Episode 165: The four career types: which one are you? – with Dan Freehling of Contempus Leadership

There are many different aspects to having a successful career.  But how do you know you’re on the right track in your career, and that you’re not limiting your own career progression?

Dan Freehling is a career coach specialising in working with top millennial leaders seeking to develop their leadership pipeline.

He explains the different career types there are, the common career pitfalls people face, and how to uncover the category your career falls into

Today’s guest

Dan Freehling of Contempus Leadership

Website: Contempus Leadership

Email: Contempus Leadership

Dan Freehling is a coach specialising in working with top millennial leaders, the author of The Career Design Map and the founder of Contempus Leadership LLC.

He partners with fellow rising leaders directly and through forward-looking organisations seeking to develop their leadership pipeline.

Prior to founding Contempus Leadership, Dan led highly rated, multimillion-dollar organisational and leadership development contracts and oversaw a flagship worldwide coaching program.  He has personally coached dozens of purpose-driven leaders at the manager, director and vice-president levels across sectors.

Dan holds an MA in Organizational Leadership & Learning from the George Washington University, an MBA from the University of Massachusetts Amherst and a BA in International Relations and Political Science from Boston University.

What you’ll learn in this episode

  • [1:26] What a ‘leadership pipeline’ is.
  • [3:30] The main challenges of transitioning to a full-time coach.
  • [4:17] The four different meaningful career types: contributor, go-getter, expert and executive.
  • [8:43] How to identify the strengths and weaknesses in your career.
  • [11:02] The danger of falling off a career path.
  • [15:17] The difference between an expert and an executive.
  • [17:33] The transition from a go-getter to an executive.
  • [20:47] The different aspects of being successful in the workplace.
  • [22:59] How to identify what you really want from your work.
  • [24:35] How to succeed in the modern career landscape.
  • [25:45] How flexible the working landscape is.
  • [27:25] How career progression works in the modern world.
  • [31:00] Ways to make your CV stand out for a leadership position.
  • [33:28] The danger of invisibility, arrogance, disengagement and burnout.
  • [37:36] How to know if you’re too arrogant and the negative impacts this can have.
  • [39:30] Exercises to keep your career on track.

Resources mentioned in this episode

Please note that some of these are affiliate links and we may get a commission in the event that you make a purchase.  This helps us to cover our expenses and is at no additional cost to you.

Episode 165: The four career types: which one are you? - with Dan Freehling of Contempus Leadership

Jeremy Cline 0:00
Where on your career journey are you? And where would you like to get to? Do you want to be the go-to person that everyone comes to if they've got questions about a particular area in which you've got subject expertise? Or do you want to be the person who's running the whole ship? That's what we're going to be talking about in this week's episode. I'm Jeremy Cline, and this is Change Work Life.

Jeremy Cline 0:36
Hello, and welcome to Change Work Life, the podcast that's all about beating the Sunday evening blues and enjoying Mondays again. If you want to know how you can enjoy a more satisfying and fulfilling working life, you're in the right place. When it comes to your career, what type of person are you? Are you the one with expert knowledge in your specialist area? Or are you someone who puts the team together and helps them achieve results? How would you categorise yourself? Does it even matter? These are the questions we're going to be exploring today. And to help us do that, I'm joined by Dan Freehling. Dan is the author of The Career Design Map, and a coach to top millennial leaders seeking to develop their leadership pipeline. Dan, welcome to the show.

Dan Freehling 1:19
Thanks for having me, Jeremy.

Jeremy Cline 1:20
So, I just used the term leadership pipeline, which is quite an interesting one. Why don't you expand for us a bit on what that means?

Dan Freehling 1:28
Yeah, absolutely. So, I basically work with two audiences. So, one is that top millennial leaders as individual clients, so they'll hire me externally to their organisation and work with me one on one. Another audience that I work with is actually partnering with organisational leaders themselves who are looking to develop, whatever the term is, their leadership pipeline, their leadership bench, essentially, their group of high potential rising leaders, who they view as the future executives for their organisation. So, basically, those two audiences make up my coaching practice.

Jeremy Cline 2:03
And I always get confused between Gen Xers, Gen Y's, millennials, all that kind of thing. So, when you talk about millennials, what sort of age group are we talking about?

Dan Freehling 2:12
Yeah, so depending on the definition, they're generally late 20s to early 40s now. So, I know a lot of people still have in their head that millennials equals college students or teenagers or something. But they're now squarely in that mid-career leader group. And I think that's an important distinction just to keep in mind when talking about working with them.

