The turtle and the shell

An experienced agency founder gets honest about feeling stuck, losing motivation and what he discovered about himself when the job title disappeared.

Steen Rasmussen built one of Denmark's most awarded digital agencies over 20 years. By most measures, he had made it. And yet for two of those years, he stayed in a role he knew he'd outgrown, unable to leave, unsure why.

If you've ever found yourself going through the motions in a career that looks successful on the outside, or felt a creeping loss of motivation you couldn't quite explain, this conversation will feel familiar.

What starts as a discussion about life after a major career transition goes somewhere much more honest. Steen traces the thread from the disorientation of stepping away, through the particular kind of loneliness that comes with senior roles, and back to the experiences that quietly shaped the way he sought fulfillment for the next decades.

He arrives at some uncomfortable realisations about self-confidence, self-deception and why high achievers so often stay stuck long past the point they knew something had to change.

Tune in to hear about:

• What no one tells you about your sense of self when a long career chapter ends — and why it catches even the most self-assured people off guard
• The hidden loneliness inside leadership: why moving up often means having fewer people you can actually be honest with
• The gap between the vulnerability high performers can show and the kind they can't — and what living in that gap costs over time
• How the very achievements that built your confidence can quietly turn into the thing keeping you from moving forward
• The moment in Steen's past that reframed everything he thought he understood about his own drive and ambition
• Why the most successful people in the room are sometimes the ones most stuck — and least likely to admit it

Full transcript

Aggelos: So, let's just start with the easy one. Beyond your role, who are you?

Steen: So if we strip away my title, who am I? Well, I've just gone through the process. I co-founded an agency 20 years ago and over the last couple of years I've been thinking about leaving, and now circumstances just aligned. So there was an opening for me to step out of.

The first instance is realizing that there is something. I have no idea how long — when I picked up the phone and answered the phone, I was naturally inclined to say it's Steen from IH Nordic or IH Nordic, it's Steen — and it wasn't. It was just Steen from Steen. So who the heck was he? That gave a lot of room to think.

I had so many options. From my announcement on LinkedIn, it took five minutes for the phone to ring for the first time with somebody offering me something. And I got so many offers. So it was a challenge to stop and refocus and recalibrate around what was it actually that I wanted.

It gave me time to stop and think. And if I look back before that, I think I used to describe myself as a top funnel guy. I went around and I talked to people and if somebody potentially was interested in buying, I wasn't the sales guy. I was just the person who initiated the conversation and helped them move on in the process. But when I stepped away from that, saying okay, I didn't have to sell anything to anybody — then what was left?

That gave me a good time to think. I've been spending time teaching also before that, but I found out that teaching has for my part been a really big part of who I am — sharing what I know with other people, just sharing the information and then them learning. I've been talking at a lot of conferences during the years, and this is one of the things I came back to — the joy of sharing my knowledge, but in a non-commercial way. It also tied back to finding myself as part of a community and being something strong for the community.

At the same time it was also having this time of recalibrating around family — saying, I'm not just my job. I'm not just the function I have in relations to other people. On the second layer, I have a role as a father. I have four kids. So being there for them and helping them become everything they can be on their own terms. My wife, the same thing — enabling, supporting her and giving her the freedom to be whatever she wants to be and just being in her corner.

And then of course the circle of friends — when I stripped away the job and got the idea of this term called your friends from work, who are actually not friends if you stop working. It's only people you relate to because you share a job. So stepping away from that job, who was left? And surprisingly, a lot of people still remained friends after I left the job.

And then of course there's the last 15% saying, well, all this is related to other people, but what sits inside Steen, what is the core? I think the core of me is a combination of curiosity and playfulness. I've been telling people my favorite dish is something I haven't tried before. The exploration of saying there are so many interesting things out there — if I keep eating the same things, I'm probably missing out. There's a curiosity in the sense of not missing out. And then the playfulness in the sense that I've been a consultant for 25, 30 years and everything gets so serious. What I want to do and who I am is trying to be more playful — not less serious, because everything is serious, but trying to approach it with a less serious approach.

