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This post is brought to you by a few of Kathleen’s travel luxuries she finds room for her in her backpack: a silk sleep mask, silk bathrobe, and silk pillowcase. She bought hers in Bali, but in case you’re not heading there soon, we’ve linked to a few recommendations.
This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!
Kathleen had a career in Boston where she made six figures. She quit to spend a year traveling, but her feelings about returning to the office led her to opt for an unconventional path. Be sure to check out her blog, My Lonesome Roads, to read more about her travels!
Thank you for hanging out with Freedom Is Everything, Kathleen!
Key takeaways from Kathleen’s interview:
“My definition of success has also changed. Being from a highly career-focused family and country, there’s always plenty of subtle pressure to always trying to achieve more, earn more, or get a more prestigious job. But that’s not what makes me happy, and I have become even more determined to live a life where success looks what I want it to look like. That means having freedom, strong friendships, and giving back in some way to the world. And having plenty of time to write what I want, not just what my clients need.”
“Know that this kind of life can seem glamorous and carefree from the outside, but it’s not all working from a sunny beach. You need to think about balancing work and life and travel all at the same time, which requires good time management skills (I’m working on those myself tbh). Staying focused on doing great work can be hard when everyone else is heading to the beach, but it’s important for your professional reputation. Be realistic about how much work you want to take on and how much income you need.”
“It is very, very easy to fall into doing what other people tell you will make you happy. That can be your culture, your parents, your friends, your boss, or really anyone. But happiness and purpose are different for everyone, and finding yours takes a lot of deep thought. Then taking action to actually make that happen takes a whole lot of courage. Lots of people talk about their dream life of traveling and writing – very few take steps to make it happen.”
“Charge more! I don’t care how much you’re currently charging or what seems reasonable – charge MORE! And then just keep charging more. You’re probably not asking for enough money, and with higher rates comes better clients as well. The worst that can happen is they say no, which happens to me sometimes, and then at least I tried.”
Table of Contents
Introduce yourself! 🙂 Who are you? What do you do for work? And what is your nomadic story?
Hi, I’m Kathleen! I’m a writer who is originally from Boston, but I’ve been traveling and working remotely for more than 2.5 years. Since August, I’ve been living in Split, Croatia (I got “stuck” in this beautiful place due to Covid) and plan to be here through the summer.
I’m a freelance copywriter and content writer, mostly for B2B clients. I help my clients create compelling content that resonates with and informs their audience, whether they’re a brand-new startup or a well-established enterprise. I mostly write blog content, but I’ve created ebooks and white papers, and I do a bit of social media marketing as well. And I also have a travel blog where I talk about solo female travel and digital nomad life as well.
I’ve been living abroad for 2.5 years and a nomad for 1.5 years when I started my freelance career. I’ve lived primarily in Greece, with some stops in England, Ireland, Albania, and now Croatia.
What inspired you to start nomading? And how has nomading changed your perspective on life?
I started nomading because in September 2018, I quit my 6-figure corporate communications jobs to spend a year just traveling the world and exploring. It was amazing – I visited 24 countries and four continents totally solo!
But when that year came to an end, I wasn’t ready to go back to life in Boston working for a big corporation again. I did, however, need to start making money again. So I decided to transition to being a freelance writer and living in Greece while I got established!
Nomading has changed my perspective on so many things in my life. I have realized how much more comfortable with uncertainty I’ve become and how that’s a necessary skill as a nomad. I realized how much more I value my freedom and free time these days and don’t see myself going back to a 9-5 job for a long time, if ever.
And I’ve realized how living as a nomad helps you find people you connect strongly with because you have a love of travel and adventure and new cultures in common. It makes it really hard to go back to “normal” life ever again, which I’m fine with for right now.
My definition of success has also changed. Being from a highly career-focused family and country, there’s always plenty of subtle pressure to always trying to achieve more, earn more, or get a more prestigious job. But that’s not what makes me happy, and I have become even more determined to live a life where success looks what I want it to look like. That means having freedom, strong friendships, and giving back in some way to the world. And having plenty of time to write what I want, not just what my clients need.