Jeremy Cline 2:33
And talking briefly about you, so you started coaching full time in May this year, 2023. So, what were you doing before then?

Dan Freehling 2:43
Yeah, so I was working in a variety of leadership development projects, essentially. So, number of roles, working with federal clients on professional development, organisational development, leadership development. In 2016, as part of my role on a contract for a federal client in the US, I was overseeing our leadership coaching programme, and I started to see, wow, this is really something that's working, that people are really engaging with, that's moving the needle on results, and started to look more seriously into it, started volunteering as a coach a few years ago, in 2020, with some first generation college students in the Bronx, started getting my coaching, training and coaching professionally on the side for a couple of years. And then, yeah, this past May, I have finally made the leap full-time into the practice.

Jeremy Cline 3:29
And how's that transition been in these early days?

Dan Freehling 3:33
It's been really great. It's exciting to make that shift of working within an organisation to working externally. So, I've been really loving it so far. And it's been quite exciting.

Jeremy Cline 3:43
What so far has been the biggest challenge?

Dan Freehling 3:45
I think it's that shift of having work to do automatically fed to you, basically, and then you're deciding how do I go about this and how do I organise the team to take this work on, to having to switch to putting yourself out there generating new business. It's a fundamental shift, I think, in how I've been operating. So, that's been both challenging and exciting at the same time.

Jeremy Cline 4:08
So, in your work, you talk about the meaningful four career types. Can you describe those to us?

Dan Freehling 4:17
Yeah. So, basically, picture a quadrant, one of those two-by-two consulting matrices, and the axes are career advancement, that's the X axis. Basically, that's what I define as confidence in yourself and from relevant to others. So, this is the idea of how do I advance in my career, it's both by putting myself out there for opportunities, but also in convincing others that I'm ready for these opportunities, that I'm going to be adding value to the organisation, that this is the right position to put me in. The Y axis is leadership. So, that's enabling people to advance a common purpose. And there's an interplay between these two that results in these four meaningful career types. So, when you're relatively low on career advancement, and relatively low on leadership, that's one that's called the Contributor. You're doing enough, you show up, you contribute to the team, you work reasonably hard, but you have other things in life that are your focus: your family, your friends, your hobbies. Work is not your primary focus, you're working to live, not living to work. Further up on leadership from that is one called Go-Getter. So, that's when you're still at the early stages of career advancement, but your leadership is high. So, you're going above and beyond, you're really taking on projects that are important for the organisation, for the team. And that's an interesting transitional stage, which we can get into further on, but you basically have that choice to make as a Go-Getter of, do I want to go into these other two meaningful career types. So, further up on career advancement, but still relatively low on leadership is one called Expert. So, that's when you have a really specialised skill set, and you're highly compensated, you're highly respected, but you're still more of an individual contributor than a true leader, where you're working through others. And then, that final pinnacle of the map is called Executive. And that's when you're both relatively advanced in your career, and in your leadership, and you're both highly respected, earning a good living, but you're also working through other people to achieve common objectives and goals. So, that's the Executive quadrant.

Jeremy Cline 6:38
Where did this framework come from?

Dan Freehling 6:40
Yeah, so I've been in leadership development for a number of years now. And then also, during that time, I got an MBA, I studied organisational leadership and learning and got a master's in that as well. So, there's a lot of this academic and theoretical backgrounds, that is really tough to get across to people in a practical way that's actually digestible. So, I've written a number of papers and conducted a lot of independent research and shared this out with people. And it's just really difficult to translate these deeper academic ideas to a practical real-world situation, where real leaders are going to use them. And this is something that I've worked on for quite a while to condense a lot of the modern leadership approaches, theories, frameworks and practical experience in working with clients and working in leadership development and organisations into something that's super digestible and approachable but gives people a strategic framework to use, to navigate a really rapidly changing world in terms of career and leadership.

Jeremy Cline 7:44
Do you find that everyone fits neatly into one of these categories? Or is it a bit more of a Venn diagram?

Dan Freehling 7:50
Yeah, it's definitely even a spectrum a lot of the time. So, there'll be times when people are sort of between categories, or in different aspects of their life, they're in different ones. I'm much less concerned with people nearly falling into them, than I am with it being just a useful tool to help you see where you are currently, where you want to go. If you look at it, and you say, 'I really don't fall neatly into one of these', then that's fine. At least it stokes the conversation, and you can think about it and act strategically. So, yeah, definitely not something that's supposed to be a rigid, one-size-fits-all approach.

