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2 years working as a freelancer – Lessons learned

I cannot believe how time is flying. The beginning of August marked two years of freelancing for me. It still feels like yesterday that I had my last day at work. That I said goodbye to my colleagues and started to work on my own terms.

On the other hand, it feels like ages ago. In the last two years, I learned so much not only for my professional life but for my personal life as well and I am happy I made that step.

I not quite live the life I have imagined before as I am still mainly staying in one place but I am happy with the way I’m living my life. I have a base here in Mexico and can leave to travel and explore whenever I want and still work and earn a living on the way. I wouldn’t want to change that!

“You may not always end up where you thought you were going, but you will always end up where you are meant to be.”

As two years are over I thought a bit about the things I learned that might be interesting for people who want to do the same thing – travel the world and work as a freelancer along the way.

Start small

As a freelancer you obviously won’t start with the same salary you made as an employee. Finding clients is something you have to do very regularly and it takes time. You have to get yourself a reputation. You have to get experience and a portfolio you can show to potential future clients.

working as a freelancer - lessons learned

Make your dream come true

So if you have the chance, start as a part time freelancer, finding your first few regular clients before you jump completely out of 9-5 life.

How I started freelancing

I didn’t do it this way. My work contract said that I have to inform my employer about other jobs I do apart from this one. I did some English tutoring as I thought about maybe teaching English but that was it. I started with no clients.

I started differently. I started with a work exchange on the Galapagos Islands. I worked five hours for five days a week and got my accommodation paid as an exchange. I had saved quite some money and lived very cheap during those first three months and started out.

I worked at the tour operator in the morning and on my freelance jobs in the evenings. Nonetheless, I didn’t make a ton of money but I also didn’t need it. I liked the way it was.


About one year ago, I found a job for a travel service which now makes the majority of my income and I got to earning more than in my 9-5 job. The way I went is not a common way but it worked out for me. Whichever way you take whether you start part time or full time, be prepared and have some savings as a back up.

working as a freelancer - lessons learned

Last month – working with a view of Cusco

Travel slowly

You cannot travel as a normal backpacker would do when you are working as well. You will be tired all the time. You probably won’t work as successfully as you could and it’s hard to stay motivated when you’re exhausted.

Most people who work as they travel, stay at least a month in one place, have their routine and explore the place on their days off and in the afternoons/mornings. This way you not only get done work better, you also get to know the country better. You will make local friends, find the places fast travelers don’t find and truly immerse in the culture of a country.

Stay in private rooms/Airbnbs

As you travel more slowly, staying in apartments/rooms where you pay a monthly rent is a better idea than staying in hostels/hotels all the time.

It is better for your money and also helps you with working hours. I know you probably start as a freelancer to be freer and work whenever you want. But it is a fact that having a routine is better for your productivity. Having your own private place is a necessity.

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Working while staying in dorms

In the end of 2014 and again in the beginning of 2015 I traveled in Ecuador and then Mexico, Belize and Guatemala. I stayed in dorm rooms as I wasn’t making enough money to afford a private room every single night.

But the thing is, you also won’t be as productive as you would be in a private room. It is impossible to work in a dorm room, so if you are at the starting point and have to live on the cheap, find quiet places in the common areas of the hostel, co-working spaces or cafes to get your work done. But often getting a room for a month is even cheaper than staying in a dorm.

Plan ahead

If you start out as a freelancer, I recommend you to take time at the end or the beginning of the week to plan your week. Make a plan what you want to get done during the week.

Then each evening think of what you want to do the next day. Always start with the biggest task first. Most people are more productive during the morning hours and it will help you to grow motivation ticking this big thing off your list.

I’m definitely that kind of person who needs lists. When I do not have a to do list for the day I end up lingering around doing nothing. Ticking off things from my list instead makes me incredibly motivated and productive and I want to tick everything off. So I stop being on Facebook.

Use productivity tools

This goes with the point before. Use tools to increase your productivity. There are hundreds if not thousands of tools out there to help you. The following tools are the ones I use to make the most of my day and get work done:


In Trello you can create different boards for different projects. For each project you can then create different lists and shift tasks from one list to the other.

For example you can create the lists to do, currently doing, done, on hold for one project. It is a very versatile tool, I use it for example for my blog content plan as well. As soon as I have a post idea, the idea is written down in the first list, followed by content research, keyword research, headline, content writing, published, promotion and done. You can add deadlines to each card.




With Wunderlist, you can also create different lists. Add all your to dos to one certain topic to the list and tick it off as you would do on a piece of paper.

You can make each task reappear on a certain day. This way I never forget regular tasks I do not enter in my Trello Board each week. I reserve for example time blocks for further learning, emails (you learn not to answer everything right away as a freelancer), social media work, invoicing etc.


In Toggl you can track your time. You add projects like Blog Writing, Social Media, Freelance Acquisition etc and track your working hours.

This way you find out how much time you need for which work which helps a lot when planning later.


RescueTime is similar to Toggl but works automatically. The app tracks which programs you use and which websites you visit.

You can then review the hours worked as well as your productivity score based on your tracked time.


The internet distracts a lot. Your notebook gives you notification when you get an email, when you get a message on Facebook. You stop working and check what is new instead.

