The Myth of the Linear Career Path with Holly Ojalvo

Holly Ojalvo has had a long career in both digital media and education.

Over the past dozen years, she has been an editorial leader at outlets including The New York Times, Quartz, and USA TODAY, developing and executing content strategy, streamlining processes, launching and running initiatives, and mentoring, coaching, hiring, and training journalists. She also founded and ran Kicker, a digital news outlet aimed at young adults.

Previously, Holly spent a decade in the high school classroom as an award-winning teacher and student newspaper adviser.

She has long been passionate about fostering collaborative and healthy culture for staff and students to thrive.


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In this episode you’ll learn:

  • What Holly does
  • How nonlinear paths can play a role in your career
  • How to frame transitions on resumes
  • Linear vs non-linear transitions
  • An iterative approach to career
  • How Holly thinks about calling and purpose in her life, career, and journey
  • How to know when it is the right time to make a career transition

Resources Mentioned:

Holly’s Twitter

Holly’s Linkedin

The Squiggly Career by Helen Tupper

Software Generated Transcription:

Dan

Holly, thank you so much for joining me, welcome to the podcast.

Holly

Thank you so much. And I’m really excited for this.

Dan

The place I always like to begin is the question, how do you begin to talk about your work in the world?

Holly

Well, that is a great question, because that’s something I’ve thought about a lot, is even how you even begin to talk about your work in the world, especially when your path has not been linear and when you’re a career switcher like me. So even figuring out how to frame your story in a way that makes sense for other people is hard. So I’ll try it out on you. And you tell me you tell me how I’m doing and trying to perfect that sort of like a meta process, right?

Dan

Yeah, let’s workshop it.

Holly

Let’s workshop it. It’s a long progress, right?

Dan

Yes.

Holly

So I guess for me, I’ve spent most of the last dozen years or so in newsrooms, you know, as a newsroom leader and an editor, mostly focused on things like content strategy and execution. I’ve run teams and verticals. I’ve also been in more of a support role. So I’ve run hiring, mentorship, coaching, internship programs, professional development, those sorts of things. And before that, I was a high school teacher. I taught English and journalism and philosophy, also several top public and private schools.

And so, you know, I’ve had two different careers, right, in education and in journalism. And there are some elements that overlap and there are some that don’t. And I guess I’m always sort of thinking about how to combine those two things in sort of different and fresh ways, because I’m just really passionate about both of those areas and in general about empowering people to be their best selves, do their best work and tell great stories. And that’s how I think about my career.

Dan

I love it.

The last phrase, can you say that last phrase again, because I feel like  that is like a mission statement.

Like do your best work.

Holly

Yeah.

Dan

I guess if that’s a phrase or a tagline that you’ve workshopped. But I thought that was like so clear and concise.

I think that that really encapsulates a lot of your work.

Holly

That’s amazing to hear. Yeah. I had it’s not like it’s not like a tagline that I could say. I just said it just so. So, yeah. You know, good thing you were recording this and this is for podcast because we may have to go back and turn that into my mantra. But now it’s funny.

Like I guess I’m the kind of person who I don’t like to be the face of things. Right. I’d rather not be if I were working in TV, for example, I wouldn’t want to be the anchor. I want to be the producer. If I if I were working in politics, I would want to be, you know, the the the candidate or the politician. I would want to be running the campaign or running the show. So I like to be behind the scenes.

I like to empower other people to do their best work and to thrive. So so far I’ve done that mostly in education and journalism. And I could stay in journalism, I could go back to education, or I could combine those things in a different way. So I guess like the threads of that. The theme of that is really setting up other people to succeed and thrive. That’s where I’m happy.

Dan

I love it. So just to rewind, to go back as a young woman thinking about the career path ahead of you look, what does that look like?

If we could just turn back time?

Did you were you planning to go into education and just be a high school teacher or something along those lines long term and then this kind of switch happened? Or would that path, I guess, at that point in your life?

Yeah. Where did you think you were headed?

Holly

So depending on how far we’re rewinding, we could go when I wanted to be president, the United States. Yes, I had a T-shirt that said Holly for president on it. I’d be happy to learn, but it was pink with green iron on letters. And I wore it around like I wore to school. I, like, wore this shirt. I wanted everybody to know that I was going to grow up to be president United States. And that obviously has not happened yet.

Dan

Not yet. And yet time.

Yeah. I mean, just to say all that desires, as a very ambitious, driven kid. And I just thought the whole world was open to me and. Yeah. And I guess, you know, originally I thought more concretely when I was in college, I really thought I was going to be a college professor. You know, my professors pulled me aside and said, you know, we really think you could be really good at this, like what we do here.

And I was like, oh, really cool. So I went to graduate school initially in a in a graduate program in my field, which was the. Is English literature, and I thought with with the aim of getting a PhD and becoming a professor, and I was in the program and realized I was miserable and I didn’t want this to be my life. And so I left the program with it and I was to call a terminal. Emma, when you leave a PhD program as if you have a disease and you know you’re persona non grata.

Thank you. Goodbye. Get out of here. And and, you know, when you leave a program like I feel like you either know what you want to do instead or you don’t. And I did not. So I left that program and wandered in the desert for a while thinking, OK, I don’t really know what what I want to do next. And I had a couple writing and editing kind of jobs because that’s sort of my skill set with language.

And then I realized, you know what, I really do love the teaching piece. And what if I go back to that? But I don’t become a college professor. What if I did at the high school level? So I went back and got a second master’s in education and I became a high school teacher.

Dan

Love it, love it, and then, like without without dating yourself too much, I guess.

Holly

Sure.

Dan

How long were you in that role before making the switch to journalism?