Jeremy Cline 8:26
So, it sounds like a relatively straightforward framework. But I'm interested to know in practice, when someone comes to you, how easy it is for that person to identify where they fit on this quadrant.

Dan Freehling 8:43
Yeah, so I think, when you really sit down and think about it, you can generally identify where you fit. I think the challenge is one of these dangerous seas. So, on the outside of this, these four dangerous seas, I call them. So, when you're too low on leadership, you're in disengagement; when you're too high, you're in burnout. When you're too low on career advancement, you're in invisibility; when you're too high, you're in what I call arrogance. Those are where people are very reluctant to put themselves. It's an honest conversation that needs to be had a lot of the time of, are you actually sitting in one of these areas, and how can you move back into one of the meaningful four. That's generally a much trickier conversation. People generally know if they're an expert in something or they're go-getter, they're early in their career, and they're trying to prove themselves. But when you get into those dangerous seas, is when it gets challenging.

Jeremy Cline 9:40
Have you had anyone who's been through this exercise and has been a bit disappointed with the result?

Dan Freehling 9:44
I have, and it's a part of coaching that is the harder part, where it's not the 'Rah-rah, I'm going to pump you up. We're going to be really excited about where you are right now and where you want to be going.' And it's the start of an honest self-assessment. So, I've had people that have landed in arrogance, in particular, which is one where you're too high on career advancement, basically, you're too self-confident, and those around you are too complementary to what you want to be doing, and nobody's giving you honest feedback. And I've had people that are initially upset with that and taken aback by that. And they've actually come back to me, on two occasions now, and said, 'You know, I didn't realise that that's where I was, or that's where I wanted to go, and recognising that was so helpful in humbling myself and getting a better understanding of what I actually wanted, rather than I want to just advance, I want to make more money, I want to get that promotion automatically, and it's why do you want to do that, and what do you really want to be doing in the world, what impact you want to be making.'

Jeremy Cline 10:56
It nicely leads on to the next question I had about whether there is kind of a place for someone in each of these four quadrants, and it's kind of a place where they can sit. I mean, you talked about a Contributor, potentially being someone who's quite early in their career and early in their leadership journey, which kind of almost implies that they should be aspiring to move up and move along. But is Contributor somewhere where someone can feel comfortable about sitting?

Dan Freehling 11:33
It's a really spot on question. So, I like to relate it to, instead of thinking of it as like career and leadership, perhaps think of it as a similar concept for diet and exercise. So, something where you don't necessarily have to be the marathon runner who eats the perfect diet to be a generally functional person in society. I'm definitely not. That would be kind of akin to being in that Executive quadrant, of having like the best of both of these, these are really something you're focused on. But there's a world that most people live in, where maybe diet and exercise are not the most important things in their life, but you still have to be at a somewhat reasonable place, where you're not falling into these dangerous seas of not moving or eating way too much or eating really unhealthy foods. So, it's really a choice of where you want to go and how important that is compared to other things. So, to the Contributor example, a lot of people will prioritise other things in their life, and that's 100% great, if that's what they really want to be doing. The trick is to make sure that you're still doing enough where you're actually in the Contributor quadrant, and you're not falling into that disengagement or invisibility, because that's when people get laid off, that's a really dangerous place to be when you're not viewed as adding any value at all.

Jeremy Cline 12:56
And it sounds like running to stay still.

Dan Freehling 12:58
How so?

Jeremy Cline 12:59
You're kind of in that space, and if you don't keep going, keep being active, if you like, then you risk just drifting further and further backwards into one of these dangerous seas that you talk about.

Dan Freehling 13:12
Totally agreed. And it's a matter of doing enough maintenance and upkeep on your career and on your leadership contributions, where you don't put yourself in danger, you don't put your career in danger, you don't lose your focus on meaning and purpose to such a degree that you fall off. And I think that's something that does happen quite often with people. They'll let their skills fall behind, they'll let their commitment to the organisation fall way behind, they're doing something, but they don't have any passion that they're doing it, they're letting their skills lag. And that's just a dangerous spot to be in. So, I think it facilitates an honest conversation in that regard, where you can't just coast and expect everything to be completely great in your life and career. But you also don't necessarily have to be trying to be a Fortune 500 CEO to have a successful and meaningful and fulfilling life and career as well.

