WOW 176 | Loneliness Of Leadership
The loneliness of leadership is not an uncommon experience among leaders. In this episode, James and Jane share their perspectives on this particular management challenge. They share some tips for leaders when they feel separated from their team and the group. They also talk about creating a shared mutual understanding of the relationship in the board room. There is so much to unpack from this conversation that you don’t not want to miss. Tune in!

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Management Challenges: The Loneliness Of Leadership

Jane, what are we talking about in this episode? What’s the series? What are we exploring?

For those of you who’ve been reading, we’ve been doing a series of conversations between James and me that have covered a number of challenges that managers face. We’ve been talking a little bit about our particular approach to those challenges, our experience of it and hopefully offering some of our perspectives about what people might want to do. This one is a first because this is our first one coming from World of Work Project and World of Work audience members. Karen Abrams, a big shout-out to her in the US, emailed in after one of our newsletters and said, “I’d be interested in hearing you talk about this.”

What she suggested which we have labeled using her phrase, “It’s lonely at the top.” Broadly what we’re talking about is the situation where you get a job. It’s more senior so you are either a CEO, an MD or a head of a division. There’s only one of you so quite often you have less around you drawn. We’re going to be talking all about that and a little bit more about the context and situation. We’re going to share a little bit of our reflections on the context, do a bit of a deep dive and then share our experiences and tips before we get out here.

This is a nice topic. It’s something good to focus on and get our teeth into a little bit. Have you been here before? Have you been this person? Have you been the lonely person on the summit of something or other?

I don’t know if I was on a summit. I have had new jobs, two in particular. One I’m thinking of is very particular where I was appointed. I sat on the leadership team but was quite separate from everyone else because my work area was starting from scratch. I was starting on my own from scratch. It was a little bit like being a founder of a section but it was also only ever a fixed-term section because it was in sports major events. Therefore, I felt a little bit separate from the leadership team, the team running the event and everything. I have been here, particularly in that scenario and yes, it was very lonely. My friends and my personal relationships felt the brunt of it. What about you?

I was thinking about this when this came in and we were exploring it. I don’t think I’ve been in a role quite like this. I’ve run teams but I’ve never felt like I was the one person at the top of something. I’ve always had a peer group around me. I’ve never run a, for example, multi-functional team where everyone’s coming into me. I’ve always felt in a place where I’ve got support and peer groups. I’ve never been in that position. I’ve spoken to a lot of people that have been there. I don’t think I’ve been there myself. Maybe one day but not yet. I’ve certainly spoken to a lot of people. I can relate to, empathize with and have some insight into it but I’ve not done it myself.

It’s probably worth calling out here the context that Karen gave us as well, which is even more specific, just because we might refer back to it a little bit. The original prompt was in nonprofit leaders and CEOs who have a board, are quite hands-off or voluntary and therefore have limited time. Whether it’s a board, a CEO or a leadership team above you, if you are living in that space where you are senior but quite distant from the group of people who are there to hold you to account or the person that holds your account, it can put you in a tricky place.

If you are living in a leadership space where you are distant from the group who are there to hold you to account, that can put you in a tricky place.

Why don’t we jump into it and explore a little bit what we might do and kick around some thoughts? You’ve been there. Why don’t I open it up by saying either, what was the first thing you’d do if you were going to do it again? What do you wish you’d done differently?

My short answer would be not what I did. That’s always a good place to start. I’ll tell you what I would say. There are two things that I found helpful when I moved to Scotland. After I left two of those roles, I moved up to Scotland on my own and started my consultancy just before I met you, James. One of the things I did before I moved was to reach out on social media and say, “I’m making this move and I would like to buy coffee for anyone who knows anyone in this space.”

Whilst if I was moving into a bigger organization, I wouldn’t approach the language quite like that. Once you know you’re moving and it’s public knowledge, reach out before you’re even in that role to peers, competitors and people in that industry space who are not necessarily directly the same as you and announce yourself open to that conversation. Number one, hands down, it was the best thing I did in the first few lonely weeks.

Those of you reading who know our relationship well, no, that’s how I ended up talking to James. I’d forgotten about that. That was directly related. The other thing on a very practical basis, which is related which I know you are going to talk more about because I know you’ve talked about how useful it’s been but very specifically is using an academic tool called Personal Boardroom, which is the understanding that there are specific roles we need people to play to help us steer our career and work.

