Freelancer Stories: Getting Started with the Freelance Lifestyle

Freelancer Stories: Getting Started with the Freelance Lifestyle

Get insights from two different freelancer's approach to kicking off their freelance careers. Get tips and lessons learned along their journey.

Peter Johnston

Aug 10


Getting started as a freelancer is often tough to start. Where do you begin? It's often tied to a big lifecycle change or shift in approach to employment. To help you on your way we decided to profile a few freelancers who each take different approaches to building a freelance lifestyle.



The Wanderer

Sofie Couwenbergh made her travel blog,, her “official” side gig in 2014 and then transitioned to full-time a year later. She always loved writing and she always loved travel and it was somewhat inevitable, perhaps, that she would someday combine the two. She said she’s a “saver” by nature and started to save money even before she started blogging. Having that nest egg really helped her get started when she quit her job, and right away, the flexibility of the freelance just clicked.

“I love the freedom freelancing offers me to work on what I want, when I want it and to be the boss of my own time,” Sofie says.

However, like many freelancers, time management can be a challenge—for better or for worse. Some people can find it hard to stay motivated with no boss, while others, like Sofie, find themselves working more.

“The most challenging aspect for me was, and is still, keeping a balance between working and relaxing,” she says. “I'm a bit of a workaholic and can do too many hours in a day if I'm not careful.” 

However, all that hard work has paid off. To supplement the blog and better support herself, Sofie created additional revenue streams by travel planning and creating detail itineraries for clients. Now, she gets new clients and watches her income increase month by month, which is exciting.

“I wished I'd found my niche much much sooner,” she says. 

Beyond demand for her services, Sofie has grown her business by being analytical. She tracks income and expenses meticulously, and uses that information to gauge where her strengths lie. Whenever Sofie starts a new project, she analyzes similar projects she’s done in the past to identify what worked or didn't work. Communities—both online and in person—have also helped her grow as a freelancer. She says Facebook groups are a great place for her to connect with other travel bloggers and creative entrepreneurs, as are going to conferences and trade fairs.

For freelancers who are just starting out, Sofie says the key is to stay organized and calm.

“If you're feeling overwhelmed, don't panic,” she says. Take pen and paper and write down every possible step you can think of having to take in the project or projects that you're working on. Prioritize and check things off one step at a time. You'll see that it's much easier to tackle a bunch of small steps than it is to tackle a big project all at once.




The Coordinator 

Valeriia Soloveva is a Contract Market Coordinator who works for Airbnb Trips in Moscow. She started freelancing lasts year and says it was the best decision of her life. When asked what the most exciting aspects of freelancing are, she gave three.

“One, I don’t need to spend so much time to get to my workplace and to get back home,” she says. “Two, I can work at night, because I’m a night owl. And three, have much more time for self education and workouts, and most importantly, I can spend the whole day with my lovely dog.”

To ability to choose when and where to work is what attracts many people to the freelance lifestyle. For Valeriia, it’s helped her unlock her full potential, and she does better work as a result.

 “I’ve started to learn myself better,” she says. “The most surprising was the fact that I’ve become so calm and much more productive that I’ve ever been.” 

The solitude can be great for productivity, but a challenge for others. As Sofie mentioned, becoming a better freelancer is all about understanding yourself, your own habits and behaviors, and how to structure your time most effectively.

Valeriia’s advice for people thinking about making the jump into freelance?

“Find out are you a person who can stay with yourself for a day,” she says.