In this episode of The Entrepreneur to Author Podcast, your host Scott MacMillan welcomes Siobhán O’Riordan, coach, advisor, and lifelong generalist to discuss her book Reframe: How Generalists Thrive in a Changing World. Drawing on her nonlinear career and client work, she unpacks the “generalist’s dilemma” of being essential yet often unseen and misunderstood. In Reframe, she offers a functional definition of a generalist built around ranging curiosity, creative connections, and context, giving generalists the language and framework they’ve lacked so they can better understand their strengths, articulate their value, and intentionally design careers that fit them.
She also reflects on the writing journey behind the book, noting that long-form writing is a very different discipline from day-to-day writing. The process forced her to clarify her thinking, decide what truly served the reader, and turn years of experience into a focused, practical guide. With the help of structure, a clear curriculum, and a supportive writing community, she completed a book that argues generalists are increasingly vital in a changing world—able to experiment, test, and take risks in ways specialists often can’t.
EPISODE LINKS
First two chapters of "Reframe" Free: big-sea-strategies.kit.com/7b06068914
Expert Author Community: expertauthor.community
GUEST BIO
As a certified coach, advisor, and founder of Big Sea Strategies, Siobhán helps individuals and teams anchor in their strengths to navigate change.
A Generalist with experience across the social sector, Siobhán has worked with hundreds of individual leaders, teams, and board members across 100+ organizations with revenues ranging from $500K to $30M. Her lifelong commitment to helping others learn, grow, and succeed is her favorite job; she taught high school history at The Lincoln School in Kathmandu, Nepal. Siobhán is a certified Gallup® Global CliftonStrengths™ Coach with a BA in History and MA in Teaching from Tufts University.
CONNECT WITH SIOBHÁN
Book Website: bigseastrategies.com/book
Website: bigseastrategies.com
LinkedIn: linkedin.com/in/saoriordan/
CONNECT WITH SCOTT
LinkedIn (@scottmacmillan): linkedin.com/in/scottmacmillan
Instagram (@scottamacmillan) instagram.com/scottamacmillan
Medium (@scottamacmillan): scottamacmillan.medium.com
ABOUT GRAMMAR FACTORY:
Grammar Factory is a Canadian self-publishing company that helps business leaders and entrepreneurs write, publish, and market non-fiction books to boost their credibility and business results. Their expert team guides clients from idea to professionally published book, offering editorial services to ensure high-quality, compelling content. Serving clients globally, Grammar Factory focuses on transforming manuscripts into industry-leading books that attract clients and enhance brands, with a strong commitment to supporting authors throughout the publishing process.
Episode Transcript
Please note: The transcript is produced by a third-party company from an audio recording and may include transcription errors.
Scott MacMillan:
You're listening to the Entrepreneur to Author podcast.
Announcer
Welcome to the Entrepreneur to Author podcast, the podcast that brings you practical strategies for building authority and growing your business. And now, here's your host, Scott MacMillan.
Scott:
Today I'm speaking with Siobhán O'Riordan, coach, advisor, lifelong generalist, and author of Reframe, How Generalists Thrive in a Changing World. Siobhan, welcome. Thank you so much for being here.
Siobhàn O'Riordan:
Thank you for having me.https://www.spreaker.com/episode/e2a-103-writing-a-field-guide-for-generalists-with-siobhan-o-riordan--68821803
Scott:
Listen, I gave a quick snapshot of your background in the intro, but could you give our listeners a full picture of the work that you do and what brought you into the space?
Siobhàn:
The work that I do, I think like many generalists, I'm often stumped with how to best explain the work that I do. So, I like to start with where my passion and purpose is. And my passion is really, has always been, I was a teacher, I was a high school teacher, has always been to really help people be their best and help them get that up and out of who they are.
And so, my purpose really is getting talent that has really been sidelined back to the table. And so, I do that as a coach and as an advisor, I work with both individuals and teams to reorient them around their strengths and kind of figure out how to just align with who they are internally, but also just how they can do that collectively to navigate the challenges and change that we're all living in.
