Are You Too Curious For A Traditional Career?

0:00From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

0:22Do you ever see someone and wonder, what does that person do? They seem to be doing so many things. So how do they focus on any of them? How do they all fit together? And then maybe the next thing you think is, and how do I do that? How do I have so many things? I've had people wonder this about me because I do a lot of things, as maybe you know, editor in chief of Entrepreneur Magazine, podcasts, book, speaking, startup advising, some other stuff. But I will be honest with you, I see this in other people and I have to wonder, what are they doing? and how are they doing it? And there is someone who I have gotten to know on Instagram, who is someone who I always wonder this about.

1:12Her name is Eloise. My name is Eloise Skinner, and I am an author and an existential therapist. So I specialize really in meaning, purpose, values, and identity as well. But also Eloise started as a lawyer and then got interested in journalism and has written a bunch of books. And then at what point did you study at a monastery or something? Yeah, I was sort of going deeper into what the point of everything was really, because I had always thought, okay, get a career, get a degree, get a house, find a relationship, settle down, that'll be your life. And quite early on, I managed to do all those things in pretty quick succession.

1:54So I was 22 and I was already in a really good corporate career and settling down and finding somewhere to live. And it just seemed very, like, a bit too abrupt. And I sort of got to this place of like, Oh, no, surely there's something else. Or is there something else? And so that took me on a pretty much a decade long quest to find out what those other things could be. And during that process, yeah, I did a lot of things I trained as a yoga teacher, I went to like meditation and mindfulness training as well. And like you said, I spent a year in a monastic community. You can see why all this intrigued me, right?

2:27It's just, it seems so varied and also so immersive. And I guess the thread here is that Eloise is looking for ways to be useful to others and also to find purpose for herself, which I think is something that we're all doing. And she has a new book out. It's called, But Are You Alive? And it's an exploration of depth and meaning in everyday life. It's for people who are searching for these kinds of things that she's been searching for and the lessons she's learned from so many different arenas. So it's sort of a mix of introductions to teachings from things like existential therapy, yoga, meditation, mindfulness, monastic teaching as well, but also really practical, easy exercises that people can try out in their everyday lives.

3:13And the intention or the purpose behind the book is to help people find a deeper connection to just the everyday experience of being a human. So after getting to know Eloise through the internet, basically for a while, we decided to actually hop on a call and talk and using her book as a springboard to talk about what it is like and how people can pull together a life and a career made of multiple parts, multiple things that they enjoy, feel passionate about, feel curious about, Instead of that traditional career path of just finding one thing, of immersing yourself in one job, that's not for everyone.

3:54So what does it look like to do more, to do a lot? That is what we're talking about on this episode of Problem Solvers coming up after the break. I just moved out of an apartment and into a house for the first time, and I have been waiting for spring so I can finally enjoy my outdoor space. And you know what can make that even better? Sunday lawn care. Sunday is everything you need to get the lawn you've dreamed of. This spring, just go to GetSunday.com slash Problem Solvers to enter your address and get a customized plan created just for your lawn. No trips to the store or hauling heavy bags since they ship straight to your home.

4:31You just need a hose to apply Sunday. You can fertilize your whole lawn in less time than it takes to watch an episode of your favorite TV show. And they only use ingredients you can feel good about. No harsh chemicals. Like I said, Sunday is offering listeners 20 % off. Full season plans start at just$109 and you can get 20 % off when you visit GetSunday.com slash Problem Solvers at checkout. That's 20 % off your custom plan at GetSunday.com slash Problem Solvers. All right, we're back talking with Eloise Skinner about her new book, But Are You Alive? question mark, and how to build a life and a career based on many things, not just one thing.

