Content Writer Rebecca Rosenberg
About this podcast episode…
CONTENT WRITER AND STRATEGIST REBECCA ROSENBERG
This time, we explore both a metaphorical freelance journey and physical one.
In 2015 Rebecca decided she wanted to travel whilst freelancing.
After building up savings and clients for a couple of years, she headed off to Europe as a digital nomad.
At first she did more sight seeing that client work, but as time went on she was ready to switch that balance. To settle for longer - both in terms of location and contracts.
Rebecca shares insights on how she made the most of her network for initial clients, and adapted to changing freelance landscapes over the years through platforms like LinkedIn, Facebook groups, and Slack communities.
She discusses the challenges and benefits of running a location independent business. (She’s currently settled in Bonn, Germany - but before that spent two years in Turkey!).
Plus we hear about the importance of community, developing her freelance business with external help in mastermind groups and with coaches. Plus getting strategic by herself with regular quarterly 'CEO retreats' - taking time out of client work, to focus on what she's building herself. Because even if she's staying put for longer geographically these days, she's definitely still going places.
Read a full transcript & get Links in the tabs.
More from REBECCA ROSENBERG
Rebecca’s website
Rebecca on LinkedIn
More from Steve Folland
Transcript of the Being Freelance podcast with Steve Folland and content writer & strategist Rebecca Rosenberg
Steve Folland: As ever, how about we get started hearing how you got started being freelance?
Rebecca Rosenberg: For me, being freelance started when I was working in full-time as a marketer. I was a social media and digital manager for a taco chain called Torchy's Tacos started in Texas and they're now in like 14 states I think, and I was working for them during this time where they were expanding to multi-state operations.
And I was loving the job. It was really fun, but I was ready for a change and didn't really want to look for another job because we all know how fun that is. And at the same time, I started seeing stuff kind of bubbling up on Instagram. About remote work and digital nomadism and work from anywhere, and that seemed really appealing to me 'cause I had been an expat before and loved traveling, and this was in 2015, so it wasn't really a normal thing yet.
So I basically just started hatching a plan and saving money and figuring out the timing for when I would take the show on the road.
Steve Folland: Cool. So 10 years ago that you start plotting, how did you go about getting those first freelance clients?
Rebecca Rosenberg: The first few, I started doing kind of side gigs while I was still full-time employed. And so that was really helpful because people already knew what I was doing. And so just leveraging that network, telling people, Hey, I'm available for freelance work. And then the same thing as I started to transition away from the job and into, you know, full-time freelancing.
I posted on LinkedIn, posted on Facebook and you know, told my network what I was doing. And I also used at the time, you know, 2017, Facebook groups were really big. I think they're maybe not quite as valuable today. Today I'm using more like Slack communities and Slack groups. But that helped me get the first few clients and then that kind of snowballed from referrals and, you know, word of mouth.
And yeah, it's changed over the years. In the last few years, I think I've started to lean more on pitching and outreach and stuff. So I think the lesson there is it always changes. You have to try different things.
Steve Folland: So, at what point did you feel confident to put this dream of yours in action to work and travel? How did that actually go?
Rebecca Rosenberg: So I started in January, I think it was January 17th, 2017. I remember the day, 'cause it was right after the presidential inauguration and yeah, so I had basically saved up money 'cause I wanted to have a little financial cushion to start with. And, you know, I had broken my lease and moved everything into storage and all that stuff.
And basically I decided where I would start. I was gonna start in Europe and I had no real plan as far as like where I would go and how long I would travel, but I, you know, knew that I wanted to make it last as long as possible. You know, the first few years I wasn't working full time on my business like I am now.
It, because it was you know, more of a means to travel longer. So I was maybe working like 10 hours a week, 10, 12 hours a week, and just looking for different options, trying out different clients and different styles of working and figuring out what worked for me.
Steve Folland: And what did work for you? So that's more that sort of digital nomad lifestyle, leaning on the traveling, and I, and I often wonder, I've not done it myself, like, how you avoid, the sightseeing getting in the way of the work, but equally the work getting in the way of the sightseeing.