Holly

Yeah, so I was a high school teacher for about ten years. And I guess when I first started teaching, yeah, I was already, because I had the two master’s degrees and because I had a couple of jobs. You know, I, I was about, I was, I was like Holly9 or 30, I think, when I became a teacher. So yeah, I did it for about ten years before I decided to switch careers. And even that came about very organically.

It wasn’t really a hard stop. I actually was I had been freelancing for The New York Times on the side. So I was a full time teacher and I was advising a student publication, which is also a lot of extra time. And then on the side, in addition to that five days a week, I was doing some freelance work for The New York Times and then it organically turned into an in-house job, which is not a typical path at all.

It’s not usually how people start in journalism or start of The New York Times, you know, just kind of really weird way to sort of lucked into a job. And that happens sometimes in your career. You know, things just kind of kind of morph into something else. Even the way I came to the Times in the first place was I just I applied cold because I use the times a lot in the classroom. And they have this thing called a learning network that still exists.

And it’s all about the whole purpose of the Learning Network is to help teachers use the times in the classroom. And I was like, hey, I’m a teacher who uses the times in the classroom. So and I emailed the person who was then the editor and said, oh, hi. You know, I guess the Times and all my classes, I use a few times articles and philosophy. I use it as models for my journalism students. Obviously, I use they use essays as models for my my composition students.

I use essays. I use articles to supplement my my literature. I use it all the time and everything. Can I give you my lesson plans. And you actually wrote back to me and was like, that’s not the way it works.

We just got to take lessons. We will use it. Thanks, but actually we don’t do that. But she said, you know, it’s funny, you know, you should reach out to me at this point. I don’t really need another writer, but I actually need like a deputy editor. Or is that something you’d be interested in? And yes, I was very interested. So some of it is timing. And I maybe just the way I approached her, I don’t know.

But just then I just became her deputy and I did editing for her five days a week. And then I ended up going in house and being the deputy to her replacement, an expanded role and, you know, just kind of went from there. So, yeah, some of it’s like some of it’s timing, some of it’s, you know, what I was doing. It’s sort of a combination of all that stuff.

Dan

I love. I love that. And I mean, I think it underscores, you know, I think a theme, a theme on this show. And I think with a narrative that I’m often trying to, I think, help us all move move beyond is the that career paths are linear. And that’s, you know, one of the things that the first connected us. You had a tweet that I came across.

I think it seemed like a lot of people came across that’s about a nonlinear career path, that it just struck a chord, struck a chord with me.

As with many people, I think that we’re all culturally indoctrinated into thinking that, like you get to you’re on the on the straight, straight path, through through your education, into the workforce. And then you know that you stay on that path till you retire or you stop working for some reason. And that’s so rarely the case. And often there’s transitions that you could never expect, many of which are even better than we could imagine. But they just happen.

They happen in ways like this happen for you. And the email, a random email turned into a new career like that’s incredible. I love it.

Holly

I mean, that’s a really interesting way of thinking about it. I hadn’t really thought about it that way, but that’s absolutely right. And, you know, I think, you know, I think one of the reasons why that tweet, which, by the way, I still to this day, I’m shocked that, you know, more than six people responded to that tweet. You know, it’s it’s you know, it’s up to a hi. I’m looking at it right now.

It’s up to one hundred and fifty six thousand three hundred twenty one thousand three tweets, you know, almost seven hundred.

Just direct messages back to me. No comments back. Unreal replies. It’s wild to me. But I think the reason I’ve thought about a lot, I think the reason is that is exactly what you’re saying. It’s common, extremely common. But still, for whatever reasons, not normalized. We still have this idea that’s ingrained in us for I don’t even know why that we should have this trajectory. You should be on this one like you pick you even here you hear students talk about this now is like, what a.

Going to do with my life, yeah, that’s just not the way it works for most people. I mean, even if it didn’t feel like education, right, I was tenured at, you know, a leading high school that was is a great place to work. And I loved it. And I could have spent my entire career there. I mean, I could have I remember being there thinking like, OK. And my head of my department was only a little bit older than me.

I remember thinking when he moved into that job, like he might be my boss for the rest of my life, like we might literally work here till we retire.

And so many people do that, which is great if that’s what makes them happy and brings them joy. And I am not a person who likes to stay still. I always want to do like something new or something different. And that’s been a blessing and a curse, you know, to some people might look at my career and you left that teaching job that I was in high school. Who would do that? And then people you left The New York Times like, what’s the matter with you?

I think I’m really stupid and maybe I am in some ways and then in other ways is exactly what you’re saying, that, you know, we don’t really necessarily want to stay still.

We want to have different kinds of experiences in life. Some of those of us are just built that way. And we’re on a non-linear path.

Dan

Yeah, I love that. I mean, so much so much resonates with me.

But I think part of it is like that the transitions, the career transition, like looking at your resume, these great places that you’ve been, a lot of people are like scared of having too many transitions on their resume. And I’m I’m curious how you think about those transitions and the story that they tell. And how do you to someone who’s listening, like, yeah, I’m in a job and I want to make a change, but I’m scared of having too many changes because then I might not be hirable in your own experience as you go from the jobs you’ve had, the transitions you’ve made, as well as being in hiring since you’ve hired journalists and such.

How do you think about transitions on resumes?

Holly

Yeah, that’s a great question, because I think especially right now, like with the pandemic and how many people have lost jobs, it’s really very depressing, I think. And I think it used to be a real mark of shame and was like, if you Google so many articles about how to explain or a career gap or a career switch and you know how to downplay, you know, the rough parts about stuff like that. And, you know, last summer I wrote an article for The New York Times about how to deal with a layoff in a way that helps you not feel ashamed about it, because I think there’s a lot of shame associated with career transitions and career switchers, especially if this transitions are not, as you were saying, if they’re not linear or they’re not on this upward trajectory, sometimes, you know, you take an off ramp and sometimes you leaves a place of your own accord because you got laid off or because place closed or, you know, there’s like so many reasons.

