Embracing the Power of Nonlinear Careers (with Siobhán O'Riordan)

What if the very thing you've been apologizing for is actually your greatest advantage?

Maybe you've changed industries. Switched directions. Collected experiences that don't seem to fit neatly together on a resume. While specialists often have a clear roadmap, many of us have careers that look more like a winding trail with unexpected turns along the way.

In this episode of The Potentialist Podcast, I sit down with coach, leadership consultant and author Siobhán O'Riordan to explore why nonlinear career paths may be exactly what today's world needs. Drawing from her book, Reframe: How Generalists Thrive in a Changing World, Siobhán makes the case that generalists aren't scattered or unfocused. They're often the people connecting ideas, solving complex problems and helping organizations navigate change.

In our conversation, you'll discover:

• Why generalists make up nearly half the workforce, yet often feel invisible

• How "looking around the corner" helps leaders spot opportunities others miss

• How to tell your career story with confidence, even if your path doesn't look linear

• What generalists need from managers, mentors and workplaces to do their best work

If you've ever wondered how to explain your twists, turns, pivots or unexpected detours, this conversation will help you see them through a completely different lens.

Your career path may not be messy after all. It might just be evidence that you're built to connect dots others can't see.

Transcript

Reframing the Generalist: Embracing the Power of Nonlinear Careers

[00:00] Lee: Hello everyone. Welcome to the Potentialist podcast. I'm your host, Dr. Lee Koles. I'm an industrial organizational psychologist, ICF and Gallup certified coach, and your go-to for science-backed strategies to step into the most powerful version of yourself. Everyone has something that they were built to do. And for my guest today, Siobhán O'Riordan, that something is helping people shine—particularly in the moments when change makes that feel the hardest.

As a Gallup certified CliftonStrengths Coach with 25 years of experience, Siobhán has partnered with hundreds of leaders and more than 100 organizations to navigate transition, build stronger teams, and lead with greater impact. She's also the author of the fabulous book, Reframe: How Generalists Thrive in a Changing World. Welcome to the podcast, Siobhán.

Siobhán: Well, it is wonderful to be here. Thank you.

[02:15] Lee: Yes, it is my pleasure. So, Siobhán, I want to kick off our discussion by talking about your book, Reframe, which I just finished reading when I was traveling. I had it on the plane with me and just was digging into it and loving it so much. So many people get worried when their career paths aren't perfectly straight—you know, when they can't just paint a perfect linear path and they feel like they may have been doing something wrong.

Like I know in my own career path, I've had stops and starts and detours and direction switches and pivots, and that's basically what got me to where I am now. Your book, one thing I loved about it was that it celebrated the squiggly or spiky career paths—those nonlinear career paths. I just want to quote one of your reviewers: "If you're tired of apologizing for your wide-ranging interests and ready to claim your role as an essential catalyst for change, this book will show you how." So, what can you tell us about the power of a nonlinear career path?

Siobhán: Thank you for having me. I'm thrilled that you enjoyed the book and that it resonated for you. I think some of the feedback I get from people closer to my age is they really saw themselves in there. They understood immediately that I had written it for the younger version of myself, and really for a lot of the people that I coach and work with.

To set a bigger table here around this question of squiggly and spiky and nonlinear careers: we're moving into a time of rapid change. We're in it, actually. I don't think it will get more rapid, and change will be felt in lots of different ways. It became clear to me that the kind of traditional career that I see as linear is often that of a specialist—someone who has deep expertise and has a very clear path to follow.

And yet we're moving into a time where a whole bunch of people like you, like me—and I'm sure a lot of people who listen to The Potentialist—don't have and have not had a linear career. They might have had the spiky career that I had, or if they were wiser, had more of a squiggly career, which is a little bit more gentle than the spiky career of, you know, you're really crushing it or crashing out.

This book is really for generalists, and generalists make up about half of the workers out there. These are people who have no definition; they don't specialize. They tend to function as the glue and in many ways are a go-to within their team or organization. While they're ubiquitous, they are invisible. Following a nonlinear career path is one thing that generalists have defaulted to, but the intention of the book is to make everything about being a generalist more visible so that generalists can create and choose the careers they want and model them.

[05:30] Lee: What you said makes a lot of sense. I know that when people decide they want to be a doctor, there is a definite career path that's set out for them. Follow these steps A, B, C. Yes, there are different choices to make along the way, but it's scripted out. Same with being a lawyer. But other careers don't have this set of steps that's predefined for people.

Siobhán: That's right. Especially for people whose curiosity isn't about going deep; it's about going wide. Generalists tend to have more of a ranging curiosity and a nonlinear approach to problem-solving. So they're a little bit more creative—connect the dots, "out of the box". Because there's no clarity for them in terms of job titles or career paths, the environment in which they operate really matters, and probably matters more than it would to someone who is a specialist.