So I'm having this energy of saying, if people want to sit around a long table looking at PowerPoint slides, they can do that, but that's not what I do best. Going back to my self-definition — I came across this amazing quote from Steve Jobs that I use to help redefine me: it's better to be a pirate than to join the Navy.

So instead of me going out and joining some other organization where I would have to fit into a role and redefine myself in relation to them, I said, okay, cool, I'll take the pirate's way into this. And that has given me a role I call a digital fixer — just somebody who comes in quickly and looks at things and fixes the situation. I use my experience, but I feel like Sherlock Holmes. I come in and I solve the mystery and I fix the problem and I find the solution and then I can move on. It's not like I have to be in the organization for months and months. The faster I can do it, the better success. That's the combination of finding back to who I am — a playful approach to life centered around curiosity.

Aggelos: I mean, this playfulness is what makes us successful in the first place, but somehow along the way we are losing it, we forget it. It's research driven — if you lose that playfulness, that joy of trying things, the quality of the outcome deteriorates eventually.

Steen: The most depressing book I read — I can't even remember the name — it was about humor and saying that kids laugh out loud 72 times a day. And if you're lucky as an adult, you laugh out loud like three times a week, spontaneously. So what is it that gets lost in that process and how can we keep that? For instance, one of the things I've been trying to do to stimulate myself and force me to smile more — when I'm walking I can listen to stand-up comedy. It's going in and getting another reason to smile.

In the old days, I would always listen to some serious business podcast that would enhance my professionalism. But it would mean that I lost myself in relations to having the playfulness.

And one of the things that has given me 20 years of pain in the workplace has been — every time my curiosity came up with something funny or interesting or groundbreaking, something that broke the mold in how to work and came up with a new process — people always wanted to productify it. "Let's make it, let's turn this into a product." I'm like, that sounds really boring. You're suggesting let's take this game and put it into a series of steps so we can repeat it? That's the complete opposite of being playful. There's no exploration in going in and defining the process. Sure, I can dance in front of you and do crazy stuff. And if you want to productify it, you do that. I'm not going to go back and spend a lot of my time trying to put a formula on a process that arose from creativeness and playfulness.

Aggelos: Since we're talking about joy at work, that leads me naturally to the second question. I'm pretty sure you will have some parts that you might be good at, that you might be doing on autopilot, but not really connect with anymore, not really identify as that anymore.

Steen: For me it's been a massive help having this fixer mindset because in the old days I would see myself as a salesperson — I was responsible for bringing things to the business. Now I can let that go and say, well, it's not selling. What I'm doing is having conversations with people, and if they have problems I can help them solve it — but it's going in and having the conversation about their situation much more on their terms, because I'm no longer committed to sending something back to the people back home.

Being the salesperson is something I've very much left behind and replaced with just being a digital psychologist, basically — being able to have that conversation about people's situations. And what I've also found out is that very often the problems we have in organizations, the mysteries I have to solve, are tied to some very specific problems — but instead of fixing the problems, people start doing workarounds. If you have Bob in accounting who is always bothering you, then you find a way of working around Bob, but it's not solving the problem. Going into organizations, I see a lot of those Bob situations where you have built a complex hierarchy of relations that is basically workarounds around processes, because it's too difficult to solve them. There's too much internal politics and hierarchy. So going in and actually pushing some of those and getting a solution — it's gratifying, but it's also something that hurts in a lot of organizations.

I was at an event yesterday, the launch of a magazine called You Can Now, and one of the articles asked a lot of people: if you could choose between a human and an AI as a manager, what would you choose? And there was a significant majority who said an AI, because then you don't have the politics, you don't have the challenges. But it's horrible, because in a sense it's putting up a friendly facade of something that has no empathy at all. But people would prefer that to the relationship with real people who don't show the empathy or don't understand the relations. I think it's a massive complication, but super interesting.

Aggelos: At least the robot is not expected to show real empathy. So we have no expectation from it. There's nothing for us to get disappointed by.

Steen: Yeah, exactly. And then there's no end to the conversation we can have — we can continue until it says it understands us. It is also why a lot of people are using it as self-therapy, because you can have this conversation, it never gets tired. The hourly rate never runs out.

