The Loneliest Part of Leadership

Several years ago, someone asked me a question that has stayed with me ever since: “What has surprised you the most about being a leader?”

I didn’t answer with strategy. I didn’t answer with finance. I didn’t answer with operations or commercial real estate.

I answered with one word: Loneliness.

After more than 45+ years in business, leadership isn’t lonely because you’re surrounded by fewer people. If anything, the higher you move in an organization, the more meetings you attend, the more conversations you have, and the more people who want your attention.

Leadership becomes lonely because responsibility compounds. Every promotion gives you more authority, but it also gives you something much heavier to carry.

As the constituency of your leadership grows, so does the weight of the decisions only you can make. One of my brothers called it L.A.T.T. – it’s lonely at the top!

There are fewer people you feel you can ask, fewer people who fully understand your constraints, fewer people who see the entire picture.

At some point, every leader realizes there are decisions no one else can make for them.

That is the loneliest part of leadership.

You Don’t Get Paid for Certainty

One misconception I see repeatedly is that leaders are expected to have all the answers, but I don’t believe that’s true. Leaders aren’t paid because they’re always right; they’re paid because they’re willing to make decisions before certainty exists.

In fact, I once asked General Colin Powell to define leadership for me, and he simply told me that, “Leadership is about generating enough curiosity in others such that they willingly want to follow you.” When you have followers, you are a leader. A human being with the responsibility of those who choose to follow your words, your direction, and your decisions.

Everyone wants perfect information, but leadership rarely affords that luxury. The best leaders I’ve known weren’t the smartest people in every room; they were the people most willing to make difficult decisions without perfect information.

Everyone wants certainty and leadership doesn’t usually provide it.

• Markets shift
• Interest rates move
• Customers and clients change
• Competitors evolve
• Technology/AI rewrites industries

You rarely get all the information you wish you had. Sometimes you have 70% of the information. Sometimes 40%. Sometimes nothing at all. Eventually, analysis gives way to judgment.

I’ve often said that experience is accumulated judgment. You don’t develop judgment by reading about difficult decisions; you develop it by making those decisions. Bad experiences are due to bad judgment; learning from those experiences helps you develop better judgment, which drives better experiences for all.

Sometimes you make the right decision, and sometimes you don’t. But every difficult decision leaves you a little wiser than before. And very few decisions need to be permanent. With more time, experience, and input, we can make new decisions that reverse the downward slide of a prior decision that proved to be flawed.

Leadership Changes the Questions You Ask

Early in your career, most decisions are tactical. You ask questions like:

• “How do I complete this assignment?”
• “How do I impress my manager?”
• “How do I earn the next promotion?”

Almost every decision can be discussed with someone: your manager, your teammates, or your mentor. But somewhere along the journey, your questions and confidants begin to change.

Instead of asking how to accomplish something, you begin asking whether it should be done at all.

Instead of worrying about your own success, you begin worrying about the success of hundreds of other people.

Instead of asking what helps one department, you ask what strengthens the entire organization.

The scope changes, the consequences change, and the burden changes.

When you’re responsible for people, decisions stop being theoretical and become personal.

• Every hiring decision affects a family.
• Every restructuring affects someone’s future.
• Every acquisition changes lives.
• Every strategic pivot creates opportunity for some people and uncertainty for others.

That’s not something leadership books talk about enough. The spreadsheet doesn’t show the human cost. Leaders see both.

The Higher You Climb, the Smaller the Circle

As your responsibilities increase, your circle naturally gets smaller. Not because people disappear but because fewer people carry the same responsibility.

When you’re managing a team of five, almost everyone around you understands your challenges.

When you’re responsible for hundreds of employees, millions of dollars of capital, or the future of a business, conversations change. You’re trying to make everyone happy while still running a company:

• Employees see their department.
• Investors see returns.
• Clients see service.
• Partners see opportunities.
• Board members see governance.

But only a handful of people see the entire picture simultaneously and that’s why leadership can feel so isolating and lonely. You realize that every decision creates winners and losers.

That’s one reason I have always valued mentors, peer groups, and trusted advisors. Not because they make decisions for you but because they understand what it’s like to carry decisions that affect other people.

Leadership Isn’t About Being Right

Great leaders aren’t distinguished by perfection; they’re distinguished by ownership.

Anyone can celebrate good outcomes but good leaders know how to own the bad ones.

When things go well, the team deserves the credit. When things go poorly, the leader accepts responsibility.

We live in a culture that encourages explanation before accountability, but leaders aren’t afforded that luxury.

