What if one of the greatest challenges in leadership isn’t decision-making or pressure but loneliness?  

In this Unfiltered Series conversation, leadership experts Amy Riley and Daphna Horowitz get real about the isolation that often hides behind confidence and success. Even the most connected leaders can feel unseen when everyone’s looking to them for answers. 

Amy and Daphna explore how this quiet loneliness shows up at every level of leadership and why it’s not a flaw but a signal—a call to pause, reflect, and reconnect. They share how to build your personal “A-Team,” drop the mask selectively, and find spaces where you can be supported as much as you support others. True leadership, they remind us, isn’t about standing alone at the top—it’s about finding the courage to lead with openness and connection. 

Key Takeaways: 

1. How to Recognize When Leadership Feels Lonely - Learn the subtle signs of isolation that most leaders overlook—and why noticing them matters. 

2. Why Loneliness Can Be a Teacher, Not a Threat - Discover how reframing loneliness helps you grow instead of hiding behind busyness or success. 

3. The Secret to Building Real Support as a Leader- Hear how to design genuine circles of trust that remind you you’re not meant to do it all alone. 

4. What It Means to Drop the Mask Safely - Find out how to be open and authentic without losing credibility or composure. 

5. Turning Loneliness into Leadership Strength – How connection and vulnerability can become your greatest sources of influence. 

Connect with Your Co-Hosts  

Daphna Horowitz  

www.daphnahorowitz.com   

https://www.linkedin.com/in/daphnahorowitz/   

https://www.facebook.com/PEACSolutions   

https://podcasts.apple.com/ca/podcast/leadership-live/id1524072573   

Amy L. Riley  

http://www.courageofaleader.com   

https://www.linkedin.com/in/amyshoopriley   

https://courageofaleader.com/podcast/   

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Announcer, welcome to our podcast series UNFILTERED.

This is where we have Courageous Conversations about topics that

are not always discussed in the mainstream or in the workplace.

Here we strip away the polished surface and

dive into the raw, messy and deeply human topics that we

don't think it talked about often enough.

We are your unfiltered hosts. I'm Amy from

the courage of a leader podcast,

and I'm Daphna from leadership live podcast

with two coaches from two sides of the world who believe that

real growth happens in the uncomfortable, unspoken moments.

From Workplace trauma to dealing with major life

changes and taboo topics like grief, imposter syndrome and

menopause. This is the space where nothing is off limits.

So if you're ready for honest, bold and

sometimes messy conversations, let's get into it.

You You can be surrounded by people all day

long. Daphna, lots of meetings, lots of conversations, a team

that's looking to you for direction, yet still feel alone.

This is one of the most common leadership phenomenons, yet we

don't talk about it much,

yeah, and that's why we're talking about

it today, right? Because it's not just about that feeling of

isolation. It's also about the weight of always having to be on

composed, capable, in control, having all the answers when

inside you really wanting to know that you can talk to

someone who really gets you so today, we're going to be having

this courageous conversation about the loneliness of

leadership and what it means to be carrying this

yes, we are going to unpack why loneliness shows up

in leadership, how it hides behind busyness and success, and

what it really means to find connection that feels safe and

real even at

the top, yes. So let's get unfiltered, yeah.

Let's talk about this phenomenon. I know you and I

both worked with leaders that talk about this loneliness that

they feel in their work days, right?

And I think we mentioned a little bit before we

started recording this whole notion of loneliness at the top,

and maybe that's a good place to start to say it's not only at

the very, very top. We're not only talking about the

loneliness that if you're sitting at the top of the apex

as CEO, founder, or whatever it may be that you will feel

actually in every layer of the organization. When you're in

charge of a team or a certain business unit or project, you

might start to feel that loneliness. So maybe let's talk

a little bit about what does this mean? What is this

loneliness? So it can be at every layer of the organization,

and it doesn't have to mean that you're only at the top. And that

feeling of loneliness can be when you've made a transition,

or when you are feeling that you're running something, or in

charge of a whole of lot of things, and all of a sudden

people are looking at you, and people are looking to see, what

do you think? What do you look like? What is your mood? So you

start to have this awareness of needing to maybe be more planned

or more aware, or more composed, more structured around how

you're showing up.

