The loneliness no one warns you about before the corner office starts the day every problem stops at your desk. Joshua Gould, CEO of thebigword, leads more than 400 employees and 15,000 contractors. He puts it plainly: “Everything is on you. And at the end of the day, there’s nowhere to escalate.” I’m Glenn Gow, The Scaling Executive Coach, and I watch CEOs hit this wall in their first year in the seat.
Quick Answer
Leadership loneliness is built into the CEO role. The CEO answers to a board that evaluates them and leads a team that depends on them, so neither group is a safe place for doubt. Glenn Gow, The Scaling Executive Coach, advises CEOs to confide in two outside sources: an executive coach and a peer group of non-competing CEOs. Neither has the power to fire the CEO or a stake in the company’s results. CEOs who build both before a crisis bring a second perspective to every hard decision.
Why the CEO seat is lonely by design
The loneliness at the top begins the moment you lose your boss. Joshua spent 20 years in the C-suite before he took the top job, and he describes the change this way: “Whatever CXO you are, you do have a boss. You never have to be alone… And then one day you become the CEO and there is no one to call in the middle of the night. There is no one to complain to. There’s no one to share blame with.”
Steve Harmon, CEO of Spartan Logistics, runs a business with more than 400 employees and over 6 million square feet of industrial space. He ranks stress as the top threat to any leader, and he names isolation as part of it: “The lack of sleep, the stress, the cortisol levels, the loneliness at the top. Nobody wants to talk [about it], but you can’t complain to anybody but your dog about your million-dollar problems because nobody wants to hear it.”
Brian Rich, Board Member of FieldPulse, sees the same trap from the investor side of the table: “The CEO role is extraordinarily lonely… They’re a little bit reticent to talk to the board because after all the board is judging them as well as others… And they’re certainly reluctant to speak candidly with their C-suite team.”
Leadership loneliness is an epidemic at the top that almost nobody names, and very few CEOs say it out loud before we start working together. CEOs feel it anyway. The ones who admit how lonely it is to be a leader are the ones who fix it first. Nobody warns you because the people who could warn you are the people you lose as confidants the day you take the job: your board, your investors, and your own executives.
Why your board and your team make risky confidants
Your executive team depends on you and your board evaluates you, so neither is a safe place to take your doubts. Colby Durnin, CEO of CREDE, learned this through his own missteps: “Earlier in my career I made mistakes where I would overshare with VPs or folks in the office or my EA because you know, you get to know and trust folks and you think, well I can also share everything with them. That’s not necessarily the case.”
Joshua breaks the pattern on purpose with his private equity partners at Susquehanna: “I drive my investors mad because most CEOs will only give a very polished view of the world to their investors. But I actually treat my investors… Part shrink, part coach.”
Joshua also admits most investors struggle when a CEO shares unfiltered operational fears with them: “Most investors can’t cope with it. Just tell me how good it’s going to be cause they’re nervous, right? They write these checks for hundreds of millions of dollars to you.”
Colby speaks from the board seat when he asks CEOs to raise problems early, before board members turn them into year-end performance criticism: “If there’s something that’s bothering you for more than a day or two, call one of us as a board member. You know, use it as an unofficial sounding board to go, ‘What am I thinking? Where am I going?’… Rather than just turning around and hammering them at year end.”
I tell CEOs to use board candor wherever the relationship supports it. I also tell them to keep at least one confidant who has no vote on their future. Here is how I map the options with the CEOs I coach:
| Who you confide in | Power over you | Stake in the outcome | What it produces for you |
| Board and investors | Hires and fires the CEO | Equity and fiduciary duty | Strategic input, filtered by your need to look in control |
| Your executive team | Reports to you | Jobs, pay, and equity | Execution help, plus boundary problems when you overshare |
| Your spouse | None at work | Your family’s financial security | Emotional balance on decisions you run with your head |
| Executive coach | None | None | Unfiltered thinking on problems you cannot take up or down |
| Peer group of non-competing CEOs | None | None | Situational advice from CEOs facing the same calls right now |
The confidant with no power over you
An executive coach is the first confidant I recommend, because a coach holds no equity and no firing authority. Brian R. Smith, CEO of S3 Ventures, oversees $1.2 billion in assets and says the same from the investor chair. He describes what a CEO under board scrutiny lacks: “What that leader really needs is someone else to talk to that isn’t going to have the right to fire them.”
Brian R. Smith also explains why independence matters for the CEOs in his portfolio: “A valued consultant [or] coach… Can come alongside them who can be independent from the board member, from the actual investor, that there can be some more comfort there in conversation and some more confidentiality.”