Scott:
Yeah. You wrote your book, Reframe. For those who haven't read it yet, what's the core idea behind it? And I guess, who did you write it for and what do you hope that they'll gain from it?
Siobhàn:
Sure. So my book, Reframe, is really for generalists who are those who have never felt quite like they fit in. These would be the jack of all trades, the multi-hyphenates, the generalists, those with a squiggle career or a non-traditional career, a portfolio career.
They're people like me. And I was motivated to write the book because this is what I would have really benefited from earlier in my career, particularly my mid-career. And so I decided to share the lessons that I have learned since then and that also that my clients and others have shared with me.
So it's really to help generalists get what specialists have long had, which is a definition and a framework and a way to really be intentional around developing their career.
Scott:
I want to come back to that idea of the definition of a generalist because I think that's important. But first, early on in the book, you described the generalist's dilemma, which is the idea of being essential but often unseen. What first sparked your desire to explore that topic?
Siobhàn:
If I'm honest, it started with my own experience of being seen by some but not by everyone and being frequently hired for roles where people just said, I need you to do what you do without much explanation. So it was being hired by people who knew me and appreciated my abilities in a way that I actually didn't have language for or really clearly understood. And I was having so many hits and misses, and I was either really crushing it or really crashing out.
So that was the beginning. A friend introduced this term generalist to me. And once I started really doing the research, and the book Range by David Epstein, I think was really helpful in this, but so were the other 150 sources that I dug into.
The reality was that generalists have been consistent, but really since we started specializing since the 50s, have really been overlooked. And the reality is they're everywhere. According to one study by OC Tanner, they did a trend report in 2023 of the 36,000 people that they surveyed, half identified as generalists.
And they were really frustrated with communicating their value. They're really frustrated with promotions and frequent job change. And so this idea of being everywhere, but essential and being ubiquitous, but invisible was the real dilemma.
And so I really wanted to give generalists a structure and framework to be seen, to help them be confident in what we bring, understanding that it's unique to each generalist and also being able to communicate clearly what their value was.
Scott:
Okay, good. So that's really helpful.
I think foundational context. And so then let's go back to this idea of the functional definition of a generalist that you've provided, really, I think for the first time. So ranging curiosity, creative connections, thriving and changing environments.
Why was defining the term so important in your view?
Siobhàn:
I was a little hesitant to define it. And I think that's in some ways indicative of what a generalist is. You don't want to be hemmed in.
You don't want to state too many truths out there because you tend to be adaptive and a learner by nature. But it was important to have a framework and that a generalist could navigate and understand and map their own growth to. And in order to do that needed a really functional definition.
So, I say functional so that if others have a definition that works better for them, they can use that or apply that. But there were three things that I really noticed. One is, and I think every generalist would agree with this, and certainly David Epstein talks about this in his book Range, is this ranging, that's the name of his book, curiosity.
And so, it's people who are curious about many things. And so this would be the Renaissance thinker, perhaps, or our friend Leonardo da Vinci, among others. But it's also people who have interest in a number of subjects.
So, unlike the specialist who is very curious about their topic and they go necessarily deep into their subject, a generalist will look across. So, they have this ranging curiosity. The second part is around creative connections.
And I like things to be orderly, so I made sure everything started with a C. And this is just how generalists problem solve. And so they tend to be a little bit more experimental and tend to be more free about borrowing different solutions or ideas from one sector or from one area and apply it to another.
And so, there's a much greater comfort with piloting, testing, experimenting in terms of problem solving. And then the third one is really around context. And I deal with that a little bit separately in the book.
But generalists are most challenged not in understanding who they are, but finding the right work environments in which they can really thrive and bring their particular benefits to an organization, an issue, or a team.
Scott:
Right. Yeah, a lot of this, and I'm sure this is true of our listeners too, a lot of this is really resonating. Well, like you said, 50% of the population sort of associates with or finds this concept of being a generalist that it really resonates with them.