Yes, I think this is important point, Daphna, that it

can happen at each of those transitions. We went from an

individual contributor to a team leader. We're just a peer on the

team, right? We're friendly with our teammates, and now we're the

leader that got the management role right? Or now we're

becoming a leader of leaders, or now we're a leader of the

business, right? There's there's this responsibility, there's

this sense of, I've got to know what to do here. People are

looking to me. I can't have the same relationships that I had

with these folks in the past. And it can bring with it a

feeling of loneliness.

Yeah, you know, as you were talking, I was also

thinking that feeling of it's all up to me, that, that weight

of responsibility, of, actually, I'm in charge if something goes

wrong, it's all on me anyway. That is a big weight to carry,

and that can feel very lonely, because who's going to really

understand it to that level?

Well, the buck stops with me, right? So I, and only I

am the person who is ultimately responsible, right? You might

have counterparts in your organization. There are other

leaders in your organization, but you've got your team and

your workload that you are responsible for.

I had a CEO that I worked with. He would say

to me often, he would say to me, at the end of the day, I am the

one losing sleep at night because of the business, and no

one else. People are coming, and they're coming for a job, and

they are, you know, getting paid for it, and at the end of the

day they can go home. And I think, and I do want to say, as

we talking about this and trying to give a sense of what does

this mean, it's not exactly true, necessarily, but it's the

feeling that we hold with ourselves when we have a level

of responsibility.

Well, definitely it's why I do what I do, because I

know when leaders are doing their job well and they're

caring about the people and they're caring about the work,

there's a lot of doing and there's a lot of thinking and

responsibility that comes with that as well. I think it's also

we've alluded to this, but I want to call it out specifically

Daphna, this persona, or this professionalism, or this This

portrayal, that we've got it all together, that I'm your

confident leader. You can believe in me. Please feel good

about your work and the work that you're doing every day,

right? I guess that's the other side of the

coin of that I'm the one who will lie awake at night worrying

about the business. So you can be rest assured, I've got this

I've got this handled, and then who do you talk to when you're

feeling stressed, when you feeling like actually, I don't

know if I've got it handled. I don't know if I'm making the

right decision. I don't know if this is the strategy to to

follow that feels very lonely, because who do you talk to? Who

can you really be vulnerable and open about some of your fears or

uncertainty or worry.

Yeah, and Daphna, when we were preparing for this

a little bit, because we like to have our conversations be

unfiltered, don't over prepare, we were liking it to the parent

child relationship, right? Of course, parents want to feel

connected with their children, but there's also this idea that

parents don't put all of their adult burdens onto the child,

like they might know that mom's stressed, right? Or there's a

lot going on with her work right now, right? Or my kids have

known when my family members have passed away, mom's dealing

with grief right now, but there's, there's a certain level

that you share that and you create that connection. And so

sometimes with team leaders, it feels like, okay, team members,

please tell me as much as you feel comfortable telling me, be

open. I'm here to here, and then can't quite feel like they can

do fully the same in return.

I love that you brought up the parenting analogy

because I think it's very relevant here. Because what's

beautiful about parenting is that we maintain connection and

a very deep and loving connection with our children,

and yet we still maintain an element of we've got this. We

are a safe, secure space and home for our children. Very

similarly with leaders who, for me, that brings in that whole

paradox of, while we encourage leaders to be real and authentic

and open and share what they can about what they're going through

and how they're feeling. They need to do that with a sense of

connection, because I think that's really important for the

team, but also with a sense of this is a safe place, and I've

got this handled, and that's a little bit of a paradox here,

because you can be open, but not totally open with absolutely

everyone all the time. I think that's the distinction here.

It's not like, Okay, I wear my heart on my sleeve wherever I

go. It's actually be discerning about who, when, what and how,

and that starts to build that kind of support system. And I

know we don't really want to go there right now, because there's

still quite a lot to discuss. But and we want to stay in that

level of tension of, what does this what is this tension that

this loneliness creates before we move into, okay? How do we

move out of it that I think it's important to to understand that

for me, that paradox, you know,

yes, and the cost, the cost of this paradox, yeah,

feeling lonely has us feeling unsupported. At times we can

feel the fatigue, the decision fatigue, all of those key

decisions are on me as the leader, I've got to make them

the pressure. I think there's huge pressure to

bring your best, know the answers, make the right

decisions, create the right strategies, set a vision. I

think there's huge pressure, and that comes with the cost.