It’s amazing. I’ve used it so many times writing out on a piece of paper the different roles I need because what helped me in both roles was I was stepping into slightly different functions like leading areas where people were reporting to me or working with me. I didn’t have the expertise in what they do. What I found helpful is it helped me understand what was missing, not the quantity of relationships I had but the type of relationships. For example, I had no relationships with people in the major event industry when I first stepped into it.

I thought about whom I need to speak to. How can I build those relationships? When I moved to Scotland, I had no experience with freelancers and I was a freelancer. I had lots of relationships but everyone had a job. I was like, “Whom can I talk to? Who’s going to understand why I’m facing these challenges around cashflow and things like that?” Those would be my two things. What about you?

That’s nice to hear. I was thinking about this. We do a little bit of prep for this. I’ve got eight bullet points or something like that. That’s the way it works. One of the things that was quite high on my list of things that is important in this space and that if I found myself in this specific place, I’d try and maybe look at before is a lot of it starts with a little bit of self-awareness, self-knowledge and self-reflection. Some of the things that you spoke about there for me almost fit into that category. Projecting myself into going into that type of role, I’d want to be clear on what I’m good at.

Make sure I’m clear on the skills that I do bring but equally as important, I’d want to be clear on maybe where I’ve got some gaps and try and have a little bit of comfort around the areas that I need help in or where I’d look for, maybe some of that technical support like understanding of self and capability. Also understanding what I need as a person to navigate through this.

Depending on our career paths to these different roles, we’ll have different strengths from a functional or technical capacity. For example, if you’re an engineer and you end up leading a tech startup, you’ll have one set of strengths. If you are maybe a fundraiser in an organization, you end up being the leader of a charity. You’ll have a different set of strengths and gaps.

Trying to reflect on your career map and the strengths and gaps that you bring is helpful. Also trying to get a bit of a flavor of what you need as a person. Some people are more individual processors and self-reflective. They can do more individual activities to help them navigate these moments of being on their own. Some people need more of that verbal processing or collaborative work.

Reflect on your career map and the strengths and gaps you bring.

Trying to understand those softer things that you need to feel comfortable in that place would probably be my starting point. That is potentially an ongoing thing that anyone can do at any stage of that and to do that as a piece of prep at an earlier stage of your career. When you go into these situations, being able to be ready would be helpful.

To give you a very live example, people may not believe this but I’m incredibly shy in situations where I don’t have a role. Give me a role, whether it’s like serving food, giving a speech, networking or facilitating. It’s brilliant and extremely extroverted. I am extroverted generally but I have a real discomfort with approaching people at social events or networking. I can go to a conference and not speak to anyone. I will walk away so ashamed that I haven’t spoken to anyone but I won’t have had the guts to approach someone so I know that.

I understand there are some things that will work for other people that don’t work for me. I always think about that like, “How can I create a purpose and reason for every interaction and situation when I’m trying to build those relationships and networks?” For example, trying to raise my profile so I can get on awards judging or facilitation. My classic is always to join a volunteer board.

That’s my go-to because I’m like, “I’ll build relationships with people in the industry,” but also, I’m there for a reason. No one’s going to be like, “Why are you suddenly talking to me?” I have a reason to be there. Self-awareness is massively important. Understanding and being realistic about what works for you is hugely important.

I like that. That’s a great example you gave of the introvert-extrovert in different situations. That shows some real insight. Projecting myself into this, what I would look to do next is bring in a network and grow a network. Getting that support one way or another with those things that are gaps and with the desire to bring weave things that I need to be able to flourish in my role is important. There are different ways to do it but I’d look to explore. One option is one-to-one coaching to process and work through and mentor. The act of verbalizing is so powerful. Even if we’re speaking to somebody who’s not a professional in our field, there’s something useful in that and mentoring brings other benefits.

There are options around that that you can do and you might touch on some of those more. Also, there are communities of practice or industry all around us. We can navigate them in ways that are helpful. To use my example earlier, it might be a fundraising community that operates at a regional or national level. Maybe that would be something to be part of or that could be more of a general business community to be part of it. Try to stick your head up, spot the communities around you, engage in them and say yes to them. Something that stood out for me when I’ve thought about people who successfully engage in communities is to view communities around you as non-zero-sum games.

