Moving abroad for success

"My new definition of success is having a life that feels like enough, where I feel like I am enough."

The Sustainable Solopreneur is a weekly newsletter about seasonal, cyclical, supportive business strategy for solopreneurs and creative souls who want more out of life than the status quo, hosted by business coach and strategist Jenni Gritters. If you’ve been reading this newsletter for a while and you receive value from it, I’d encourage you to sign up for a paid subscription.

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Today, I can’t wait to introduce you to Kathleen O’Donnell. She’s someone who manages to marry stability with flexibility, as you’ll see in this interview about her decision to move abroad. Kathleen is thoughtful, meticulous and intentional. She’s also epically creative. When I started asking around about folks to interview for this series about taking the third door option, Kathleen’s decision to move to Greece (and her approach to business in the midst of this move) immediately came to mind.

Here, she shares what success looks like for her as a solopreneur who’s building a business and life overseas.

Kathleen, how would you describe your work right now?

I’m a freelance writer, mostly in the B2B space, and started working for myself five years ago (even though sometimes it still feels like yesterday!). I write social content, longer-form blog content, and I do some copywriting too. I’m a team of one and have been the whole time, but I did set up an LLC and an S-corp last year to make everything more official.

I used to work almost exclusively with B2B SaaS startups, but diversified when the industry was really rocky last year. Now I have a fairly diverse spread of clients, with a lot of them in the HR space where my corporate background was focused.

What does embracing a “third way” look like in your life?

I spent my career before freelancing in the corporate world, in finance and insurance, and I was generally a person who really valued stability and had absolutely no desire to work for myself. But then I took a year off of work to travel the world (lucky me!) and that completely changed how I wanted to live my life going forward.

I decided to leave the U.S. and move to Greece, and live as a digital nomad. There was no legal path for me to live there full-time at that point, and I needed a way to support myself, so I thought, why not freelance? It was naive and optimistic, but I had my heart set on it and lots of corporate connections and I somehow made it work.

I left behind a much more traditional life in the U.S. to live a very different one in a very different place. I’m very happily single, choosing to be child-free, and I’m just generally pretty uninterested in the traditional markers of American adulthood like having a car, a big house in the suburbs, and working 40 hours a week until I’m 67.

For me, having a life that is free of the expectations of other people has been really challenging but it’s worth the struggle. I have purposefully created a very different but incredibly beautiful life that I love, and while it is not easy in a whole host of ways (learning Greek is basically another full-time job), it’s satisfying and fulfilling on a much deeper level.

What does embracing a “third way” look like in your business?

I have really, since the beginning, seen my business primarily as the means to an end: living in Greece. I really love my work and my clients, but I am not in this for status or prestige or really big paychecks. I don’t care about “expanding” or “scaling” or getting to the next level. I just want to do good work with good people, and then go live the rest of my life. It’s such an enormous shift from how I operated at work when I was younger, and the kind of career I thought I wanted! But it’s exactly what I need at this time. I wake up most mornings still in awe of what I’ve managed to create for myself here.

Tell us about moving abroad, and why this decision has worked for you.

Moving abroad is absolutely not for the faint of heart, particularly moving to a place where the culture and the language are so different from the U.S.! The bureaucracy alone in Greece is absolutely daunting in a way that’s hard to explain if you haven’t experienced it. It’s really, really hard (both legally and culturally) to move abroad.

But those difficulties have made me find an inner strength I didn’t know I had, and that helps me approach my business with more confidence and much less fear than I would have before I moved. I know how resilient I am, how determined I am when I want something, and how to try new things even when I’m not sure they’ll work. (Also when things go badly: Now I know a lot of interesting new curse words in Greek!)

Also, living in a culture where there are such different priorities has been amazing. It’s impossible to summarize a whole people but Greeks generally prioritize life outside of work (and leisure and rest and enjoyment) in a way that really resonates with me. The first question people ask you is not what you do for work. It’s totally normal to spend three hours on a workday drinking a coffee with a friend in the sun and gossiping (this is my idea of heaven). It’s normal to take at least two full weeks off work in August, and more time off throughout the year. Naps are totally normal and even encouraged.

Work is not life here, even though people here do work very hard and are very entrepreneurial (which is also energizing!). It’s not all positive - salaries here are really low and employers can be exploitative, so Greece is not a magical paradise for workers by any means. But the pace of life and the ability to live a really full life that is less materialistic and more community-focused is something I could never give up.

What do you believe about the “rules” people teach us, related to work? What good has come from choosing another path?

The traditional ideal I grew up with was that achievement and working really, really hard at an Important Job are the only ways to have a good life (and then to give it all up once you have kids, which is another whole subject!). But those rules are not the only way to have a satisfying life, I’ve found.

I almost never work 40 hours a week. I took 5 vacations from work this year alone. I don’t want to grow my business by hiring more people and becoming a boss, at least right now. My new definition of success is having a life that feels like enough, and where I feel like I am enough, and that’s pretty modest by those standards. I’d rather take more time off, or go to the beach on Fridays, than work more and earn much more than I actually need without being able to enjoy it.

I love this perspective. With all that in mind, what’s the Kathleen version of growth in this season?

One of the very complex things about living in Greece (on my specific residence permit) is that my ability to stay here is contingent on my income. I do need to keep my earnings from the business high enough to meet certain permit requirements. In leaner months, that’s a pretty scary thought! I also can’t go out and supplement my income with another job. So part of my plan for the next 2.5 years (until I have permanent residency) is just keeping my business income high enough for that, which is challenging but worth it. Plus I’m buying an apartment here, so I’m focused on earning enough for all those unexpected expenses I’m sure will crop up!

But for the farther-ahead future, I’m really focused on setting up a stable but flexible foundation for my future self, for whatever she wants to do with her life. My life has changed so radically in the last six years that planning another six years ahead in detail just feels impossible and unnecessary. I just want to build a really solid financial foundation so that I can pivot to whatever feels right then: taking a month or two off to write a novel, spending the summer working at a coffee shop on an island, buying a hotel in a tiny town and running that while writing for pleasure. Whatever future Kathleen wants, I want her to have! And with a paid-off mortgage, a fully funded 401(k) and permanent residency in a few years, she’s going to have so many exciting options.

If you’re debating whether or not you should make a massive life change like moving abroad or starting your own business (or both at the same time, if you’re me!), I really recommend giving it at least a little bit of a try. You can always move back! You can always get a full-time job again! But if you’ve got that little voice inside of you telling you to try something different, to break a rule you’ve always followed, to try a totally new way of life, you owe it to your future self to at least give it a chance. You’re capable of so much more than you think! And breaking out of the usual is one of the best ways to find that out.

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I highly recommend following Kathleen on LinkedIn to see the latest from Greece!

Curious about my background? I (Jenni) am a writer and business coach living in Central Oregon. My goal is to teach everyone who will listen that it’s possible to build a simple, stable, successful business that support your human needs first. Join my group coaching program, SUSTAIN, for more conversations like this (and a community of people who are all about the path less taken — including a lot of expats!), and follow me on Twitter & Instagram.