There's also physical cost. We've seen the research that

says, first of all, we spoke about research as well, and

there's plenty of research to say that more than 50% of

executives and CEOs feel that loneliness, and they feel that

it impacts their performance. And secondly, the physical and

emotional impact is huge, whether it's burnout,

depression, physical health, you know, really literally ailments,

heart disease, and all of those come with those pressures of

feeling like you're very alone in the situation. Connection

helps to build health, and we know that as we're talking

about the impacts, the cost of this loneliness at the

top, I'm like, I feel like, then this becomes compounding, right?

Like, because when I'm feeling overwhelmed and I need to make

decisions and I'm burnt out, and the responsibilities with me,

like, I'll withdraw. Many folks faced with those kinds of

pressures isolate. I gotta put my head down. I got to figure

this out.

Yeah, yeah. Rather than having those be the moments

that I reach out and connect in a meaningful way, yeah, instead,

we're putting our foot on the gas even harder. I got to figure

all this out by my lonesome.

No, and I think that this is even an indicator.

That could raise a red flag for people that are experiencing

maybe the loneliness, but aren't even maybe able to label it as

loneliness. Something that's coming up for me is, how would

someone know that they're experiencing loneliness, unless

they're really feeling lonely, and maybe it's not an experience

that everybody can connect to but I do think that sometimes

it's that exactly what you said, that level of isolation. I'm

hunkering down, I'm working out harder, I'm putting in more

hours. I'm busier than ever. Just take a moment and look at

that. You know, do you really need to be in that space? Are

you bringing people in to your workspace? Are you sharing the

load? Are you sharing the conversation? I think that's

maybe an indicator of loneliness, or a symptom of

loneliness. If there are any more of those, maybe like it had

me

think about a giving support, getting support

continuum Right? And how much are you giving support,

listening, providing ideas, helping to remove barriers for

others, or just being with others, emotions and reactions

you're giving that support. I love that, how and who and from

whom and where are you getting?

Getting it exactly when you're noticing

you're on the giving end, the holding space, giving answers,

making decisions. You're the one that everybody comes to. That's

actually an indicator as well. And I had another one come up

for me, which is that feeling of no one really understands me. I

think that is a very big one. People just don't get me. They

don't get this, they don't get the pressure. They don't get

what I'm doing, they don't get how much I'm responsible for.

