Why Leadership at the Top Is the Loneliest Job in Business

14 Aug 2026 · 17 min · 5 chapters

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In short

Executive isolation—why CEOs/founders feel lonely despite busy schedules, and how to address it to prevent burnout and poor decisions.

Guest backgrounds

No guests. Host Jeannette (Jeannette Linfoot) speaks from 30+ years running large global businesses and one-to-one work with senior leaders.

Key claims

Isolation happens as peer groups shrink and leaders must protect teams while carrying stakeholder pressure. Ego can stop vulnerability; “showing vulnerability and asking for help” is strength. Leaders must make final decisions (including redundancies/restructuring), and emotional support boundaries can’t be fully blurred. Unaddressed isolation can cause burnout, impaired judgment, relationship strain, and business performance decline.

Notable examples

Her international travel (70%); burnout leading to hospital and surgery; “ships that pass in the night” with her husband. Mentorship/coaching provides a confidential, judgment-free support system.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Understanding Executive Isolation

0:45 to 2:52

Discussion on the loneliness experienced by leaders and the importance of addressing it.

“So I don't know, I mean, does that sound like familiar to you?”

Reasons for Isolation in Leadership

2:52 to 8:38

Exploring the factors that contribute to isolation at the top levels of an organization.

“So that can often mean that, you know, you end up in this period of kind of silence, really.”

Consequences of Unaddressed Isolation

8:45 to 13:14

Discussing the dangers of ignoring feelings of isolation and the impact on health and relationships.

“So, you know, I just think it's a difficult place to be, but we need to talk about it.”

The Importance of Mentorship

13:14 to 14:03

Highlighting the role of mentorship in overcoming isolation and improving leadership.

“I would love to be able to help you on your career journey, on your business journey.”

The Reality of Leadership Loneliness

14:03 to 15:20

Learn about the common feelings of isolation among leaders and the importance of support systems.

“In fact, it's just part of the responsibility.”
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Transcript

Automatic transcript. May contain errors.

0:09Welcome back to Brave Bob Berlin. I'm Jeannette and you know today what I want to talk about is something that most leaders feel but very few people say out loud. you know because from the outside being the CEO the founder the boss the person at the top of the org chart you know it can often look like the dream can't it you know and for yourself you may have spent years and years and years getting to that top position but actually when you get there you realize it can be the loneliest place in the world you know but all that's going around you at that time can make people often feel in those big jobs and those big positions that they can't speak honestly and can't actually show the vulnerability that is so important you know and I can tell you from 30 plus years of running large global businesses and now working closely with leaders one-to-one that what it actually feels like more often than not is just really lonely you know and you can be surrounded by I don't know a team of hundreds thousands and you know but actually you may sit on board meetings every week have a packed calendar and still feel like there is genuinely no one you can turn to who truly understands the weight that you're carrying.

1:22So I don't know, I mean, does that sound like familiar to you? Because certainly I can honestly say that I have been in that position many, many times throughout my career and it can just feel so isolating at the top and it's dangerous. It's dangerous if it's left unaddressed. So, you know, let's actually talk real. Let's talk about it and let's get into it because, you know it's so important that here at Brave Bold Brilliant we are building a community and a community has each other's backs. A community talks about the real challenges as well as the opportunities. So you know I'm going to take you through eight key points that really have sort of resonated with me throughout my career.

2:07So the first one is you know why does isolation happen in the first place. Well, you know, the reality is that the higher you go in an organisation, the fewer peers you naturally have, you know, around you, inside your own kind of world or organisation you're in. You know, the pyramid often looks like this. So, you know, that means just by very nature, your peer group can become smaller as you, you know, build your career up the ladder. And, you know, you can't always be fully honest with your team, your board, or even your family about what's really going on. Now I'm not saying you're dishonest in these roles, you're not dishonest, but sometimes you feel like you have to maybe protect the team.

2:49Very often I found in my time in very you know senior leadership positions whether it's a CEO or an MD or as a business founder and entrepreneur myself today you know that sometimes you're the sandwich between you know sort of the pressure that's maybe going on from the stakeholders, the shareholders and the board at a macro level versus, you know, actually protecting the team so that they can get on and focus on what they need to do. So that can often mean that, you know, you end up in this period of kind of silence, really. And I think, you know, from my perspective, when I look back through my career, I would definitely say the ego played a part, you know, because I was incredibly ambitious.

3:30I'm still incredibly ambitious today. But when I was building my career, you know, I came from a very very humble beginnings you know very working class family a family full of love don't get me wrong but in my head I you know I wanted to achieve more I wanted to be more so as a result of that you know almost sharing vulnerability and saying I'm struggling a little bit right now or I don't have all the answers back then I almost saw that as a sign of weakness and and not being a strong leader. So I kept quiet and I took that burden internally to myself. So I think that can often happen. But as we progress in leadership, what you begin to see actually is that showing vulnerability, asking for help is really a sign of strength.

