Episode 1. How one freelance content writer straddles two continents: Interview with Ruthie Wyshogrod

Welcome to episode 1 of All The Freelance Women Podcast! 

Today’s guest is Ruthie Wyshogrod, a freelance content writer and the founder of Jiri Content Strategy and Writing, living in Israel. She shifted to freelancing after having several disappointing and even excruciating full-time job experiences, and has moved back and forth between the U.S. and Israel several times in recent years. Her story illustrates the power of freelancing to help people shape their lives, which in Ruthie’s case means having a better daily work life, moving internationally, and pursuing work that fits her passions.

Show notes

Bio and links

Ruthie Wyshogrod is a writer and content strategist who helps mission-driven organizations reach their audiences through high quality, engaging content. As the owner of Jiri Content Strategy & Writing, Ruthie offers end-to-end services including pagers, white papers, case studies, blogs and web content, presentations, and message development. 

Jiri Content Strategy & Writing: www.jiricreative.com

Memorable quotes

“Nobody likes to have to get to work at a certain time. And everybody wishes, they had more vacation time… it deeply bothered me that I had to count every single vacation day.”

“I really love the lifestyle. I really love the flexibility. I love running a business. It’s very empowering.”

“I have the flexibility to change directions, shift directions, and reinvent myself every day… In terms of learning how to navigate as a businessperson, every day is something new, and that is very, very empowering.”


Katherine: Hello, and welcome to all the freelance women podcast, which brings you the stories and perspectives of women and non-binary freelancers of all types from around the world. I’m your host, Katherine Gustafson, and today I’m speaking with Ruthie Wyshogrod, a freelance content writer and the founder of Jerry content, strategy, and writing living in Israel. She shifted to freelancing after having several disappointing and even excruciating, full-time job experiences, and have moved back and forth between the US and Israel several times in recent years. Her story illustrates the power of freelancing to help people shape their lives, which in this case means having a better daily work-life moving internationally and pursuing work that fits her passions.

Hi, Ruthie, welcome to the podcast. Thanks for speaking with me today.

Ruthie: Hi, Katherine. Thanks for having me.

Katherine: As a freelancer who’s always plied my trade from one country, I’m interested in how you’ve managed to move internationally while pursuing your writing career. I know you’ve moved back between the US and Israel a few times, and you’re currently in Tel Aviv and are planning to move back to the states in a few years. So what I’m wondering is how does freelancing help you make such international moves while maintaining your career path?

Ruthie: I think that there’s something about being an independent, that potential clients view differently as if you’re an incoming for a job interview with a resume that we’re all your experiences, like in a different city or a different region or a different country. I think there’s more of a recognition that as a freelancer, kind of you’re being examined more for the quality of the actual work that you produce, and a little bit less, and some, obviously this isn’t applicable always, but that you’re kind of less examined for the name recognition on your resume and more for what skills you can actually offer.

Katherine: That makes a lot of sense. Can you tell me a little about that journey, how you got started, and what you do, and why you felt like that wasn’t being recognized properly in certain places?

Ruthie: I started my career in nonprofit development. I started here, I moved here, right after college, and I worked in fundraising in the kind of Jewish Arab coexistence space. And I kind of fell into that very unintentionally, because that’s what happens when you’re an English speaker abroad, and you want to work in the nonprofit sector, that you just immediately get boxed into development.

I kind of fell into it, but I liked it. And then we moved to Philadelphia. And, when we got there, I kind of had a bit of a bit of a loss professionally, because I realized that it wasn’t grant writing wasn’t my passion. My passion was the issues that I was working on. And I didn’t want to just get a development job in some other nonprofit and the thing about Philadelphia is it’s less like a global city, I guess, compared to some of the other major cities around it. And so a lot of the kind of types of organizations that I would naturally kind of feel at home didn’t exist there. They all have offices in New York and DC and so, therefore, they don’t have offices in Philly. And so I kind of like I didn’t know what to do, I didn’t know if I should just get a development job. I did apply for some I got some offers, but I just couldn’t see myself writing grants for like, just an issue that wasn’t like my issue. And so I actually left the nonprofit world. I spent a year in a project management role in the corporate sector, mark, check that off the list for the rest of my life.