Please tell us the detailed story of how you started your freelancing business.
I have been writing professionally my whole career, for 12 years, before I started freelancing. So while my success might seem like it happened fast, it’s really because I had a really good background in my chosen skill. I really jumped into freelancing headfirst because I just wanted to get back to living in Greece!
When I returned to the US from my year of traveling, I just needed something to get me started. I found an opportunity with a digital marketing agency based in Texas that was looking for a freelance content and copywriter, and they truly trained me on how to do those jobs. I’m really grateful I started out with such a great group.
From there, I started branching out to find additional work to increase my income. I have been able to find lots of great clients who pay well on Upwork and actually make the bulk of my writing income there for both content and copywriting. I also have a few clients I got through my networks, both former colleagues and then recommendations from clients who enjoy working with me. Having a mix of income sources is important to me, so I’m not too reliant on a single client.
Since launching, what has been most effective to acquire/retain clients?
My main priority as a freelance writer is actually not just my writing skills, though those are great – I’m also focused on being 100% reliable to retain my existing clients. From working with freelancers at previous jobs in the past and also talking to my current clients, I know how hard it is to find freelancers who can write well and also deliver on time, every time. It’s a tough combo! And I pride myself on delivering just that. I don’t miss meetings ever, I don’t miss deadlines ever, and I will always deliver what I promise. That helps me stand out with great clients because they know they can rely on me absolutely.
To deliver this, I’ve had to be selective about the kinds of clients I work with, and to that end, I’m always increasing my rates. People who pay you more value your work more! And that way, I have only a manageable amount of work on my plate to get done. I use organizational tools to stay on top of deadlines and make lots of to-do lists. I usually aim to work about five hours a day but flex my workload around my life, so sometimes I have a very long day if the weather the next day is beautiful and I want to go to the beach at 11 am. I love being able to do that!
What are the 2-3 favorite places where you’ve lived/traveled to and why?
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Greece is my favorite country, and also a great place to live and work. The cost of living is quite low, the people are welcoming and friendly and outgoing, and it has a growing nomad scene, so it’s easy to meet people. Plus, the weather and the natural beauty just can’t be beat. I love living in Athens, which gets a bad rap but is actually a really young and vibrant city with a lot going on.
I have also really grown to love Croatia in my time here! The weather is also beautiful though the cost of living is not as low as in Greece, but it’s still reasonable for the quality of life you get here. Split also has a growing nomad scene, which will only get bigger with the Croatian digital nomad visa, which was introduced this year as well. And locals here are really hospitable and friendly once you get to know them!
What advice would you give to someone who’s thinking about nomading?
Know that this kind of life can seem glamorous and carefree from the outside, but it’s not all working from a sunny beach. You need to think about balancing work and life and travel all at the same time, which requires good time management skills (I’m working on those myself tbh). Staying focused on doing great work can be hard when everyone else is heading to the beach, but it’s important for your professional reputation. Be realistic about how much work you want to take on and how much income you need.
There will also be periods of loneliness as you move on to a new country yet again and leave behind people who have become friends, and the same thing makes dating a challenge as well. It’s hard, and so far, I haven’t found a way to make it easier, but it does mean I’m creating strong friendships, and I’m grateful for that.
But fortunately, meeting people while traveling can be easy. I’m quite shy naturally, but I’ve found a few ways to make this work for me. I usually join coworking spaces which is an easy way to meet other freelancers and nomads. I also join Facebook groups in the cities where I visit for expats and digital nomads, and they usually have lots of meetups and events you can attend to meet people.
Once you’ve met a handful of new friends, you’ll start meeting even more people, and then you’ve got a whole new social group! This was one of my biggest fears before I started nomading due to my shyness, but I’ve been pleasantly surprised at how easy it is to meet people while traveling.
As a woman, what should other people who identify similarly (and who haven’t traveled much) know about traveling/nomading?
Lots of people were (and are) very concerned and confused when they hear I’m a woman traveling and living abroad alone. I just checked into a new Airbnb yesterday, and my hostess was quite surprised I came without a boyfriend!