Jeremy Cline 14:09
Talk to me a bit about this kind of division between Expert and Go-Getter and how they converge on Executive. I'm thinking about my background in law firms, then you would typically get the rainmakers, who I suppose you'd call the go-getters, the ones who get in the external business. And then, you'd get those who were the real technicians, I mean, the brains the size of a planet, if you had this really thorny technical issue that you just couldn't work through, then you'd go and talk to them about it. And yes, there were people who did both, but there was usually a bias towards one or towards the other. I mean, does the Executive quadrant naturally arise when you get the combination of those two? Because I guess I'd have thought that, either they'd be more on the Go-Getter side, or they'd be this sort of different breed of person where, actually, they would kind of help those people, the rainmakers and the technicians to get the most out of themselves.

Dan Freehling 15:15
Yeah, so there's a shift that comes in when somebody goes from being that expert, the highly specialised technician in the law example, to being someone who's running the firm, or as a partner, or something like that, where it's kind of higher level of leadership. So, I think that's a transitionary state for that person where they have to go from, I'm an expert in the minutiae of this particular type of law, and I'm a world-class expert in this exact area, to, okay, now, part of my job is thinking about the firm's strategy, and how are we positioning ourselves, and how are we growing our internal talent, and how are we working together as teams, and all of these other leadership areas are what bring someone up from that Expert to a true Executive. And I think there's a tendency for people to keep doing what has worked so far. So, in the example of that highly specialised technician, what's worked for them so far has been, I'm going to become really skilful at knowing every element of this type of legal area, and I'm going to know all the nuances of it, and I'm going to keep researching it and staying up on it and knowing who's involved in it, to get to being a true leader. That person no longer has to keep becoming increasingly expert at the minutiae of this thing. They need to shift their focus instead to how am I enabling the people in this firm to advance our common mission. That's a fundamental shift that's tough for people to make when everything so far has been going in that expert direction, and they have to shift gears if they really want to be the executive. Part of this map, though, is that there's nothing wrong with staying in that highly specialised technician space. You can make a great living, you can make a lot of money in it, you can be really well respected. But if you do want to become a true leader, that's a different skill set, and it's a different area you need to flex.

Jeremy Cline 17:26
Can you talk about the transition from Go-Getter to Executive in similar terms, if you're going up that axis?

Dan Freehling 17:33
Yeah, so Go-Getter to Executive would be less of the rainmaker. The rainmaker, in my mind, is more of a person who would be in that Expert quadrant, but their expert skill is in business development, basically. And that's a really distinct skill; that's like sales ability a lot of the time, it's quite a lucrative skill that you can do that well. But Go-Getter is more of that, think of like an early-stage associate or something in a law firm, who's really trying to go above and beyond, do things that benefit their team, prove themselves in the organisation, and they're really trying to make a name for themselves in the firm. And that's a great place to be, but it is temporary. So, it's really tough to be permanently someone who's just going above and beyond all the time and putting yourself out there to make a name for yourself. There comes a point when that person has to make a choice of, if they want to continue to advance, do they want to go that expert route, do they want to become an expert salesperson, the rainmaker, do they want to become an expert technician, or are they looking to stay in that above and beyond, putting the firm first leadership position and shift over to Executive. And a lot of the time, people will go in multiple directions on this. So, they might say, 'Okay, now it's time for me to become an expert on this particular nuance of copyright law.' And after they do that, then they'll say, 'Okay, now it's time for me to shift to becoming an organisational leader.' And they'll go up to Executive, but you can also go from Go-Getter straight across to Executive, in the sense that you might not be the best actual lawyer in the organisation, but your skill set is in management and leadership, and that's what's valued to get to that Executive quadrant.

Jeremy Cline 19:27
Okay, so actually, it's more like, you've got this box with the four quadrants, and it's much more fluid, bouncing around between the boxes, and possibly not bouncing back towards Contributor, but possibly bouncing between Go-Getter and Expert, and possibly ending up in the Executive quadrant.

Dan Freehling 19:48
That's exactly right. And a lot of this is in understanding that there's seasons in life and career, and that sometimes you might be starting a family, and you might have been in Go-Getter, but right now, your focus is on the family, and you want to purposely go back to Contributor, where you're doing enough to stay there, but your focus is elsewhere, your attention is elsewhere. And later on, you might want to pursue expertise in something, and you go over to there. And later on, you might want to go and leave the whole firm and become an executive. So, it's definitely fluid, and you can strategically choose where you want to go next along this journey.