And that's super interesting, but at the same time, that was one of my reflections from yesterday — it's also the AI's business model. In reality, it has no empathy. The reason why there's empathy there is to keep you engaged in the conversation, because then you spend your tokens and you need more tokens. So the longer you talk with it, the more money it makes. It's kind of like a psychologist — except it has no empathy, no understanding. It's the psychologist asking, "So what do you feel about that?" — having these reflecting questions back at you so you solve your own questions. So from that perspective it's interesting, but it's also the business model.

The empathy has been put in there to engage us and to keep us in the conversation, so we feel, "Well, I have to go on a diet now because I promised my AI." And it doesn't care, it doesn't mean anything to it.

Aggelos: So what you left behind is the salesman identity, let's call it.

Steen: Yeah. But also the other part of the salesman — the marketeer — in the sense that my communication is now really related to communicating and not positioning. Peeling off some of the marketeer and being a more authentic me in my communication. It's super interesting, but it's also a complication, because it makes it more difficult for me to stop being a pirate if I decide one day to join the Navy again.

Aggelos: What made you take that decision? I would like to hear what emotions emerged when you were selling or marketing that piled up towards that decision.

Steen: I think it goes back to the general perception of the salesperson and the marketeer. Neither is perceived as something really positive from the outside — it's somebody that convinces you to do something you don't want to do, basically. And even though I feel I can say I never sold anything to anybody that didn't get more out of it than it cost, it's still the self-perception of: what are you doing, what is your role? Well, I'm in sales and marketing. And then you put yourself in a bucket where other people just pull their prejudice out and say, "So you're that guy."

And that opens up something in relation to self-perception in general. One of the things that can create the fiercest arguments is when you push somebody on their self-perception. If I define myself as an amazing speaker on stage and you come and tell me I sucked, then you are hitting me where it hurts.

Aggelos: It becomes a personal attack.

Steen: Yeah, exactly. And that's why I try to teach my kids too — if somebody says, "You're always so lazy, you're always doing this or that," they shouldn't take it personally because it's just what the other people have interpreted. It doesn't define them. It's not a personal attack. Very often it's a symptom of something they might be doing that can be perceived that way, but it's just the other person's perception. So they need to consider: if that's the vibe I'm giving out, if you see me as lazy — why would you see me as lazy when I don't feel lazy?

Aggelos: I want to move to my third question, which was about loneliness and the times that we might feel lonely even if we are around people. I don't know if you relate to that at all.

Steen: I think so. My co-founder kept coming back to it, saying that one of my problems was that I was too far ahead in relation to where the market was. So feeling alone with your thoughts — he was just flattering me maybe, but it was something he brought up on a recurring basis: "This is not now, this is something the market is ready for in three to five years, if it continues in that direction."

Being somewhere where your curiosity pushes you — you skip like a stone, one thing takes the next and you're just jumping forward, and you're standing in a situation where you can really clearly see something that nobody else necessarily can see. You can feel really alone there.

And then the other side of that — which has also been a kind of strength — has been in relation to commercial thinking. Being able to look at something and say, okay, this is a business, this is a business process — what is the commercial objective and how can we support that? The best example: I was teaching a class in Sweden in commercial analytics, and the first thing I did on the first day was show them a website and say, okay, what is their business? And having them reflect on that. Well, it's an e-com website, they sell stuff. Yeah, but it's actually more complicated than that. What is their business? And trying to see how far you had to push people for them to understand there was a business behind it at all.

Because the reason why companies hire anybody is because they think the business will be better with them in it. If I have two candidates, I would hire you if I think you're better for the business than the other person. So it's not necessarily about your qualifications — you could have done 10,000 things. But if the other person has half the experience but the skill set that matches the business needs better, then they would be the better candidate.

Getting people to see that — so when you get rejected from a job, it's not you. When they say we went with somebody else that we felt fit better, that is the ultimate truth. Either you didn't sell the value you would bring to the business well enough, or you simply weren't the right candidate. So it's not about diminishing you. It's about communicating what's there.