Recognize that the community around you is not for you to extract value and insight from. It is for you to contribute to. Maybe giving before you get, contributing by having that more collaborative mindset to offer into that community and see what returns. Take that engaged approach to give and support the communities that you’re in with the knowledge that if you do that well, you’ll build relationships, gain insight and learn from others. That piece around giving before you get is helpful when trying to build those relationships and have something to bring and offer.

WOW 176 | Loneliness Of Leadership

Loneliness Of Leadership: The community around you is not for you to extract value and insight from. It’s for you to contribute to. Give before you receive.


I want to talk about mentoring as the mentor versus the mentee briefly because I cannot tell you how stimulating it will be for you. If you are managing a group of people but you’re feeling quite distant because they’re all managing their functional areas, one of the most powerful things you can do is mentor people outside of that group who might have similar experiences of work. You might mentor them from a career perspective but that will stimulate you mentally and help you relate more to those people as you start to build relationships as well. Giving before you get can work on so many levels because you can also take so much from it as you are giving.

You get all kinds of benefits from knowledge and connection to well-being and all those things. All too often we feel too busy to engage in that space or we feel a bit awkward maybe sometimes networking without a purpose. That’s why it goes back to me to be clear on what it is that you can bring. What is it that you’re offering? How are you given into that community? That opens up opportunities in your communities. That’s something that I’d push for.

It also brilliantly allows you to lean into your strengths at a time when you’re feeling a bit not strong. When you take in that new role and you’re managing people quite often around people who don’t have the same skills as you, it can be incredibly lonely and intimidating. You’re like, “I’m working with a board. They’re all more experienced than me. I’m managing these 3 or 4 people in a multifunctional team. Most of them have more experience than me in their role.” You can quite often feel a little bit discombobulated, uncertain or wrong-footed.

When that’s happening, then looking to other places you can lean into your strengths to keep your confidence going powerfully. Talking about self-awareness and what you need, one thing I’d probably mention is we talk a lot about skills-based people development around the building by the borrow. We’ve talked about it before. Are you going to build the skills internally? Are you going to buy them or borrow them somewhere else? That works well when you’re thinking about yourself as a solo operator at the top.

You can borrow them or friends, peers or communities of practice and exchange. You can buy them executive coaching seats at programs. You can build them because the other thing you can do is develop the skills and the people in your team, if not to create peer support, at least to be able to be a more engaged participant in the technical or the strategic conversations you want to have, even if they don’t understand the fuller picture.

Develop the skills and the people in your team, if not to create peer support, at least to be a more engaged participant in the technical or strategic conversations you want to have.

I wanted to pick up on something. You said something that I wanted to explore a little bit more. You might be able to get yourself a seat at a table. Would you say a little bit more about that? As part of a cohort or something, what were you doing?

I was thinking about buying in either individual or group support. We’ve talked about coaching, mentoring and things like that, which would be one-to-one. Also, there are programs where quite often are called masterminds. There are programs you can buy into where you can buy a seat in a program of 10 to 12 to 16 to 20, however many people who are specifically in your same scenario. For senior leaders, those things do exist. Sometimes you would buy into a leadership development program, which might be slightly more cost-effective than something like a mastermind.

Following on from that, thinking about some of the things that we’ve spoken about so far in a question that we sometimes ask in some of our programs. What do you think the balance is between developing skills, knowledge and capabilities? The flip side is developing as a person and self-development. Where do you see that focus being for somebody in this role? If you were going into it again, what would stand out?

To quote all the academics in my life, the phrase that everyone hates is it depends. It depends on the self-awareness piece you were talking about where your strengths and witnesses are. I do think there is a slight challenge when you come into this lonely position at the top where you have to do some basic knowledge growing about the roles of everyone around you. Whether it’s a board or a senior leadership team and the team below you that you don’t necessarily aren’t as familiar with, you do need the basic language to be able to connect with them well.

WOW 176 | Loneliness Of Leadership

Loneliness Of Leadership: There is a slight challenge when you come into this lonely position at the top where you have to do some basic knowledge growing about the roles of everyone around you.


You also need the space and the skills in decision making, reflection strategy that is often only brought with engagement with other people and stimulation from external materials. How do you get those external materials? Some people don’t listen to podcasts because it’s very much like an individual thing. For some people, it’s in a room with discussion. Generally, if you don’t already have at least the basic soft stroke communication skills and people skills coming into this role, it’s almost impossible because you’re coming into it in a place where not only is it already a tricky role but you are also not necessarily got the things you need in place. It does depend on what timeline you’re on.