And you interviewed, surveyed, and have coached many generalists, both while writing the book and I'm sure outside of that as well. What surprised you most from those conversations that you've had with generalists?
Siobhàn:
I think what surprised me most was just here are some people who have had really profound successes, have been frustrated with some failures and knowing how smart and capable and successful they have been, that they really didn't, that this narrative of their ability to understand and claim what they particularly do well to really see their own value is always striking to me. It's something that I also struggle with. I introduce myself a little bit differently each time I talk to someone based on what the context is.
But people really feeling that they don't really, they're not clear on what they bring because they're not a specialist. So I'm, I'm, I'm always struck by that. And I'd say that's fairly consistent.
The challenge to communicate value. The second one is the difference a mentor can make. So people who have worked with people who really understand their value and they have a really great mentor, and that might've been a former manager or a leader in some organization, they'd often have greater success because they, they often will travel with that person.
And that's something that came out in the survey I did of about a hundred folks. So mentoring can be important.
Scott:
Yeah, I can imagine it would be. Well, let's talk about that idea of articulating value more clearly. How can someone who identifies as a generalist start using the ideas from your book to do just that, to start articulating their value in a more clear way?
Siobhàn:
I think the first thing that generalists need to do is forgo the pursuit of being a specialist and forgo being an expert in a subject, unless you are the kind of generalist who focuses on one specialist area and, and then hops to another. So there are a few that, you know, become an expert in a number of different fields, but others who are not, and I'm thinking folks who generally work across an organization or work across organizations or teams or issues or ideas. The first thing is to let go of being a specialist.
Do not try to take on the mantle of expertise that a specialist has and embrace the expertise of being a practitioner. So the best generalists are those who are really highly self-aware and they have an ability to self-manage their own expertise as a practitioner. So they know how, what they're curious in, how to be curious, and they know how to learn just enough to address solutions.
And they know very much how to discern the right working environments. So one is embrace being a practitioner. The second is really focus less on your skills, which are what we can learn, and more on your strengths, which is, which are the inherent talents you have and how do those strengths explain your individual unique abilities as a generalist.
That's the hardest work. That's the work that I do a lot with, with clients, both individually and groups and teams, but it's really the most important work. And, and, and in that work, you really find out what it is you're good at and actually what it is you were going to say no to and, and seek partnership in et cetera.
So I think really being clear on what your unique value is based on the strengths you bring and how they show up in terms of how you're curious, how you problem solve in the best environments for you to work in. And I think that the second half of the book is, well, my intention was that it was super pragmatic. It was like, here's some roles to consider.
Here's things you need to know how to do. This is how you grow and develop as a generalist. And I think really, you know, breaking it down, you know, once you have your narrative, you can really break it down into nuts and bolts around how you want to build your particular career.
Scott:
It's really great advice. You talked about, you know, the, the need to partner as a generalist. And, and of course, if, if 50% of us are generalists, the other 50% are specialists.
So we have to be able to work together with other generalists and, and of course, specialists as well. What does great collaboration look like between generalists and specialists?
Siobhàn:
Oh, that's such a good question. And, you know, it might be a good question just for what collaboration always looks like, you know, I think, I think the one fundamental piece of the most important piece of advice around collaboration is get to know the people that you're collaborating with and really understand what do they think they bring in terms of, of, of, of what they do well, what do they need in order to succeed? What, what do they not do well?
And, you know, and, or where are they kind of trying to learn and improve? And I think having those foundational conversations are really important. And particularly when people default so much to hierarchy, generalists tend to work in a more lateral way.
So they work across organizations. And so often can be the people who come into contact with people who are on the front line versus also in the C-suite. Many of them are in the C-suite.
But really understanding who the specialists are, what their value is, but also what it is that a generalist can do for them. And that specialists are, see the value of what a generalist can do for them. Does that make sense?
Scott:
Yeah.
Siobhàn:
But I think the, the, you know, my number one rule around collaboration is you better know who you're collaborating with. Because if you were going to engage in really complex problem solving, you need to have some foundational trust that's based on recognizing and seeing who the other person is and what they bring and what they need, which is, you know, an area of vulnerability for many.
