Pivoting careers in a changing market

In this episode, we are going to talk about the idea of finding a new era with your career. Maybe it's because business is slow. Maybe it's because you're like me and you're feeling disconnected, and maybe you're seeking out the opportunity to work in an office again and build connections with coworkers. And maybe it's the market. Maybe it's out of your hands and you're feeling like you need to transition into something a little bit more viable because the market is changing, the tools are changing, like AI is here to stay, it's not going anywhere.

Kaleigh: Is freelance writing something you want to keep doing, Emma? Is it something you want to pivot away from completely into something totally new? How are you personally thinking about this right now?

Emma: Yeah. It's interesting you're talking about, like, the step-by-step actions that we talk about on the retreat because it is totally what we do. And many of us have a tendency to say something very broad, like, I want to change my career, or I want to offer some different kind of service for freelance writers, or just think big about what that change is going to be. The advice that I got on our last retreat was to think about: what is the one next step that I can take?

So, if we're talking about my advocacy business, for example, the next step is reaching out to three advocates and asking: Is there any work that I can help you with on a pro bono basis that would give me experience? Or, can you refer clients to me who can't afford to pay for advocacy services? Or maybe the step is signing up for a certificate program or a course.

It’s not necessarily an all-or-nothing wherein one day I'm doing this, and the next day I'm doing that. I think the retreat is again an interesting case because the first retreat we did was targeted to freelance content marketers and freelance writers. One thing I recognized from being on the retreat is that we have a couple of people who were more adjacent to freelance writing and not totally in that world…and we got so much value from those diverse voices. Similarly, when you and I ran our retreat back in 2019, we didn't market it to freelance writers. We marketed it to women solopreneurs. That was the criteria. And sorry, this is a long way of saying this, but Renee and I decided the next retreat shouldn't be for just content marketers. It should be more generally for service-based business owners. 

I'd love to hear if you have any other ideas about how to wrap your brain around embarking on something new.

Kaleigh: I've been testing the waters this the past six months by trying a lot of different types of work. For me, that's included experimentation with AI. So for example, in December, I took an agency gig where I was tasked with pushing out five AI-assisted drafts a day because they were going for volume. They had this workflow using Chat GPT for most of the sections, but there was still a ton of prompting the tool and editing and fact-checking. They made it sound easy breezy, but it was soul-sucking. But I'm glad that I tried it.

I have also done more editing work on AI-generated drafts, and that's a lot of work because they're so not ready to go. For some companies, it's like, "We don't care. As long as it's optimized and good enough, push it out the door." For me, that doesn't sit well. I don't like having my name or my work associated with a half-baked product. 

I keep trying to figure out: What is my relationship to these tools? How can I leverage them to be more efficient in my own work? They are great for still very specific things. But as far as drafting goes and in the content marketing work that you and I have done historically, it's still got a long way to go. I haven't quite found a comfy relationship with the tools yet. 

And so again, I find myself wondering: Should I take an in-house job? If I do that, I will have to get out of my own way about the mental block of downgrading what I make annually.

Because these in-house jobs come with benefits and perks, but the salary is less than what I was making as a freelancer, it's a push-and-pull question of whether I should give up the freedom and flexibility and the potentially larger income for the security, peace of mind, and connection that I'm so desperately craving. 

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Emma: Yeah. The most difficult thing for me has been like, well, what is that thing? Right? Because it's like, okay, you can make these small pivots in directions that are interesting to you or that you feel that you're good at and follow your interest. And then I think there's also this aspect where it's like, well, if you have some goal to do something different, then you also kind of have to make a decision about what the difference is at some point, right?

Kaleigh: Yeah. And I would go back to what we talked about in the first episode and say that therapy has been really helpful at navigating all this because in a way, a therapist is a form of a business coach because they're helping you learn about yourself. They're helping you learn about your limiting beliefs, which our friend Linda talked about at the very first retreat we co-hosted together. And if you recall, I was very resistant to those ideas. I was like, this is a little woo woo for me. Like, I don't need anybody to tell me that I'm in my own way. I know myself better than you do. And of course, I was the one who needed to hear it the most because I was resisting it so hard. 