If you’ve got a long runway into this and a year to make your impact and stuff, you can build the skills. One of the tricky things is navigating who does what for you and whom you need to do what’s for all of your stakeholders. That will be in the job and then outside of the job for you to keep you sane, functioning and developing. One of the challenges around that is in this particular role, it’s very hard to get a good challenge. Your board or senior leadership team wants you to deliver the results, have a chat with you every 6 to 8 weeks and hold you to account for when finances or something else is going downhill or outcomes.

That’s it. If they’re a senior leadership team, a big organization, they’ve got other jobs and other responsibilities. If you are a nonprofit, they’ve got other jobs. They’re volunteers. One of the challenges is I don’t think I’ve ever felt in this job like I’ve got critique from the people below or above me. I’ve always had to go and find the critique. One of the challenges about that is you say, “What do I need?” I can know self-awareness but unless someone is appraising my work effectively, my thinking or my decision-making, I don’t know what I need because I don’t know if I’m getting it right or wrong.

That’s a massive challenge because quite often, certainly at the top, if you bring proposals to the board or the senior execs, they’re not going to give you a four-hour debate about what’s right or wrong. They’ll throw it back, refuse it and say it’s not good enough or it’s not right and these are the three reasons. What you quite often need is space and time with somebody who understands the context to talk through what’s gone wrong and what you need to do differently. That’s hard. For me, it’s finding that person to bounce things off and talk things through who’s going to be honest with you about why someone might not think what you’ve done is the right thing to do because you lose that.

Do you think that’s something you can get within an organization? Do you think that’s something you can find within the team that you have or that’s something that needs to be external?

It’s hard when you first come in. That’s like any team. We’ve talked about new managers. Generally, it’s pretty hard early on anyway. What’s particularly tricky is strategic decisions are normally made pretty early. Not like the first few weeks but certainly the first six months, you may not have had time to develop that internally. I’ve never successfully done a job like this without external counsel or someone I can go and say, “This is what I’m going to pitch to them. Tell me what you think is wrong with it. Tell me what you would critique it as.”

Find the people who hold the positions that you are connecting with, whether that’s your board or senior leadership and whether that’s your staff or your managers. Find comparable people to be able to talk that about so you can build your awareness of other people’s perspectives on that. In some senses, it’s an extreme stakeholder, map and engagement plan. If you grew your stakeholders, not just to be the ones you’ve got but also to be the ones that can help you be at your best, how can you constantly connect and communicate with them? That’s good. The other thing I would say very practically is to learn how to buy your time. Be articulate about how long you are going to be listening for and not making any major changes because that’ll buy you a bit of time to build relationships.

I’ve written down speed and listening as two words I was thinking about picking back up on but I did have another question which is, how do you get a shared understanding of that relationship with your board members? We talked about self-awareness and with self-awareness comes a desire to pin down our leadership style, who we are and something in that. How do we go on to create a shared mutual understanding of how we’re operating in that boardroom? What do we do in that space to try and do that or can we?

I would describe it as not dissimilar to how you and I would discuss project management, program management and change management, which is you have to create a narrative of the journey that you are confident about communicating and a narrative to whose job is what. The reason I say narrative versus deciding what his job is that generally in my experience with board or very senior leadership teams when they’re divisional and they’re one step away or board members. They’re going to be in that meeting for half an hour before and then afterward.

Constantly reminding themselves and gravitating themselves back to what their purpose is and articulating what you need as a leader from them at that moment and space is important. It’s about having a good awareness of who might be willing to help more. I’ve had board members in the past who have said, “I can’t be available every week to talk to you but I can if you need an hour and a coffee at lunch break every so often, talk to me. I can bounce things around and we’ll cut straight to it.” That’s been helpful but it’s hard. Board members all have a different idea of what they’re there to do.

Therefore, you can tell them what you want them to do but they will still drift back to what they think their purpose is. You have to take the win. That’s why I would never rely solely on the way. In another team that wasn’t so lonely and wasn’t so senior, I would be confident about being able to find peers and support within the team. That’s one of the reasons you have to go external because you need that balance against the people who work for you and are therefore worrying about running their teams and the people who are holding you to account who have limited time resources and their number one job is to make sure that you are effectively discharging the strategy and keeping the organization compliant.