So I think. Yeah, and it goes back to really to the whole like common versus normalized thing, I think is really common to switch jobs. But we still have this idea that, like, you’re going to be somewhere for the rest of your career and you’re going to have a retirement party and get a gold watch. You know, like I just like because we think that we think that’s like what version with the good news. I think inside of that is that it is becoming so much more common to transition either jobs, industries or both.

Yeah. And, you know, it’s funny, like I’ve definitely talked to as a hirer, as you say, and I’ve hired many journalists and I’ve I’ve read thousands of resumes and cover letters and I’ve interviewed probably thousands of people. And I’ve I’ve heard a lot of people. I definitely have noticed a change in those conversations, you know, where people don’t necessarily feel as bad as they used to feel, you know, over the years that you can tell that things are starting to move and change.

But there is still some shame associated with that. And you can tell when people start to feel a little anxious in the interview, like, OK, here comes the part where she’s going to grill me about while I stayed at that place for a year. You can kind of bracing themselves, right. Or like going into their little explanation that they’re like, OK, they’ve kept it like they’ve prepared. They have the reason why, you know, and I sometimes try to, you know, put people at ease in those conversations and just say, like, I don’t I don’t actually look at that negatively.

I think it’s super interesting that you used to be a working scientist and now you want to be a science journalist. I think you bring a lot to the table. When I ever I’ve said things like that, people almost every time feel very surprised, like, wait, really? You think that’s a good thing? We really think that’s not a bad thing. You think that could be a plus like. Oh, they feel surprised. They feel relieved.

They feel comforted by the fact that you might think of that as a plus, that they’ve they’ve had the fortitude to switch something that they’ve, you know, put themselves out there, that they have had to learn something totally new, that, you know, there’s so many ways to think of that as a plus.

But we’ve been conditioned to think of it as a negative, like, oh, you switch, you move around, you don’t commit. So I think there’s a lot of ways to reframe it that I think can be very, very powerful.

Dan

I love that.

And I think as I was thinking about this conversation, think about the. A specific piece of how do we tell the stories around transitions, particularly for, you know, as you’re in a job interview?

What I think is really exciting that’s happening is how much people are resonating with this idea that, you know, that career paths are not linear for most people and like to go into those conversations at least like giving yourself at least a hope that the person on the other end of the conversation, the person that’s doing the hiring, doing the interview, has had a taste of that.

Holly

Yes.

Dan

Like to break it down like they’re not a robot, they’re human. Right. And that I feel like the transition say something about being human, that we are all in process, that we change and grow, and that it speaks to, you know, our desires to, you know, take on the next challenge and grow and our skills and experience.

So I don’t know I don’t know if that resonates with you at all, but I don’t really think about, like, this exciting thing that’s happening that, you know, so many people have liked your tweet. Some of those people are hiring people. And those people like you can look at those transitions differently than we look at them when they’re on our own, if that makes sense.

Holly

That’s right.

No, it absolutely makes so much sense. And, you know, another way I think about it, too, is about risk greatly. People are taking risks in their lives, in their careers. And I took a huge risk leaving a tenured job, which, you know, people think of as cushy or whatever. Right. I took a huge risk of leaving The New York Times to launch my own startup and be an entrepreneur. I’m actually a ridiculous risks and other people take even bigger risks.

And companies, they need some people who are steady and they’re going to stay there for a long time. And they also need some people who are going to be have a little bit appetite for risk, you know, for innovation and, you know, how are you going to ever have new ideas and think differently if all you ever have are people who have never left the company and it’s hard to inject that energy right. You kind of need both.

Some people bloom were planted and grow towards L.A. and some people need to be replanted.

I don’t actually garden, but maybe this metaphor works the way, you know, I just feel like there’s I think you kind of need a little bit of both. And, you know, I mean, I’ve heard from people over and over like, oh, when people are hiring, you know, companies hiring you, all they want is someone who’s done that exact job for years. And I do think that is safer. There’s less risk there if you know that person has done this exact job and they’ve been good at it.

You know, I think that your job, if you are a career switch or transition or however you want to think about it, is to frame your experience in a way that is a positive, that is a plus. Like I I’m going to bring fresh energy. I’m going to inject new perspective and new ideas, and I bring something different to the table. And this is how it’s going to be really valuable. You know, if a place is not open to hearing that, maybe there’s not ready for it, but there are places that that are for sure.

Dan

Yeah, I love that.

I know that on that tweet thread, you link to a bunch of great resources, a few books that I’ve read, some that I haven’t that I want to, but one that you’d link to range.

Dan

Why Generalists Triumph in a Specialized World, which is a fantastic book that I recommend just about the very idea that so often the innovation, the growth, the next phase of whatever it is that needs to be brought about comes from outside of the, you know, the specialized world that cultures, that businesses this is live in, which I think is for anyone listening who’s interested in this idea. That’s a great, great book. Yeah. Explores that and in great, great detail.

Holly

Yeah.

I need to read that book myself. I mean, that’s another way to think about it. It’s not just like the the study people and the risk takers, it’s also the specialists in the generalist. I think like a lot of industries and a lot of organizations need both of those to write like I’m a I’m a generalist. I often work with specialists in newsrooms or what have you. But I have a lot of soft skills. I have a lot of transferable skills.

So in some ways that makes career pathing really challenging and daunting. It’s like I’ve got this I’ve got this set of skills and guestrooms. I’ve thought about it as like I have these I have these pieces to a puzzle and I don’t know what the puzzle looks like. And the puzzle pieces can be combined in different ways. Like, I don’t know I don’t know how to assemble at this time, you know, like I just thought about myself that way.