Jeremy Cline 20:25
And a point that struck me was how you said that, when I think of expert, I think of technical experts, so it could be expert in a particular area of law, or maybe if you're in engineering, then you are a particular technical expert on some aspect of engineering. But I think what you're saying is that technical expertise is just one aspect, but there could be other aspects, including sales, customer care, that kind of thing.

Dan Freehling 20:56
That's exactly right. It's really that confidence from those around you and your ability to add value. And that can take a number of forms, and it can be exactly that, it can be communications, it can be sales, it can be customer experience, it can be any number of things that don't necessarily have to be the technical expertise in what the firm does.

Jeremy Cline 21:17
Could it be leadership?

Dan Freehling 21:18
So, that's the interesting part of this, where the leadership aspect of it is fundamentally not about building your own confidence in those around you; it's about the opposite of that. It's about enabling those around you to achieve common goals. And oftentimes, people conflate the two, but they're sort of fundamentally different aspects of how you are in the world. And that's why I have them as the two axes there. So, a lot of the time, people will just think, the way to become an excellent leader is to just know everything there is to know about leadership and to have all of these angles. And that's definitely a part of it, that's definitely a part of that career advancement and how you get over to there. Then, there's that fundamentally different element of it, where it's not about you, it's about working through others and working with others. And it's a big shift for people to make, especially in a technical mindset, to get to that, it's not about me.

Jeremy Cline 22:24
Presumably there are people who kind of think that what they should be doing is going for the Executive quadrant. But when you dig in a little bit deeper, it doesn't necessarily completely sit all fours with who that person is, their strengths, their values, and that kind of thing. What sort of conversations do you have for that person?

Dan Freehling 22:47
That's exactly right. And that's a big benefit of using a framework like this, is in providing some way to structure that kind of a conversation. So, you go through your career, exactly like you said, and a lot of the time, the Executive is the best thing you can do. If you're ambitious and want to make a difference, you should be an executive. And people just automatically want this. I think there's a real maturity and a real strategic skill to being able to sit back and say, 'What do I actually want? What do I want in This moment? What do I want longer term?' And what you'll often find is, people will come in to a coaching engagement, and they'll just automatically think, say they're at a school, they'll automatically think, 'Okay, I want to be the principal, because that's the best thing.' And when you really dig into it, they want to be outstanding, world-class teacher. They want to be really, really digging into that subject area. Similar for a law firm, somebody might say, 'I want to be running the firm someday', automatically, and that might not be what they want to do. And that's the beauty of coaching, is that you can then have those conversations with people and help them to figure out what they really want to do, not what they think they should do. And then, once you have that decision made, what strategically do you have to do to position yourself to get there? It's a really helpful tool in enabling those kinds of conversations.

Jeremy Cline 24:22
Is it a decision that you need to make? Or is it something that you can kind of play around with bounce around with? Is it something that you can keep your options open on?

Dan Freehling 24:35
So, in my mind, it's both. And what I find is really critical to succeeding in the modern career and business landscape is this strange combination of both being highly adaptable, and highly unique. If you can figure out how to do both at the same time, then you are extremely well positioned. So, in this case, I work with a lot of fellow millennial clients. But strangely, they're actually pretty adaptable, automatically. They've just had a lot of life situations, and coming into the job market at a particular time, and sort of understanding the way that the career market is going, where they're very onboard with being super flexible and adaptable. And now, they're wondering, 'How do I do that and do something that's unique, that's personal, that's purposeful to me?' And marrying the two is where the real trick is here.

Jeremy Cline 25:39
So, these people are flexible and adaptable. Is the world of employment on the other side equally as flexible and adaptable? So, if somebody, say, wants to go down an Expert route, but then once the option to pivot to either Go-Getter or even leadership, I mean, is that realistic, or does this start to create a situation where you've got a CV, and you just kind of can't see the thread rolling through, and it kind of seems like a rather crooked path?

Dan Freehling 26:17
I do think that being adaptable and flexible like that is critical. I think a lot of times people will shoehorn themselves into, you know, oh, I've done this kind of thing for so long, there's no way I could ever do something different. And I think the way that the world is going now, not only is that an option, that's a requirement more and more, being able to pivot continuously, understand the changes that are happening, and flex and adapt. Yeah, it's just not only something that they can do, it's something that everyone increasingly needs to do and will need to do more and more.