One question is if you approached 100 people who were 1 year into a role like this and asked them how many of them would do it the same again, what proportion of people do you think would feel that they got right?

I’m going to say two things here and neither of these are reflections on the people I’ve known who’ve done this job because they’ve all been brave, brilliant and imperfect. They’ve been in the game. I admire people who take this job because having done it a couple of times, I don’t think I’ve ever done anything as hard ever. What I would say is generally they’re moving at such a pace. They don’t always look back. Therefore, it would be difficult for them to articulate what they would do differently but they would almost, I suspect, certainly think they should have done something differently.

The biggest mistakes I see people use and I see this very frequently, is people not reaching out and not understanding the power of coffee or Zoom. People don’t get how for some people with certain preferences that can be game-changing for you to get you off the train of thought. The other thing that’s incredible is holding the space long enough. You were talking about time and pace. Almost everyone panics. They need to be seen to be making major changes, even if it’s not a big drama problem. Even if they haven’t been recruited to solve a problem, people worry in this job that they’re not being seen to do anything.

It’s a very weird job because you’re trying to take in everything and then plan in your head. I imagine it a little bit like being a ship’s captain. You might be part of a bigger fleet but you need to understand all of that and your people on the boat to make the decisions, who goes where and who does work. You’re not in a storm. You don’t have to do it at the moment but quite often people want to be seen to make major changes and those noises.

Get good at holding your space and say, “For the first three months, I’m only going to be listening and no major changes at all.” Repeat that about 40 times. People are getting patient but you got to hold your line. You got to say, “No. I’m learning a lot and this is what I’m learning. This is what I understand. You’ve got great expertise and I don’t think there’s a rush. Let’s make the changes once and make them well.”

As you were talking, a few things occurred to me. One, I’m going to check out straight away, which was a little bit of a metaphor. You avoided a military one and went for a naval one but one that was in my mind as you were speaking is a phrase that people use sometimes to talk about football or soccer here in the UK. They talk about people having lots of time on the ball. Somebody seems to always have lots of time on the ball and this is about them and their ability to make things look fluid and in control. There’s something in that metaphor about appearing to have all that time and measure that’s interesting.

Something else I was thinking about is the relevance of a sector and function that we’re in. In some areas, if you’ve got a quarterly P&L target and that’s how you’re measured and targeted, maybe you have less time to produce more things you want to and you are held in this way that’s potentially unhelpful for some types of things. Whereas in other industries, you’re maybe on a four-year cycle and that’s a different thing. It’s important to be clear on those things.

You’re 100% right and to add on that, my advice would be if you’re taking a job like this, be realistic about how quickly you can turn things around. Have that conversation before you take the job. What are the time scales of changes? If the team is performing to X level and the delivery continues to keep performing but over time grows, it’s great. If there is an ambition to significantly change something very quickly, you’re going to struggle if you don’t know that function as well or those multiple functions. It’s going to be much harder.

The last thing that was on my list of bullet points at that minute was due to the fact that everyone I’ve spoken to who’s been in a role like this and has had space to reflect, which has done things a little bit differently. With that comes the knowledge that we will be imperfect as we go through this journey. Probably everyone’s going to be imperfect going through this journey. Something that stands out is how we are okay with failures.

This is industry, location and function specific but some industries are good at owning some of that imperfection along the way or better and some individuals are and some are less. Try to navigate to be better at recognizing that sometimes we make mistakes and that’s part of this and not let that knock us down. We need to learn, get better and navigate through these things but we need to be able to keep learning, evolving, changing and holding onto that as we progress.

You are right and it’s very interest-specific. What I would say is that one of the particular challenges of a role like this and the loneliness of it, which I’m feeling alone in this, is that it is very rare that anyone’s telling you you’re doing a good job or even that you got anything right. Everybody else in an organization, generally there is a specific responsibility to let people know when they’re doing well. In this senior or CEO role, it’s pretty rare.

There are some board members who are greater at the moment but in the wins in between, a month and a half from any board meeting, when you’re sitting there and you think you’ve scored a meaningful relationship conversion, even if there’s no money attached, even if the pipeline for the funding or the client is a year down the road, it is no one’s job to celebrate with you. That makes it much more likely that you’re going to lose confidence and that negative bias that we all have is going to creep in of, “What am I getting done?” People are like, “I did not do this well.”