These are bigger skills. And feeling alone in relation to them... but also, and this is related to work — money and finances. Being in a situation where we have 40 people, we have 10 customers who have not paid their bill yet, so technically we have all the money — but it's not there, and now we have to pay salaries. I could talk to my co-founder, but we had already kind of agreed on that situation. So feeling alone in that situation — you cannot go to the employee and explain. You can just work around it and make sure they get their salary. That's an extreme sense of loneliness. And sometimes also making tough decisions.

But I actually feel that's also one of the things I get to talk to people about now. If you're a manager in a lot of organizations, you have your area of responsibility, but you don't necessarily have somebody to talk to about the decisions. You sit as a CMO having to decide the marketing strategy for next year. You cannot really go to your people because they expect you to already know and be on top of it. And you cannot go up in the organization because they expect you to be on top of it, they don't care, and they don't have the knowledge sphere. So you're sitting there alone with nobody to talk to.

Being that person who comes in and says, "Hey, I can come and spar with you — you don't have to be alone with this" — I think that's a lot of loneliness sitting with decision-making in organizations that you don't really think about. Because you think that when you move up, you will have a network, you might have friends — but they won't necessarily spend their time deciding what you're supposed to do with your job. And they will also in a lot of cases assume that you're on top of it — that if you're the CEO of the company, you became the CEO because you know. But very often you don't. So who can you talk to?

Aggelos: That's very true. Very often you don't. In my network at least, nine out of ten people — or even more — don't know what they're doing. Even the most confident founders, people you wouldn't even imagine feel as insecure as everyone. No one knows what they're doing.

Steen: Yeah. And we live in a time where we have to signal that we know what we're doing. We cannot show weakness, because then we apparently are not the right one for the job. So the one who's best at faking it till they make it gets on top.

Aggelos: But when a lot of people fake it till they make it, I don't know about you, but to me it starts becoming a little bit of noise.

Steen: Yeah, I agree — it ties back to why would people rather have an AI than a person as a manager? Because the manager doesn't know what they're doing really. And especially in human conversation, it gets complicated and messy — we have relations and other agendas and things. You're accountable to your boss, but your boss is accountable to his boss. So he cannot just promise you a raise because you need it. He has to be accountable to the business first.

Aggelos: I think the word here that we are both looking for is trust.

Steen: Yeah.

Aggelos: There is a trust issue at the moment. At least the AI won't try to fool me. It might hurt my feelings, but it will be transparent.

Since we're talking about the network of people around you while you are running a business — is there someone that you can be completely honest, completely transparent, completely vulnerable with about your thoughts, your doubts, your fears?

Steen: I would say there are two levels to it. One is — because I was aware of this situation and not wanting to be alone — I have managed to establish a good extended network of professional relations to go in and discuss professional issues. Is this the right decision? Is this the right platform? How do we handle this in relations to people? That's all the outward facing things from my role. So yes, I had good relations with people and was opening up and having conversations with them. But on the other level — the personal level, the imposter syndrome and all the other things that you get — I think there were only a few people I actually felt I could open up on that level.

You could show everybody the turtle shell because they could technically see that anyway. But inside the shell was me — the actual turtle — that only very few people saw. It's the two different roles we have: our own uncertainties inside as people, and the activities we do on the outside that we can discuss and justify. The turtle image is quite precise — everybody could see the shell, but very few got invited inside.

Aggelos: I mean, few people is a lot compared to the average — in most cases it's none. What I hear frequently from founders or high performers is that they have people around them, but each of them doesn't necessarily get it. You might have your family close, but they don't really get what you're going through. If you're lucky to have them, you might have your partner, your husband, your wife — but there is always a dynamic of "I have to prove something, I can't be fully vulnerable." And even if there isn't that dynamic, they don't always get you. They might offer some words of affirmation, some support — but it's not really landing. That's what I hear a lot from people like you. Do you relate at all with that?

Steen: Yeah. I can relate to it, especially through time. The first company I started, I was very much alone with everything. Badly the way I left the company and everything — that was 20 years ago. I was very alone with that, but there were a lot of emotions coming out on the other side and I had to have a lot of conversations with people around the process to tackle it.

I was sitting alone with this situation, but then I had to process it, I had to open up. And I think it meant that when I started the second company, a lot of the people I had opened up to around the first process — I had those people along the way. Because you have to mess up once really bad to have good people in your corner. And that has helped me a lot in the second process.