But the truth is, most places abroad actually feel much safer for me than being back in Boston. I’ll walk home at Split at 2 am alone, which I would never do anywhere in Boston. Being a woman has dangers everywhere, and you, unfortunately, can’t avoid them by staying home. But you might be surprised how much safer you feel living somewhere else.
What scale is your business at today, and what are your future goals?
I have about 10-15 clients at any one time and work with them anywhere from a few times a week to once a month, and I earn about $4k-$7k per month, depending on my workload at the moment. It took me over a year to get to this level, but currently, I feel like my business is quite sustainable, and I’m working with high-quality clients I enjoy.
I don’t have a desire to own my own agency or manage other freelancers, however, because I like the freedom of being my own boss and the sole employee. So I want to scale to a point where I can earn enough to also have time to focus on my own writing part of the time as well, and still have time left to enjoy life. That’s my version of success, not earning as much as possible.
For someone interested in becoming a freelancer in your field, what’s the best advice you would give? And what books, podcasts, thought leaders, or other learning resources do you recommend?
I would advise them to start out slowly instead of jumping in like I did! It took me a while to make a sustainable income. Maybe start it as your side gig while you have a full-time job still! But it was what I wanted at the time, so I don’t regret it.
Also, this is especially important for female freelancers – charge more! I don’t care how much you’re currently charging or what seems reasonable – charge MORE! And then just keep charging more. You’re probably not asking for enough money, and with higher rates comes better clients as well. The worst that can happen is they say no, which happens to me sometimes, and then at least I tried. Sometimes they’ll agree right away to whatever you ask, and sometimes they’ll at least increase their offer. It’s the best way to grow your income without working 100 hour weeks.
If you only had a few minutes to live, what are the most important life lessons you would share with the world?
Life is very short, and you never know how short it will be – so go live your dreams and take risks! Don’t put anything off you will regret not doing until the uncertain future.
Also, be kind to everyone you meet. You never know when you will meet them again, even if you travel around a lot. The things we regret most in our lives tend to be failures of kindness, as this beautiful speech from writer George Saunders reminds us.
What digital tools do you use for your work/business?
I use Asana with one of my clients to keep us all aligned on upcoming content, and I also use Slack. But I work with them very frequently, so we need to communicate a lot. We also have a weekly Zoom meeting.
With all my other clients I work with less, I use Trello to stay on top of upcoming work. I also will sometimes schedule an intake Zoom call with a client if they want it, but otherwise, we mainly communicate via email or Upwork, and that works well as I prefer to have as few meetings as possible. And I use Wave to manage my income and invoice clients.
What do you travel with that you couldn’t imagine traveling without?
I currently live out of my backpack and don’t have a home base, so my list of belongings is very short. But I do always travel with a silk pillowcase, silk sleeping mask, and this beautiful silk bathrobe I bought in Bali as my little luxuries. Falling asleep in new places is always a challenge for me, and having a solid bedtime routine and my familiar soft things around me is a big help.
What is your philosophy on being happy and/or finding meaning/purpose in life? And any recommended resources for people navigating this journey?
It is very, very easy to fall into doing what other people tell you will make you happy. That can be your culture, your parents, your friends, your boss, or really anyone. But happiness and purpose are different for everyone, and finding yours takes a lot of deep thought. Then taking action to actually make that happen takes a whole lot of courage. Lots of people talk about their dream life of traveling and writing – very few take steps to make it happen.
And you’ll probably upset some people along the way who don’t understand or are threatened by your life outside their norms. That’s ok! If you know what you’re doing is right for you, you can go for it, and you’ll find a team of people doing the same and supporting you along the way.
If you’re passionate about FIRE (Financial Independence Early Retirement), please share how this has impacted your life, what your journey has been like, and what other people should know about FIRE!
I’m just starting to explore FIRE, and it’s one of my goals in the next year to figure out a plan to become financially independent by age 45. That way, I can focus on my own writing and traveling!
How can people learn more about you and your work?
I write about living abroad, traveling solo as a woman, and digital nomad life on my blog mylonesomeroads.com. And you can keep up with my latest adventures in Croatia on my Instagram!