Two of the managers and leaders that I worked with were amazing at this. They were drawing me into their celebration of success as their number two. I was off running another part of the team but they would set up informal communication to be able to celebrate what their wins were with me and me then to be able to go, “Well done. That’s amazing.” I didn’t understand for some of them even why they were important but they told me they were important.

I would tell them, “I thought that was amazing. Well done.” That matters because when you are lonely like this, to your point, we can be kind to ourselves generally but we’re not very good at being kind to ourselves as humans. Some of us are better than others but sometimes it takes someone else to help us be a bit kinder to ourselves. You make a great point about that.

Sometimes it takes someone else to help us be a bit kinder to ourselves.

I was going to riff on what you’ve said there with a lead into another one of my bullet points, which was well-being is hugely important in this. When you’re talking about the sharing of success with others, I think of that as a positive emotional thing that contributes to well-being and boost us and does all those good things. There’s a need for more focus on our wellbeing. We need to carve out time for ourselves as I’m speaking out here. There are a couple of bits to that. Understand what you need to be at your best from a well-being perspective, which could be social time, exercise or doing kind of things, whatever these different things.

It’s also important to be a little bit selfish about carving out a little bit of time for you to reflect, grow, learn and continue to develop in that role. If you don’t do that, it feels like there’s maybe a risk of a little bit of repeating mistakes and not feeling the momentum and maybe a bit of a downward spiral around that potential as well.

I was pulling a funny face because I’m thinking back to how many times I’ve got that wrong. In my experience and when you are in that slightly lonely solo operator role in a senior leadership position, it becomes very hard to create a culture because there’s just you. When you are a good leader and manager and you’ve got a lot of experience in it, you’re quite used to creating cultures that are going to help people thrive, be healthy and look after themselves wherever they can. Sometimes it’s harder than others in different organizations.

When you’re on your own, it all feels a bit pointless and you are like, “I’ll crack on.” It’s very easy not to do the things that you know intrinsically will help you be better at being as operating. Also, it’s very easy to forget what keeps you working, happy, healthy, motivated, engaged and excited. You make an incredibly important point. I would say the risk is huge. What I can say from experience is when you don’t do this and I’m thinking of a particularly appalling month for my partner who had to deal with it where I got myself into a mess, in terms of quite a big bid, we were pulling together and I was mentally a mess.

I hadn’t done all the things wrong. I hadn’t drawn on the sport I’d been offered. I hadn’t talked to my friends about it, not the work but how I was feeling. I hadn’t set up space and time for myself to be well and healthy. I’d set a lot myself in the back room and I tried to wrestle my way out of it. I was surprised I failed. No matter how resilient you are as a human, it is easier when you are working mostly independently in a leadership role. It is easier to slip into, “This is the way I need to get it done.”

You become blinkered. You try to push and work harder, not more cleverly and not with a recognition that the things that will make you more likely to do the job well will be going for a run, going out on tours, a swim, a pint with your friends, even though it’s driving you crazy, whatever it is that helps you reboot, reflect and feel well. There’s no one to pull you out of it and that’s hard. On top of that, you’re like, “I don’t want to talk to anyone who knows about this because it’s confidential. We might do well out of it. I don’t want to give a game away to other people. I could talk to my friend over here but my friend over here is in a competitor and it’s a big client bid.” It’s difficult.

I’ve got one point I want to share and I’ve got a question or a reflection that’s come up as we’re speaking through this. The point I wanted to touch on that is helpful and that it’s something that we all work on over time is trying to make space to be clear on your values and non-negotiables from a behavioral perspective. If you develop that sense of what your values are and what’s important, then you’re preloading some of the decision-making that makes it easier to navigate with things that come up in the workplace. I was going to chuck that out there as a reflection.

We’ve talked there about the importance of focusing on well-being and making space and time and all of that stuff, which I standby heartily. I’ve never been in a role exactly like this but I’ve been in roles where for protracted periods, I’ve had to work intensely. High immersion, high contribution and all those types of things or at least I’ve felt that I needed to. As a personal reflection, I have at times found that I feel or I can feel resentful about that. When things grow and the scope of the work gets larger and it becomes more encompassing, I can find myself unhappy and resentful.