4:19It's not a weakness at all. So that leads me on to the second point, actually, that the pressure of being the strong one you know because everyone looks to the leader for certainty don't they even when you might not feel certain yourself you know the business might be looking for you for the answers you know the performance of confidence even in private moments of doubt so why admitting struggle can feel like weakness even though it isn't so this is so important and you know the third point is the decisions no one else can make for you. And there are ways, of course there are, you want to create an environment where you're taking on board the input from your team, from the rest of the board, from your senior leadership team.

5:04But when push comes to shove, ultimately the book stops with you. And that can often be about making those really unpopular choices and unpopular decisions that can mean the difference between is the business going to survive or is the business going to fail? And that can often mean, you know, having to exit people or say farewell, you know, maybe a redundancy program, a restructuring program. And these are decisions that affect people's livelihoods and lives. And unfortunately, I've had to do that many, many times through my career. I've had to say farewell. I've had to restructure organizations.

5:39I've had to take cost out, you know, because of the external environment sometimes you know and that weight is different from any other role in the business and whilst you may come across like you're very confident and comfortable making those choices it doesn't mean to say that we don't feel it we're all human beings at the end of the day you know so I just really think it's important to talk about this you know and the reality is you know that your team yes they can support you but they can't be your support system really not truly when you're when you're in some situations. There's naturally a boundary, isn't there, between the leader and the rest of the team.

6:21And that doesn't mean to say that you don't enjoy being in each other's company, you don't respect each other, but there is a line. There is a line between. And the risk of blurring those lines when leaders lean too heavily onto their teams for emotional support, well, that can be dangerous as well. So that's another reason why you can feel quite isolated and quite lonely at the top of an organisation. And it's not actually, you know, it's not about distance. It's actually about role clarity. But before we continue, I want to speak directly to those of you who are listening and thinking, I know I'm capable of more, but I need structure.

7:04I need some help. Because here's what I've actually learned after, gosh, more than three decades in business. You know, ambition without clarity creates frustration and motivation without structure. It really does fade very, very fast. So that's exactly why we created Rise Academy. You know, and Rise Academy is not theory. It isn't fluffy motivation, although you will be motivated. And it certainly isn't another online course that you never finish. It's actually a fully structured growth environment for ambitious entrepreneurs, leaders and founders who absolutely are ready to do all of these things.

7:49Sharpen their strategy, elevate their leadership, increase revenue with intention and build businesses that actually support the life that they want. And inside Rise Academy, we focus on the foundations most people skip. Leading yourself, leading your teams and leading the business. It's about clarity, standards, decision making, commercial intelligence and execution. Because scaling, it really isn't about doing more. It's actually about doing the right things and doing the things right consistently. So if you're serious about stepping up into your next level of your leadership, your business life, and not just consuming content, but actually implementing it, then Rise Academy was absolutely built for you.

8:38So you can find all the details on our website, go to www.brave-bold-brilliant.com. And now, let's get back to the show. So, you know, I just think it's a difficult place to be, but we need to talk about it. So, you know if you don't address the isolation if you don't address the fact that you may actually be struggling a little bit in that big number one job you know what are the dangers of that is your body will tell you let me let me and I've had a see I've had burnout I have had burnout where I've ended up in hospital I've ended up having surgery and all sorts of things so burnout is a very real thing but if you're an ambitious leader which you know I'm sure you are I know I am myself sometimes we think we're invincible and but when you're in particular in the top job and you're not addressing that isolation it can really lead to burnout poor decision making you know your judgment being a bit impaired and that isolation can compound over time until it affects your health it might affect your relationships and the business performance you know those leaders that wait too long to get support you know it can actually cost them more than just the job and the results you You know, so I've certainly been there where, in particular, I mean, I used to be traveling internationally 70 % of the time.

10:00You know, I'd be coming in, you know, in from Heathrow. My husband would be going out for a business trip and we were like ships that passed in the night. And there were plenty of times where, you know, our relationship, you know, is a danger of us going east and west. So it can also affect your relationships. And it takes a strong person to recognize what's going on and to stop. But what genuinely helps really and what doesn't help is you don't want just generic networking to kind of scratch the itch. It's really about having a safe place, a trusted network of individuals that allows you to have confidential, judgment-free space to think out loud.

10:45Peer relationships with others who understand the specific pressures of the top job. And this is exactly where having a business mentor or a coach comes in. This is why when I work one-to-one with a business leader, it could be an executive, it could be a senior leader in an organization, it could be an entrepreneur. What we create is that absolute safe space to be able to talk about everything that's going on. Because at the end of the day, when you're leading a business at the top, actually, you know, the lines do get blurred between business, personal life, relationships, health, etc. So when you're actually going into a mentoring relationship, it's critical that you have the trust.

11:29It's critical you get the right person that you gel with and you can rub along with. because the chances are you might be starting talking about something that's a business related topic but actually often leads into other things that are going on in your life so you know if this is actually landing with you you know all i would say is make sure that we're connected let's get connected on social media you're going to find me janet uh linfoot with two n's and two t's in janet all over linkedin instagram facebook you name it and of course with the podcast you know on which is on Apple Podcasts, is on Spotify and of course if you like watching videos then our YouTube channel you know hit the subscribe button because we're here to really share the realities of leadership that often don't get talked about honestly.

