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6 Months of Freelancing: How It’s Going Now

Posted By in Freelancing and Location Indepedence, Travel Musings | 27 comments

6 Months of Freelancing: How It’s Going Now

A few days ago, Brent and I handed over the keys to our apartment in Chiang Mai and said farewell to Asia permanently after more than 2.5 years.  That means it has been almost 5 months since I wrote this post filling you in on our first month as full-time freelancers. I think it’s about time for another update, wouldn’t you say?

I’m Still Here

freelancer girl working on laptop

Before I started freelance writing full-time, I read the warnings of others bloggers and online entrepreneurs advising would-be digital nomads that this lifestyle isn’t all typing up romantic travel stories on the beach while throwing back cocktails. I believed them, but part of me still imagined that working online would be far more glamorous than it actually is.

I thought I’d have so much time to travel around Asia over the summer without the limited vacation of a full-time job weighing me down. Instead, I’ve been bound to my laptop. When I did travel, I actually felt less free than I once did during vacations. Carefree sightseeing was replaced by dashing around a completely unfamiliar city looking for a Wi-Fi signal and a quiet place to work.

The highs and lows I wrote about when Brent and I first came to Chiang Mai are still very real. Yet, despite all the struggles and successes we’ve experienced over the past few months, we’re still here and we’re still making it work. We earned enough to live, travel, and even save a bit during our time in Chiang Mai. When doubts arise, this overriding fact still trumps them all.

It’s Still Kind of Scary

girl in kuala lumpur malayasia

It gets a little easier every day, but I still haven’t become completely comfortable with the unpredictability of my freelance income.

The inherent uncertainty of this career feels acceptable when I have more than enough work, but when I find myself without a major project, the paranoid parts of my brain start convincing the sane parts that I’ll never get hired for anything ever again. That’s about when I start accepting low-paying jobs just to tame the anxiety. It’s a habit that’s putting me on the road to burn-out, and one that I’m trying to break.

In order to make this lifestyle work over the long-term, I know I need to learn how to gratefully accept the breaks when they come, and then work like crazy when the projects roll in again.

Freelancing and Blogging

The trips I haven't written about...yet

The trips I haven’t written about…yet

If there’s one thing that has universally sucked about freelancing, it’s the effect that it has had on this blog. Those of you who are regular readers may have noticed that my posting schedule has dropped from twice a week, to something more like twice a month.

It feels like every time I sit down to write a post, I get offered a new project that takes precedence over this blog. Freelance projects equal an income which the blog, sadly, does not. I’ve thought about re-focusing on monetizing the blog a little more, but that requires a major investment of time with little hope of immediate financial return in the beginning – it’s not something I feel confident or financially stable enough to commit to right now.

Beyond that, freelance writing keeps me in front of my laptop at least 8 hours a day. I find myself reluctant to try to squeeze blogging in there too, adding even more screen time to my life (because, you know, fresh air and birds and life-outside-of-cafés and all that other good stuff). I’ve also never been one to slap half-baked posts online just for the sake of churning out regular content.  I only want to post when I have time to sit down and really think about what I want to say.

I still haven’t figured out a solution to this issue. I do know that I want to keep blogging and that’s not going change. I’ll continue to bring you the best content that I can, as often as I can, while I work towards finding a balance between writing for pay and writing for fun.

Where to Next?

Me in Barcelona - almost 3 years ago now!

Me in Barcelona – almost 3 years ago now!

Returning to what I mentioned at the beginning of this post – yes, Brent and I are no longer in Asia. And we have no plans to return anytime soon. So where are we now?

If you follow me on Facebook you already know that we’re in….Stockholm! We’ll be spending a few days here before continuing on to Spain, where we’ll be doing our first-ever house sit in Los Barrios, a town found about 30 minutes away from the border with Gibraltar.

Brent and I spent 8 months in Europe when we first left Canada in 2011. It was basically my first time traveling and looking back now, I had absolutely no idea what I was doing! I’m pumped about having the chance to re-visit some places with a new perspective, plus check a few more off the bucket list.

Our house sit will last for about 6 weeks, and then, for the first time in a very long time, our plans afterwards are still completely open.  


…….Any suggestions?



  1. rebecca September 26, 2014

    Keep up the good work! Glad to hear the freelance is going reasonably well. Stockholm would be amazing!
    My recent post Lazienki Park in Photos

    • waysofwanderers September 28, 2014

      Definitely! I actually kind of miss teaching sometimes – it was nice to have an excuse to move around, plus there are more than a few students that I'd love to see again 🙂

  2. loveandroad September 26, 2014

    Hi Jessica,
    I was reading your article and looking to my wife freaking out to finish our next post…
    We are blogging from only 3 months and realized that we are working more than our 9-5 jobs. The good thing is the mobility 🙂 now we are writing from Istanbul…
    Keep up the good work and enjoy southern Spain. We did a 2 weeks pet sitting gig in La Linea de La Concepcion and LOVED the area!
    Safe travels!!!!

    My recent post Morocco: dream trip and cultural shock

    • waysofwanderers September 28, 2014

      Good to know! We accepted the house sit pretty spontaneously, so I'm not sure what to expect. And agreed, the mobility really makes the longer working hours worth it.