Will Jones, CEO of Thompson CFF, manages an operating budget above $40 million and serves more than 10,000 clients. His first question to any leader is direct: “My first question would be is do you have a coach? Or even better, who’s your coach?… If you’re an executive leader, an owner, an entrepreneur, if your answer to that’s no, you’re already behind the 8-ball. You need to have a coach… You need to have somebody that you can go to with problems that you can’t go down to your team with.”
Damon Lembi, CEO of Learnit, has helped upskill more than 2 million people. He describes the gaps a CEO keeps even from family: “A lot of times it’s lonely to be a CEO and you don’t have anybody to turn to. Maybe there’s things you don’t want to talk to your wife about or maybe there’s things that you can’t share with your team. So you need somebody to help cover your blind spots.”
Sam Hodges, CEO of Vouch, helped take Funding Circle to a $1.5 billion IPO. His filter for a confidant matches the one I use with clients: “Go to people who have no direct connectivity to what you’re doing, but frankly just a vested interest in seeing you be successful.”
Will adds a confidant most advice skips. “One of my biggest coaches is my spouse… I lean on my spouse to give me discernment. My wife knows me better than anybody knows me in this world.” He calls himself more head than heart and relies on his wife to balance his decisions. I support that choice. I also pair it with a confidant outside the family, because a spouse shares the financial stake in every risk you take.
Why peer groups of non-competing CEOs work
A peer group gives you CEOs who are making the same hard decisions this quarter. John Volturo, CEO of Evolution, sees the pattern across the leaders he works with: “Most of the time what I find is really successful for CEOs is to belong to something. And that thing is typically some sort of a group of like-minded people, whether it’s a mastermind, whether it’s another group where they can just really run things by others without the fear of judgment.”
Karl Hughes, CEO of Draft.dev, bootstrapped his company with no venture partners and felt the missing network: “In the first year or two, I didn’t have much of a peer network… I found myself in this feeling very isolated. I had to make all these big decisions on my own… You can read books, but books are broad knowledge, not situationally specific.”
Brian R. Smith’s firm builds peer relationships on purpose. S3 Ventures brings the CEOs from its 80-plus portfolio companies together for a two-day summit every year: “We want them to meet each other. We want them to find a someone who could be a friend, a confidant, whatever… So that so-and-so can talk to the second person and figure some things out and encourage one another along their journey. Cause it’s a long and tough journey.”
Bryan Murphy, CEO of Smartling, joins outside boards to get the same peer access: “The reason I sit on a couple of other boards is because I learn from the other CEOs… Being a CEO is kind of a lonely place, you know what I mean?”
Will pushes back on the standard formats. He says networks like Vistage “generally don’t work for me,” so he built an informal group of non-competing CEOs that fits his schedule and priorities. I give CEOs the same freedom on format. Pick a forum, a mastermind, an outside board seat, or a group you assemble yourself. Hold one rule firm: no competitors in the room.
What white-knuckling does to your body
Isolation shows up in your body before it shows up in your results. Joshua ran $100 million in revenue across 80 countries in his early tenure with no established board behind him, while facing lawsuits, client departures, and payroll pressure: “It was very, very lonely when those lawsuits hit, when the clients want to leave, when a new technology threatens the business, when you’re struggling to make payroll… I remember feeling like someone had punched me in the stomach in the first five minutes because… all the worst problems from everyone’s day would rise all the way up to the top.”
Steve found his outlet on a treadmill after he took the top job: “When I ascended to the CEO role… I started jogging. I hate running, but I got on the treadmill and I started moving because I thought more clearly on the treadmill than sitting on my couch.” He pairs exercise with prayer and calls the two the key assets he would recommend to anybody.
Asad Zaman, CEO of Sales Talent Agency, has facilitated more than $550 million in salaries. He became a CEO at about 32 and describes how the load changes with age: “I just had more energy then. And I have a little less energy today. My nervous system gets tired a little bit faster… It’s also important to not just try to white-knuckle yourself through life and to recognize that we get older every year and we change and we evolve.”
John built a framework around having nothing to prove after surviving a brain tumor. He describes the drain of constant performance at the top: “We’re trying to prove that we can get the job done, that we know what we’re doing. And what that leaves is this idea that we’re seeking external validation and that external validation is draining because we end up performing all the time.”
SC Moatti, Managing Partner at Mighty Capital, has watched CEOs hit the wall of isolation again and again. She uses long trips and outside coaches to step back: “When I’m on these long trips, I get to reflect on things and… I can be on the business as opposed to in the business… And then I have also coaches… Who help me see things that I could see if I was not in the system all the time.”
How to build your confidant system in 30 days
Every new CEO I coach gets 30 days to hire an executive coach and join a peer group of non-competing CEOs. In the first two weeks, hire an executive coach who holds no equity in your company and reports to no one on your board. Ask one question in the first session: which problem on your desk have you told nobody about? That problem becomes the agenda.
