Working remote without a giant leap: Robbert's story in Thailand

I am Robbert Oelp, 54, self-taught, content creator, entrepreneur and father of three children. My work is broad: I create podcasts, write articles and blogs, am a local journalist, produce videos and documentaries and manage social media channels. I also support a business investment zone with organizational and practical work in communications and events. In the Netherlands, I have my own video and podcast studio.

I mainly do things that I enjoy doing. As a generative content specialist, I am versatile and have found my own way in this. Whereas my generalist outlook was previously seen as a threat to development, I have now been able to embrace that same generalist knowledge as my specialty.

What connects all this work is that I like to create cohesion, connection and crossmediality. One good conversation can be the basis for months of content. That’s not a trick, but a way of working that gives peace of mind. And which, not unimportantly, also travels with me digitally, literally in my backpack.

Remote working for doubters

I am not a digital nomad with a laptop on a beach at sunset. I’m also not someone who cancelled everything one day and left without a plan. I am a doubter. Always have been. Someone who thinks long and hard, tries things carefully and rarely takes big leaps. But also someone who has learned that keeping thinking sometimes keeps you right where you really wanted to go. I make changes in small steps. Maybe sometimes those steps are a little too small, but for me, as an “anxiety hater first class,” the right thing to do. And so I began to move. Slowly. One step at a time.

Before I had children, I traveled a lot. Asia in particular felt familiar, as if the pace there better matched who I was. Less hurry, more space. Less separation between life and work. On a Thai island, I once thought: what would it be like if you came here not only to travel, but also to work? That thought didn’t disappear. It remained somewhere, waiting for the moment when it was allowed to resurface from an overstuffed backpack.

How remote working began out of necessity

Then came children. And a divorce. For years I was caring almost full-time for three young children. There was little childcare and little flexibility. So I worked from home. Not because it was hip, but because I had to. There was simply no other solution. I was difficult to reach, often “in meetings. I made phone calls in the barn, because in the house there was too much noise from children playing. What was later called ‘remote working’, or in corona times ‘hybrid working’, I was already doing then. Out of sheer necessity.

Only much later did I realize how formative that period was. And how pleasant it is that private and business are allowed to intermingle. That it’s a different way of thinking and working.

When I became seriously ill in a short period of time and had to undergo major surgery, I discovered that this way of working could travel with me even then, modified, necessarily more flexible. Recovery was paramount and work was on the back burner, but it was there. Not because it had to be, but because work became an important part of my life that moved with changing personal circumstances.

Somewhere then the realization dawned: remote working has become a way of living for me. The couch at home, your own office, waiting at the coffee machine at the garage, at an airport, in a coffee shop abroad, on a subtropical island to even a hospital bed can at times feel like your office.

From necessity to choice: my entrepreneurship

But back to another tipping point, years earlier. Before becoming an entrepreneur, I worked in salaried employment for about 12.5 years. My first job, in which I felt like a fish out of water. After an acquisition, however, the situation changed completely. I ended up in a reorganization and was labeled “redundant,” a situation I understood, by the way. Not resentment, anger or sadness, but a situation that forced me to set a new course.

I did not see an appropriate new role within the new organization and was looking for another direction. That moment felt less like a blow and more like a direction. I suddenly knew for sure: I don’t want to be employed anymore. Not because it’s bad, but because it no longer suited me. Entrepreneurship was not a leap of faith. It was a series of small decisions. Often with doubt, sometimes with fear, but always with the feeling that I was staying closer to myself.

In retrospect, I see how this way of life was also parenting. Not by big words, but by example. My children saw that work and life do not have to be opposites. That you don’t have to give up on dreams, but sometimes park them, to pick them up again later. That you can do first and only then think about money.

The life you lead is ultimately the message you pass on.

Working from Thailand as an entrepreneur

As my children grew older and more independent, that old dream returned. Tucked far away in the backpack, it swirled up again and again. Not big, not loud, but present. Silently it planted a seed in my mind. I began traveling to Thailand again. Briefly at first. Always with work with me. As an entrepreneur, I am never completely off. With an eSIM I am reachable, conversations run via WhatsApp and deadlines travel with me. Sometimes it’s also just nice to do “something” business-related, to work on your visibility.

A client once said, “It feels like you’re just sitting here.” That touched me. Apparently distance is mostly in our heads. Another client appended, “Actually, communication is exactly the same as when you are in Holland.” Slowly, distance no longer made a difference but was no more than a question, “Are you in the neighborhood or should I be jealous that you are also filling up vitamin D at the same time? I’m not jealous!

Remote working in Thailand: living instead of traveling

I go to Thailand twice a year for about three weeks. In the first few days, vacation is still the focus, but after the first week, it’s all about the combination. My working days vary. Sometimes I work long days, sometimes only a few hours. I work in hotels, cafes with good wifi, at tables that are temporarily my desk. Sometimes at the university where my partner works, among conservatory students or quietly in the back of a lecture hall.

You naturally build a rhythm. You get to know people. It becomes less “being on a trip” and more “living somewhere. I was in Bangkok from the beginning of January, then a few days in Chiang Mai and now I’m staying in Phitsanulok, central Thailand. I am one of the few tourists here, although it doesn’t feel that way at all. Thais look at people in a different way, with a lot of mutual respect.

Entrepreneurship with more freedom

In 2024, I gave my work a name: Content Tiger. Not to sell, but to give direction. A name helps to make choices, become visible and take yourself seriously. My desire is to help companies and freelancers with online visibility, precisely because I am technically and substantively broadly educated. Audio, video, editing, not through quick templates, but through craftsmanship. This blog is not a promotion, but part of that process: showing where I stand and what I am working towards.

Remote working did not give me a carefree life. Indeed, it is quite difficult at times, especially with children living at home and the realization that you are not “at home” where everything feels and is familiar. But it also gives peace of mind. Space. And a different perspective. A wider world with more possibilities.

It requires discipline, clear agreements and honesty. To clients, but especially to yourself. And it delivers something that is difficult to express in money: the feeling that your life is moving along and that you experience freedom. Free enterprise, with a twist.

Extend remote working step by step

Currently, I work remote about six weeks a year, spread out throughout the year. That feels good. And at the same time, it’s a start toward more. I want to expand that slowly. More often per year. Longer at a time. That means making choices, finding new clients and adjusting structures. Not all at once. Not recklessly.

And what did I learn? Dream big. And dream a thousand times bigger than your very biggest dream. Not because anything is possible, but because dreams create movement. Do first, think about money later. Direction comes before return. Start small, but begin. Even small steps will get you further. Be clear to clients. Include them in your change. Don’t stay where you are if you know where you want to go.

I didn’t turn my life around. I have moved it. In small steps, in which location is no longer the base, but only a part. Each step shows that the world is not getting smaller by distance, but rather bigger, with more possibilities and perspective. Even for doubters and fear mongers like me, there is room to come to remote work. Even in small steps.

Would you like to follow me? Take a look at my website: contenttijger.co.uk or check out my Instagram: @content_tiger or TikTok: @contenttijger