Lee: Right. I feel like this is a topic that's been coming up a lot lately. There was David Epstein's book, Range, which came out in 2019. It was just this big splash talking about how you really need range in your career in terms of being able to maximize critical thinking and all the different technologies that are opening up today.

He wrote that in 2019; little did he know how much we would really need some range in our careers with what was to come. In fact, I was just recently at a graduation for a liberal arts school, and they were talking about liberal arts and that need for range. Now, you talk about generalists, and I know I've talked to you about this before—I wish there was a sexier title for the word "generalist," because it doesn't sound super exciting or like something someone would aspire to be. But just so that you inform our listeners, can you tell us about generalists and what kind of jobs they would have? Someone who could be in the C-suite?

[08:00] Siobhán: For sure. Actually, I would say they probably dominate in the C-suite. We know about 90% of those in the C-suite have had general management experience, and about 40% actually identified themselves as generalists. These are people who have had the benefit of being a generalist.

I'd be curious if they had a mentor, because often people who are successful in their career have someone helping them navigate the unknown. They might also have followed their curiosity and taken some risks to try new opportunities in which that ranging curiosity allowed them to succeed. Then, when they went into a new role, they were able to connect the dots a little bit differently than someone who had just stayed in a linear path.

Lee: I'd love it if you could tell me about the "superpowers" of a generalist. What is it about a generalist that makes them so likely to wind up in the C-suite or in a leadership role?

Siobhán: In a leadership role and in the C-suite—and I would venture to bet in the future—generalists depend on specialists for expertise and information, but because they're already looking across, they have an advantage. A leader needs to look ahead and around the corner. So there's already a longer-term habit of looking across instead of deep.

This isn't specialist versus generalist, it's specialist and generalist, but since generalists have been ignored for a long time, we need a little bit more attention on who they are. They have that practice already of understanding that their curiosity can bring them to new places of discovery. If they're paying attention to their curiosity and being intentional about how they use it, they're in many ways practicing for what leaders need to do, which is look ahead.

There's often a desire for solving certain types of problems. I sometimes call them "problem invaders," and they will often bring a creative, out-of-the-box approach to solving those problems. You see that a lot in entrepreneurs who then become leaders in their own right. The other thing is the environments that they create as leaders for organizations often reflect what they valued in their own experiences coming up.

[10:45] Lee: I love that. I want to repeat one thing you said: "A leader needs to look ahead and around the corner," and generalists have this curiosity they can use to bring them to new places of discovery. So, knowing there's something else out there they want to learn, instead of only having their head down thinking about one particular issue.

Siobhán: Right. And this shows up before anyone gets into the C-suite. Curiosity, when it's unbridled, can run rampant and cause distraction. You might make the best trivia partner, but you're not necessarily going to be someone thinking about how to solve problems in a creative way.

One of the things generalists really need to do is understand their curiosity and be able to drive that with some intention. They also need to understand the kinds of problems they like to solve and where. Are they the kind of generalist who's going to jump in, fill the gap, and meet the needs right away so the rest of the team can move forward? Are they someone who connects dots and might be working across teams? Or are they a big systems thinker thinking about change at a systems level?

One of the things I end the book on are the qualities that a "mature generalist"—I couldn't think of a better term.

Lee: An evolved generalist.

Siobhán: Evolved, that's good. Because they are always practicing. The idea is they are inherently adaptive because their curiosity is driving constant learning.

[13:15] One of the skills an evolved generalist needs is understanding how to listen. That's not just listening for information or response, but really listening for what's being unsaid. This goes towards that idea of leadership—being able to see around corners. They also need to understand how to discern in order to make decisions, and understand the difference between discernment and judgment. They're often making decisions in times where absolute information is not available, so they're discerning shapes out of ambiguity.

Another key factor is a technical skill: understanding not only how they make decisions, but how they give and receive feedback, because that's really the mechanism of learning. Finally, they need to understand their curiosity and know how to curate ideas and bring them into problems they want to solve.

Lee: Right. So curiosity is at the root, but they need to channel it with intention. They need to understand what their strengths are, what kind of problems they are drawn to, where they are best able to fix things, and where they are most likely to succeed individually or with teams.

Siobhán: Exactly. You and I, as strengths coaches, are both strengths-obsessed and understand the value of individuals really understanding their inherent talents and developing them. It's exponentially important for generalists because they'll never compete successfully with specialists around special skills, knowledge, or expertise. Since there's no one type of generalist, you have to really understand who you are individually.

Your strengths and really owning them can help you understand where you function best. Are you someone who likes to fill the gap? Are you interested in project management roles? Chief of staff, COO, consultants, coaches, and other solopreneurs are all typically generalist roles. I'm a people person; my value as a generalist is always going to be related to people. I'm interested in helping people use transitions to transform. That's informed by my understanding of my own strengths that make me the kind of generalist that I am.

[15:45] Lee: Now, you mentioned adaptability as a characteristic of a generalist. We are living in an era where adaptability is one of the most important strengths someone could have. What would you offer a generalist in terms of harnessing that adaptability to maximize their potential?