And again, this is this is stuff that I've been working on in therapy and uncovering. And I think that's a point that I wanna make is that learning how your own mind works and the filter you put on the world and how you perceive ideas and people and concepts is going to help you better understand yourself and what makes sense for you in your career.

Because this is a huge chunk of time that you're investing yourself into. This is not just a job at the end of the day. It's how you're spending your life. And life is short, and you kind of unless you're enjoying what you're doing, like you said, getting meaning from the thing that you're doing, you're gonna feel the friction of that if you're not. And I think it's it's all about understanding how to overcome that friction and do the thing that does feel meaningful and authentic and important within your day to day life.

Emma: Yeah. And I think also practical. Right? I think that there's plenty of people that have a career that is maybe not like the world's most fulfilling, but it allows them to live the life they want to live, whether that's like some more flexibility or traveling or just like benefits that like make them feel comfortable if like something goes wrong with health or community from colleagues. Like I guess community from colleagues isn't exactly practical in the same way, but like there is more than just kind of the work itself.

I am curious if you can talk and I'm happy to like go through this exercise too, if there is a particular limiting belief that you have about yourself that you think prevents you or maybe hinders you from embracing a new type of career or a new type of, you know, professional identity?

Kaleigh: That's a good one. I think a big one for me is I really struggle with the uncertainty piece, especially right now going through this period of change where so much is already uncertain to self inflict more uncertainty on my life feels very reckless and feels very scary. And so I'm looking for I think again, that's why the full time or in-house job feels so appealing because it does feel like a little bit of stability amidst all this change and chaos that I'm I'm going through.

And I'm someone who took the leap when I was in my twenties to start freelance writing full time. And that was a period of life where when you're young, like, you you haven't had enough range of experience to really be scared of things. Think now that I'm 36, I'm a little bit older and I have experienced some more painful things. I am more cautious and that's good and that's bad.

But, again, I'm trying to figure out what is the thing I need right now to make me find that meaning. I think that that's the thing that's really important to me is, like, feeling the meaning, feeling the connection. And like you said, I love that you called out, some people don't find this with work. They find that meaning in their family or in their friendships that they have or in the things that they do outside of work. We're not saying you have to figure out the work thing because it is the meaningful piece.

I want you to talk more about that too because you are trying to strike this balance of maintaining your family life. You've got two little kids at home. Like, where does the work piece sit in your pie right now?

Emma: Yeah. Well, I think when I first came back to work after my maternity leave with my daughter, I just had, like, so much rolling around that I really wanted work to be something that I could plug into, do the work, work with the clients. I would have a little bit of time for me, make some money, all of those things, and then I could just plug into it. And I think where I ran into a block with the freelance writing was that the market had changed that I couldn't just plug into it. I was going to have to work to pitch, to change my offerings.

Because I think when we talk about like making a big career change, there's like a couple aspects of it. One is that like sort of the service that you're offering. Like, is it still freelance writing services? And maybe the way you change your career is you offer those to someone else or in some other capacity or you're working on helping local businesses with everything that they need for marketing, which includes so much content generation. So I think there's kind of like the thing, the service, which may or may not be different. And then I think there's, or maybe I missed this up, there's sort of like the, there's like the audience or like who the clients, the type of clients you're gonna work for.

And then there's the service itself. So, is it going to be freelance writing? Are you going to offer a business strategy instead? Are you going to offer more general marketing consulting? Are you going to go in-house and work for a nonprofit in a fundraising role because fundraising requires so much communication?

