January 30, 2025, 5:46 am | Read time: 12 minutes
Do you dream of traveling whenever you want and even earning the necessary money along the way? TRAVELBOOK author Anna Wengel (now Chiodo) has been doing just that for years as a traveling author. Here she reveals 11 tips on how to make it work.
For years, I had the dream of working while traveling. I finally realized it and spent a long time on the road as a so-called digital nomad. If this idea appeals to you too, but you don’t know where to start or what’s important, you should read on. Perhaps one or two tips that have emerged from my sometimes awkward attempts, minor and major failures, as well as perceived successes, might help you to realize your dream and earn money while traveling.
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Don’t Let Yourself Get Intimidated
The most important and, therefore, first tip is this: Do you have a dream? Don’t let anyone, including yourself, tell you that your dream is unattainable. We are often our own biggest critics. And sometimes, we make the world and our possibilities in it seem smaller and grayer than they are. Mostly out of fear or shame, we sometimes hear fearful or angry voices in our heads telling us that we could be doing this, this, and that wrong and that we are not good enough anyway and should just leave it alone. Remember, failure is just one perspective among many—and perspectives can be shifted. Your dream is achievable, even if it looks impossible at the moment.
My life dream also didn’t start out logical or follow a straight path—and it still doesn’t to this day. I had and still have fears—and sometimes fell flat on my face. Yes, there can be setbacks. Yes, sometimes things don’t go as smoothly as you’d like them to, or they even don’t work out at all. But that doesn’t mean that your dream is wrong. Take as long as you need to get over a setback. But then, it’s crucial to dust yourself off and rise again. That is important. As well as thinking about what you can learn from the situation. And then move on.
Trust in your dream. It’s easy to say and not necessarily easy to do, I know. But it’s the only way to keep going. And it works because (and if) I and you want it, we commit to it, and just keep going. And if not, I can only advise you to take a closer look at your own fears and the story you are telling yourself in your head. Pushing them away or running away from them doesn’t work. If you want to live your dream and you are blocked by fears, go deep. To confront this, you need to acknowledge and feel the fear. If at all possible, even accept it. You may never get rid of your fears completely, but you will learn to live with them. (Note: If you are unable to get a grip on your fears, therapeutic support may be advisable.)
A Clear Vision
For me, the whole traveling-and-working combo started with a huge longing for Portugal. Each farewell to the country left me heartbroken, dreading the return to my life in Berlin. At some point, the longing was so great that it was clear: I wanted to move there. I wanted to be in Portugal and somehow write and make a living from it. I didn’t have much more of a vision at the time. Over the years and trying out different paths, my vision of life has become clearer, and I have a kind of roadmap. My tip: The clearer the vision, the clearer the steps to realize it.
You can start with these questions, for example:
How often and for how long do you want to travel?
What standard of living do you want while doing so?
How much money do you need each month?
But the most important thing is the feeling. That feeling that makes you want to travel and earn money on the way. On the one hand, it won’t go away (if you don’t follow it, it will probably just annoy you regularly), and on the other hand, it serves as a driving force and a kind of compass in moments when you don’t know what to do next.
Step by Step
Discarding one life to start another on a whim is possible, but it can be incredibly overwhelming. Once you have a vision, i.e., a clear idea of what you want, you can think about a plan. In other words, divide the way there into small steps. This way, you won’t be faced with a huge, insurmountable, and incomprehensible mammoth task, but first one step, then the next, and then the next.
Find Allies
I’ve already said that you shouldn’t let others ruin your dream, but I actually recommend that you don’t tell them your dream in the first place. Or at least until it is solidified. Nobody needs to hear that their deepest desires are unattainable. Talk about your dream and its realization with people who will encourage you, support you by asking helpful critical questions, and who may even think with you about how to make it a reality. If you don’t have such people, you can look for them. Other expats in your desired location, for example, or a coach.
Earning Money While Traveling? Keep an Open Mind When Choosing a Job
Which jobs allow you to work while traveling and earn money abroad? I would say almost all of them. Because most jobs can either be done anywhere or adapted so that they also work elsewhere. At the beginning of my journalistic career, I thought that I would perhaps work as a permanent employee at a print newspaper and travel on my vacation days. Today, I work as a freelance travel journalist, author, and coach and travel as often and as long as I want. That’s not quite what I thought ten years ago—but it suits me better.
However, you can also look at your own work experience, hobbies, and other passions and think about what could be turned into an on-the-road job that you would enjoy. And if you want to travel for a fixed, longer period of time but are happy in your job, the sabbatical model may also be an option.