Rebecca Rosenberg: Yeah, it is a delicate balance, I must say. One of the things that I did was try to plan to like stay longer in each place. You know, if you're staying three days in a place, you really don't have time to do work and sightseeing. You know, a lot of people, I think when they digital nomad, they do like once a month they'll move locations.
I was moving even faster than that and sometimes that was too fast. But yeah, just giving yourself time to like be in a place and maybe take the first few days, sightseeing, or sometimes I would split it into, you know, morning and afternoon. And yeah, it took a bit of trial and error to see what worked for sure.
You know, as I started along the way, wanting to invest more time in my business and realized this was really gonna become something sustainable, you know, I switched that ratio a little bit of like more work, less sightseeing. But now I live in Europe, so it's still like every day is an adventure and something new.
Steve Folland: Yeah, because this is the thing, right? So. I know we're fast forwarding slightly, but how long did you do the digital nomad thing where you are regularly moving to being perhaps more location independent? Would that be the right phrase, where you've, you stay for much longer in a, in a particular place.
Rebecca Rosenberg: Yes. I love that phrase: 'location independent', 'location independent business owner', et cetera. I mean, the digital nomad term is a little bit strange, but it's the one everybody knows. So yeah, for the first few years I was basically yeah, moving around. I actually had a home base kind of here in Bonn at that time as well.
My partner at the time, now, husband was living here, and so I would kind of use that as a jumping off point. I would go for a month traveling around, say, you know, Eastern Europe, or I would go to Africa for a month or something and then I would come back here. Still, you know, traveling around locally in the region and just getting a little bit of rest and then coming and then leaving again to go somewhere.
So I did that. For the first almost two years, I guess. And then after that I got a job, like a part-time job in Spain as an ESL teacher. And this was partly a way to have a visa. And I had you know, healthcare and a little bit of steady money. It was not really well paid, but, I think that was kind of the transitional period for me of like moving towards maybe a more. I'll say sedentary or like more standing still kind of lifestyle. So I lived there for 10 months and I did basically 10 hours of work as an ESL teacher and about 10 to 12 hours a week of business building and working with my freelance writing clients.
And then after that, the pandemic kind of started to happen a little bit, you know, a few months after that. And so that kind of naturally slowed me down. But it was interestingly around that time, after two-ish years, I was ready to slow down anyway. So then I started looking for more long-term visa options here in Germany.
If we wanna fast forward even more, I eventually ended up in Turkey for two and a half years before coming back here.
Steve Folland: Wow. And throughout that time, where are your clients? Are they also anywhere or are they mainly in America or..?
Rebecca Rosenberg: My clients were mostly based in the US and still are. I have a few UK based clients. I have a Canadian brand that I work with, but I did mostly work with US brands. I think partly just because that was what I was familiar with. You know, they needed English content, of course, and I know the market. So that was an interesting compromise with time zones, et cetera, which is definitely one aspect of digital nomad life that anyone who's tried that and freelance life in general, you know that you run up against those challenges.
Steve Folland: How did you overcome them? Like how did you deal with clients across those different time zones? I mean, maybe that freed you up to do more traveling when they weren't expecting you to work.
Rebecca Rosenberg: It actually, it has some positives and negatives, of course, like the positive is that, if I'm here in Europe or on this side of the world, I'm getting work done while they're asleep. So I used to always pitch it to them and be like, yeah, like the, the assignment will be in your inbox when you wake up.
Right? And I can get a lot of stuff done without people pinging me and emailing me. So that's great. And I am a little bit ahead of time here so I can even, you know, turn in the assignment four o'clock my time and it's like it's there 9:00 AM for them. And then on of course, the downside is that if we have to have meetings, you know, a strategy call or something, that means I'm often potentially doing it over dinner time or something like that.
