Digital Nomads Daily Podcast Cover Facing The Realities Of Online Entrepreneurship with Anne

22: Facing The Realities Of Online Entrepreneurship with Anne

Get ready to go behind the scenes of the digital nomad dating world and build an online business with Anne. She has been nomadding for four years and runs a podcast agency along with two successful podcasts. In the first part of this episode, we chat about the challenges digital nomads face in dating. Then we continue the conversation about facing the reality of building a business and taking the entrepreneur path. Anne reflects on what she learned and shares valuable tips about preparing yourself mentally and setting realistic expectations. Don’t miss out on a fantastic conversation about the digital nomad lifestyle!

“As entrepreneurs we learn so many lessons. I think entrepreneurship is basically a self-development journey on steroids ”

Featured image of digital nomads daily podcast shownotes 10 years traveling the world with digital nomad daisy

The digital nomad Lifestyle and online entrepreneurship aren’t that glamorous

It’s true, the digital nomad lifestyle is less glamorous than shown on social media and in this episode we talk about two of the challenges Anne experienced as a digital nomad. The first part of the interview covers her dating life as a digital nomad and why it’s so difficult for digital nomads to date. The second part of the interview is about how to build a successful online business as a digital nomad. She shares some of the common challenges as a traveling online entrepreneur and how to overcome them.

Why dating is difficult for digital nomads

Loneliness is a common topic in the digital nomad community. Sharing this amazing lifestyle with someone else is a dream for many nomads. But why is dating so difficult for digital nomads?

“It felt like the pool was so small because there are locals, travelers, and then there are the digital nomads…”


Anne shares that in her experience, one of her challenges was that the pool of digital nomads is very small. Meeting people is pretty easy throughout the journey as you meet travelers, locals or expats. It gets harder when you finally make a special connection but one of you is leaving. So pretty early on, you have to decide to keep hanging out or walk away. This type of commitment is overwhelming and why dating can become very complicated. What helped her was to be open-minded and flexible. She advises that if you like the person to share how you feel and if it’s mutual to be flexible with your plans.

When she met her boyfriend in a hostel in Thailand she wasn’t interested but could use some company during dinner. They got along and decided to go to an island. It wasn’t part of her plan but she liked the idea and was flexible and open-mind. It wasn’t really a date but there was definitely some romance! What’s funny is that Anne’s boyfriend wasn’t a digital nomad at the time! He learned about this lifestyle by seeing her working remotely and wanted to pursue the same lifestyle. Anne and Nienke Nina also talk about how to date safely and more tips for digital nomads dating.


Building an online business while traveling the world

Becoming an online entrepreneur and traveling the world gets extremely glamourized on social media. Anne shares that she totally underestimates the work part of this lifestyle. As a freelancer, she worked many hours and was basically sitting behind a screen all day long. Of course, she would go out and go on adventures but it was a lot of hard work in the beginning.

“I was like, okey I’m going to do this business now, and I expect to be able to live off this immediately. My income will grow and grow and I will definitely will be very rich before the end of the year – that did not happen”

Luckily she transformed from a virtual assistant to a successful freelance career and built a podcast management agency. The agency business model enables her to work with other talents and to do the work she loves. On top of that, she is working fewer hours and has more flexibility in her schedule. We collected some of her most valuable tips for freelancers and creative entrepreneurs, read the article.


Key takeaways of this episode

  • Be open-minded and flexible when you’re dating
  • Give yourself time to build a sustainable business and have patience
  • Create a financial buffer to cover your expenses so you have less stress
  • Set goals for the near future and for what you want to achieve in the long run
  • Start your online business as a side-hustle and go full in once it’s making money

This episode is fun, honest and very insightful. If you dream of becoming a digital nomad or a creative freelance who wants to build a business, this is your episode!

Photo of Digital Nomad Daisy traveling the world
Quick links:

Follow her journey on Instagram @thepodcastbabes

Check out her podcast @annes_nomadstory/s

Visit her website via

Follow Digital Nomads Daily on Instagram @digitalnomadsdaily

Meet your host Nienke Nina Instagram @nienkeninatravels