Jeremy Cline 26:54
So, is there something to be said then for perhaps not having quite as much strategy when thinking about your own career? So, rather than going, 'This is where I'm aiming for, and so to get there, I'm going to do da-da-da-da.' Maybe you instead kind of go, 'Well, the thing I'd like to do early on is this, I've kind of got my eye on maybe doing this for the future, but I'm not going to get hung up on that, so let's just start with what I'd like to do now.'

Dan Freehling 27:21
That's exactly the right approach. And that's so much of why I made this model the way that it is. So, I think the traditional approach to career mapping is, okay, by the end of my career, I want to be this particular kind of position. And to get there, I'm going to take this university track, and then I'm going to be in this type of job, and then I'm going to get promoted to this kind of job, and then promoted to this kind of job, and then I'm going to reach this endpoint. And I think that's just fundamentally the wrong way to look at it as we're moving out of this industrial era mindset. And the right way to look at it is having strategic direction that you can be pursuing. But it has to be pulled back; it can't be so hung up on every little minutia of job title, or his particular programme, or anything like that. It has to be that broader direction. And then, along the way, you have to continuously revisit, adapt, revise, change, based on your changing circumstances, based on the new knowledge that you've gained. This is just one way to help do that, in a way that's not, okay, there's nothing you can do at all, you just have to let the wind take you where it may, it's instead saying you can pursue strategic direction, and you have to be flexible at the same time.

Jeremy Cline 28:44
I've got in mind the person who thinks that the decisions they make now are going to either rule in or rule out stuff in the future. And so, it's much more of a rigid, rather than flexible approach. I wonder if you've got an example of someone who can kind of demonstrate to this person that, actually, you can be more flexible and still get to this different position, even if that's not where you end up. So, someone who decides that they're going to go for more of an expert position, but then that hasn't necessarily ruled out for them leadership, taking on team leadership roles.

Dan Freehling 29:28
Yeah, so I'll use my wife's example, it's an easy one that doesn't violate any confidentiality. So, she was in education, and she was an excellent teacher, and she was an English teacher. And she was thinking for quite a while that what she wanted to do forever was to remain as an English teacher and to get increasingly more expert at that. And then, opportunities come up, as they do in life, and she was able to join a new school that was starting. And she stepped up into a leadership role as an assistant principal. And that's something that she's really thrived at, and it was something that she didn't think she ever wanted to do. She never wanted to be in administration. And she's now in that. And then, what the future holds is still up in the air. So, for her, she's probably going to stay as assistant principal for the long term, but there's many people in education who then pivot out and go into some sort of related educational consulting, or leadership development in general, outside of that, or even leave education entirely and go into another field. It's something where, I think, you have to just keep your options open as to what the future might hold and be able to grow and pivot in those different directions.

Jeremy Cline 30:43
What was in your wife's CV that meant that she was able to be considered for an assistant principal role, rather than kind of being pigeonholed in this sort of like, you're just going to be a good, and then a really good, and then an absolutely outstanding teacher forever?

Dan Freehling 31:01
Yeah, I think this is a really critical point. So, she had taken on some progressive leadership roles and was doing, I forget exactly what it was, but something like a department chair or something like that. So, there's always those opportunities where you incrementally grow your leadership capabilities. But I think the thing now is being ready to take on opportunities as they come and raise your hand for them. And you might not know exactly where they're going to go, but being ready to do that, and not pigeonholing yourself into, I'm only able to do this, and the only way that I can do something different is if I have passed some sort of industrial era test on, check, I've passed the leadership test, and now I can become a leader. It's much less of that and much more of being willing to shift and put your team before yourself and put your organisation before yourself and really take on those stretch opportunities that allow that.

Jeremy Cline 32:05
And I think a critical point that you've made there is that you might, say, apply for and start working as in some kind of a, air quotes, 'technical role'. But chances are that, even though it's not in the job description, maybe not what you were expecting, there's going to be opportunity there that you can use, that you can, as you say, put your hand up in order to demonstrate more leadership skills and abilities.

Dan Freehling 32:36
I think that's exactly right. There's two general paths that people's careers take. So, one is, you'll start off in something technical, and then branch out into something more pulled back and leadership. And then, sometimes you'll start off with something more in that general organisational leadership thing, like an assistant or associate or something where you're not highly technical, your job is to kind of look out for the organisation and the team, and then people in that might shift into something more technical. So, there's all of this interplay of the leadership management and the technical hyper focused, and figuring out which way you want to go at a particular time is something that's always in flux and always evolving.