If you want to work productively, you should turn off those notifications. You do not have to do this for each website/program individually. Install SelfControl on your notebook and add certain sites to your blacklist. Then choose how much time these sites should not work for you and start working without distractions.

Pomodoro Clock

You think working longer will bring more results? Wrong. It is proven that making regular breaks will make you work faster and with better results.

A proven tactic is to work with the so called Pomodoro Clock. You work for 25 minutes on ONE task (don’t multi task) and then make a five minute break. Continue with four of those 25 minutes and make a 20 minute break.

Give yourself just one task to do during those time blocks and you will notice how focused you are.

Pomodoro Clock

Pomodoro Clock

Try to find regular clients

Customer acquisition takes a lot of time and is not the most fun of freelancing. Apart from that you do not want to depend on new clients all the time as this means you risk a very irregular salary.

Try to find regular clients instead. I don’t say you should only work with regular clients and don’t do any customer acquisition at all. Try to find a balance, even though you know you are going to make enough money this month, do not stop to look for clients.

Find a niche

If you do translations do not apply to all translations out there. If you are a writer, don’t apply to all writing gigs. Don’t apply to all programming jobs. You get me.

You might think the more applications you write, the better. But that’s wrong. Find a niche within your field in which you are experienced when possible, passionate about and become an expert.

With more experience in one niche, you are considered an expert, get picked as the freelancer to go to easier and get paid better.

Keep learning

Don’t stop learning. I bet your industry is changing all the time. Even though it’s not, there is still a lot out there you can and should learn.

Improve your application skills, learn html skills when you work as a writer or a translator. Train yourself further and further to become better and better.

I take several hours a week to learn. I read books, I read other blogs and I take online courses.

I recommend you to do the same. It’s different than school, you can choose for yourself what you want to learn and it will make you so proud when you apply a new skill successfully.

This way you can also find new jobs because a degree is not necessary as a freelancer. You need to convince your client that you are the right fit. Show your achievements, your portfolio and always be yourself.

working as a freelancer - lessons learned01

On my first day as a freelancer

Write unique applications

I know it sounds tempting to apply to 100 jobs with the same application letter. Writing unique applications takes a lot of time. But your client will notice batch applications.

Read job offers carefully and try to respond to certain parts of the offer. This way you show that you read the offer, that you show true interest and you stand out of the masses.

This is especially important when starting out as a freelancer as you cannot prove a certain level of experience fellow freelancers have.

Job Boards

Most people turn to job boards first to find freelance gigs. Competition is big. Pay is bad most of the times. Nonetheless, I find them the perfect way to start as a freelancer when you don’t have any contacts in your social environment to work with.

As mentioned above, write individual applications, stand out and show your expertise. Sometimes there are very good offers among them. You find one time assignments as well as regular clients here.

If you found your niche yet, you should also research for job boards especially made for it. There are job boards for programers, designers, translators and writers. On these job boards, the probability of finding a good client is higher than on mass job boards like Upwork.

Use motivated days to the fullest

You will notice that there will be days you burst with motivation and days you seem to not getting anything done at all. This is totally normal.

When I feel motivated I try to get as much done as possible. Even though I maybe completed my to do list of the day and could stop working, I keep going and start with something I would have done the next day.

As I do not know how it is going the next day, I use my energy and motivation to the fullest. Every day is different as a freelancer and you always have to motivate yourself to do something. There is no one who tells you that you have to do it, so make the best of motivated days.

working as a freelancer - lessons learned

Working on Caye Caulker (Belize), Merida (Mexico), Cancun (Mexico) & Esterillos Este (Costa Rica)

Decline when it doesn’t fit

I’ve done some jobs that actually do not fit to my expertise and interest. I guess a lot of freelancers have been there. I did translations for an online jewelry store. In this case pay was good, so I did it anyway but honestly I do not really have a clue about jewelry and it was not a job that was done easily.

If you feel that the assignment doesn’t fit either it’s in terms of its niche or in terms of payment, consider declining it.

Try not to compete with workers from India or the Philippines, you cannot cope with that. You cannot work for the same payment they do. That is why niching down and becoming an expert is that important.

Take time off

I find it hard to forget about work. I think about new ideas and things I have and want to do all the time. While eating, while trying to sleep, while sitting in a bus and so on.

When you work as a freelancer you are 100% responsible for yourself and it is difficult to turn that switch off. But it is important to take time off.

Try to learn to not think of open deadlines and undone tasks on your to do list when you take a day off or finished your day. This way you won’t burn out, your creativity is bigger and you can start again with clear mind and strong focus.


I told you, you should become an expert in a certain field. No matter how much expertise you have, there will be days you think you cannot do it. That you are not good enough, not fast enough, whatever.

Find help for those days. Tell yourself or find someone who tells you that you can do it.

If you need an ego boost from once in a while, create a document where you add all the positive feedback you got in the past. It can be work but you can also add personal feedback to it if you want to. Then, when you have a low confidence day, get back to that document and read what you have done in the past. What you already have achieved in your (short) freelance career. If you were able to achieve that, you can probably achieve the task ahead of you too.

Would you consider working as a freelancer to be able to travel? If you are doing it already which lessons have you learned so far?

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2 years working as a freelancer – Lessons learned

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