On Work and Travel

By: Smith Schwartz |

A few weeks back, I had an email exchange with a friend-of-a-friend who’s considering taking a break from the daily grind and moving to Ecuador for a short period of time. We’ve been having a nice back and forth about work, travel and logistics and I realize that even though we’ve been working and traveling for over a year, I haven’t really talked much about the work side of things publicly, and that’s something I’d like to do more of. She was kind enough to agree to let me publish a portion of our exchange.

Her letter:

I’m not exactly sure how we settled on Ecuador as our destination spot, but somehow we did…and now we are really stoked to go. We are hoping to head there in mid-January. I am nervous about a few things–mostly, leaving my job and all my stuff. (But also, really happy for the adventure and challenge.)

Have you worked while on the road? My boyfriend is a freelancer, so he plans on working along the way. How did you work out stuff like insurance?

Also, I’m not sure how much pre-planning we should do before getting there–like, do you have a place to stay set up and everything? I tend to over-plan while my boyfriend is more apt to wing it. We only plan to be there for 6-8 weeks, but I’d like to spend time enjoying it, not being stressed about where we are staying, etc.

Anyway any advice you have on the basics would be great to hear! Thanks a million in advance!!

Smith at work

My response:

I am so excited for your plans. Taking a risk is always better than sitting home wondering “what if?”

We’re actually back in Chicago now, but leaving soon to visit family for the holidays and then off to Hawaii for Jan-Feb. I’m pretty excited for something a little “easier”.

Perhaps you’ll find that a little break from the working world will help you as you move forward or even make a change in your career. It certainly did for me. I learned things about myself and gained perspective in a way that just isn’t possible when I was working everyday. That said, I’m now back to working full-time, but I’ve made a pretty drastic career change.

I came from the museum world. I had some really fun jobs, but they were low paying and I felt stuck. There aren’t a huge number of opportunities for advancement and you can only live in certain cities. I loved my coworkers and the work I was doing, so leaving was hard, but I was hopeful I could figure out something that was a better fit for the way I wanted to live. After a year of hard work and the ups and downs of starting over (which I’m still going through), I’m now working as a front-end web developer/designer and I really love it.

My husband is a software engineer, so he was able to work out a situation where he kept his full-time employment, (insurance, etc.) as we traveled. This has been huge for us and things really would have been a lot different if this situation hadn’t worked out. We were determined to do it either way, so we saved my salary for about a year and a half prior to leaving to practice living on one salary and to have a cushion just in case!

I definitely land on the side of planning ahead. Living in a new country is fantastic, but it can be hard, too. I always secure a place to stay ahead of time, not only for peace of mind but it’s harder to fine long-term lodging on the spot. I’ve actually just booked out all of our lodging until the end of March next year, so yeah, I’m kind of nutty about it, but it makes living without a home a little easier knowing that you have some spots lined up.

Also, I’m guessing you’ll need a reliable wifi connection for your boyfriend’s work? We’ve had pretty good luck on Airbnb with lodging- I would ask all kinds of questions before booking about wifi and figure out where you can go in case of an outage (coffee shops, libraries, etc). There’s nothing worse than having no wifi and trying to look for wifi! Also, check around to see if there are any co-working spaces near where you’ll be. We’ve found those as a good break to working from home and it’s an easy way to meet locals.

I also wrote a lot about this on Apartment Therapy. Here’s a Pinboard I made of the articles I wrote that are specifically about travel. (Yes, I’m a nerd.) Some of them might be helpful to you as you prepare. Also, I’d highly recommend starting a blog. It’s great for everyone to hear what you’re up to, it handy when trying to meet people on the road and it will help you record and process everything as it’s happening.

Keep in touch and keep me updated!

If anyone else out there is considering a nomadic lifestyle, please be in touch! I’d love to hear from you.