And again, back to grant writing, but in a completely different setting. I worked at a children’s hospital in Philadelphia in a public health research center. So I was writing research grants like to NIH and National Science Foundation, which is a whole different world than the types of kind of private foundation grants that I had previously written and also topically, very different. I learned a ton there, it felt like important work. In the day today, it was not great, basically, I mean, I don’t know how much you want me to go into, like the details of how miserable my jobs were. But basically, like, it was a variety of factors about the way that the organization was structured that I was sitting in, and the fact that as a writer, you’re often kind of alone, like you’re kind of in an aisle. But I was like, quite literally alone, because I actually sat in an area of the office where no other office or cubicle around me was inhabited. So I actually would go entire days, like, very regularly without seeing or speaking to another person at work, and I, like actively tried and begged and cried for them to do something about it. And I tried it, I suggested, like so many different solutions, and it just didn’t really, they kind of just didn’t know what to do with me. And it was also my first time working at an organization of that size. And so like, that was a whole adventure have kind of learning, learning how to navigate the bureaucracy, but also, like, slowly coming to the conclusion that I was in a position of very little power and influence and that, like, I really like wasn’t going to be able to get through to whoever I needed to get through to, like, make it better for me.

So and then also, during all those years, I started to work on the side with, with a couple of the organizations that I had been employed at in Israel, doing all kinds of one-off projects from like, they needed an extra hand to get a report in or someone that I had worked with was kind of starting a new organization. So I helped her build the initial like fundraising infrastructure for that, all kinds of things like that. And eventually, I realized that like, I can do that full time like that, I can do that with like other clients too. And it was a really, really long process. I think for me, it felt, for me, like a really long process. Like I actually, I find this really interesting because, on the binders groups, I like read a lot about people’s journeys into freelancing and like, you feel a lot of cases where like, someone was let go from a job and that was like, what made them take the leap or like, even a lot of kind of more recent graduates who seem to just go straight into it, I was terrified to do that, like, I basically didn’t allow myself to, to kind of make freelancing, my main thing until I had like, so much freelance work that I was essentially working like, a 200% position. Because I was also working with her,  I’d get up at 5:30 in the morning for like, calls with here, from six to eight, and then go to work, and then come home and like, do all of the work from my calls. Just like work on weekends. And it was a lot.

And eventually, I went down to part-time at the hospital. And I did kind of start taking the freelancing a little more seriously, I worked with career consultants that helped me kind of define what it is I’m offering that has since evolved. And come up with a name for my business and actually start to like to think of myself as a business owner.

I think that’s like that was like a really big shift. And eventually I actually in the process of looking for clients, I found one, but they were looking for a full-time position but it kind of seemed perfect in every way shape, or form. So I actually left the hospital took this job and left that job after six weeks because it was I don’t like I don’t want to share the name of the organization or anything but it’s like the boss there was like it was like a very, like emotionally abusive and unhealthy environment. And I was able to identify that thankfully very, very quickly and get out very quickly. But ultimately, it was a good thing because it was what let me finally take the leap to being fully invested in my freelance work. And so that happened in the spring of 2019 so like a year and a half ago. And since then I’ve been doing this full time and since then we also moved back here and I established a company here. And now I’ve been very fortunate to have a full workload sometimes overfull workload for that entire time, including during the beginning of COVID. And to not have to really do any publicity online work is word of mouth.

And oh, and I guess I didn’t really mention what I’m doing. I’m writing and when I kind of established the company and like thought up the branding for it and stuff,  the way I describe what I do is that I write content for mission-driven organizations. So that can mean nonprofits that I’m writing grants for, but I’m actually not really doing that right now. It can also mean working as part of a marketing team for a startup that has some sort of a social mission, in addition to its financial mission. That is something that I’ve really been struggling with because I think there is this subconscious pressure to make sure that I always have work. And as a result, I’m not very selective with the clients that I take on. And as a result, I have a full workload, because I essentially take anything that comes my way. Now, I’ve been very lucky that everything that’s come my way has been good. And that I’ve worked with clients, I work with people that I enjoy working with, I find the work to be intellectually stimulating and challenging enough. And then make me happy with the money I am making.