12:18So the power of one-to-one mentorship is so so critical. I can honestly say that through every single stage of my career when I've had a pivotal change I've actually reached out and I've had a professional mentor I've had coaches at different times as well and the two are slightly different but a mentor is someone that has been there they have a lived experience they're able to advise you into in certain situations and you know whether I got my first director position when I decided to leave corporate and go down the portfolio route when I was setting up our own property investment business you know I had a mentor all those different stages because what you need changes over time so if you haven't got a mentor it you're missing out honestly it is the one game-changing thing that you can take control of and you know it's about having someone that's walked the path you know not just sort of studied it from a theoretical point of view and that clarity comes from an outside experience perspective with you know unlimited access between sessions is what I do when I work with people I don't just we have a monthly session so we have the accountability and the focus but I make myself fully available 24 7 because when those big moments show up you know you actually need to make sure you've got someone that's going to be available to support you so if you're interested if you feel that you need a mentor and I can tell you now it's the best thing you'll ever do, reach out, let's have a conversation.

13:51I would love to be able to help you on your career journey, on your business journey. So, you know, reframing isolation as a leadership stage, not a personal failing is important. You know, almost every single leader goes through this. You know, you are not uniquely broken. You're not broken at all. In fact, it's just part of the responsibility. But naming it removes, it removes that kind of, you know, power really that it's had over you. And it's the leaders who thrive are the ones that build support systems deliberately and not just by accident. So, you know, be intentional with what you do.

14:28Leadership at the top can be the most lonely place. I know, I've been there. You know, and if any part of this has struck a nerve with you, you know, if you're leading at a level where you feel like there's actually no one you can be fully honest with, please, you know, please know that's incredibly common but it doesn't have to stay that way that's exactly the space that we create in our one-to-one mentoring work so reach out to us drop me a message send an email so we can actually jump on a call and really understand what you're looking to achieve and then what I'm able to do then is tailor a absolutely bespoke mentoring program and relationship just for you and that is going to absolutely transform your journey 100 % I have no doubt at all and so you know as I say if you want to take away one point let it be this feeling isolated at the top it doesn't mean you're doing it wrong it means you're carrying real weight and it's the leaders who last are the ones that actually have the right support rather than trying to carry it all alone and if this episode resonated with you you know please do subscribe leave a review share it with you know someone in your network who's a fellow leader that might need to hear exactly this right now because they are not alone.

15:42You are not alone. And remember, it is by being brave and bold that you are going to unlock your brilliance. So I will see you next time. I really hope you've enjoyed this episode of Brave Bold Brilliant. Remember, check out our new website, www.brave-bold-brilliant.com. You're going to find loads of resources on there that's going to help you with your leadership journey and with the businesses that you're trying to scale up and grow. So take care, everyone and remember there are no limits to your growth but it is by being brave and bold that you're going to unlock your brilliance.

From the publisher

Jeannette addresses a topic few leaders speak about openly: the intense isolation and weight of carrying top-level responsibility. Drawing from over 30 years of experience running global businesses, she breaks down why executive loneliness happens, the dangerous path to physical burnout when vulnerability is suppressed, and why relying solely on internal teams for support can blur crucial boundaries. Janette offers actionable wisdom on reframing isolation as a common leadership phase rather than a personal failing, illustrating how intentional, one-to-one mentorship provides the confidential space required to navigate high-stakes decisions effectively

You'll Learn Why:

Executive isolation naturally increases as your peer group shrinks, often trapping leaders in silence due to ego or the urge to protect their teams.

Suppressing vulnerability to project constant strength can lead to severe physical burnout, impaired judgment, and strained personal relationships.

Relying too heavily on your internal team for emotional support blurs crucial organizational boundaries and dilutes role clarity.

Partnering with a dedicated one-to-one mentor provides the confidential, experienced environment needed to process tough choices and sustain long-term success.

Whether you're a founder, CEO, small business owner, entrepreneur, startup leader or executive, these lessons will help you make smarter hiring decisions and build a stronger, more successful business.

🚀 Want to accelerate your business growth?

Join Rise Academy today and gain access to expert business coaching, leadership training, proven growth frameworks, live coaching sessions, and practical strategies designed to help you build a thriving business.

About Jeannette Linfoot

ABOUT THE HOST

Jeannette Linfoot is a highly regarded senior executive, property investor, board advisor, and business mentor with over 30 years of global professional business experience across the travel, leisure, hospitality, and property sectors. Having bought, ran, and sold businesses all over the world, Jeannette now has a portfolio of her own businesses and also advises and mentors other business leaders to drive forward their strategies as well as their own personal development. 

Jeannette is a down-to-earth leader, a passionate champion for diversity & inclusion, and a huge advocate of nurturing talent so every person can unleash their full potential and live their dreams.

Podcast Description

Jeannette Linfoot talks to incredible people about their experiences in business and life, gaining first hand insight into how they unleashed their potential to become Brave Bold Brilliant.

From the boardroom tables of big international businesses to the exciting world of entrepreneurs it's all about stepping up to the next level while staying true to yourself.

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