If you spend your time protecting your image or reputation, you stop protecting the organization.

The best leaders I’ve worked with possess an uncommon willingness to say four simple words.

“That was my mistake.”

Those words don’t diminish credibility; they build it.

Leadership Isn’t About Being Liked

One of the loneliest moments in leadership is realizing that doing the right thing and being popular are often two different things.

Every leader eventually has to make decisions that disappoint people. That can be declining an opportunity, changing strategy, restructuring a team, or letting go of someone you’ve worked with for years.

Those aren’t enjoyable conversations. But leadership was never supposed to optimize for comfort. It was supposed to optimize for stewardship.

Leadership requires distinguishing between what is comfortable and what is necessary. Sometimes, the best decision in the long run is the hardest one in the moment.

Loneliness Creates Clarity

I’ve also learned that solitude and loneliness aren’t always something to avoid.

Some of the best decisions I’ve made happened after I stepped away from the noise.

Leadership today is full of distractions: emails, meetings, phones, opinions. If you’re not careful, you’ll spend your entire day responding instead of reflecting.

One habit I’ve tried to develop over the years is creating space to think: not to react; just to think. Leadership requires reflection because reaction is rarely strategic.

Creating space to think has prevented far more mistakes in my career than moving quickly ever has.

Build a Circle That Challenges You

The answer to leadership loneliness isn’t surrounding yourself with people who agree with you. It’s finding people who will challenge you.

I’ve always believed that if everyone around you agrees with every decision you make, one of two things is happening: Either you’re hiring the wrong people or you’re listening to the wrong people.

Every leader develops blind spots and benefits from honest feedback. It’s why the best leaders start by creating psychological safety in their organizations. Your inner circle should consist of people who care more about telling you the truth than telling you what you want to hear.

The strongest leaders I know intentionally seek disagreement. Disagreement isn’t disrespect and constructive disagreement sharpens judgment.

If everyone around you agrees with every decision you make, you’re probably missing something.

Strong leaders don’t surround themselves with loyal followers. They surround themselves with independent thinkers.

Leadership Is a Privilege

The loneliness of leadership isn’t something to complain about. We often describe it as if it’s a burden to endure. But it actually means people trust you.

People don’t ask you to carry responsibility because your title says CEO, president, managing partner, or founder. They ask because they believe you’ll make decisions that serve something larger than yourself.

They trust your judgment, they trust your character, and they trust that you’ll make difficult decisions when easier ones are available.

That’s an incredible responsibility and it’s also an incredible privilege. So yes, leadership can be lonely, but it isn’t a burden. It’s simply part of the responsibility you’ve accepted.

Would I rather every decision be easy? Of course. Would I rather every choice come with complete information? Absolutely.

But if leadership only existed when certainty did, we wouldn’t need leaders; we’d need administrators. Leadership exists precisely because uncertainty exists.

The goal isn’t to avoid the loneliness. The goal is to become the kind of leader worthy of carrying it.

How to Handle Leadership at the Top

Even after 45+ years in business, I still have moments where I question whether I’m making the right decision.

Call it imposter syndrome, pressure, or loneliness at the top. Whatever you call it, we’ve ALL felt it before and just don’t talk about it much as leaders.

After a certain point, there are very few people you can be completely candid with. And because of that, the hard truths often go unsaid.

But it’s also where poor decisions can start to happen: in isolation, under pressure, without an honest perspective or a place to think out loud.

That’s why having someone in the room who can challenge your thinking objectively matters more than most leaders realize. Find yourself an advisor, a mentor, or someone who can help you feel “unstuck” during difficult moments and decisions.

Final Thoughts on Leadership and Loneliness

As I’ve reflected on my own career, I’ve realized that the loneliest moments weren’t the hardest meetings or the biggest transactions.

They were the quiet moments before the decision. The moments when everyone else had shared their opinion, the data had been reviewed, the advisors had spoken, the arguments had been made, and then the room became silent.

Everyone looked to the leader.

Not because the leader knew everything but because someone had to decide.

That’s the moment few people see and it’s also the moment that defines leadership.

So yes, leadership can be lonely.

But perhaps that’s because real leadership has never been about status, authority, or recognition. It’s about accepting responsibility when responsibility has nowhere else to go.

If you’re fortunate enough to lead, don’t resent those moments; honor and respect them.

They remind you that leadership was never meant to make your life easier.

It was meant to make other people’s lives better.

And if that occasionally feels lonely, perhaps that’s simply the cost—and the privilege—of carrying the responsibility well.