Jeremy Cline 33:22
The last couple of minutes, I just wanted to dive a little bit deeper, so to speak, in the dangerous seas that you talked about. So, invisibility, arrogance, disengagement and burnout. Can you just talk briefly to those and what makes them dangerous?

Dan Freehling 33:37
Yeah, so these are, as I mentioned, the sort of uncomfortable part of this model, of this framework, because nobody's really upset if they're a Go-Getter, or they're a Contributor, all of those are reasonable places to be. Where it gets uncomfortable and honest is in these dangerous seas. So, basically, burnout is the too high in leadership. So, this is something that's an ongoing endemic issue in organisations now. Basically, you're not just being a Go-Getter, or you're not just being an Executive, where you're putting your organisation over yourself in a way that's sustainable, that makes sense, and that you can actually be beneficial to the organisation and others through; you're shouldering so much burden for the organisation, you're working around the clock, you're putting people's needs above your own to such a degree that you just can't sustain it. And this is something that's happening a lot in organisational settings now. So, that's the burnout one. Too low on leadership, this is when you're not just to the reasonable though of being a Contributor or the reasonable low of being an Expert, but you're actually below that. That's what's called disengagement. So, this is another of these endemic issues in organisations right now, where you just don't care about what the organisation is doing, and you're not contributing to your team at all in a way that is really a dangerous place to be. Because that's something where there's a disconnect there, where you're not feeling part of something. So, there always has to be at least some level of leadership, but it doesn't necessarily have to be an extreme high or an extreme low, because those are actually not sustainable places to be. Similarly, on the career advancement, way too low on career advancement is what I call invisibility. So, why isn't anyone noticing me? How come I'm getting overlooked for all of these positions and opportunities? A lot of people who are long-term unemployed will find themselves in that position, where it just seems like, no matter what they do, they can't seem to get traction, they can't seem to get people to notice them. And that's because it's on that extreme low of career advancement. And that's obviously a dangerous place to be. So, the key to get out of that is both increasing your self-confidence, but in doing things that grow relevant stakeholders' confidence in your abilities to perform and add value. Arrogance is another really interesting one. So, that's the extreme high of too much career advancement. And a lot of people will stop me and say, 'How can you have too much career advancement?' What does that mean? I thought career advancement was good.' And what that means is that your self-confidence is too high, and the confidence of those around you is too high. So, an easy way to understand this is in looking at some of these former rock star careers, rock stars, like literally rock stars' careers, where they've had some amazing albums that they've put out over the years, and they've been really incredible and artistic and new and different, and then, the stuff they're putting out now, they've been surrounded by Yes men for so long, and they're so full of themselves in their own head, that they're not actually putting out anything good now. And that's a dangerous spot to be, and that's something that's not just for that example, obviously, but in the case of an executive or an expert who's gone too far in terms of drinking their own Kool Aid, and putting themselves first and having people around them telling them what they want to hear, that they're not actually humble enough to be adapting and changing and growing.

Jeremy Cline 37:10
So, I can see very clearly what could make invisibility, disengagement and burnout dangerous, where it can lead to. Burnout, I mean, it could very much have an effect on your health and visibility you've talked about, being overlooked and that kind of thing. Arrogance, what's the potential end result of that, if left unchecked?

Dan Freehling 37:35
Yeah. So, I think it's resting on your laurels and not adapting and changing and growing. And then, everyone around you kind of saying, 'Okay, this person is past their peak, they're past their prime.' And that's quite a dangerous spot to be in as an organisational leader, to be viewed as someone who's just full of themselves and has their head in the sand. Because eventually, whatever it is, internal stakeholders, customers, clients will start to notice that and say, 'What they're doing is not as good as it once was, and they seem like they're not keeping up.' And that's quite a dangerous spot.

Jeremy Cline 38:10
How would you know that you're in that position or that you're sailing in that direction?

Dan Freehling 38:15
So, this is probably the most common, I have a quiz that goes along with this, that's the sort of current state and the desired future state, and often people will have Arrogance as their desired future state, based on their answers to the quiz. And it's always surprising. Because we have this cultural mentality that more is always better in a career advancement, that you should always be the best, and you should always be striving to do more and achieve more and be more ambitious and all of that. There's a point where just going more, more, more, more, more, is no longer serving you. And what you actually want to be doing is being really intentional about why do I want more, what do I want to be accomplishing in my career, what is my lifestyle that I want, all of these kinds of questions come into play, and it's less of just flipping that lever, and I want more.