You know, we try to do it where it's their morning and my afternoon and people are really understanding about that, but sometimes schedules just don't align and I have to take a later call. But one thing that's also good about it is that, you know, being a content writer, I'm writing, you know, blog articles or email series, or a case study or a report, and once we've exchanged the information about what needs to get done, which can be done through a call, or sometimes a brief, you know, we might not even need a call, if we've already established the working relationship and a lot of the knowledge is already there then I can, you know, I work on deadlines, so it's not like I'm having to check in every hour or every day with these people.
So you just kind of have to find the balance. I did have to work through those boundaries of like, okay, I'm not taking on any sort of client work that requires a daily check-in, or sometimes even a weekly check-in would be too much.
I might take into account, are they on the East coast or are they on the West coast and you know, 'cause that's a three hour difference. So you have to just think about little things like that. And I've worked it out over time.
Steve Folland: And you are still mainly getting clients through like the groups that you join online and being helpful and getting to know people that way.
Rebecca Rosenberg: Yes. Actually, I would say the last two clients I think came from LinkedIn, just like LinkedIn outreach, or them seeing my content and reaching out to me because they felt like we had a similar approach to content and their way of thinking. I, yeah, I use Slack groups. To all, a lot of the Slack communities I'm in will have like a channel for, you know, jobs or gigs, et cetera, that you can kind of reach out to.
But it's also, again, about just being helpful and being visible in those communities. And then, yeah, I've been lucky that things have, you know, referrals. I have a process in my offboarding questionnaire where I, you know, kind of ask for a referral or just put the, put the idea in their head like, Hey, do you know anyone who might need my services?
If not, no pressure, no worries at all. But it still kind of reminds them even if it's not at that time right when they fill it out, that maybe a month or two later they know someone who's asking for a writer and they'll remember me.
Steve Folland: Nice. So are you quite systematic about the way you run your business? I like the fact that you have offboarding and you're automatically asking for referrals. I'm intrigued.
Rebecca Rosenberg: Well, I would love to say that I am super systematic, but I am not. I mean, I do have some systems worked out. I think I realized. Over time, like I've been in different communities and gone through coaching programs and played around with my systems and tried to figure out, you know, do I need to have a fancy onboarding forum and a welcome kit and do I need to have, you know, different freelancers have lots of different project management tools.
I do try to keep it pretty lean. You know, I have, when I get a new client, you know, I have some basic information that I send them. I like to have a kickoff call where we explain things. I have an intake form which is more extensive for some projects than others. And then I have an offboarding form.
But, you know, during the project. Pretty simple. We work through email and Google Docs, et cetera, and you know, I try and help them be a good feedback giver, et cetera. Like you know, I have little policy, not policies, but yeah, like ways I like to work where I say, you know, instead of every person from every department giving feedback, please limit it to one point of contact, you guys can, you know, corroborate and commiserate. Behind closed doors and then give me that feedback on a document so that it's not... 'cause that can really slow down the process and also kind of like muddy up the waters of the messaging if we have too many cooks in the kitchen.
But yeah, I've just tried to find what works over time and I think for me, I like keeping it pretty simple and I think clients for the most part, appreciate that it's really easy and streamlined to work with me.
Steve Folland: Yes. To having one person just give feedback. So are you someone who's quite goals driven?
Rebecca Rosenberg: I try to be, yes, because I think one of the biggest challenges for a lot of business owners is you work a lot on client work and that's your first priority, and then it gets, you know, time runs away from you and your own planning and your own marketing, et cetera tend to kind of like fall by the wayside.
That definitely happens for me, so, what I started doing is a quarterly, I call it a CEO retreat, so it's like a quarterly planning session. There's been times in my business where I've done it monthly. There's been times in my business where I had like every Friday, or every Monday was like Marketing Monday and Planning.
But over time I've realized like quarterly works really well. I can't always fit it in every month. So what I do is, yeah, I take, I usually go away from my house or from my coworking, from my town. Let's say I go to somewhere an hour away or half an hour away, just gives you new scenery. Staying in a nice Airbnb or a nice hotel and it puts you in kind of the mindset of, I'm here to work on this, instead of, Hey, the laundry could be done right.