People just don't understand. I think that that is that's

something that comes up for you as you going through your day to

day. That's actually an indicator of that level of

isolation that you might not be

noticed, that I like that, yeah, because those feel

like really real words that could go through our heads, and

very real words that I've heard from leaders sitting across from

me, we can also check in with our energy. Daphna, human beings

have a natural sense of wanting to belong, right? Even though we

talked about in our introversion episode that there's different

needs for processing out loud or spending time thinking and

talking through with others, but we have a natural sense of

wanting to belong as humans, and if we feel like we don't have

our team or our community where we belong and where we can

really show up our full selves and lean on others,

yeah, and that actually is really also, I feel

there's a bit of nuance there as well, in terms of, yes, we want

to feel that we belong, but when we say, when we've been promoted

to a level of leadership, or now we the CEO, we can't feel like

we fully belong. On some level, there's always a little bit of

distance. So maybe there will be the company party where there's

a barbecue and everybody comes together, and it feels really

good, but when you are leading a team, there's always that little

bit of nuance of, do I really belong in this space? Can I

really share what's going on for me, or do I have to keep some of

that back? And yeah, I mean, I often talk about the leadership

gap, because that's exactly. What's there. It's sitting in

where you are relative to where your team is. And there's there

might be gap, I know in some companies, it's bigger or or

smaller, and that's something to look at as well in terms of

competence. But I'm not talking about the competence here. I'm

talking about the feeling of being part of the team. You

certainly can be and you can create that connection, but

you're also just a little bit separate,

yes, and definitely you're having me think I work

with many leaders, specifically in fast moving industries. The

example I'm thinking of right now happens to be from a tech

industry. Some of that gap is very much desired created. I

know many leaders who encourage their teams to have their teens

channel without them on it, right? I forget how they

referred to that. But players only, players only where they

feel like they can say to each other, just like siblings would

say to each other some things they might not say to the parent

or the Guardian, right, that they can have their discussions

about what is and is not working. I know that gap, like,

needs to be, you know, like, in some

ways, to be there interesting. I know my

kids have a group, and I feel very left out. I would love to

know what they are talking about, without us, the parents,

but it's true, there's something in that peer connection that is

really important, that it needs its own space as well. So that's

actually a lovely thought as well. Very interesting. So

where, if you're the leader, which group are you going to be

part of? You know, right? Yes, and feel incredibly lonely. So I

think should we maybe look at, how do we shift this narrative a

little bit, the tension, the loneliness, the Who do I really

speak to? How can I really show up? And I think it's really

important, and we mentioned it a little bit before, but it's

really finding your real circle, finding the people. It's the

when, what, how, and I don't know what, I had four of those

before, but who, who, who? Because I really believe that

it's not about, okay, I'm just going to be open. It's actually

really choosing the people that you can feel comfortable with to

open up when you've had a hard day, or when you made a mistake,

or you made the wrong decision and there was a big what you put

like an oopsie or whatever, you know, failure, or whatever it

was something didn't work out the way you wanted, find people

that you can talk to about it. Because I think that's really,

really important,

yes. And as leaders, you're going to have to probably

design this, create it yes, because this is a phenomenon

loneliness at the top, because it doesn't get organically

created for us.

So we gotta be don't wait for it. Yes, yeah, don't

wait for

it. Intentionally build this circle. It could be

your counterparts. It could be leaders at your level. It could

be other trusted leaders or mentors inside of your

organization, outside of your organization, it can be friends

and family to as well.

Yeah, I don't know if I'm dating myself with

this analogy, but okay, I call it the A Team. Did you ever

watch The A Team? Yes, and you know how there were four of

them, and each one had a very specific role and a very part, a

specific part to play with their own personality and their own

style. And I think you've got to, I don't

remember it as well as you do. Daphna, I like this.

Okay, regardless, build your a team,

your outstanding a team that's going to be different people for

different purposes or different roles. So have your coach, have

your trusted advisor, have your mentor, have your partner, have

your all the people that are going to help you feel

supported, develop and critically challenge your

thinking when required, help you to just vent and offload if

that's what you need, and share some of the emotional burdens,

and, you know, help you brainstorm to think through some

of your very important decisions that you need to make.

Very well said, Daphna and I would add only that

make sure at least one, maybe a couple of those folks are ones

that you can reach out to when you're feeling messy, when

you're when you're really in the thick of it, you could be upset

or have some emotion flowing in that moment. Who is someone that

you can trust? In those moments, yeah, that know that that aren't

going to think, oh, Amy's just a disaster. Well, I know that this

is just a moment, yeah, right, and I can support her in it.

You know, I think that as we're talking

about this, and I'm getting the feeling that this is a difficult

conversation, because I think there are two elements to this,

and I know that a lot of the executives and CEOs that I work

with have their a team in place. They've got a really good number

of advisors. Yeah, that they will really interesting and not

even, not even the board of directors or the official

advisory board. It's an unofficial advisory board,

because they still have to maintain a certain image or

level of composure and competence towards their own

board. So it's people they can go to outside to discuss

dilemmas such as hiring or decision making or strategy or

anything like that, but that is very kind of professional and

and expert level. And I'm just hearing some of my clients say,

but I don't need therapy, and I don't need to talk about my

emotions, and I don't need to, you know, so I'm saying

sometimes it's important to have, like I said, the A Team.

Have someone on your a team that is also that person that you can

speak to when you are feeling down, as you said, when things

haven't gone well, and you can just offload and share that

without worrying about making a bad impression or what they're

going to think about you, yeah.

Or you can drop that mask selectively,

exactly, selectively that's good

intentionally, yeah, intentionally and selectively.