5:16I started by saying to Eloise that I think a lot of the people who listen to this show probably feel stretched because we are interested in so many things. We're so curious. I think it's the reason why you become an entrepreneur or are attracted to that mindset and that lifestyle. And you don't just want to think of yourself in one way. You don't just want to do one thing. And so how do you actually start to create that life for yourself? How do you actually start to understand how to pull things that might seem separate together? I mean, it's a huge question. And it's really the question of how you want to design your life or your working life, which I think is maybe one of the most exciting and interesting questions you can explore.

6:04So yeah, maybe the first thing I would say is if you are feeling like that, I know for a long time when I felt like that, I felt really overwhelmed, anxious, stressed, sort of disappointed in myself that I couldn't just settle, like really irritated with myself for just not taking the opportunities that I had to go into a career and just like get on with it. So I would say the first thing is maybe, well, you're not, you're definitely not alone. There's like millions of people who have done this before you and will continue to do this kind of thing. And also that I think it's a really valuable thing to recognize in yourself, this kind of diversity of passions and interests and all those sort of multi-dimensional elements of yourself as a working person, as a human as well.

6:43The first thing I guess I would say is to figure out what you actually want, which is sounds obvious, but I think is one of the most sort of fundamental questions that we often skip over because the next layer is maybe about the practicalities or, you know, what jobs are going to do and the salary you want and where you want to live. But fundamentally, I think one of the questions is like, what is it that you're looking for? Or like what kind of values and like what kind of meaning are you looking for in your career or in your working life? And when you say that you're, you're thinking really fundamental, right?

7:13This, it's the difference between what do you really want? I want to be a writer versus what do I really want? What I really want is to feel like I am making a living off of my creativity or something, right? Like you're, you, you want it to be abstract enough that it isn't anchored down to one particular task. Yeah, exactly. It's sort of this overarching or maybe like underlying is better sense of like, what is it that you're looking for in lots of different roles and projects? And one method that you can use for this, which I think maybe even I wrote about for entrepreneur a long time ago was the five why method, where you start with a question and you sort of drill down.

7:52It's like a, I think it was originally like a manufacturing technique to find out where there were problems in the supply chain or something like that. But the idea is that you start with a broad statement of like, what is it that you want? And someone might say, okay, I want to be a doctor. And then you go, and then you start with why, and then you go down into, okay, I want to have a really safe, stable career that helps people. And then you go down again, you say why, and you're kind of going down and down and down until you get to the core of whatever it is that you're looking for. And it doesn't always work.

8:19It's not like a perfect method. It doesn't always get you to a perfect answer, but what it does often do is indicate where the true values are underneath the job roles and the titles and the responsibilities that you have. And for a lot of people, when they do this exercise, what it actually comes down to is a sense of like giving something or some sense of like service or some kind of greater, not necessarily like a great benevolent mission to save the world, but like something that connects you with either other people or like the world in general. So for a doctor, it might be you're helping people, you know, you're making people's lives better or something like that.

8:52It doesn't always get that answer for people but often there's like this bigger sense of like what it is that you're looking for and then once you have that sense you can sort of work back upwards and think okay if I don't want to maybe I know that I really want to help people or I want to make people's lives better in a very practical way by helping them with their health for example if you are doing the doctor example then you can extrapolate sort of back upwards and think okay if I didn't want to go to medical school maybe there are other places that I could find this sense of if you know what it is that you're looking for you can find other places to explore it, if that makes sense.

9:23Yeah. Why do you think that this is an important path to go on, which is to say to start this journey very internally instead of externally? Because I bet a lot of people might think, all right, well, I'm not fully satisfied doing this one thing, but you know what I really like is I really also like glassblowing. So why don't I do some glassblowing? And then also I think what I really like is, right, and then what they end up doing is cobbling together a pretty incoherent set of things that they're doing, some of which are making money and some of which probably never will, which is also totally fine.