What I do find is if I get to the stage where I’m in that situation when I submit to that and accept that this is what I’m doing and the other stuff becomes subservient to that purpose that I’m working in within a period, then I’m okay with it. If there’s something about when I’m fighting the all-encompassing nature of a particular time and feeling like I’m missing out, resentful or out of control, then I dislike it. Once I accept that this is going to be my entire existence for X amount of time, then I’m okay and I can let go of the other stuff. What do you think about that, if anything? You can refer me to counseling if you would like. That’s an option.

You’re right. What I’m trying to decide is whether that is a temporary coping strategy that is effective at the moment with dealing with high-stress and intensive work periods or whether it’s healthier long-term. I’m not sure what I think about that. A little bit, it depends on your perspective of the power of work and what you need from work. What I would say is making your peace with the work that you do and the role that you need to perform at that moment is helpful. If you are going to go down that making your peace and accepting that’s what it is, then boundaries become even more important.

WOW 176 | Loneliness Of Leadership

Loneliness Of Leadership: Make peace with your work and the role you need to perform in that moment.


Boundaries become important in this stuff anyway. It’s very easy for you to become the job when you’re working solo because you don’t have a team and a specific identity within the team. It’s like you and the job become synonymous. You do have to have boundaries, even if you’re working incredibly intensively. The best example I can give to you around the intensive work and loneliness thing is when I used to work in events generally. I’ve talked elsewhere on the show about I overworked people and myself enormously.

What I also was good at was that we had very clear boundaries about when the intensive work period was and that helped. You are right. Making your peace with it, that’s what’s happening but then also knowing that it will end. You have to know that it will end when you’re working intensively and you have to let other people know that it will end too. Otherwise, it can feel overwhelming and it’s not possible to accept it. You might not feel resentful but you’re going to feel pretty broken and want to leave at some point. It’s tricky. It’s an interesting question. I’m honestly not sure.

Your point about the separation of self and job is something that I can relate to in a different context where I’ve been involved in a small business in a quite small place. If everybody knows that you are associated with this thing, then that’s your identity and it’s hard to separate that. One of the things that I found most trying about that period of my working life was the inability to separate and have a separate identity or a private identity. I felt there was something interesting in that and trying to maintain that separateness, the individual identity, the permission to be something else.

If you work in sports, retail or community, I’m not saying these are the only places. You will relate to what James said 100% because people are going about their lives not in a work context while you are in a work context. The example I always give and I’d be interested to know about yours is when I was working in a national governing body in sport but I also played that sport. I would go for a Saturday to burn off some steam, playing some tennis and someone wanted to have a conversation about the decisions that had been made on the court two weeks ago or on a rule change that had happened and they wanted to give me a hard time.

That intensifies that boundary relationship because you’re like, “I can’t even hold my boundaries, let alone anybody else.” I am respective of your job. If you’re reading this and you have that challenge, I don’t know what your advice, James would be in terms of dealing with it but from my perspective, I had to go and play another sport. I had to go and get another hobby. I had to step away from playing tennis for a while because I was like, “I can’t be living and breathing my work even in the one day a week that I don’t think about it.” How did you deal with it?

I moved as well. Ultimately, that’s what I did. I couldn’t navigate away. Maybe it would be different but I’m older, bolder and all those things. Maybe I associate with Baldwin more and that would give me a separate identity.

People do. They move. People who work in communities quite often run the local shop and they’re like, “I’m going to move to 5 miles down the road so I don’t bump into my customers every day.”

That’s what I needed to do. Maybe it would be different now but certainly at the time, I didn’t have enough breadth of identity around what I was doing to give me that separation. Maybe I’m there. I’m not sure of it but I am. Have you got any other points? We’ve meandered a lot in this but it’s been quite enjoyable to see.

We have been meandered quite a lot. There are a couple of things that I would add. Adding onto the well-being thing, I’m a massive advocate of celebration rituals for yourself. Get yourself set up with, “This is what I’m going to do every time I have a little win and success.” People on the show will know what I talk about. I take myself out to lunch sometimes and that’s me marking that something good’s happened and I might even text my mom. My mom loves me very much. She doesn’t care about my business but I will still text her and let her know I’ve had a good day.

Celebration rituals. The other thing that I wanted to mention was if you are reading and this is you, be conscious that by the very nature of you being more separated, people are probably less honest with you. Sometimes that’s for a kind reason but it means that you have to work a little bit harder to make sure that what you are hearing and how you’re interpreting it is a close approximation of people’s perception versus niceties. People say nice things to me and did all the time.