  3. cubiclethrowdown September 26, 2014

    That's great that the freelancing work has been going so well! But yeah, still being at a computer 8 hours a day, not exactly mai tais on the beach is it! Housesitting is a great gig for freelancers…have you guys considered just looking for another housesit somewhere else after this one?
    My recent post Time to Go Again: Canada Highlights

    • waysofwanderers September 28, 2014

      That's definitely on our list of potential plans. I get email updates with new listings from like 4 different house sitting websites every day, so we'll see what comes along over the next few weeks.

  4. Alana - Paper Planes September 26, 2014

    I'll be heading back to some European cities for the first time in years as well and looking forward to revisiting them. Like you, when I was there before, it was my first time really traveling and I know I missed out on so much! Enjoy!
    My recent post Book It: 3 Beach Reads

    • waysofwanderers September 29, 2014

      Yes! And I'm sure since you spent such as long time in Asia too, you'd agree that it's exciting just to be in a completely different part of the world.

  5. Naomi September 26, 2014

    I've just started freelancing (although balancing it with my full time job) and it is crazy how little time there is! I get the whole thing about being glued to your laptop though, I feel so antisocial at times but then I feel the guilt too. Such a catch 22. But there is of course huge benefits too, feeling like a cool, grown-ass business woman is pretty damn cool – although I doubt an actual business woman would refer to themselves as that haha!
    My recent post The many benefits of learning a foreign language

  6. Charlie September 27, 2014

    Looking forward to reading about your first house sit! After 2 months of freelancing, I was super lucky to find a job at a company who want 4 hours writing 5 days a week all the time. It's really made travelling and house sitting awesome as my work is always done by midday. I was thinking about what an effort it would be to have to juggle and search for more freelance work all the time and not have that kind of simple time schedule. Very admirable that you're making to work – and good luck!

    • waysofwanderers September 28, 2014

      That's great! I've had some steady clients over the last few months, so fortunately I haven't had to look for new projects either (*fingers crossed*). Although, it'd be fantastic to be locked in to something even more regular and consistent.

  7. francaangloitalian September 28, 2014

    Thanks Jessica for your honesty! People often think that blogging and online work is all good and gives you tons of free time to do what you want, it's not always the case as you said, but it does make you location independent which gives you so much flexibility. If you want my advice take it as it comes, regarding what to do after your housesitting, go with the flow, by the end of it you might have another housesitting assignment lined up somewhere else, who knows? Sometimes not having plans is the best plan 😉
    My recent post A Beginners Guide to Enjoying Animals on Holiday – Without Harming Them

    • waysofwanderers September 29, 2014

      Definitely! Although it makes us a little nervous, we've never really had no plans before and it feels foo to just go with the flow and have the freedom to say "yes" to any opportunities that arise.

  8. Joella J September 28, 2014

    Great update Jess- glad to hear how you've been getting on. House sitting in Stockholm sounds great too. Oh and I can completely understand not wanting to log after 8 hours of working online already. Enjoy the feeling of having no plans after your house sitting- I love those time when you feel free and you can choose to go anywhere!

  9. midlifewanderlust1965 September 29, 2014

    Well done on reaching 6 months freelancing. Due to circumstances I am looking at freelancing and blogging full time. Reading about yourself Jess helps to inspire me.
    My recent post Sun is Shining – Day 2, 14/09

    • waysofwanderers September 29, 2014

      Thanks so much! I hope it goes well for you – it can certainly be challenging but its equally rewarding.

    • waysofwanderers October 6, 2014

      Yes! Tangier is like an hour away by boat, so that's definitely happening!

  10. christina October 6, 2014

    thanks for shining a realistic perspective on 6 months in on the freelance/blogosphere! just beginning my journey and I appreciate the candid light on what to expect. hope you get to enjoy some more of your own time in Stockholm — and KUDOS to you for sticking to it!

    ~christina http://www.currentlyexploring.com
    My recent post Travel Resources

    • waysofwanderers October 7, 2014

      I ended up with a little work lull in Stockholm which worked out well!

  11. @Nomaderhowfar October 9, 2014

    Hi jess! Just came across you on twitter and headed over 🙂
    Freelancing is something i think we will one day look into – i come from a media background and we both love the blogging field, turning into an almost part-time job alongside work as we prep for long-term travel in australia!

    What sort of work do you do with your freelancing?


    • waysofwanderers October 9, 2014

      Awesome! It's mostly writing, and mainly travel-related, but I take whatever comes along. I'm also trying to move into more social media management and editing because, honestly, writing 24/7 is a little draining and I'd like to mix it up a bit.

  12. Jenni October 19, 2014

    Hi Jessica,

    We were just thinking about you guys and we're wondering if you were still in Japan. I guess now we know the answer is no!
    We stayed with you guys in Takayama a couple of summers ago. How time flies!
    Have fun in Spain and let us know if you want to have a short break in Rome, we're still here and have staked out all the best pizzerias and gelaterias.

    Jenni & John

    • waysofwanderers October 19, 2014

      So good to hear from you guys! We're actually thinking about spending a few months in Italy after Christmas, so we'll definitely hit you up for advice if we end up there. It would be awesome to see you both again :).

  13. Giedre October 25, 2014

    Come to Munich!! It will be amazing here once the Christmas markets start at the end of November — last year I went to about 25 different ones in the city metro area alone, so you would have plenty of new experiences to write about. Let me know if you're ever in the area and I can show you around. I love your blog!! <3 🙂

  14. Apartments Barcelona April 26, 2016

    Excellent article and we are glad you enjoyed Barcelona, one of the most amazing cities in the world

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