And but that can be daunting. But it could also be positive, like, wow, I’m so flexible and I can do different things. Like I had people who are specialists say to me, why you’re so lucky. You can do you could do twelve different jobs or more. There’s so many different ways to combine, he says, or like what I am is this like I have a friend who is like I do sales and he’s like, when I look at your career and I think about the jobs are interviewing for it.

Wow. Look at the variety of things that your conversations that you’re having and jobs that you’re he’s like, if I’m going to do it a job, it’s going to be in sales. And that’s what I’m good at. That’s what I do. And I do think I kind of think it takes all types. I think you need people who are specialists who really know what they’re doing and they can go deep. And I think I’m hopefully I’m not just telling myself this.

You know, I do think there’s there’s something to be said for it, for the value that General is open to. Yeah.

Dan

Totally, totally agree. Yeah. Well, I think back to that the question of of you know, that students at. So what am I going to do with my life and I don’t know.

You mentioned earlier in this conversation one of the, I guess, real negative effects of the linear narrative is how much more pressure is on that question to get it right. And I know from my own life, you know, another reason why I host this podcast.

Another reason why I have these conversations, because my faith has been so not living here. I was a youth pastor, a photographer. I’m an entrepreneur now doing things that I never would have even imagined myself doing, you know, Dan0, 15, Holly0 years ago. But I felt so stuck for so, so long because I didn’t know how to answer that question of what am I going to do with my life. And a better question, you know, I think would be, you know, where do I start?

What do I want to do next .

And I don’t know how different work would feel if that was the starting place instead of like one final answer that you get stamped on your forehead for the rest of your life or something.

Holly

Yes. Yes. It’s funny because we tell young people, you know, follow your passion. And then I have other advice, like, that’s the wrong way to think about it. Don’t think about it as a passion thing about like what you’re good at and where you can add value about that. Or you think about, you know, obviously your major. Right. You have to use that the rest of your life or, you know, there’s just all kinds of different ways to frame that up.

And I think I’m always thinking about the way I always talk about it. I don’t even know how I got into using this phrase is say I’m looking for my next adventure. I’m thinking, you know, I love that. Or I thought about my next chapter, everything like a book, a novel, like an epic, some really long with lots of different things happen. You know, if you think about what I’m going to do for the next chapter, I don’t think about the rest of my life anymore.

I know not to think about it that way. Yeah, it happens to be for most of my life. It’ll happen that way. But I’m not going to think about it that way yet. I’m going to think about what’s going to come next and how I am going to leverage all my experience in the past. But, you know, the stubbornness that you’re describing, I’ve definitely felt that I don’t want to, like, pretend like it’s all great and I’m just transitioning my way through in this fluid way and it’s all jolly and amazing and so special, you know, and it’s an adventure.

I mean, adventures that have scary parts and they have bad parts and bad stuff happens with your adventure sometimes.

And I’ve definitely experienced that myself. And I think, you know, we’re talking about normalizing the non-linear career path. I think you need to normalize that to like sometimes you’re going to feel stuck.

And, you know, I think we as a culture, we tend to prize that the narrative of like the person who doesn’t pick themselves up and dust themselves off and just goes forward and they just figure out what to do next minute. I think we just like a lot of stories about that. I’ve seen stories. I’m sure you have to turn. The pandemic person lost their job like five minutes later they launched this new business and they’re making it work and amazing.

And the people who were stuck or who get stuck for however long and really feel paralyzed or frozen or whatever, whatever metaphor you want to use, like that’s not something that we celebrate. We don’t celebrate, you know, going deep and being introspective and having conversations with people and trying to figure it out. That’s not the part that feels cool, is not the part that you get profiled for, you know. So I feel like that’s that’s more invisible.

And then I think people feel ashamed of it. They don’t want to be open about the fact that they’re stuck because that feels like it reflects on you. Yeah, and I’ve definitely I mean, in so, you know, I lost my job last May, which I wrote about is for The New York Times. And I’ve definitely had phases in the past, you know, eleven months where I felt very stoic, very frozen, you know, as you’re saying, like, what do I like to do?

Well, you know, what would you’re a generalist. You like to do a lot of things. What am I good at doing?

Dan

Totally.

Holly

As a generalist? I’m good at doing a lot of things.

So, you know, like, I tried different things on for size. And I’m like, well, they all feel kind of equally interesting to me. I do. I stay in journals. I love journalism school, but I go back to education, love education. Maybe I do that or maybe I combine these pieces in a different new way. I could do that, too. And so, like listening to what you really want and really you are best at and what you’re really good at is not always clear when you’re this kind of person.

So, yeah, it can be. The downside is that can be really, really challenging.

Dan

Yeah, yeah. Yeah.

And while you’re in that you don’t liminal in between space, it’s, you know, there’s, there’s pressure especially you know, when you have bills to pay, mouths to feed, like it just adds a whole another layer of complexity and struggle and even pain.

I would say for people, depending on your situation, I think what you’re saying is really, really important.

You don’t we don’t want to gloss over right now. Hard, those transitions can be and they are we don’t want to enter into them lightly.

Holly

That’s right. I mean, people people have different kinds of bandwidth rendering into them and where they’re forced into them or both.

Dan

Right.

Holly

So but I think, you know, being really intentional, making sure that you have your support network around you, people who are good sounding boards where you can you can bounce ideas around.

I mean, there are there are a lot of resources out there about finding the right thing. And it really resonates with you and helps you if you need help with your journey. You know how to think about your next the next chapter. You know, there is stuff out there. You know, I I’m actually in a program right now that is that is designed to help people kind of move forward in that process. So, you know, there are there are things like that out there.

And it’s been a really interesting process for me to be to be part of that kind of program now.

Dan

And I’d love to hear a little bit more about that. And, you know, what sort of what some of your takeaways have been.