9:55And it makes a kind of sense, but it also probably stretches them very thin. This, for whatever it's worth, is definitely been my approach. I have not, in a meaningful way, stepped back and thought, what is it that I want that underlies all the things that I'm going to do? instead what I have tended to do is just kept trying out stuff that seemed in front of me or oh I now have the ability to do this or now people are asking me if I'll do that so why don't I do it and see what I think and sometimes I like it and I keep going and sometimes I don't and sometimes of course you just spend a lot of time on something and then much later figure out that it doesn't really serve for your purpose but what you're suggesting is more intentional but also interestingly it doesn't actually start with action.

10:43It doesn't start with doing a new thing. It starts with spending a lot of time interrogating yourself. Yeah. And I think for what it's worth, I don't think that it is a perfect answer to any of, I think the big questions about your career and your working life, they're not going to have like a one size fits all solution. Like you have to start here and this is like how you do it. And then, which I honestly think is what I believed it would be when I started on my own personal journey to finding meaning. I really thought there would be like an answer. If I worked hard enough, this is what we've kind of been taught, at least our legal education system is like, if you just work hard enough, you'll get to an answer that will be like the right answer.

11:22But coming out of law school, trying to apply that approach to the real world, it wasn't entirely successful for me. So yeah, for what it's worth, I don't necessarily think this is the approach that will resolve everyone's issues. And I think the other approach where you just try things, I think that's also incredibly valuable. And as long as you're reflecting on those things and seeing whether they do actually fit. You're sort of trying things, but you're trying them with a sort of sense of awareness about how they're going and whether they fit with you and your values. It was something that you just said that reminded me of this really interesting insight that I had a while ago.

11:53What you were talking about was how you were taught in law that if you work hard enough, you get to the answer. I was talking to a professor of writing a little while ago, and she told me about this distinction that I'm going to tell it to you, and it's not going to sound like the greatest revelation in the world, but I find it to be a useful construct. I'm just curious for your reaction to it, which is that she said there are well-structured problems and there are ill-structured problems. Well-structured problems have one right answer. So for example, two plus two equals four. That is a well-structured problem.

12:22Ill-structured problems do not have a right answer. And creative problems, for example, are ill-structured problems. There are a million ways that you could write something. But also, frankly, the question of figuring out what you want to do with your life is a pretty ill-structured problem. There isn't like an actual answer that's out there that you can find. And the point that you made there about what you absorbed from being in law, I think is probably very similar to what a lot of people absorb just from whatever their backgrounds are, which is that they've been told there's an answer somewhere.

12:54And so that means, of course, you got to go find that answer and then be satisfied with that answer. And that's not quite true because life is not a well-structured problem. It is an ill-structured problem. Yeah, I love that. I mean, you see it everywhere. We're told pretty much from the beginning of our educational journeys into our careers that like there will be an answer or you can find like find the right fit for you and like do this quiz and you'll find out what your perfect career is. And like you just keep going like that. And I think it's so tempting to think, oh, there is a there's a route out there that is the right route.

13:26But like you said, nothing is going to map perfectly onto your life. And even if it does for a period of time, your life is going to change again. And you have to do the problem solving thing again. and then you have to keep coming back to it. And I think it can be, well, for me personally, I found it very frustrating because I was like, I'm really trying. I'm trying so hard to figure out like what I'm supposed to be doing here. And none of the techniques or tools or anything that anyone is offering is really working because like you said, you can't like squish your life into a box and just be like, this is the answer to everything.

13:55But yeah, so I love the idea. I love the distinction between the two different types. I think there are elements of your career that could be thought of as like the well-defined problem. well-structured problem where you can um sort of get an answer to like okay if i need if i want this type of career i need to do this internship and then i need to like spend three years doing this so there are elements that you can sort of map out like that but the broader questions i think definitely fall into the other category you had introduced me to a phrase that had been around since the 1980s so i'm a little late to it but i first heard it from you in this piece that you wrote for entrepreneur.com which was the portfolio career which is an interesting idea in thinking of your career as a portfolio, as a collection of things rather than as a singular thing, which again, I think is probably very different from somebody in law.