Jeremy Cline 39:15
Are there any practices or habits which can help you to sail or can help you avoid sailing into any of these seas? So, just an exercise or two, which someone can do, which just kind of can keep them in check against all of these?

Dan Freehling 39:34
Yeah, so I think the easiest thing to do would be to take the quiz that goes along with this, and to just get a good sense of where you think you are now and where you want to go. So, you can go to careerdesignquiz.com and take that, see where you land. So, that's that sort of pulled back approach to it. And then, actually, with each chapter in the book, there's a practical real-world exercise for that particular area of the map. So, depending on where you land and where you want to go, there are some really tangible practical exercises to it. So, just a couple of examples on it would be, if you find yourself in invisibility, one of the exercise there is to just have one single networking conversation with somebody. And it can help to really get people out of their head and out of this, you know, there's nothing I can do at all to get myself out there. And you can have literally one conversation with a person and just ask them about their career or their trajectory, what they view as future trends in the field. And that alone can help to kick people out of this invisibility area, because they're starting to get themselves out there. The arrogance one, there's an exercise that goes along with that, which is to get a reverse mentor or mentor in an area where they want to learn and grow more. So, it's finding some aspect of something that they want to work on. And that can be business, that can be personal, finding someone who excels in that and asking if they'd be willing to help guide and mentor them as they learn that. And that can help to foster a better sense of humility and learning in them, and that can then translate into other areas of their life too.

Jeremy Cline 41:14
Fantastic. Brilliant. And apart from your own book, which I'll put a link to that in the show notes, any other books, tools, resources, which you recommend that people take a look at?

Dan Freehling 41:24
Yes, there's so many of them out there, and I just advocate always looking at new resources. One that I'm currently reading is a book called The New Reason to Work, and it's by Roshan Paul and a contributor. That's basically a look at this new era that we're in of purpose and impact no longer being separate things that you have to do, separate from your career, but you can actually build and develop a career that includes impact and purpose in it, and that being something that's increasingly both desirable and possible now. And so, it's something I highly recommend to anyone interested in that purpose and impact space.

Jeremy Cline 42:03
And if someone wants to find you, or find your quiz, or find your book, where should they go?

Dan Freehling 42:10
Yeah, so my coaching practice is called Contempus Leadership. So, they can go to contempusleadership.com. And that has everything about the book and the practice and all of that there. They can also buy the book, basically any bookstore can order it, they can get it on Amazon. And the free quiz is at careerdesignquiz.com.

Jeremy Cline 42:32
Links to those will be in the show notes, as usual. Dan, thank you so much for coming on and sharing your insights. I've loved discussing your framework with you, so thank you so much.

Dan Freehling 42:42
Thanks for having me, Jeremy. I really appreciate it.

Jeremy Cline 42:44
Okay, hope you enjoyed that interview with Dan Freehling. I really liked Dan's model of categorising where you are in your career, and also exploring with him how you can move between the various different categories. It was clear to me that things can be quite fluid. And maybe we don't need to be worried about being pigeonholed as a particular type or in a particular area. Just because you're the subject matter expert, maybe the techie person, that doesn't rule you out from moving into more managerial positions. The key, as Dan was explaining, is to take up opportunities to explore those management positions. So, if there is an opportunity to maybe lead a project, put your hand up, if that's what you're interested in doing. I thought it was also quite timely to discuss the dangerous seas. I mean, disengagement is something that we all know is happening in the workplace at the moment, and invisibility, I mean, that's something that can be harder to avoid when you're working remotely. You may be working from home, and you don't see your colleagues as often as you would if you were in an office together. So, definitely worth thinking about what you can do to avoid sailing into those dangerous seas. A full transcript, summary of everything we talked about and links to resources are on the show notes page for this episode there at changeworklife.com/165, that's changeworklife.com/165. And if you feel like you're in a particular quadrant, and you can't figure out how to get to the next, then don't forget, help is at hand. You don't have to figure out all these things by yourself. And that's one of the things that I work on with my coaching clients. So, if that sounds like something which could be interesting for you, then do take a look at changeworklife.com/coaching, that's changeworklife.com/coaching, where you can find out a little bit more, and also book an introductory call with me to find out just what it's all about. There's more to come in two weeks' time, so if you haven't subscribed to the show already, make sure you do so, and I can't wait to see you then. Cheers. Bye.

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