Holly

Yeah, so so the program that I’m in is called Evolved Me. And it was started by two women who also had inflection points in their own careers for different reasons. One left the workforce to raise a family for a while. And then after 10 or 12 years, I was looking to return and not sure how to how to do that. And the other one, the other founder was in a career that she found was very closely aligned with her identity for a long time and then decided she really didn’t any longer feel really that it was aligned with her identity.

And then therefore, what now? And so the whole program is designed for women, specifically mid career women who are at an inflection point for whatever reason, maybe they’re returning to the workforce after taking care of family or for some other reason, maybe they’ve been laid off. Maybe they’re just thinking about making a career switch or for whatever reason, they’re looking to pivot or do something new. So they created this whole method to go through. And there’s a curriculum thing on them.

And it’s like an eight week curriculum just starts with the discovery phase. You discover what you’re like. Superpowers are which direction you kind of want to go in. The whole thing called the DARE method. DARPA is a is an acronym. So the first part is discover. The second part is called Amplify. You you you craft your pitch, you amplify your strengths, you try to get over any kind of imposter syndrome you might be experiencing. You try to think about your personal brand.

The third part is called refresh and you refresh your resume, you refresh your LinkedIn, all your personal branding. And the last part is embar because after all that, you’re ready to kind of move out into the world. You’re building your network. You’re thinking about how to have conversations and interviews in effective ways as we’re talking about how to frame your experience in your past and how to leverage all that for the future. And as part of that, you’re in like a what’s called the accountability group.

So you’re in like a subgroup of women in the program. And you meet separately once a week as a small group. And that’s been incredibly powerful and amazing. I’m in a group of five just incredible women in completely different industries and we’re all experiencing some togetherness.

We’re in this little together. And it’s just the conversations we’ve had have been very rich, very supportive. You know, that that’s like a new sounding board that I have separately from my other ones. And so it’s been it’s been very powerful. And the whole idea of that process is that it’s not linear. Again, with that whole it now linear career path, anything even that process is not linear. It’s framed as, you know, as a like a virtuous cycle.

So you can cycle through it. And some of us feel like we’re at the end of it. We’re not really done. And they’re reminding us, you know what, go back to the beginning, go back to the discover path. Maybe since you’ve been through this whole pipeline, going back to it, you’re going to see it differently. It’s going to hit differently. So it’s an iterative process. So, yeah, you could you know, anyone can join that that process and and try to do it.

Or you can just kind of do pieces on your own. But it is powerful to connect with other people. Definitely. You feel less alone.

Dan

Yeah, I love just that iterative approach.

Holly

Yeah. Me too.

Dan

Because I think when it comes to these big questions of work identity, meaning you use the word calling, whatever words you want to use to describe that like that we’re continually growing and changing.

Different parts of ourselves are bubbling up to the surface. And we have to continually come back to these questions of who am I when it comes to work, who do I want to be and what do I want to give voice to the work that I do. And so it has to be an iterative cycle, even if our path on paper is very linear for those, you know, for the minority of people who stay in one job for a really long time, even within that job, if they’re really performing at a high level, they’ve had to find a way to grow within the boundary of that role and make space for all.

Of the change that’s happening inside of them, it’s all I. All of this is just to say, like I think the cycle piece is so important that we have is circling back to who we are and what who are we becoming, I think big questions.

Holly

Yeah, it’s interesting because, you know, the discovery piece is at the beginning, but you’re also discovering along the way. So the fact that it is it makes sense is just organically happening anyway, because you’re having these conversations. We’re doing all this work with all this homework involved. There’s like these experts involved. It’s it’s a very rich program. And you do make discoveries along the way. So you’re naturally sort of iterating you’re naturally sort of it sort of recursive and building on itself.

That’s happening anyway, even as we’re moving through it. And then, you know, we’re encouraged to keep going back through it. So that’s really helpful. And then there’s a lot of meetings, there’s videos. And then I’ve been doing other reading on my own, as you mentioned, range. So one book I’m reading now is called Impact by the founders of a nonprofit called She’s the First Christian Grant and Tammy Tibbits. And so they founded a nonprofit that’s, you know, that with a goal of helping girls become educated so they don’t have access to education.

And then, you know, they wrote this this book that I’m reading, it’s it’s really powerful. And the subtitle of the book is a step by step plan to create the world you want to live in. And it really is about where can you add value? Where can you, you know, draw on your powers to think about where you can have impact. That’s another way of thinking about your career and all these different ways of sort of framing the process of thinking about your career.

So where and how you can have impact is a really interesting way of thinking about what job should I have or what career should I have.

It’s about like, you know, what kind of impact should I have? And then I can. I had a really wonderful conversation with a friend recently who was like, no other way to think about it is what do you love to do? They think about what you really love and figure out. Just start doing that and it will lead you to something else. So there’s like all these different starting points, right. You can think about what you’re going to think about the impact you want to have, think about what you love, you know, think about the service you can provide whatever it is, like those different ways of framing it.

But for me, like maybe one way is not the right way. Maybe it’s all those ways. Maybe you didn’t think about all those things to connect the dots and put it together.

Dan

I love it. I love that I’m curious for you, this is kind of circling back, maybe even to where we started this conversation.

Holly

Speaking of iterative.

Dan

Exactly the sort of cycling. Yeah, well, just zooming out the big picture and like words like calling and purpose. And like, I’m curious how you think about those words in your life, in your career and your journey.

Holly

Yes.

So it’s interesting because I think there are some roles or some careers that are more aligned with the idea of a calling. Right. I think education for me and I think for a lot of educators is one of them. When I was a high school teacher, I felt like it was a calling. I was called to help teenagers learn and grow. It definitely felt that way for many journalists. I think it feels that way. You know, you want to uphold the First Amendment, you want to shed light on the dark places.