The one thing that’s missing is that really like, I’ve kind of veered too far away from that kind of mission-driven work. And I’ve never really made an effort to, to like, actually try to identify the clients, I’m going after based on that niche and to actually target them and seek them out and like try to market myself to them. So I kind of see that as my next like, I’m coming up on a year, since we’ve been back. And since I like to establish myself here, and for the coming year, that’s kind of what I see is like the thing that I want to focus on.

Katherine: That’s so great to have that type of awareness of a larger picture. In order to do that, would you need to change your marketing strategy or even start a marketing strategy? It sounds like most of its been referrals?

Ruthie: Yeah, I still think that the strategy would be mostly networking and word of mouth more than kind of any sort of like advertising beyond that, just because I also, at this point, at least, I don’t have an interest in expanding like, I don’t want employees they don’t want I want to keep it as a one-woman show. And so like, I don’t, I don’t actually have the capacity to take on that much. So I’m really just looking for like, one or two quality clients that align more with my values. And I think the best way for me to find them is not as much to invest in redoing my website or like advertising on LinkedIn, but actually just through my network and conversations and seeking them out kind of more quietly. But I can’t really speak to whether that’s the successful strategy because I haven’t started it yet.

Katherine: Can you tell me a little bit about how you go about deciding what to do like you have made a specific company with a specific type of branding and you have a niche you’re focusing on I know a lot? And you also decided to make a company as opposed to just going under your own name. I know a lot of people, I’ve seen a lot of questions from freelancers about how do you make these decisions since it really is like you’re the CEO of your own little company, even if you’re just working under your own name. And so I think it’s hard to decide what to do, basically. And so I’m wondering if you could share kind of what your thinking has been or what your path has been, in making those types of decisions?

Ruthie: I guess I’ve two parts to my answer to that. The first is that it’s been mostly trial and error. In terms of kind of how I define the work that I do initially, it was it did result from work with career consultants through a lot of kind of self-exploration exercises, which I paid someone to guide me through, but you can completely do on your own one exercise that like, I guess, is worth sharing. Because I think it’s been like, really, really, really integral. And in this process for me, is, is basically imagining, it’s really just an imagination exercise. To imagine your ideal day. And really plan it out. Write it out on paper, in a lot of detail. Like, what time do you wake up in the morning? What do you do in the morning? What’s your morning routine? Do you exercise? Do you start working really early? Do you take your kids to school? When you go to work? What does that place physically look like? Are you working in an office at home? Are you working in a high rise tower? Are you working in an industrial space? What do you wear to work? How do you get to work? And then what does your workday look like? Are you by yourself? Are you with other people? Is it a combination? Do you have a lot of meetings? Do you have a lot of phone calls? Does it change as a kind of stay the same day today?

So really like thinking about your perfect workday. And perfect doesn’t mean a special one of a kind, like, what is your perfect regular workday look like? Interestingly, I did this exercise in 2017. And a few months ago, I had this realization that my days are really close to that. That’s, like, really, really cool. So So I guess, and then that kind of leads into the second part of my answer to your question, which is, even though it’s a lot of trial and error, I think it’s really important to actually start with some sort of idea or vision of where, where you’re aiming to go, whether that’s things like what is your lifestyle going to look like? Or whether it’s what types of organizations and clients will you work with? What kind of work will you actually be doing?

