Our overriding goal was simple: live in Mexico for 2 months, and see how well we can keep up our family and professional endeavors. In case you missed my initial mention of the trip, this was not a vacation. In every aspect possible, we wanted a sustainable lifestyle- something we could have kept up indefinitely.

Make Money

Financially, our goal was to come home with more money in our bank account than we had when we left. Grabbing cheap airfare and subletting our apartment got us off to a great start; working for the duration of the trip carried us through successfully.

Be More Productive

Despite potential tropical distractions, I was actually able to focus more on my work than usual. Creating a wide-sweeping auto-responder on my email and leaving my cell phone at home (kind of– more on that later) drastically cut down on less-than-vital communication. No TV. No newspapers.

Authentic Living

As part of the “make money” goal, and due to a desire to have a more culturally “authentic” experience, we kept our accommodations pretty simple. Unfortunately, we took it too far. It’s true that most Mexicans (at least in the towns we visited) don’t have air conditioning, microwave, washer/dryer, and drinkable water. In that sense we lived somewhat authentically, but it wasn’t sustainable for us. The simple fact is that if we moved down there long term, we would have those modern conveniences, and we would bring our car. Dealing with a toddler who has diarrhea and a severe diaper rash when the nearest laundry facility is a 15 minute walk away is not something my wife and I care to go through again.

Time Together

This one was easy: the lack of social commitments and the fact that I worked at home most of the time made it possible for me to spend a ton of time with my wife and daughter, both one-on-one and as a whole family.

Unfortunate Surprises

This was our first experiment in living the vagabond lifestyle, and based on the above points we’d call it a success. However, it wasn’t all roses, particularly for my wife. There were a few hard and unexpected lessons learned:

• Rather than adapting to all the lifestyle differences over time, each stomach bug we caught, meltdown that our daughter had, and giant flying cockroach I had to kill had an accumulative negative effect that sapped our adventurous spirit and left us all a little anxious to get back to home base (I partially blame “Authentic Living” from above). At this point I’m just not sure how well we could pull off doing this for 6 months at a time.
• Raising a busy toddler on the road was just plain hard. We didn’t have our usual support network of friends and family. We only spoke a little Spanish. There were times when my poor wife thought she was going to lose her mind from lack of simple and easily accessible activities that wouldn’t leave her exhausted. Sure, a trip to the beach is blast for everyone, but it takes a lot of work.
• My laptop had a major problem, and trying to solve it in rural Mexico was the pits. Slow and intermittent internet connectivity got really annoying too, although I can’t say that it had much of an effect on my overall work productivity (fortunately).
• Our increased time together as a family had the unintended side effect of further blending our roles and making us more dependent on each other than we usually are. That’s actually a wonderful thing to some extent. I think married couples need to be more interdependent. However, now that we’re back in the States, reinstating our usual routines and roles is going to take some adjusting.

And so the big question is: will we do it again? We both say yes, but our timelines differ. If you’d like, you can help us out by recommending our next destination- just leave it in the comments.

For a full travel travel log with lots of photos, check out the site Chelsey made just for this trip, as well as a few posts on Jed’s personal blog.

One night he crashed at our apartment. In the morning I was surprised at how he struggled to wake up. I just assumed he was some kind of insomniac. I teased him a bit about being lazy, and he shared his life motto with me:

Work hard, play hard, rest hard

We’re now two weeks into our two month Mexican excursion, and I’ve been doing my best to apply that motto. I don’t have any tangible examples or formula- it’s just matter of keeping an overall sense of deliberateness about what you do. It’s related to other GTD and 4HWW principles of avoiding distraction, fighting procrastination, and being focused on your goals, even if that goal is to rest and relax. I’ve kept my same wacky schedule, but somehow I just seem to be getting more out of each day; more productive work, more time with my family, solid rest, and even some hard playing. Perhaps it’s just the change of scenery and being away from home.

Or maybe its the street tacos

1. We found an awesome deal on flights
2. We used Home Exchange and VRBO to get incredible deals on some beautiful rentals. No tourist-packed resorts for us.
3. With the help of our assistant, we found somebody (via Craigslist) that is going to sublet our place while we’re gone.

wow.

Thanks to a comment left on my cheap travel post, I’ve been using Kayak a lot lately. Today I booked an incredible deal on a multi-city itinerary. Check this out: Chicago -> San Francisco -> Guadalajara -> (stay for 3 weeks in Ajijic, then bus to Sayulita) -> Puerto Vallarta -> Salt Lake City -> Chicago. Total price with taxes and fees and paper ticket shipping: $568.89. Unbelievable. After spending 2 or 3 weeks near in Ajijic near Lake Chapala, we’ll take a bus down to San Pancho and Sayulita for another 4 or 5 weeks. After that it’s back to visit family in Utah for the holidays before returning home to Chicago.

I still use Travelocity when first checking for the lowest price on trips that have completely flexible dates. Once you get it narrowed down to +/- 3 days, Kayak is is the way to go!

5 years ago we were fresh out of college, fresh into grad school, and pinching every penny. My time didn’t have the income potential that it does now. Those factors, combined with my incessant optimizing, made booking travel a nightmare. I would spend hours searching every possible combination of times and flights to try and save $20. I once remember asking my brother if he could come pick me up at an airport that was 6 hours away because it was $50 cheaper to fly there. Even when I found a good deal, I couldn’t pull the trigger, thinking “what if something cheaper shows up tomorrow?” If you need ideas on how to go insane, that should provide some inspiration.

Things are different now. I prefer to spend my time doing other things, and I’m working on satisficing for all but the most important aspects of my life. Here are the steps I now take when planning travel for within the U.S and Canada.

Why put something in writing when you can make a flowchart?

There are ways to save another $5 here and there (sites like sidestep and bookingbuddy will scour a billion sites), but based on my experience over the past 5 years, I think this gets close to the “minimum effective load.”

Notes and Resources

• I fly Southwest whenever possible
  • super low fares
  • no fees for canceling a trip (HUGE)!
  • the most baby-friendly airline (in our experience)
• Southwest DING! sends alerts for super-cheap fares to your desktop. I’ve flown Boston to Chicago for less than $50 each way (including taxes and fees)!
• If and when you use Priceline (I recommend them for car rentals only), low-ball them. Last time I ignored the “you’re never going to get this price” screen and did in fact get my price.
• Hotwire for hotels is a bit of a gamble. If where you stay is really important to you, only take high-star ratings, or simply skip Hotwire.
• Set up Travelocity RSS feeds

Finally, if you’ve got a great tip, please share it in the comments.