Are you gonna work in internal communications at a company? Like, these are all things that I think when we're thinking about making this change and going back to the idea of pivoting, it's like, it's almost like, have you heard that old meme of like, everything is content? There's, like, that Bo Burnham song that he has, like, all of this content or something. And it's, like I mean, obviously, it's, a joke, but, like, if you have really strong communication skills, it can translate to a million things under the sun. And so I think that that's, like, worth remembering here that, like, it's not just, oh, I'm gonna, like, make this gigantic pivot.

Kaleigh: And I think it's also important, we've talked about this in previous episodes too, like, you gotta keep learning. You can't just keep using the same skills you've had all of these years and not expand that offering at all. So you have to keep an open mind about what can I learn, what can I offer that's new that maybe is kind of emerging within the freelance content marketing space? Like, I've seen a couple people really pivot hard into repurposing and repackaging content because it is a hamster wheel, and there is so much need for fresh content all the time. Again, this is, like, how can you think creatively about the skills that you have and putting them into new formats?

Emma: Yeah. I was also gonna say that I think it would be really helpful to maybe share some examples, like end the episode with some examples of, like, things that we've heard about freelance writers doing because I have a few examples that I think are interesting. So I have one friend that worked as, like, a freelance social media writer and like a thought leadership writer, like she would help like executives build their social media platforms.

And so that's like one option that I've seen. Another option that I've seen is someone saying like, I'm going to go all in on like writing a novel and like really publishing that novel and, like, for real, not just kind of, like, this pet project on the side. And I could still do my freelance writing work, but I'm gonna, like, lean heavily into being an author of fiction and, like, make my life basically about that or make my career about that. I'm trying to think of some other, like, tangible examples of people doing this because I do think it's helpful for people to see. Like, I've seen someone that was doing, like, kind of basic content services pivot to offering, like, I believe she calls it like story mining services for executives.

She helps them actually kind of similar to what I was mentioning that other person was doing before, but kind of like with their messaging and how they show up. It's almost like she switched over to working on brand building and brands consulting rather than just kind of like this writing aspect. Those are like a few examples that I've seen. I've seen like someone else who has leaned much more heavily into the community side of her business rather than the freelance writing side. I'm curious if you have like any other examples of sort of pivots that you've seen in our worlds that are interesting to you.

Kaleigh: We are gonna do a full episode on this, but I have seen some established freelance writers really lean into the content creator angle. And so become kind of influencers for people who are interested in freelance writing or building a freelance business. And when I say that, I mean, they're doing the they're talking to the camera on Instagram. They're really leaning into YouTube and TikTok. They are selling products about how do you become a better writer, how to become a better freelancer, things like that.

And so it's it's pivoting into more of a creator than a freelance writer being the actual writing work being the thing that pays your bills. And instead having, like, info products, retreats, courses, and we're gonna talk more about that. But I it's funny because I think back to myself and like I I've dipped my toes in the water with that about probably seven years ago. 

Emma: Yeah. It's interesting you talk about people sort of becoming influencers in the freelance writing space because I think there's also an opportunity to say like, okay, I have these communication skills. Like, is there something else I really love or am interested in or know a lot about that I could share a ton of knowledge on? 

I think if you do something like that, like you're working on a YouTube channel, those are services that can, that knowledge can then be like, you could become a video editor, right? Yeah. Whether freelance or internally, right? Like if I leaned into that, I could do video testimonials and case studies, like if I got really good with like camera equipment and stuff.

But if you do wanna make a pivot and you know it's to a different kind of business, like you probably need a business plan with like revenue projections and like how you're gonna actually like switch from one thing to another. And it is a good opportunity to find a coach or business strategist because I think it is a difficult thing to really do on your own. Yeah. So that's what I think about it.

Kaleigh: I think the bottom line here is just you have to make it piecemealed in a way that's realistic for you to take steps towards it. You can't just say, ugh, I'm paralyzed because I don't know what to do because this goal is too broad. You have to be specific about what you wanna do. Try a lot of different things. We've always been a big proponent of that. Test it out. See what you think of it, and learn and adjust as you go.