

Lonely at the Top

by Alex Judd

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The sentiment that leadership is lonely isn’t new. That’s why we’ve all heard this cliché: “It’s lonely at the top.” Many of us have probably used it at some point in our careers.

If you’re like me, you’ve probably waffled on your degree of agreement with the idea.

  • Agree: There have been moments where I have leveraged it as an explanation. It helps explain decisions, opinions, perspectives, and feelings in others—but also in myself. It gives people the ability to shrug their shoulders and simply say, “Well, it’s lonely at the top.” It’s in these moments that I enthusiastically agree with the idea.
  • Disagree: But then, there are times when I really think about it, and I can’t wrap my head around the cliché as a viable explanation. I question every part of it, and then I question myself. If leaders are leading well, shouldn’t they be surrounded by people? So how could they possibly be lonely? It’s in these moments that I write off the idea as an oversimplification at best and a pity party at worst.

These two competing viewpoints have waged war in my mind and life for a while. And there wasn’t really a clear advantage to either side. That’s kind of a problem for a person who makes a living trying to understand, work with, and coach leaders. It’s an even bigger problem because it’s difficult—if not impossible—for anyone to solve a problem they can’t comprehend.

Occasionally, it would look like one side was pulling ahead. Then, inevitably, a new example would come raging forward that would turn the tides in the opposite direction. I eventually gave up hope that I would ever reach a clear belief.

But then, one phrase changed everything. At the risk of sounding cheesy and dramatic (even though I’m definitely a bit of both), it was a light-bulb moment. An epiphany. A revelation that brought about a sense of resolution.

It was an early Saturday morning, and I had the coffee shop all to myself (perfectly ironic). Absolutely wired because I was already almost done with my second cup, I was tearing through Doris Kearns Goodwin’s Leadership in Turbulent Times. When I reached the last paragraph on page 229, I’m pretty sure my jaw dropped. 

In five words, this book won the war. It wasn’t even a full sentence. Just a preface. Here it is.


I read it five more times, astounded that such a big idea could be captured in such a concise way.






That’s it. That. Is. it!

It’s not a lack of company that makes leaders lonely. It’s a lack of empathy.

As humans, we don’t just need people who know who we are. We need people who know what we’re going through. And the more we set ourselves apart, the harder these people are to find.

Nowhere is this reality experienced more fully than within the exercise, practice, and performance of leadership. Think about it: The nature of leadership is responsibility. If you’re the leader, you are responsible—for the wins, the losses, the growth, the stagnation, the failures, and the successes.

And you’re not just responsible. You’re ultimately responsible. 


That’s why one 30-minute conversation with a person who “gets it” is more energizing and life- giving than three half-day meetings with people who don’t. It’s also why you can be surrounded by your team, customers, family, and friends and still feel completely and utterly isolated. But here’s the hard truth: That’s not their fault—it’s yours.

As with most things, you and I are the problem. That means that you and I have the opportunity to be the solution. I’ve been, observed, worked with, and learned from leaders who are devastatingly lonely. I’ve also been, observed, worked with, and learned from leaders who are no less successful but remarkably more joyful. And what I’ve noticed is that all the leaders who experience the latter (joy, community, success, and fulfillment) practice three habits (spoiler alert—they all involve sharing).

Habit 1: Share the Details

It’s tempting to leverage this “ultimate responsibility” thought process to justify the idea that if you’re a CEO, you can only connect with, talk to, and learn from other CEOs. And heaven forbid they have a smaller company than you do; that would be a waste of time. 

But this is a gross misinterpretation of this principle. (On a side note, I also think it’s one of the underlying forces that’s causing the deep-seated dissension and polarization of our country.) What’s more, it’s counterproductive. Because if you walk this out, then the more successful you become, the fewer people you can connect with; and the fewer people you can connect with, the more lonely you become; and the more lonely you become, the less successful you become. 

Simply put, the plan implodes on itself over time.

We must stop to consider that the reason why the people closest to us can’t understand what we’re going through is because we’ve never taken the time to actually share it. A great “look- in-the-mirror” test for this is to see if your family and closest friends know what you do day-to- day. Too often in the lives of leaders, th e people who are closest to them have zero clue what they actually do.

So the answer—and this is as hard for me to write as it is for you to read—is to slow down. Give people outside the office the opportunity to know, feel, and experience what you go through every day.

Give people outside the office the opportunity to know, feel, and experience what you go through every day.

The big part here is every day. Not just in the moments of crisis or celebration. Every. Single. Day. 

Because they’ll never be able to feel the magnitude, depth, sorrow, and joy of the big moments if you don’t let them in on the small ones.

Let me be clear: Most of the time, this will feel boring, unproductive, and maybe even selfish, especially for a growth-oriented individual. This is a lie. You have to think about your closest relationships as a bank account. Every single time you slow down enough to talk about what you’re going through, you’re making a deposit. The currency is context. Sometimes these deposits take two minutes. Sometimes they take two hours. But every time you make a deposit, you’re giving someone who cares about you the context that will be necessary to process the peaks and valleys the way you do. 

And that is invaluable.

Action: Find one person outside the office you trust. This can be a spouse, family member, close friend, pastor, counselor, or mentor. Tell this person that you’re going to start intentionally sharing more details about your life and work so someone else will understand what you’re going through and you won’t be isolated. Then, actually do it.