So the only rule I really give myself during these is no client work. And I do some goal setting. I do reflection on like, what went well over the last three months, what do I wanna do more of? What do I wanna do less of? I usually do some marketing stuff, like take time to maybe write a article that I've been wanting to write, draft up some LinkedIn posts, my email list, et cetera.
But yeah, so it's planning and implementation, no client work allowed, and I find that they're really great. They, you come out of them feeling like really energized and excited about your business instead of just feeling like, okay, I'm slogging through deadlines. So it's been really great for me.
Steve Folland: I love that a quarterly CEO retreat and you are actually going away as well.
Rebecca Rosenberg: it's a great way to incorporate my passions and my business.
Steve Folland: That's made a real impact?
Rebecca Rosenberg: I think so. I mean, I come back from it really excited to do, actually more excited to do the client work and I feel less stressed about like, oh, these things, these marketing tasks or this planning, this strategic thing is still sitting on the back burner.
You need to do that. You know, that mental load is gone and, and just gives you more clarity. I mean, sometimes I end up changing some messaging on my website or I'm revamping my packages and what my offerings look like. So yeah, it's really a great way to make progress in your business.
Steve Folland: Let's talk about your marketing though, because you've mentioned a few different things. So it would be cool to hear what you do. 'cause you, you've said that for example, people have found you on LinkedIn because they like the content that you put out, you made reference to emails that you send. So how do you market yourself?
Rebecca Rosenberg: I used to market myself on Instagram and LinkedIn, but I realized that, so I work mostly with B2B companies, so B2B Tech and finance. And I realized those people, they might be scrolling on Instagram for fun, but they're not necessarily looking for a service provider there. So LinkedIn has become my platform.
I try to be consistent with posting like two to three times a week. Sometimes I'm better at it than others, and I have kind of a document where I just like have a stockpile of ideas. I try to go back to that often, and so that might be on the CEO retreat or if I have time during my week, like going back and refining some of those ideas.
I'm always jotting down as things happen. You know, like, Hey, I am on a podcast. I should share that with people, right? So yeah, I do LinkedIn marketing. I do a lot of, I would say just networking. Also, just like relationship building. Like I'm love getting on a virtual coffee chat, maybe in a Slack group that I'm in, or in a community that I'm in or on LinkedIn.
And those, I think relationship building and, and those like more one-to-one things have been really amazing 'cause people get pitched all the time, right? So these conversations are not a pitch session. It's really just like, Hey, I want to get to know you. It could be another freelancer or it could be a business owner, but they have actually ended up.
Turning into client work a few times. So it's like if they do, that's a great bonus. And if they don't, then I've met someone that knows more about my work. And it's that thing that I mentioned before, like maybe three months or six months down the line, they're thinking about, they're ready for content and they remember this great conversation they had with me.
Steve Folland: That's so nice, especially because as well, it brings in that human interaction. 'cause I was wondering about that, and I know you mentioned coaching, so I was wondering whether you have people around you that you talk business with and maybe some of that has been more formal.
Rebecca Rosenberg: Yes, I do, and I have in the past. I try to always invest in something, whether that's a community like being freelance or the Copywriter Club has been a community that I've been involved with. They have a few different programs. Sometimes I've worked with one-to-one coaches or like group mastermind programs, and it's so valuable to just be able to talk to other people who are balancing the same, you know, work-life balance and being all the roles, you know, as freelancers, we're HR, we're Sales, we're Marketing, we're Operations, and you know, only other business owners are the ones who are gonna get that. So I love being able to, you know, share just those struggles, share the wins.
Or like, a lot of times we're getting really into the nitty gritty of questions of like, this client said this to me, how would you handle this? Hey, I'm thinking about. Offering X, Y, Z. Does that sound good? Where do you think I could improve it? Or what are, so they'll really help you pick apart your idea as someone who has been there.
So it's so valuable.