And that’s something that for me, I’m kind of always like, evolving around, because I always said, like, I want to write all the time, but writing all the time gets lonely and boring sometimes and, and I’m realizing that I really enjoy, like the dynamics that I have with some of my clients where I’m a more kind of integrated part of their marketing team, which means that I do write a lot, but I also sit in on a lot of meetings and work on kind of shorter things that are the kind of like change the pace that my mind is working at. So I guess, I would say, the way I go about making the decisions is trying to have a direction in mind setting some sort of a timeline. Like I mentioned before, that I’m kind of coming up in a year and now I want to try to be more intentional about the clients that I find, that was actually something planned when we moved back here. I said okay, I’m gonna just go for it and get it set up. And I’ll reassess in about a year. And kind of get a sense of like, what’s working and what isn’t, and like, I did that and I’ve identified like, I really love the lifestyle. I really love the flexibility. I love running a business. It’s very empowering. The thing that’s kind of missing is the actual content of what I’m working on. And that’s what I want to focus on for next year.

Katherine: That makes sense. I had a question just backing up a little bit, when you were taking on freelance work on the side of your full-time job, was that kind of with a plan to increase it in order to eventually become a full-time freelancer? Or was it just kind of that you liked doing it, and it was just increasing on its own, or it kind of organically, I guess I’m trying to get at whether you kind of just evolved into being a full-time freelancer more or whether you kind of saw from the early on that that was your goal?

Ruthie: I’d say it evolved, it definitely started, I didn’t start taking on freelance work with the intention of becoming a full-time freelancer, although I’ll say that I have always since I entered the workforce after college, I’ve always felt like, I’m more bothered than the average person by the dynamic being an employee.

Katherine: I completely agree.

Ruthie: Nobody likes to have to get to work at a certain time. And everybody wishes, they had more vacation time. But like it deeply bothered me that I had to, you know, count every single vacation day, like, religiously and that like there was there. I mean, and of course, this is also like, a result of the organizations that I worked at, and that this isn’t experienced. And this is, I think it’s also changing a lot lately, but like those kinds of things like that, that feeling of like being kind of not trusted, even if I was trusted by my supervisors or my bosses, this, this, like, a general sense of like, there needs to be these policies in place, because like, the organization like somehow doesn’t trust you to be an adult. It just really always bugged me so when I started freelancing, it wasn’t, it wasn’t with the intention of going full time, although I did always have those feelings in the back of my head. And so eventually when it evolved to the point where I made that decision. I did have this natural, like, an instinct that it would be a lifestyle that suited me. But in terms of the kind of evolution, I think, it’s like I said before, I guess I’ll kind of expand on this a little. It took me a really, really long time, once I kind of realized that I could become a full-time freelancer until I actually did it.

And what made it happen, ultimately, was that I left a job, but I think it was also I think there was also like a deeper mental shift. Like, I think it just took me a very long time to build up the confidence. That to build up enough confidence to take the risk, because I think, ultimately, I think it’s very rare that someone’s going to be in the position where from one day to the next they have this like perfect increase in their freelance work that enables them to quit a job and just like continue at their same income level there definitely is a point where you have to make a decision that you’re going to take a risk of taking a pay cut, or just not having a steady income basically, in order to build it up. But I guess another thing I’ll say in terms of that process is that as soon as I did make the decision to be a full-time freelance. I pretty quickly found an anchor client who found it through personal connections and networking. And I found a client that I’m still working with today. I’ve been with them for over a year. And they take up now they take up initially they took up about half of my time now they take up a little more.

And I mean, that’s huge that like that is first for anyone who’s like very risk-averse, like I am like, I don’t think that I would have lasted if I had started with just piecemeal projects here and there. I like had to have that, like, I’m on retainer with this client. So like, I had to have that guaranteed monthly income just to have the peace of mind to be able to find other clients and to like, actually feel like I can take this seriously.

Katherine: Yeah, the stability is, is key, I think, to be able to have the room mentally and emotionally to also look for what’s next.

Ruthie: I think so logistically, like, I, I think that having a good chunk of your monthly income taken care of you just spend less time on administrative stuff. This just gives you a little bit more freedom to take on other work that you want to take on and to, you know, have more time.