Set up Broadly
This was a setback for me: I moved to Portugal with what felt like financial security from two clients. One of them disappeared from one day to the next because the magazine was closed down, and I no longer had enough income. Shock, mental horror scenarios, panic, stressed-out actionism, and slow acceptance followed. After a few short months, I had new clients—and I was relieved. I learned three things from this story: 1. Panicking doesn’t help at all; 2. it always goes on, as long as I take care of it; and 3. as a freelance writer, it’s a good idea to have a broad base. More clients, a little more security.
Calculate the Money You Earn While Traveling Well
It’s best to consider the question of money before you go. I strongly recommend accumulating savings. This way, you at least have a temporary buffer in case something happens to the planned sources of income. But it’s also a good idea to have a rough idea of your monthly expenses. Approximately, what will you need for flights, accommodation, and food? Depending on the country, the cost of living may be lower, for example, if you are staying in Southeast Asia. In other countries, such as Australia, New Zealand, or the US, they are usually more expensive on average than in Germany.
But here, too, it depends on your lifestyle. For example, if you are traveling through New Zealand in your own van or house-sit your way around the world, you will tend to need less money than if you are taking a road trip through the US in a rental car and staying in hotels, motels, and the like. But, as mentioned before, it depends on how you want to live. Also consider the expenses that continue at home. If you want to reduce these, it can help to terminate current contracts and sublet the apartment.
Allow for Time
If you want to work while traveling and have deadlines that you have to meet, I recommend always planning a little more time. I learned this in India: I had promised a client that I would write a text by the next day, which required a fair amount of research. Then the power went out in Arambol. For almost 24 hours. I think this is where I got my first gray hair. About three hours before my deadline, the power was back on, and I was not only drenched in sweat, but also deeply stressed. I managed to meet the deadline, but ever since, I’ve set my deadlines well into the future and started working as early as possible when traveling.
Another time factor: Depending on your destination country and job, you may first have to find a place where you not only feel comfortable and can concentrate, but above all have a good internet connection. You should allow for this time, too.
And the third tip comes with possible time differences: Depending on your job, attendance obligations and customer requirements, you may sometimes have to be on the phone with someone in the middle of the night, or be at a meeting online. This can perhaps be better planned, but being willing to work spontaneously and at impossible times is helpful to keep clients happy.
Also interesting: Why EVERYONE should travel alone sometimes
Don’t Forget Your Loved Ones
Being able to travel as often as you like is a dream that some people have. But there are also downsides. In addition to illnesses, unwanted animal guests in bed, or even threatening on-site experiences, I have missed one thing in particular while traveling: My family and friends. This can go on for a while, maybe even months, but at some point I always reached the point where I missed my parents, grandmas, best friends, and my friends’ children, who I felt were growing up far too quickly.
Therefore, think about how long you can do without your loved ones and then fly to them. It can be a short stay or a long one, and then you can leave again immediately. But it helps to savor the travel life you desire without the constant shadow of homesickness. Of course, these extra costs need to be factored in for this to work. And if you miss your loved ones at home too much, this may mean that long-term travel doesn’t work for you, and you need a mix of home and travel. Then the next tip will help:
Keep an Open Mind
If you leave your familiar surroundings and everyday life to live your dream, you will continue to develop and change. The same is most likely true for your dreams. Stay open to these changes. If a dream or a path you have already chosen no longer feels right intuitively, say goodbye to it. Or change it where necessary.
A small example: My dream started with being a war reporter, went on to travel and work as a journalist, with a small detour as a yoga teacher, and is currently a journalist, author, and coach with a permanent home and lots of travel. I can almost certainly say that something will have changed in ten years, at least I hope so.
Enough and Not Too Much Work
I promised myself that I would divide my everyday travel life into work and adventure, because I am mainly on the road to discover a lot. At the same time, I sometimes tend to fill myself to the brim with work and then get completely stressed out. This is usually due to fear. Of things not working out at some point. Fear that a client will think it’s stupid if I’m not always available.
At times, this fear has resulted in grueling days of ten to twelve hours of work. Not only was it exhausting, I also didn’t notice anything about my surroundings as a result. But at some point I realized this and now calculate my work better and in a healthier way for me. Of course, planning is helpful here too. My tip: Think about how many hours you can and want to work with a good feeling, calculate jobs accordingly—and stick to it.
This article is the second part of the series “Working while traveling”. In the first part, our author Anna Wengel (now Chiodo) reports on her own experience as a traveling author (read part one here: Travel Author Explains: ‘This Is How I Earn Money on Vacation’). In the third part, you will learn about a few jobs that are well suited to traveling, and Anna gives tips on how you can turn almost any job into a travel job (read part 3 here: 5 work models that allow you to travel for as long as you want).