Scott:
And you're right. That is good advice for collaborating in general. Of course, when we're, when we're sharing our, our knowledge and our expertise, there's a variety of different ways that we can do that.
And you chose to write a book. What did you find valuable about the process of writing?
Siobhàn:
Oh my gosh. I have a lot to say about writing a book. And I am someone who tends to welcome change and, and, and challenges.
I like things, I like things that are new and exciting. And I thought, oh, this will be a new and exciting thing to do. I do a lot of writing.
I mean, I have a regular writing practice, a writing group. I'm an avid reader. Writing a book is really different from all of those.
I think Kelly Irving of the expert author community, when you express to her that, you know, long form writing is a totally different game. She's like, exactly. And that's why her community exists.
So what I learned about long form writing is first the profound benefit. It was to me and I think to my readers to get really, to know my own mind and my own thinking and really discern what was relevant versus what wasn't. So I think when, you know, people read this book, there's so much that was written that's not in the book.
That was actually my own practice around trying to understand what generalists need. So the, the, the long form writing being its own journey was, was an amazing one to go on. Challenging.
You know, you go through these times where you're not sure it makes sense. You're not sure you're going to finish it. You're not sure it's going to be of value.
So I think that's just part of the journey. What made it an easier and maybe even a better journey than maybe some others go on is that I did follow a curriculum that really helped organize my thoughts, create an outline and follow through on that. Even though I did start writing the book in the middle, I actually went back and followed the order.
So I learned that lesson as well and writing in communities. So the idea of being accountable to yourself because you were with others who needed that you were helping them to be accountable to themselves is a very powerful way to actually get something done, but also to do it with people who are also in the process as well. So you can, you know, share some of the ups and downs.
Scott:
Yeah. Yeah. Writing in community can be such a powerful thing.
And I'm glad that you highlighted Kelly and the Expert Author Community. We'll be sure to put a link in the show notes to EAC because that's a really great community for anybody who's on that writing journey for listeners who sort of feel like they are a Jack of all trades type person who doesn't fit into one box. What would you most want them to hear today?
Siobhàn:
I end my book and, you know, Jack of all trades, Jill of all trades, there's, you know, there's that word, the J of all trades. It's the one people know, and yet it also is sort of captures some of the limitations of what it means to define what a generalist is. The one thing I want people to know are two things.
I end my book with three words, which is, I see you. And it is not lost on me that when generalists feel seen and understood, there's not just profound relief, but I actually think there is, it clears a pathway forward for them to actually do the work around claiming their own individual narrative. Second, and maybe even more important is that generalists are needed now and increasingly will become more important as we navigate change.
So generalists bring something that specialists can't risk. They bring an ability to practice. They bring an ability to test new ideas, to pilot, and to take on risk in a way that specialists can't.
And so we need generalists to understand their individual value so that they can contribute more readily to how we collectively address the challenges ahead.
Scott:
Wonderful.
Siobhan, where can people find you and learn more about your work?
Siobhàn:
I'm on LinkedIn. If you can spell my name, you'll find me there. So, it's Siobhàn O'Riordan. And also my company and website name is Big C Strategies. And I am also on Substack these days.
Scott:
Wonderful. Very good. Well, we'll be sure to put those links in the show notes.
So even if somebody can't spell your name, they'll be able to just click on it and get to the right place. Siobhàn, thank you again for joining us and for sharing such thoughtful insights about the world of generalists. Reframe is a powerful guide.
It's really a fantastic book for anybody who's ever struggled to explain what they do or where they fit in. And I know listeners will take a lot from this conversation.
Siobhàn:
Well, thank you, Scott. It's been a pleasure publishing with you. And I really enjoyed the journey.
Scott:
Thank you.
As we wrap up this episode of Entrepreneur to Author, remember this. Now is the time. Time to write, time to publish, and time to grow. I'm Scott MacMillan. Until next time.