Habit 2: Share the Responsibility

It’s easy to read the phrase “share the responsibility” and immediately think “delegation!” And while that’s true, I’m referring to a very specific type of delegation.

Too often, leaders delegate tasks. While this is okay (and perhaps even necessary for a team to grow), it doesn’t relieve the loneliness issue at all. Remember how I said that the thing that sets leaders apart is responsibility? This means that one of the things you’re going to have to delegate to avoid loneliness is real, actual, true responsibility.

This means you aren’t just handing off tasks, outcomes, projects, or even teams. It means that you’re handing off ownership.

Let me be clear: I’m not talking about giving away equity or position. I’m talking about empowering someone who isn’t you with the opportunity to be ruthlessly responsible—for the wins, the losses, the growth, the stagnation, the failures, and the successes. (Sound familiar?)

The inevitable consequence of this action is that you lose control.

The inevitable benefit of this action is that you lose control.

But this isn’t about you losing control; it’s about someone else gaining it.

That means that someone else knows what it feels like to be emotionally impacted by the highs and lows. Someone else knows the stress of not hitting the budget. Someone else experiences the gratification of exceeding expectations. This will be good for your team. It will be good for your company. It will be good for your family. It will also be good for you, since the undeniable result of having that “someone else” on your team is that you’ll no longer feel alone—because you won’t be.

You could have a PhD in organizational leadership and still fail miserably at this. I think the important thing is that you try it. Because it’s in the trying that you push fear out of the driver’s seat. So be about the business of finding people who have the propensity to care deeply about the work, then actively share real responsibility.

Action: Think of one person you could give more ownership to—not because they’re guaranteed to succeed, but because they’re guaranteed to care. Then, proportionate to the person’s level of competency and integrity, hand off something that really matters to you.

Habit 3: Share the Mess

Although this is the last habit, it’s probably the most important.

You see, there are countless books, articles, and speeches out there that tout the idea: “No one expects you to be perfect!

But I think, for some of you, that’s a lie. 

That’s right. I said it. 

The idea that no one expects you to be perfect is an absolute lie. Some of you have teams, colleagues, friends, and even family members who expect you to be perfect. You know why?

(This part is way better if you scream it as loud as you can.)


(See, wasn’t that good? Now, back to normal.)

Don’t get mad at me. I’m just sharing a message that I repeatedly need to hear. Think about it: We hide mistakes, refuse to admit failures, conceal our feelings, and direct attention away from our setbacks.

This is really gratifying, and (dare I say it) fun. It’s fun to be looked up to, revered, respected, admired, and thought of as flawless. That’s what makes it so tempting. It’s also what makes it so dangerous.

Because, when you play this game, you intentionally deprive people of the opportunity to see you as imperfect. When you choose—and it is a choice—to establish this as a pattern, you’re training people to stop seeing you as human.

They see the power-washed, filtered, polished, perfect version of you, which isn’t you at all. 

Therefore, even if you go all-in on sharing the details and sharing the responsibility, you’ll still feel profoundly alone. People won’t be connecting with you. They’ll be connecting with the mannequin that you’ve chosen to present. (Twist. The. Knife.)

But we all know this isn’t sustainable. One day, there will be an imperfection, mistake, or failure that’s too big to cover up and too profound to ignore, which means the people who trusted, admired, and looked up to you will see it. And they’ll be outraged. Why? Because you chose to perpetuate the lie that you’re perfect, and you just broke your promise. They counted on you, and you let them down.

Wow. That’s a pretty gloomy outlook. Sadly, it’s a reality that’s playing out in the lives of thousands wrapped up in the illusion of perfection. 

But here’s a brighter version of that scenario: You begin setting the tone for the future by being really honest in the present. You let people in on the gritty, flawed, and imperfect nature of yourself. You use phrases like, “I let you down,” “I screwed up,” or “I got this wrong.” Don’t be weird about it. Just be real.

You begin setting the tone for the future by being really honest in the present. You let people in on the gritty, flawed, and imperfect nature of yourself.

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These admissions of imperfection will do wonders for your team, your friends, and your family. They will do even more for you. Every time you share your imperfection, which is your humanity, you unclog important pathways that lead to conversation, connection, and trust. Equally important, you reset expectations to align with reality.

Over time, this trust track will create the opportunity for you to not simply share what you’re doing but what you’re feeling. For the first time ever, you can courageously share things like, “I’m afraid of this,” “I feel guilty about that,” “I’m ashamed about this,” or even “I’m so glad about that.

For some of you, it will be the first time in a long time that you’ll have people on the receiving end of those trust-laden statements who actually get it. Not only that, but they’ll even feel it. And in those moments, loneliness will seem like a mere afterthought—because you’ve already done the necessary work it takes to be the type of leader that people follow and connect with.

The most beautiful part of all this is that, just as before, you’ll end up being looked up to, revered, respected, and admired. Only this time, it will be sustainable—because this time, it will actually be you.

Action: Identify an imperfection that you’ve relented sharing because you’re afraid. Then, have the courage to share it with someone you trust.

Alex Judd

Alex Judd

Alex Judd is the CEO of Path for Growth where he helps business leaders chart the route towards healthy growth for themselves and their companies.

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