Steve Folland: Where do you find a coach? You know, like if people are listening and thinking, oh, I, I've, I've heard of some people talking about coaching, but I'm never quite sure how I know who would be a good coach for me.
Rebecca Rosenberg: Yeah, it can be a bit of a process to find one because you know, there's always people telling you online, 'I was so successful I did this and you can too if you buy my course'. Right? I think for me it was getting turned onto things accidentally, like through a blog or like I mentioned, the Copywriter Club. They have a podcast. And so I listened to their podcast for a long time and you know, I was like, okay, I'm getting value from that and I'm loving the things they're saying. And then you find out that they have a program.
A lot of coaches and communities will have like a free Facebook group or a free Slack group so that you can kind of dip your feet in. And then they will also have like a paid tier.
So I'm in a couple of content marketing communities on Slack. One is called Super Path, another one is called Top of the Funnel. And they both have like free channels where you can just meet other people and then if you're interested and you like, are enjoying, you know, the content and the support that you're getting, you can take it to the next level.
So that's more group based, but private coaches, I think it was. Just a matter of maybe finding them online and then consuming their content and building that trust or finding them through a referral. Like I'll ask people in my community and then that, you know, that's a real life testimonial of, Hey, I enjoyed this about it.
This maybe wasn't my favorite, but you know, you're different. So I think it depends on, you know, your needs and everyone's different, but that's how it worked for me.
Steve Folland: How about work life balance for you? This must have changed a lot over time. You've traveled the world, but perhaps more like today when or when you're in Turkey, you know, like when you're more settled, how's, how do you get a grip on that?
Rebecca Rosenberg: It's always changing. Yeah. So I realized that for me. Working in the morning is best. That's like when I feel creative and fresh. So I try to do like the deep writing, you know, deep focused work in the morning. And then, you know, we've talked about how I work with clients overseas and so I usually tend to take like a longer break in the middle.
So after my deep work stretch of like four or five hours, I will take a break of a couple, you know, three hours, and then I make sure to check in again. While it's, you know, my clients overseas are awake and make sure they don't need anything, and I can do some communications or calls. So that has been one thing I've tried to do is like, figure out what schedule works.
I've also, you know, I, I, a lot of people use like a Z Cal or a Calendly link. I have that so that if new prospects or something wanna schedule a call, they can do that, but I only have it available on certain days so that I'm not having a call on a Monday or a Friday evening. And I just, I know like these are my days for calls, so I can plan my evenings if I wanna, you know, go to an event or go to the gym or something.
I know those days are gonna be free from calls. So a couple of strategies like that, and... work life balance. I start my day with yoga, so I like to make sure I get like a little bit of movement in at the beginning of the day. 'cause as the day goes on, it's things always pile up and take precedence. Those are a few things that have worked for me.
Steve Folland: Now, Rebecca, if you could tell your younger self one thing about being freelance, what would that be?
Rebecca Rosenberg: If I could tell my younger self one thing about being freelance? Well, I already kind of talked about this before, but I would tell myself to embrace community sooner rather than later. Because I think I, I spent too long just sitting in a room by myself trying to figure it out all on my own. And yeah, having that community really makes a big difference.
And I guess if I can sneak in a second thing, it would be always be marketing. You never want that pipeline to be empty, so even when you think you're fully booked, you need to still be talking about what you do online and in person.
Steve Folland: Brilliant advice your youngest self would be, would be glad to hear it. Rebecca, thank you so much and all the best being freelance.
Rebecca Rosenberg: Thank you so much for having me. This was super fun.
Episode sponsored by Riverside
Record high quality video & audio with Riverside.
Plus let AI help you create social media ready clips.
Massive time saver.
Even stream to the likes of LinkedIn and YouTube, record webinars with an audience in your own branded studio… and then repurpose that recording with AI summaries and video clips ready to go before you’ve made a cup of tea to celebrate.
See how recording with Riverside can help your freelance business.
It’s free to get started
- use code BEINGFREELANCE to save 15% on a paid plan 🎧🙌