But it's also that sometimes I feel you need people to not just say yes, but also push. Very often it's like the AI saying, "Sure, okay" — they can completely understand you and they know where you're coming from, they know what you've been through, but maybe sometimes you also need someone to say, "Pull yourself together and do this now, move on, do something." And I've probably been too self-confident to allow people to do that. It's my mistake of not letting them in. Back to the self-perception saying, "No, you can pat me on the back, but I got this." When technically, looking back, I say, "Well, dude, I didn't have it. Why didn't you tell me? I thought I got it, but no, I didn't."

Aggelos: This is something I experienced firsthand during the years of my consulting in the past. Most of the founders I was working with — aside from the fact that they were quite volatile as people, which is totally understandable, being a founder, a CEO is an extremely stressful situation — what I remember from this time was this craving for trust. And this trust was in lots of cases built by challenge. The more you would challenge them, the more they would trust you, because they would trust your intention in the process — okay, you are not trying to sugarcoat me, you're trying to help me. So after some challenging, some healthy sparring, they would sort of submit because they would trust, and they would be more vulnerable. That's close to what you're saying, but you also said that you didn't feel you needed that at this stage.

Steen: So this was the self-perception that I felt — I was in control of the situation. Sure, I wanted to talk about it, but I felt it was up to me to do something. And I probably had the illusion that I had more control in the situation than I actually had.

But it's this wonderful book, Leadership and Self-Deception, saying that a lot about our role is about looking through the cells of self-deception and the lies we tell ourselves — who we think we are is not necessarily who we are. And that clarity often just comes afterwards. It's not like we sit in the bathtub and then have an epiphany saying, "My God, I'm completely wrong here." Something has to break normally to make it appear, or you need to have conversations that push you in that direction saying, "Okay, I'm wrong."

It's such a fine balance — if somebody pushes you too hard, you might go defensive instead, and push them away. Because change is damn inconvenient. Changing the way we live our lives and what we do every day, it's just bothersome. People are like water — we take the path of least resistance. And the path of least resistance is normally the path we took yesterday and the day before. Suddenly trying to do something different is hard and takes a lot of energy.

Aggelos: From our conversation so far, I feel like you have undergone stages of change. You mentioned leaving behind the identity of the marketer and the salesman, and now you are more towards connecting with people. You also mentioned vulnerability and that you became more open across the years. I don't know about your family or how you were raised, but I'm very curious — have you decoded what made you who you are? Because you seem like a person who is a CEO but under transition at the moment. What made you the person that was self-confident but not really vulnerable at the beginning? Salesperson, marketing person — but then a transition towards something else. Who expected things from you?

Steen: It is getting personal, but it's fine. When I grew up, I was always surprised in my school that I was by far the student with the most degrees of freedom. When we had play dates, all my classmates were supposed to call their parents and ask if they could have a play date after school, and they would get a yes or no — more often than not, a no. They were expected to come home and do certain stuff. And for me, I got a degree of freedom that was extreme compared to them, because I just had to let my parents know where I was and then be home for dinner.

It seems like a strong thing, but on the other hand it's also a non-committed thing. A very personal thing — I remember, I don't know how old I was, we had gone on a vacation somewhere in Germany. And the last night before we were going home, I woke up because I was afraid they would forget me. And so it's the hindsight of freedom in the sense that you don't feel the care.

It continued until I started high school, when I got a friend there, a female friend, whose parents were both teachers. They took me under their wing as well. So it was actually her and her family that had the expectations of me and pushed me forward more than my own parents. My own parents, they loved me and accepted me as I was, and there were no expectations of me doing anything. They just wanted me to do whatever I wanted, and that was fine. But it was also a low investment from their side.

So we lived together and they were my parents, but they didn't really shape me. They let me shape myself. And then I met her and her family helped shape me. Her expectations were what pushed me to start studying. And then I just came out into working, and having roles in different work where I naturally progressed and was a success. It gave me the momentum to move on, and the combination of what we talked about — the curiosity and the playfulness — pushing some innovation even when I was very low in the hierarchy and not a powerful person in the organization, but still coming up with some significant ideas.