You want to comfort the afflicted and afflict the comfortable is like one of the ways that journalism is described. You want to you know, you want to expose malfeasance or it feels like a calling. So it’s interesting that I happen to have two careers that really do I think for a lot of people who are in them feel like a calling. And I think, you know, I think it speaks to the real sense of purpose and mission. So, you know, I think I’m a definitely like a purpose driven person, a mission driven person like everyone am.

I start over from the very mission driven and mission. So, you know, not everyone feels that way. So for some people, work is more transactional. Like, they just they want to do the thing and make a living. And they have a really rich life outside of it. And that’s really where they get their their energy and that’s what feeds them and nourishes them. And that’s great to me that I don’t think there’s one way to feel.

I don’t think everyone needs to feel like their their work is their mission or their purpose. But I think if you are someone who for whom that resonates, that you want to do something that feels like a calling or what have you. And I feel like that can either manifest as one thing. Right. So you are a journalist or an educator, your clergy member, you’re like you’re saying before that something used to do. You don’t want to do something that really does feel more like a calling.

But I, I think sometimes a calling can feel finite, you know, to go back to what you were saying before. But you don’t even take your own path and you can feel sort of like, wait, I have this calling, but yet I want to leave it. I’m also called to leave the call to do something different. Like what does that mean? That can feel like a crisis. I think sometimes.

Dan

Yes, I’ve been there.

Holly

Right? What does that mean like I want to leave. They say “Me too. Me too.” What do you mean that they want to leave the classroom. And you know, me leave the classroom? You know, like so I think that can be really complicated for people because I think maybe people wonder, like, what was this authentic for me? One thing I think about a lot is imposter syndrome. And I think that could come up to it was I just was faking it all along. And this wasn’t really my calling. Or you were saying before, when you grow into a role, sometimes when you’re not quite 100 percent ready for a role, you feel like an imposter, but maybe you just need to grow into it.

There’s like lots of reasons. I think people feel like a fraud in their in their roles. But I think now. Do you think a calling can be a plus? And it can also be really complicated by these reasons. It sounds like you’re talking about yourself. Yeah.

Dan

Oh, absolutely.

Well, I think especially especially in in faith, you know, the faith context  of that word calling when it has a capital C on it, it just has this whole additional layer of complexity because it’s from God, you know, like, oh, my, like you know.

Holly

Yes.

Dan

Yeah, yeah, yeah.

And we could go down all the theological, you know, rabbit hole there.

But I think what’s been really helpful for me, as you know, in my own work and really as I work with people around these ideas, is to think of calling as something very distinct and separate from a job that has more to do with identity and. Yeah. And you to use the word impact. I think that’s a really important, important word.

I think it’s helpful to think about it like what is the change that you want to be a part of making in the world that can have, it can have a few different, you know, a few different manifestations. But what happens is there’s typically some sort of themes that connect it all, which I see very much in your work journey.

And the job itself is not the calling. It’s it’s an avenue of expression, an opportunity to activate, to flex that muscle.

I guess you could say.

Holly

Yes.

Dan

And I think that that’s a much healthier way to to think about those words. Does that resonate?

Holly

Oh, my gosh. So strongly.

I mean, I’m thinking about even at the beginning when you said, like, how do you describe your career? And I said that line that you were like, oh, that sounds like a mantra.

Like because if I’m if I’m called to help people, you know, thrive and be, you know, do their best work, that can be expressed in lots of different ways. I can do that inside of journalism and help empower journalists to do. Incredible, important work where I can do that as a teacher and help students grow and become the person that in self actualize right on the path to learning and and having the skills and the knowledge they need to move on that.

Or I could do it in X, Y, Z, other ways. Right. Like if that if it’s really about the purpose and the impact you want to have and not about the job. I’m so called to do those things, but I’m just going to do them in different ways and in different industries. It’s more like a theme.

Dan

Yeah, yeah, and it feels  more invitational instead of a yeah, it’s sort of like final and final, like to me at least it doesn’t.

Yeah, it feels, it feels it feels freeing and liberating and less like here’s the cage that some outside force put you in instead. Like here’s an invitation to go on an adventure and find more beautiful ways to exercise this thing in the world.

Holly

Absolutely.

It has the adventure piece, now it’s a tree. It has a creative piece too.

Dan

Yeah.

 Just romantic and poetic. You know?

Holly

I love that because it is such a different meaning.

It’s interesting is that when you think about, like your life story, your life journey, you think about the way we tell stories or like the hero’s journey. Right. It’s kind of is part of that. And you’re part of the hero’s journey is like resisting the call. So sometimes maybe you resist to be fit into that box and just feel more creative. It does feel more risk oriented. It does feel like more varied.

But there’s still like a theme. There’s something that you have this you have this purpose or you have this this aspiration. I guess that’s another way to think of as a calling. You think of a calling is as an aspiration. You’re aspiring to do something but that’s separate from the job or the title or the industry. That can be true for you in lots of different ways. I could show up at lots of different ways. And you can you can have value in lots of different ways and places with different kinds of people.

And that’s what’s going to get a variety to your life to if again, if you’re the kind of person who wants to to make those kinds of moves, I think there is a poetry and a beauty to it.

Dan

Mm. I love that.

I love that. We’ve talked about kind of these inflection point and the decision to to take the leap I guess. And I’m curious, you know, for people, because a lot of people are on the cusp of something who are listening or wanting that in their work.

And I’m curious for you, in your journey, the transitions that you’ve chosen, because not all of them, you know, were necessarily chosen, but the ones that you have made that decision to transition, you know, whether it be from a teacher to going full time with journalism or whichever ones, I’m curious how you think about when is it time for you to make that transition?