I very rarely felt like someone was close enough that it was in their interests to be critical and that’s the problem. When you’re in a team, it’s in other people’s interests to be critical of you in a healthy way. It’s not necessarily when you’re far apart. Watch out for that and look for people who will happily do that with compassion.

Compassion’s a great word across all of this. That feels like we’ve talked about a lot of things that are helpful and things we would do in that situation, have done in that situation, heard from other reflections and things to ponder on without reflecting and pondering on. One of the things that would be super useful to do in this type of situation, which is hard to bring in that little bit of a reflective practice we talked about is the need to invest in learning and development.

Making space for that and a little bit of that reflective practice, be it a little bit of diary keeping or looking back at the end of the week be a helpful thing to do. Align to that. I was going to ask, reflecting on what we’ve talked about here, does anything stand out for you? Have you got any key takeaways or things you’ve learned in this conversation?

Personal and professional. From a personal perspective, I’m still conflicted about how much I loved those jobs. I still found it incredibly difficult, challenging and lonely. I still felt like I was never intellectually and emotionally challenged in the way I was. It was like fighting the good fight. That’s how it felt for other people. My team could crack on and do what they needed to do when I was able to navigate but it took its toll massively.

From a professional perspective, I need to pay someone to help me to hold my boundaries and manage my well-being. We’ve talked about this. When I am able to make my well-being a priority at the exact moment that I know I’m under pressure, I do better work and I’m happier. Everyone around me is happier but I’m bad at it. I struggle to maintain that focus and space for the world’s humbling and it’s not just about peddling faster.

The world is a humbling place. I’ve got a couple of bits that I know are things I could do better but are probably helpful for many. The first one is to ask for help more. I’ve had a few times where I’ve run businesses or teams, particularly in the business world. I wish I’d asked for professional help earlier and just done that. It would’ve just been better. Asking for help earlier on is a good thing to do. The last little thing that I was reflecting on is you chatted throughout all of this and we thought a little bit about the separation of self from the overall identity. Something that’s in my mind is about trying to be clear for purpose and having the agenda not be about me.

This is maybe a personal reflection for me but it probably links to maybe a bit of self-awareness and what’s right for us. For me at least, I feel drawn to a little bit of being of service. If I feel that I’m on somebody else’s agenda or I’m at that service role, then whatever level I’m at if I’m providing service, doing something that feels purposeful and I’m clear on the fact that it’s almost somebody else’s agenda, that makes it easier for me to navigate some of this potential isolation, loneliness and complexity because it’s not about me. It is a bit but it’s not about me. That’s something that would help me try and navigate that so that’s a reflection.

To add one last point, which is to watch out, not from your perspective but for people in that situation. If that resonates with you, what are the risks that you have to watch quite mindfully to slip into a martyr place where you are doing it for everyone else but no one else is calling you out for it? It can feel very quickly like, “Why am I doing this? I’m doing all of this stuff. I’m far away from all of their stresses because I’m above that noise.” Therefore, it’s very easy to start feeling like I’m doing a thing for the organization. You have to be careful about that. It’s bad for them but it’s far worse for you because you stop feeling engaged and you’re helping people.

We’ll call it a day there on this conversation. What’s next for you, Jane? Have you got anything lined up?

I’m speaking to a lovely client. James, you and I are facilitating it. We’re doing a lovely conversation about conversations, which is always a bit matter. Just leaving the conversation as I always do when I talk to you about stuff, feeling a little bit reflective and thoughtful about how I could have done things differently and what would that might mean for us going forward. What about you?

I’m feeling reflective like you. I’m pondering on the less haste, more speed you talked about turning, carve out the speed. There’s something in that but I’m still mulling over how to go more slowly. It’s something that’s on my mind a little bit. In terms of what’s next, we’ve got a workshop. One of my friends who I used to work with is visiting Edinburgh. I’m going to go out to dinner so I’m going to go and eat a tasty dinner and do that later on. That’ll be nice.

That sounds like a brilliant way to round off a day where you’ve had a conversation with me and I’ve had one with you.

Thank you very much. Until next time. It’s been great to talk to you.

A big thanks to Karen Abrams for giving us the start of this conversation. It’s goodbye for me too.


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