And honestly, even though I left the first consultancy I started in a bad way, the core idea of the business was mine. Those were thoughts I had created, that I had shared with the other guys in relation to how to think. They were just really good at putting it on formula. So at some point they could see they would be better off if I wasn't there — they could start delivering on it. And that gave me the momentum to move on and keep building and keep growing, knowing that I actually really provided value.

And I think it came back even stronger when I started doing presentations. I remember I was sitting in London at one point, I had done a presentation in a community, and a guy comes over to me saying, "Hey, you don't know me, but I've been watching your presentation for the last couple of years you've been here. And I just want to say, I don't know how many times you have saved my ass."

Aggelos: That's very sweet.

Steen: So you get this confirmation saying, okay, I am making a difference. And by making this difference and being out there and getting the acknowledgement, it becomes bigger than just being a salesperson or marketing person. It's more than a role. It becomes, I don't know, an honorary title, something. But also supporting the value of being authentic and being able to shed the sales and marketing and leave it behind and saying, I don't need that. The value is in the authentic communication and being me.

Aggelos: Looking in the past from your current maturity and experience, what do you think the child that you mentioned — the child that just had to go home for dinner — what do you think that child needed emotionally back then?

Steen: It needed the acknowledgement. And you can see it's probably still there to some extent — the third party acknowledgement, other people patting me on the back and saying I'm there and I'm super cool and I'm good at what I do. That means something. It's a support system that works for me, getting out there and getting the acknowledgement that maybe, as a kid, I didn't get at home. When I came home and showed my grades, it was like, "OK, as long as you're not failing, then it's good enough." The standard was mediocre. As long as I wasn't worse than that, it was good enough. So the recognition from other people — I think that has been a strong part of the growth and the momentum.

But it has also locked me in situations — by getting recognition from some people, it has kept me in situations longer than I should have stayed. The agency that I left — I have been considering leaving for a couple of years. What took me so long? Why does it take me so long to actually do it? Why did I feel that I had it under control? Why didn't I move on before?

I think it's just getting the pat on the back and the acknowledgement — and the agency got awarded best analytics house in Denmark 10 years in a row. It's very good for your ego. But it's not very healthy for your soul.

Aggelos: It builds dependence.

Steen: Yeah, it gives some level of dependence — being there, being afraid to really move on. Because then what? And I feel that was the big release and the freedom I felt by stepping out and just being me and saying, OK, this is me being me.

Aggelos: Have you experienced any deprivation of this validation from the external environment at any point? The reason I'm asking is because typically people that come to such realizations like the ones that you shared today, they have seen the other side of the coin.

Steen: Maybe the threat of it — in the sense that a large part of my validation has been the community and the external circles. At one point we had another guy coming in to be CEO instead of my co-founder. And one of the things he said was he wanted to stop doing events and stop being external. Where I said, well, that's not going to happen because it's a significant part of who I am. I will move that out of the company if you don't want to support it, but I will not stop doing it. I guess that's the closest thing — and when we talk about it here now, the feeling in that situation was some degree of fear of losing the circle of affirmation.

Aggelos: That moves me to the last question. This has been a mind-blowing conversation and thank you so much for being so open. If you could speak to yourself in the past — which part of the past would you choose? The beginning of your career? Later? The childhood that you mentioned? What would you tell this person?

Steen: A couple of things. The first thing is get the paperwork in order. It's really lame, but making sure that your agreements are on paper and you have the terms and conditions of stuff, because otherwise you might paint yourself in a corner where you're not making the decisions that you want because you don't really know what your position is.

Quit while you're ahead. Don't stay until somebody else says it's time for change, when you know it's time for change. Be aware that change is good.

And then — let the turtle out of the shell. Let the turtle express something in relation to what is keeping it in its shell. Knowing that it's vulnerable, but it's not going to be any better if you never let it out. Speaking up from that perspective is something that should have been done.

And basically get on stage earlier — getting those affirmations and knowing that you're good enough. But even if I travel back in time and told myself that I'm good enough, I probably wouldn't believe it. So the real thing is helping establish that support system to actually build the room to be the authentic me.

Aggelos: Thank you. That's very strong.