Siobhán: Adaptability is really an assumption between ranging curiosity and a nonlinear approach to problem-solving. One of the things I encourage generalists to think about is how they are adaptive. Often, a desire for variety or variability in our careers is a sign of this adaptability. Sometimes our ability to do one thing over a certain amount of time—like fill a gap—and then let specialists take over is another sign.

Adaptation is a big subject. We're adapting to AI, automation, robotics, climate change, the impact of viruses, and a multi-generational workforce. Generalists are uniquely positioned because of this adaptability and ability to learn. They can help mitigate risk for specialists by testing new ideas—like how AI can be adopted—and taking on risks that might be too high for specialists.

They can model what it looks like to be open to failure and learning as they evolve. They can also help inform working environments that are inherently more inclusive because they allow individuals to bring their best.

[18:20] Lee: What do you say to the people who say, "Siobhán, I don't like my 'messed up' career path. I want a linear one. I look at my path and it's squiggle lines and spikes and twists and turns. How do I market myself for a job or a promotion?"

Siobhán: The first thing I would say is: I feel you on that. I, too, longed for a singular vocation I could follow and become an expert on. But my true self would come marching through, break up that dream, and I would find myself doing something new.

The first important step is self-awareness—externalizing how you think about yourself to bring some space and objectivity. When you look at yourself as you would a friend, you will start to see consistent themes, talents, and strengths. It's less about the packaging and more about what's consistent. We can't default to the packaging that exists already in the work world.

A lot of recruiters are looking for people who are adaptive, but because we don't have the titles or shorthand yet, we have to own it and describe it ourselves. Your narrative has to start with the reason you're a generalist in the first place: the problems you want to solve and the approach you take.

Lee: I love this. You've given us some gold here. It's less about the packaging and more about the consistencies—those themes that arise. We have to understand our own narrative if we're going to communicate it to someone else, not apologizing for the changes, but articulating the problems we solve and the strengths we bring.

Siobhán: That's right. There's a fun exercise I can send a link for. In accepting this about yourself, you are accepting what you do well and also what you don't do well.

Lee: Right. It's good to know what works for you and what doesn't so you can stick with one and avoid the other.

[20:45] Siobhán: Exactly. Successful generalists don't necessarily have an easy title, but we can tell our story and drive our own work so that success shows up. It's most important that you understand how you work first, because each generalist is different.

Lee: Each one of us is good at certain things and we have certain problems we like to solve.

Siobhán: Yes. And I can imagine managers thinking, "Oh, this is just going to be one individual need after another. How do we create a culture where all these generalists can thrive?" It's actually not that hard. There are common factors. One of them is freedom. Generalists need room to explore, learn, and go down a rabbit hole here and there, which is ultimately in service of problem-solving.

Some might need to be on teams, some might need a mix of solo and team work. Most of all, they need access to and mutual appreciation with specialists. They need that learning to be successful and help meet company goals.

Lee: I would love for you to state clearly: what is it that generalists need to thrive?

Siobhán: They need self-awareness and an ability to self-manage. They are more successful when they have an active network and mentors who can support them. They need a manager who understands they are a generalist and will help develop their generalist attributes, not just the default specialist professional development. The best managers will assess performance around what a generalist does best—which is often connective work—and give them opportunities to be curious, to pilot, and to try things.

According to a study OC Tanner did in 2023 of 36,000 employees, half of them identified as generalists and were frustrated about being invisible. They're already in your organizations, but they're often underutilized because they're trying to fit into a specialist role. They are the "glue" on the team—the person people call when there’s a problem because they trust that person to think differently, bring in fresh ideas, and talk to people others wouldn't have thought of.

Lee: I love that—the glue, the one with fresh thinking. This has been so insightful. If you could offer one piece of wisdom for how our friends listening could untap and maximize their potential, what would it be?

Siobhán: I would have to say: know your strengths. It's the same for everyone. Really understand in a deep way what your individual talents are and become expert at using them as you would any tool. If you're an amazing chef, you understand which knife you use for which activity. You should know your talents in the same way. Those strengths are yours; they are your differentiator. When you use them intentionally, you will find your way forward.

Lee: Right. Whether or not you're referred to as a generalist, no one can take away your strengths—that's your special sauce.

Siobhán: And generalists can't compete on skills; they can compete using their strengths and understanding their core characteristics around curiosity, how they solve problems, and the environments in which they operate best.

Lee: Thank you so much, Siobhán. Friends, you can learn more about Siobhán by going to beiastrategies.com. And don't forget to order yourself a copy of Reframe. It's on Amazon and lots of other places. Thank you once again, Siobhán. I really appreciate you being here. My hope for everybody listening is that you move forward in your day feeling proud of your career path, whatever shape it may be. Remember, you already have everything you need inside you. I'm just here to help you unleash it.