Katherine: Yeah, I absolutely agree. I found that over the years. At first, I didn’t have any real like, anchor clients, and it was just like, the hustle was totally constant. And now it’s still constant. I’m used to it. But it’s not nearly the same intensity, because I have some that I know, I can count on month to month. I’m almost out of time. But one last question I had was just if you could talk a little bit about traveling back and forth from different countries, and how you feel freelancing has helped you be able to do that if you feel that way.

Ruthie: So I’ve only traveled once, I’ve only moved countries once, while I was freelancing full time. And I guess I’m surprised at how simple it was. I think that’s also because of the types of clients I’m working with right now, all of my clients, even though almost all of them are based in Israel. They’re all companies that operate globally. So first of all, just in terms of like, the kind of attitude about working with someone who’s kind of going back and forth, and kind of has multiple international bases, I think that’s more familiar to them. And they know how to work with that. So something that’s really important to me, in moving around a lot between countries I think it does influence the clients that I choose to work with because it’s important for me that I don’t get too local.

So that when, in three years, I move back to the States, and I’m not really sure yet where I’m going to be in the States, I don’t have the same experience essentially, that I had as an employee where my portfolio is kind of not relatable to clients there. So I think freelancing lends itself well to working internationally. But it still needs to be done smartly. I don’t think that every type of work and every type of client base is well suited to this. And I think that as much as we talk about the world being so global and being able to work from anywhere more, more than ever today, I still think there are limitations, like the the the ability to physically be able to work from anywhere by like being on my laptop in Israel, or in New York, or in a guest house in Bali.

Like if you’re looking long term at like actually building a business that’s sustainable and building a name for yourself. You do still have to be strategic about how you’re working. Otherwise, you’re kind of, in some ways, like the world is still very local, and it’s easy to be forgotten if you’re off in another country and your client bases elsewhere.

Katherine: That makes sense. I’m glad you made that point. Because I think a lot of times it’s just freelancing is pouted are spoken about as oh, just freelancing and you can travel the world and on one level, that’s true, but it’s way more complicated than that and it does take a lot of strategic thinking and planning about how that’s actually gonna work.

Ruthie: Yeah, and of course, then you get in also to the logistics around like regulations and taxes, and how are you actually like, legally working I can only speak to that specifically to like Israel in the US. And I don’t think that that’s, like, so interesting to your readers. But those are also things that like need to be taken into account.

Katherine: Yeah, I mean, I think that could be just that point is, I think very applicable to a lot of people, just you gotta think about the legal aspects of things and the logistical aspects of things. And it’s easy to kind of fly by the seat of your pants into freelancing. And that’s on the one hand, a good thing because you can just start and do things, and we shouldn’t let the fear of taxes and logistics stop you. But once you get started, there’s going to be a time when you have to think about such things.

Ruthie: And it’s really important to think about it because you can really get in trouble if you miss those things it can be really tricky.

Katherine: In the last minute or two, maybe can you tell me just kind of what you like best about having a freelance career.

Ruthie: Two things. One, I have the flexibility to change directions, shift directions, and reinvent myself every day. I’ve never learned more in any job previously, I wouldn’t say that I’m learning as much as I may have learned as an employee about the actual content that I’m doing and working on because I don’t have an organization of resources behind me. And I also don’t have a lot of time to like, do enrichment and professional development stuff. But in terms of learning how to navigate as a business person, every day is something new, and that is very, very empowering. And it makes me less afraid to try new things. Because you realize that anyone who’s ever done anything, didn’t know what they were doing when they started and like, you really internalize that. I find that very exciting, and now I guess that’s it.

Katherine: Well, I want to thank you so much for speaking with me today, and best of luck with your freelancing.

Ruthie: Thanks. It’s been a pleasure to be here.

Katherine: Thanks to everyone out there for listening today. Check the show notes to find the link to Ruthie’s company Jerry’s content strategy in writing. You can find more episodes through our website, allthefreelancewomen.com sign up for our email list to be notified when new episodes are published and get other interesting info and perspective from freelance women around the world.

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