Monday, July 14, 2014

My experience on a working holiday

This past June I went on a working holiday for the first time. I heard about other freelancers doing it and thought I'd give it a try. To give you a little more detail, I went to Europe for about a month, but instead of taking the whole month off I planned on working at least some.

People may have different reasons not to take a regular vacation and disconnect from work completely. In my case, here's why I did it:
1) I had already taken a full week off in February when I went to Mexico (which was fantastic!);
2) The month of May had been particularly slow for me and I needed to keep working to reach my yearly financial goal;
3) I didn't think it would be a problem to alternate work with fun activities; and
4) I didn't want to leave my clients for a long period of time.

I made a plan based on two certain things that were going to happen during my trip: I was going to spend about 3 days in Paris, during which I knew I did not want to work because it was my first time in this wonderful city, and I was going to work as an interpreter at a conference in Palermo for a weekend. For the rest of the time, I wanted to see family and friends, enjoy the breath-taking beaches (see photo below), take on a few good jobs and keep the blog going.

On June 2nd I set an auto-reply on my email and left for Paris and then Palermo. The first week went as planned: I toured Paris and worked at the conference. After that, it was really hard to find a balance between work and holiday. I mean... just look at the color of the water!

Mondello beach

I think my mistake was that I didn't take into consideration some important factors. First of all, I could get sick. I know this sounds silly especially since I hadn't had the flu for years, but guess what? After all that travelling and a weekend of full speed interpreting I came down with the flu! That meant no beach, no fun, no work. In addition, I didn't establish from the beginning how many hours per day/week I wanted to work, as I can't control the exact workload I receive. So, as per Murphy's laws, I would receive work when I already had plans or sit at home with nothing to do. Lastly, for me spending time with people I love (and see once a year) is way more valuable and important than money.

I ended up working a lot less that expected, taking on a few small jobs from regular clients and a 5000 word translation linked to a job I did the previous month. Instead, when I got over the flu, I spent a lot of time laying on the beach, eating great meals and catching up with family and friends.

If you are considering going on a working vacation ask yourself these questions:
- How many hours a day do I want to work?
- What's my financial goal during my time away?
- Is it possible for me to establish a schedule without knowing my workload?
- Will I be able to focus on work/relaxing, without one influencing the other and spoiling the experience?
- Am I willing to cancel my plans last minute if I receive a good job request?

I didn't think about all these questions until after I went away. But even if I did, I think I would have still given priorities to what I value, and that is family, friends and living life. After all, I work to live and don't live to work. Can you blame me?

Calatubo beach


  1. Great post!!! I absolutely loved reading this!
    Thank you for sharing some of your failures in order to equip other people :D

    1. Thank you! I try to be realistic and share what I learn.