Working online and pet-sitting: the remote life of Heleen

Heleen Olland
27 October 2025
6 minutes reading time

My name is Heleen, I am 56 years old and for about 2 years now a digital nomad who loves to travel and has a great love for animals. How this comes together I tell you in this blog. After following the coaching of Alieke Ingerman of Working Remotely, she asked me if I wanted to write a guest blog. I was pleasantly surprised and immediately agreed to this request because I find writing super fun and there is plenty to share about my lifestyle, which is a tad different from others.

Remote working as a virtual assistant

I am a virtual assistant, have my own businesses and also babysit animals in the homes of the owners abroad. In this unique combination that came about because I followed my heart, things come together for me that I embrace. Like having freedom with my own business, living abroad, discovering and experiencing other cultures and taking care of animals. In the Netherlands I did not really feel at home and for a long time I knew that I would prefer to emigrate.

After a year as an au-pair in America at my 20e and having worked in the airline industry for more than 16 years, travel was in my blood. Packing a suitcase is therefore not complicated and I get on a plane as if it were a bus. This also makes it easier for me to be in different places, to adapt and thus be flexible in this.

Heleen with orange outfit in Scotland lake view with sunset

Dog-sitting as a pet sitter abroad

A few years ago I already took my laptop with me while on vacation in America and worked from hotels. Among other things, I worked as a freelancer for the Defense Department. I liked this so much that I wanted to do this more often. A former colleague gave me the golden tip to check out the website of TrustedHouseSitters, a British platform where pet owners and pet sitters can get in touch with each other.

Before doing my first two dog-sits in America (Montana and Washington State), I initially babysat my American friends’ dog in Maryland while they were on vacation. I had a wonderful time and it tasted like more. Traveling, working online and my love for animals come together perfectly in this way. As a pet sitter abroad, I also get to visit the most beautiful places in many different destinations.

Time for change, on to a remote lifestyle

After 2 months, I returned to the Netherlands to terminate my lease with the intention of putting it in for a longer period of time with pet sits in America, Canada, Great Britain (Cornwall, Scotland) Ireland, Germany, Sweden, France, Austria and Belgium.

As far as Europe is concerned, Scotland is currently at the top of the list as a favorite. I have been here many times and am here again now for 6 months in different places. I have a click with the Scots, they are super friendly and relaxed and the scenery is stunning. It’s great to take a long break during your work day and go for a walk in nature with the dog.

I worked for a long time as a virtual assistant through recruiters, but wanted to fulfill another dream by following my heart and that is to restart 1 of my companies with my own coaching business. With this relaunch I am currently busy behind the scenes and it gives me a lot of energy.

Heleen outside overlooking the mountains workplace of Heleen with mountain view

How has Working Remotely’s coaching helped?

Because I had been working remote for 2 years, at first I wasn’t quite sure if I should take on Alieke Ingerman’s coaching. I did it anyway because I had an inkling that she could surely help me with tips and triggers that I could move forward with. Meanwhile, I had been following her on her LinkedIn for a while and got a good idea about Alieke and her expertise.

In my case, the focus was on combining travel and work so that I can better shape my remote life. Both in terms of work that suits me and practical advice on working productively remotely, such as filling your calendar for the necessary daily structure and right balance between work and free time at your destination. We also went to work together with ChatGPT (which I still knew little about) for specific issues and talked about my online business that I am starting and the added value of having a good website, about which Alieke shared her knowledge.

And not unimportantly, Alieke is enormously flexible and can move well with the coachee. She thinks with you, does not judge you, leaves you in your value and puts it in a very positive light. This made me really look forward to the online coaching sessions. It was also nice for me that she understands my life as a digital nomad, because this lifestyle is really different from most people.

The fact that Alieke asked me at the last session if I would like to write a guest blog and indicated that she would like to hear about my progression in the coming time indicates that she is very committed to her coachees.

Sunday sunset with red sky behind the trees special colorful cottages in Scotland

My future plans

To keep things varied, in the short term I am still looking for a role as a virtual assistant for a few hours a week. It is proving challenging to find this in the Netherlands, as not many organizations are yet flexible when it comes to working remotely. I would also like to work for a foreign company.

In addition to developing my coaching business, I would eventually like to take a commercial approach to babysitting animals. After all, this is where my passion lies.

There is so much more to see in the world and I feel strongly that I want to get out of Europe to explore other continents. I love Canada, Australia and New Zealand and plan to expand my horizons to these countries next year. I like to stay in cooler climates and autumn and winter are my favorite seasons.

My tips for going remote

  1. Find out which roles fit you well and which are remote. This is where I went to work with Alieke.
  2. Still finding it exciting? Then start initially, like me, during a vacation from a hotel or Airbnb to see if you like it.
  3. Follow the coaching program from Working Remotely! No spon.
  4. Take actual steps to just do it for a period of time and enjoy the people you meet and what you all experience!
  5. Should you love animals, travel costs are a lot lower because you have a free roof over your head with babysitting an animal abroad through TrustedHouseSitters.

If you enjoy continuing to follow my adventures as a digital nomad and whatever else I do, feel free to connect with me or follow me on LinkedIn or Instagram. My website www.heleenolland.com will be going live soon.

More inspiring stories from digital nomads

Het remote werkavontuur van Aisling in Tanzania en Zanzibar

Overwinteren in Portugal, Jacky doet het al jaren

Maartje werkt al 13 jaar remote met haar gezin, vanuit verschillende landen

Back to overview

This blog was written by a guest blogger for Working Remotely. Would you like to share your expertise on a topic related to remote work? Or do you have an inspiring experience you'd like to write a blog about? Then send your idea to [email protected]. You can read more guest blogs here: Experiences | Working Remotely.

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