In weeks three and four, join or build a peer group of non-competing CEOs. I tell clients to aim for CEOs one stage ahead of them, because those peers solved last year the problem you face this year. Screen out anyone who sells to your customers or recruits your people.
From day 31 forward, run every major decision past one of those two sources before you act. I watch CEOs who follow this rhythm make faster calls with fewer reversals, and they stop waking up with the dread Joshua described.
Frequently Asked Questions
Is it true that leadership can be lonely?
Yes. Glenn Gow, The Scaling Executive Coach, sees leadership loneliness in nearly every CEO he coaches, and the podcast guests confirm it. SC Moatti, Managing Partner at Mighty Capital, says CEOs hit the wall of isolation periodically and calls it “part of the journey” of running a company. The loneliness comes from the structure of the role, so it hits confident, well-supported CEOs too.
Why is it lonely at the top for CEOs?
The CEO has no boss to escalate to, a board that evaluates them, and a team that depends on them. Glenn Gow points to that three-way squeeze as the cause. Colby Durnin, CEO of CREDE, says early-stage CEOs often see the board as “the group that’s there to hammer me.”
What is a famous quote about leadership and loneliness?
One of the most direct comes from Karl Hughes, CEO of Draft.dev, on Glenn Gow’s podcast, describing his first two years of bootstrapping with no peer network: “I was shocked by how lost I felt being like, wait, what do I do next?”
What does “sometimes the person who tries to keep everyone happy is the most lonely person” mean?
It describes the leader who performs strength for everyone and shares doubt with no one. Damon Lembi, CEO of Learnit, describes his early version of this: “You figure that you had to be the smartest person in the room, you had to get everything done yourself, be the hero.” Glenn Gow coaches CEOs to drop the hero role and surround themselves with people who will tell them the truth.
Who should a CEO talk to when they feel isolated?
Glenn Gow recommends two confidants: an executive coach and a peer group of non-competing CEOs. Both have no power to fire the CEO and no stake in the company’s results. Asad Zaman, CEO of Sales Talent Agency, relies on trusted CEO peers such as AJ Bruno of QuotaPath.
How do CEOs cope with loneliness at the top?
The CEOs who cope best build outlets outside the company before a crisis hits. Sam Hodges, CEO of Vouch, found that outlet in his cohort at the Aspen Institute Finance Leaders Program, a group with no connection to his business. Damon Lembi, CEO of Learnit, describes the turning point from his own career: “Once you learn that when you surround yourself with great people… That’s when you can really scale.” Glenn Gow tells CEOs to schedule these outlets like board meetings, so they happen in good quarters and bad ones.
Should a CEO confide in their board?
Selectively. SC Moatti, Managing Partner at Mighty Capital, advises CEOs to put the board to work on specific strategic tasks, which gives board conversations a purpose beyond performance reviews. Glenn Gow supports candor with the board where trust exists, and he still tells CEOs to keep one confidant who has no vote on their future.
Should a CEO share personal struggles with their executive team?
No. Glenn Gow tells CEOs to take emotional venting outside the company and to ask their teams for honest feedback. Sam Hodges, CEO of Vouch, urges leaders to “figure out a way to get unvarnished upward feedback from within your organization,” and he admits that gets harder as the company grows.
Does a CEO need an executive coach?
Yes, and investors say so too. Glenn Gow sees coaching as the fastest fix for CEO isolation because a coach holds no equity and no firing authority. Brian Rich, Board Member of FieldPulse, says CEOs “don’t have a lot of people to talk to, which is why coaches are so important.”
Are CEO peer groups like YPO or Vistage worth it?
They work when the format fits you. Colby Durnin, CEO of CREDE, applies YPO forum principles when he advises CEOs to treat board members as sounding boards. Karl Hughes of Draft.dev says classic books like Good to Great gave him no guidance for surviving the bootstrapped early stage. Glenn Gow advises choosing the format that fits your schedule and keeping competitors out.
How does CEO loneliness affect health and decision-making?
It raises stress, costs sleep, and pushes CEOs to decide alone. Steve Harmon of Spartan Logistics warns about “a leader who’s not hyper attuned to the fact that they are under stress.” Glenn Gow sees isolated CEOs make slower, more defensive calls.
How can a new CEO prepare for the loneliness of the role?
Build your confidants before you need them. Bryan Murphy, CEO of Smartling, sits on outside boards and says, “I always learn something from the other CEOs that I work with as a board member.” Glenn Gow gives new CEOs a 30-day plan: hire a coach, join a peer group, and run every major decision past one of them.
What You Do Next
Pick one decision on your desk that you have not said out loud to anyone. Bring that decision to an outside voice this month. Glenn Gow works with CEOs on exactly the problems they cannot take to their board or their team, and he has no stake in your company and no vote on your future. If you want a second perspective before you make that call, book a conversation with Glenn and bring the decision with you.