Holly

Yeah.

Dan

What are some of the signs, I guess, that you say, OK, there’s more for me on the other side of this and it’s time for me to leave what I’m doing now and and pursue this other thing.

Holly

Yeah. So when you say that to specific transitions in my transition field life come to mind, well, that’s one I talked about before, actually, the three of them. So what I talked about before was when I was in graduate school and I was just like, I’m really not happy doing this. This thing I loved as an undergraduate, I no longer love. And also the career prospects look bad. Just everything here looks bad because. No, that’s a good story for me here.

And it was a crisis, actually. And I actually really felt like I was going to let my professors down and I reached out to them and very apologetically. And that was really hard because I thought they were going to be really disappointed. And they actually came back and said, no, we’d be disappointed if you did something you really didn’t want to do. So, you know, so there’s that. I mean, if you just are really miserable, I guess that’s really that’s one you’re just you have to know yourself and you have to listen to yourself if you just like I thought I would like this, but I don’t.

And just to be honest with yourself about that, that’s one thing that can really kick you into a transition, though. The other two I’m thinking about. So leaving teaching, like you said, that was big. And, you know, I had started to really feel a little bit burned out as a teacher. And I did not want to be that burned out teacher that I think we’ve all had. You know, we’ve all had great teachers, which I definitely have.

And I’ve also had the teachers who were a little burned out, a little checked out.

And I knew that I always wanted to be the teacher who just gave everything like, you know, left it all in the field, you know, and I would sometimes go home and make barely even be able to move or a couple of hours because I would just have to use all my energy during the day with my students. And I was just that kind of teacher. And I just gave everything, every ounce that I had into the classes. And just like interacting with students and supporting them after hours and whatever.

So I realize it was really starting to take a lot out of me. And I didn’t want to be the checkout teacher and I recognized myself. I was just like, I don’t have it in me right now to continue to be the kind of teacher that I can be, that I should be, that these kids need and deserve and that I really want to be. And if I’m really going to if I’m not really capable of being all in, I need to take a break from this.

So that’s what spurred that transition. And I you know, I had this happen to have this opportunity at the Times. So it just sort of all came together for me, because I’m sure if it didn’t, there would have been a bigger crisis. I can imagine it would have been hard. So we just I had this opportunity and know I remember when I went in to give notice, I was like I wasn’t looking for another job. When this opportunity presented itself, it was sort of like, OK, good, I can go leave teaching for a little while.

Maybe I’ll go back. Maybe it’ll be a brief respite, who knows. But, you know, I need to do something else and recharge the batteries and do something different and not not be doing something where I was. Living in the same way teaching can be so so that was one and then leaving the Times also. So it was just like I had this idea that just was like, you know, you know, as Morpheus, as in The Matrix, like a splinter.

In my mind, it was just like it just kept kind of eating at me. I had this idea of something that I thought should exist and didn’t exist that I thought I maybe could bring into the world. And it just became like I just couldn’t ignore it. I just got really excited about it. I thought I had a lot of potential. And, you know, I just thought, OK, I sometimes have to take a risk. And I had a lot of support from my spouse and the ability to do it.

So that was just like this pressing idea that I just got more and more excited about and just just kept me up at night. It wouldn’t leave me alone. And so that was like a totally different reason, you know, transition. So, yeah, I’ve been through it different for completely different reasons.

Dan

I love it.

Well, I think a commonality between them is that you’re. Listen to yourself. What was that? What was going on in what? In what was that like? I can’t keep doing this for forever. And the others. Yeah, there’s something else that’s speaking to me that’s trying that wants to be expressed.

Holly

Yeah, that’s right.

Dan

I think that’s a fantastic answer to that question. I love it.

Holly

And I think that’s right.

And I think, you know, one of the conversations in my accountability group involved me is, is about listening to yourself and trusting yourself and trusting your gut. You know, we’ve all bounced ideas around, like trying this on for size, like, does this feel right? Or like I’m in training for this position that we’ve all been sharing with each other. And, you know, at some point we’ve all reminded each other. Now you really need you need to listen to yourself, that it is really important and sometimes it’s sometimes even that is hard or feels hard.

Dan

Yeah, I love it, yeah

Holly

Yeah, I mean, even that is like it sounds really easy, but sometimes it’s worth.

Dan

Yeah, totally, totally different personalities. You know, I think self care is not something that comes naturally to me, you know, like and I think that that goes along with it, like listening to what you need and responding to it and finding ways to give yourself that. It’s not easy. It’s not easy. A lot of us have been trained or trained ourselves to kind of just grit your teeth and bear it through. But that’s not always healthy.

Holly

That’s exactly it. That’s exactly it. And so they don’t really listen to the little voice or whatever it is like you, until you really learn how to even listen to it. That could be a process for people right there. Yes, I think it’s one of those things. It sounds to me like, oh, listen to yourself. Sounds like, you know, it’s like a like a pretty little thing you’d see on Instagram and like, really pretty Letterio like liking it.

And then you’re like, what does that mean? Like, do I have an inner voice? You know, like I think for some people is something you need to learn.

Dan

Mhm. Yeah.

I love that. I love it. Just as we move to wrapping it up here, just as people are listening and you know, maybe they’re in one of these stuck in between places.

And I’m curious if you have any words of encouragement or camaraderie or hope or anything that you just want to offer to people who are in those kind of hard, hard to stay in places.

Holly

Yeah, well, a lot of camaraderie.

For starters. As I said before, I’ve definitely had my moments of stubbornness and feeling frozen and feeling, you know, like let’s be honest, I’ve had moments where I feel pretty low about it, like, oh, I’m never going to work again. I’ve had moments where I thought, am I ever going to get unstuck? I’m so frozen, like fully frozen. Like, this is the tundra. This is the ice cap. I’m not I don’t know how to thaw this out or I don’t know how to listen to my inner voice.