14:41Somebody in law, if they're at a big law firm that's going to absorb all their time, they are a lawyer, period. But most people aren't quite that. I guess in a way it's similar to the way that we now would describe multi-hyphenates, but it feels like a bit of a way into at least seeing a very complex and abstract thing that we've been talking about in a more concrete way. So what I'd love to do is first talk about what that means and your guidance for how people can wrap their heads around if they've identified a portfolio career as a thing that they want, then how to make that in a coherent way.

15:17So let's talk about that. And then you've teased a couple of times and we've talked about it already a little that you've bounced around a lot in your own career and I've done a lot of things. And so I know that you, like me, like anybody who's doing this is in the constant process of figuring it out. But I think that once we lay out the portfolio career, talking a little bit about how we've been figuring it out would be pretty useful. So let's start with the portfolio career. Tell me a little bit about that concept and how we can start to make sense of it for ourselves. Yeah, absolutely. So as you mentioned, it's been, the term has been around for quite a while, although I think it's really gained popularity, especially maybe even during the pandemic years where people were thinking, okay, now I have my commute time back.

15:57That's like five extra hours. I don't have to spend walking to a train or sitting on a bus or whatever. Now I have a little bit more time to do this other thing that I actually am really interested in. And for a lot of people, those things became side hustles or like little business ventures or even just passions that they really wanted to be part of their lives in a bigger way. So I think, yeah, it's gained a lot of popularity in the multi-hyphenate or multi-dimensional career, things like that have been, I think a recent growing trend. But when it was originally conceptualized, it was sort of this idea that you could split your work up into different segments.

16:29So you would have like the work that you do that earns you money. And then you would have the work that you do that is like of service in the world. And then you would have the work that you do around the house, like your home responsibilities and things like that and your passion projects as well. So the idea that your work could comprise these different segments. And I think maybe that wasn't recognized as much, like you said, in the more traditional sense of a career where you're just a lawyer, you're a doctor, you're a teacher. you're doing your main career as a singular thing. But I think what the portfolio grid concept does is give you a space in which you can bring in all sorts of different aspects of yourself as a human.

17:03And you don't necessarily have to put all of the pressure on one single job to deliver all of those things. You can actually have different projects and they can sort of feed different elements of yourself. So, okay, if that sounds good to me, but I maybe haven't cobbled that together, let's imagine someone who is maybe a few steps behind us in that we've already surrounded ourselves with a whole bunch of stuff. But let's say that you haven't, or let's say that you really, you're doing something, it's fine, but it's not enough. It's not everything. There are all sorts of other things you want to do.

17:34Maybe some of which you know, maybe some of which you don't. Where do you begin? Yeah, I mean, maybe, I think maybe we've identified two possible approaches to this problem, which could be a potential. I think there's potential for like, I don't want to keep introducing book ideas to you, but there's another book idea. which is the two different approaches to doing this, which is one, just come at it from and like try different things and like go for it. And number two is to reflect on it and think like, what do I want to do? And like, what are my building blocks? So I guess one approach would be you have different passions, just create some space.

18:07I mean, it's not always that easy, but if you can create some space in your timetable to try different things. So that could be, for example, if you know that you love writing, it could be like writing a blog post or it could be pitching someone a quick article or even like small things like writing a couple of lines every day that contribute to a bigger project that you're working on something like that but you're building it into your timetable in quite I think personally it had to be quite a disciplined way if you have a job that's taking up most of your main hours and then just trying to build those things out over time experimenting with them seeing what you like seeing what you don't like seeing what's successful trying to put stuff out into the world is always helpful if you're trying a new thing so if you're writing if you're podcasting like getting some feedback from other people can be really getting that sense of accountability, I think can be helpful.

18:52That's the sort of try it first method. And then I guess another option would be to sort of start from just the perspective of yourself and what you want to achieve and what you want to do and what interests you. So sit down with a blank piece of paper and think like, what are the components of say an ideal working day or an ideal day in the life of a portfolio career? If I had one, what kind of things would you want to be bringing in? And even if you don't know specifically, like you may not know that you want to lead a workshop on well-being or something, but you might know that you want to work with people and you want to teach people something and you want to like craft some materials to share with the world or whatever it is.