And know that Simon Sinek, who's really I love his work and his

approach, talks about people you can cry with, and he was

incredibly open and vulnerable in the interview I heard with

him, where he said he's got a few really good friends that he

can pick up the phone and say, I just need to talk to you

something happened, and I need to let off some steam, and I

need to cry, and I know like bringing up the whole crying

thing is going to generate, you know, others, but

show emotion. Be able to show emotion exactly of

whatever kind

it is, yourself, and be real. And as

you said, Let down that mask a little bit.

Yeah, I want to recap and then add one more these ways

that we've been talking about shifting from isolation to

connection. You've said, find your circle. Design it

intentionally. Design that trust in our world. Drop the mass

selectively. And then we'd also say, slow down.

I think that is key in the busyness of our day

to day. It's so easy to just move on to the next thing and

ignore what's going on and just stay busy.

Keep reacting, keep reacting, keep reacting. But are

we checking in with ourselves? Because we need to do that, to

slow down and see where are we energetically? Do we do we feel

like there's no one to talk to, or no one gets me in this

moment? Do we feel like we've given all the support today and

haven't had any supportive moments for ourselves?

Yeah, and I want to offer a reframe for our

listeners. I think this is really important. I think for

me, this is the crux of this whole topic, and I know we

discussed it as well, is that this loneliness and the symptoms

and what it looks like and what it feels like is actually a

signal. It's a signal not a flaw. It's a signal that comes

to tell you, here you are. You are at this place. You're

feeling these feelings because you've reached something, you

have accomplished something, and maybe it's a sign that something

is required of you, whether it's a learning or something that you

need to be doing differently, or something that you need to be

paying attention to, in terms of who do you need to bring into

your circle? Now, it really is all part of your evolution and

growth process as a leader. So see it as a signal and ask it.

What is it asking of us? Now, this feeling, what is this

feeling requiring or wanting from us? And then we can really

take it to that next level of okay, what is the signaling to

me?

Yes, I love this Daphna, and it's such a powerful

reframe. It's a signal, not a flaw. Because really, if we're

growing in our leadership and we're stepping into one of those

transitions that we talked about earlier, or a new level of

responsibility. There is going to be, by design, times where we

don't have the structures and the systems and the people in

place to best support us in those moments happen, yeah,

there's going to be those gaps as. As we grow, and how do we

make sure we you got to intentionally set up something

in those moments. Otherwise it's going to become naturally

isolating, and it might for a time. But then how do you

reframe and shift to those connecting activities

Exactly, exactly, and to really, maybe

even take it a step higher and say, Okay, I'm welcoming this

now. I'm welcoming this as part of my journey. You know, yeah,

this is uncomfortable. It's unpleasant. I'm noticing it, and

it's really a part of the journey. I love what you said.

It's a given. It's a given. As you go higher up in the layers

of an organizational structure, you are going to feel it more

and more by design. It's just how it is, but it indicates

you've achieved that you've reached a level of

responsibility that is high. You are successful. So that comes

with some stuff that you need to notice, acknowledge and and

really give space for and understand what's required to

manage it.

Yeah, so it's a question and a moment of

stillness that invite you all to sit in you can hit pause right

now or after you finish listening to this podcast

episode, right What are you experiencing? Is there

loneliness existing right now?

Acknowledge the growth that indicates and yeah,

ask and choose. This is asking of us. What is

the learning here and who do I need to bring in? I think that

is a big question. Who do I need to bring in? It's a moment of

reconnection, and it could be reconnection with someone else.

I guess it could be a moment of reconnection with ourselves as

well. Do I need to bring myself in? Do I need to take a moment

just to do something that will make me feel more connected to

the leader that I am, the person that I am, the life that I'm

living.

Yeah, yeah, yeah. Beautiful. Beautifully said, we

all are the only ones that can answer those questions in the

moment. Troy, yeah, we've given some guidance here today, but

know that this is a phenomenon that happens in leadership.

Completely normal, completely normal. And

if you know someone who needs to hear this, please share it.

Leave a comment. Pass this episode on and let us know what

other topics you'd like us to talk about on future episodes of

unfiltered, let's keep this dialog going.

Yes, we would love to and until next time, stay

courageous, stay curious and stay unfiltered.

That's a wrap on this episode of unfiltered,

where we have courageous conversations about topics that

are not often discussed in depth. We hope this conversation

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alone. If

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