What is it telling me? I’m not sure. Or yeah. Just like just lack of clarity, lack of direction. I felt useless. I felt like I’m wasting my life. You know, I feel like one of my career add up to nothing. I mean, I felt all of these all the the the negative thoughts you can think I’ve thought them so comaraderie definitely. I mean, if you feeling any piece of that, people out there listening like you’re not alone.

You’re not the only person thinking about your career this way. You’re far from it. There are lots of people, even people who like, you know, you might look at their LinkedIn or just on paper, they look successful. They look like they’re happy in their jobs. Often I find lots of conversations with people, especially over the past year. And people who have been in their jobs for a long time have confided I’ve never felt fully happy in this job.

I don’t even know why I stayed this long. I should be doing something totally different. I wasted all these years and they feel stuck because they can’t leave, because whatever reason they’re dependent on that job for whatever reason and they feel stuck and they feel like they’re wasting their lives. So it’s not only like only if you’re between careers or something like that, that you feel these feelings. People feel these feelings at all kinds of different junctures and for different reasons.

So I would say that if you do feel this way, this is me. I also really do want to normalize not just the not having a but just having a non linear career path, but normalizing feeling stuck about your career, normalizing, giving voice to that normalizing, wanting to explore a little bit, normalizing, being unsure of where to go and needing some guidance. I feel like that we need to make that not shameful and not embarrassing and not silence.

Dan

I love it.

Holly

So I think that’s really a woman. So definitely a lot of camaraderie. I mean, words of hope and encouragement. I do think these kinds of conversations are really helpful. So I think you have people that you feel to start with, just like friendly people, you feel like you can trust that you can open up to and share your doubts or your sickness or your paralysis or your doubt, your questions. You’re having conversations with people, whether they’re people in your personal life or your professional life, that can be really helpful.

You know, one thing I recently did, I asked former colleagues if they would share a word with me about something that they think I’m good at or best and something they think I should work on, which is exposing. That’s an awkward question to ask. And it was hard for me to even ask it, but it was so worthwhile. That’s something that’s been helping helping me think about my career, what I want to do. When you think about things like one of my best, her, where if I added value and where if I had impact to get that kind of feedback has been really helpful.

So people are giving it voluntarily, that’s all. But if you want if you can, I’d be grateful, if not when I said I would take it in the spirit of generosity and people have said very kind things. They’ve taken me by surprise and people have given feedback that make me feel seen and nothing that I’ve been shocked by the like. I can’t believe that person thinks I’m not good at this particular thing. It’s like, oh yeah, they’re right.

Like I was struggling with this thing where I am struggling with this thing. They’re right about that. So they can really help you feel seen and understood. And it can also be very validating, like, OK, this is something I struggle with and that’s good to know that like other people realize. Maybe I need to get help with that in a certain way. Whatever the thing is, so I feel like that can be really helpful. So, yeah, I definitely think conversations are really helpful if people are open to reading the kinds of books we’ve been talking about, the Grainge and impacter, lots of books.

There’s another one that people recommended that that’s what it’s called the squiggly career about a linear path thing

Dan

Yeah, I need to check that one out.

Holly

Me too. I need to do that, too. And then, you know, even my programs like the one I’m in, there’s other websites. There’s other programs. If you want something that’s a little more structured, if you’re a person who benefits from structure and go find something that has structure. And I think there is hope. I think there’s stuff out there for people like us, I think. But do you think that can be enormously comforting to know you’re definitely not alone?

It’s not just you. That’s a weird thing about you. This is just it’s a very typical thing in life. And and just finding your way out can be hard, but but it’s not very possible.

Dan

Yeah, you’re in good company. Yeah, I think that.

Holly

Very much said.

Dan

Those are just great, great words of just knowing that other people are in it. Yeah. It’s just so, so important.

Holly

Yeah, it is important. I mean people can reach out to me like I’m very findable. I have had people reach out to me for guidance and help of different sorts. Just words of these kinds of words. Having this kind of conversation. You know, I’ve advised people on their resumes or their cover letters or their interviews, like how to frame this kind of stuff. I mean, I always happen to be reached out to and I know there’s lots of other people out there, too, who are having these kinds of conversations, are just finding your way in to people who want to have these conversations can be really, really helpful.

Dan

I love it. I love it. Well, thank you so much for that. And for people who are just resonating with you and want to connect with you or follow along with your work, is there anything specific you’d like to invite them to?

Holly

Oh, well, I’m available on Twitter, like you said, that one tweet, which will never cease to amaze me. You know, my DMS are open, so people want to reach out to me. I’m very open to that. So my Twitter handle to people who are on Twitter is h e O.J. That’s another story for another day.

Unfindable.

You know, people can connect on LinkedIn. Those are probably really easy ways to find me. There’s no one else on the planet with my name. So I’m so looking for Holly. Well, that was very easy. So, yeah, I’m very open to reach out. So people want to have a chat, I’ll say. Yeah, I mean, just listening to this podcast, I mean your podcast. Is it a gift to people who are in this space?

Dan

Oh, thank you. I hope so. That’s my intent. So thank you for that.

Holly

I’m sure. I’ve no doubt. Yeah. Yeah.

Dan

Well, thank you so much for just your openness and vulnerability and wisdom and everything. It’s just been so fun to connect.

Really appreciate your time with us today.

Holly

Pleasure has been for me, this has been really, I feel like this was almost like a therapy session.

So thank you. Thank you, Dan.

Dan

Little career therapy.

Yes. Yes.

Dan

Yeah. This is great.

Holly

 But I speak to the point of how useful it is to have these conversations. It really is. So thank you. Thank you so much.

Dan

Absolutely.

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