19:27So I guess that would be the way of maybe mapping out those like central elements that you want to bring in and then trying to get practical about them, thinking like, what is the first step I could take to kind of bring some of this stuff into my life? Yeah. A lot of what you're describing there reminds me of this piece of advice that I got that I've repeated a lot. And it came from Katie Milkman, who is a professor at Wharton who studies behavioral changes, wrote a book called How to Change. And I had interviewed her for my book. And she said to me that, well, in response to this question, which was like, what's the thing someone can do to start thinking about a change to make in their lives?

20:05And she said, this is going to be, it's going to sound really simple, but experiment because we tend to think of things that we do as long-term commitments, but they don't actually have to be. If we think of them as long-term commitments, we probably won't do them because it sounds scary to commit to something. I don't know if I want to do this. So what if you just think of it as an experiment? Everything that you do is an experiment. You're going to run it for three months. You're going to see what happens, whether you like it or whether you do not like it. Either way, you are better informed than you were before.

20:32And therefore the experiment was a success. And I feel like in a way what you're describing there is that. It's different approaches to it and what's the root of the experiment, how you want to run the experiment. But ultimately, let's just do some experiments. Let's find things that you like. Because in the piece that you wrote for Entrepreneur, where you have these four steps on how to build a portfolio career, the first one was, well, I mean, the way that you wrote it was to make a list. What we're describing is either making a list or kind of activating a list of trying a bunch of stuff. But then step two is to evaluate it, which I thought was really interesting, where, you know, after you either put down a lot of thoughts about what skills or talents do you have, do people recognize in you?

21:11What are your key passions or interests? These are the sort of list making things. But you can also make a list in terms of experiences. I'm going to try a whole bunch of stuff and now I've got a list. But the part two is to evaluate it, to then look at the patterns of the things that you were doing and see not just that you like liked one particular experience, but maybe that there were a couple experiences or a couple ideas that you liked, or if you made a list, just a couple of words that keep showing up that speak to a broader pattern of something that is meaningful, because that's really informative.

21:42Because it's one thing to say, I liked doing this last Thursday. It's another thing to say, I understand why I liked that and therefore what other things might fulfill me in the same way. Yeah, I love that. And I think that has been something that's been so helpful to me on my own portfolio career journey, because I have ended up doing so many things, many of which seem sort of unrelated on the face of it. And I've always found it really difficult to sort of draw those together and understand them a bit more as part of a unified whole. And I think that's been my journey of like trying to reflect on things and think, okay, it's not just a random experience, but like it's an experience that resonated with me because I like doing a certain type of thing or like being with people in a certain type of way or like teaching or whatever, like a broader sort of theme that's going on over or above all of the disparate things that I'm doing in my life.

22:29So yeah, I think it can be really valuable to, I guess the heart of most of this stuff is like noticing or observing what's going on. And I don't know too much about the job design field, but like the field of like applying design thinking to your career, where you're really trying to like, like you said, run little experiments and think like my career is actually much more flexible and open than perhaps we have been told at school or university. And instead of thinking of it as just like a series of steps that you have to climb to get up to some place that you're just going to sit and be happy forever at the top of your ladder.

23:02Instead of thinking of it like that, you're actually thinking of it as a design process, like this process of experimenting and like gathering things together and seeing themes and drawing it and being a little bit more creative and like open and maybe even playful with it. We're going to take a short break. And when we come back, More with Eloise. As spring arrives, I'm sure that you, like me, are super excited to finally get back outdoors and start moving. But to do that, we need nutritious, convenient meals that energize us and keep us on track to reach our goals. That's what Factor does. It's America's number one ready-to-eat meal kit and can help you fuel up fast with ready-to-eat meals delivered straight to your door.

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