The Road to Californication, Part 1

The Backstory

I took a week long trip to the Azores in August 2015 with the Wifey. Not only was it my first time really traveling, it was my first time out of the country! We loved the sights, culture, and people so much that we decided to look into moving there.

Working remotely from Portugal as a Software Developer was possible, and the salary was more than enough for both of us to live on pretty comfortably. So, we filled out forms to request an official background check by the FBI, a prerequisite to getting a six month visa for Portugal.

I worked hard to find a remote job and finally landed one a month later this past October. Not only was it remote, but the technology stack involved things that I was learning by myself for fun. Win win!

After a few months of sleepless nights and uncertainty, the progress of the tiny startup of a company I work for (six developers, including CTO and CINO) exploded.

We merged with an existing company in December which allowed developers of both companies to physically meet and work together for the first time. Since we had all only interacted with each other online, it was both great and very cool to spend a week hacking and living with people from all over the world (Poland, Boston, Delaware, London, Hong Kong, Los Angeles).

The progress we made that week was nothing short of amazing, and while we usually do a bang up job remotely, no one could deny the effectiveness of physically being together. To promote this, my employer decided to bring me closer to where where most of the team resides. Hence this roadtrip!

As for the Azores? Both Tiff and myself decided that we would go with whichever option could be completed first. A week and a half after deciding on California as an option, I accepted a one year lease for the apartment at around 10AM. ON THAT SAME DAY when checking the mailbox a few hours later, I saw that I received the necessary papers from the FBI...

The Trip

The Grand plan is a 55 hour, 10 day trip (05/23/2016 arrival), to our new home in Hollywood, California. We're making stops to some very notable places in the US where an AirBnB has been reserved at each place:

  • Asheville, North Carolina
  • New Orleans, Louisiana
  • San Antonio, Texas
  • White Sands, New Mexico
  • Joshua Tree National Park, California.

The only exception on lodging is Joshua Tree where we'll be camping out in a tent. Two days are alloted for each place: one to drive and another to explore. I'm still working on both days.

The plan was to leave Boston, 03/14/2016 @ 1AM. Unfortunately for Tiff I take forever to pack - we ended up leaving at 4AM instead. 3 hours of sleep, 14 Hours of driving, 7 states, 920 miles and one speeding ticket later, we arrived at our AirBnB in Asheville, North Carolina.

It was great that gas was cheap ($1.90/gallon), we spent about $100.


I've seriously come to think about Asheville as the Eastern Hipster Capital of the US (as opposed to Portland, Oregon being the overall). It has the feel of Watertown, MA with the historical beauty of Boston. It's way less cluttered and much cleaner. Small, interesting mom and pop shops outnumber franchises/chains by a large margin.

Man buns, beards, and bars were everywhere. It's awesome. We even got to buy food from a co-op store! I would also go so far to say that about a third of the people there have dogs. Bringing Hadouken places was great for us because of the leniency + great for him because everyone just had to brighten his day by saying hi.

There are also a myriad of places where many forms of art can be enjoyed. It seemed like Museums, galleries, and theatres were on every block.

To name a few things that I like about Asheville which I plan to come back and experience more of:

  • bars, bars, bars, and more bars
  • foooooood
  • hot springs
  • hiking trails
  • historical awesomeness
  • art

The Next Trip

After a few hours of sleep, we're going to leave Asheville and start a 10 hour drive to New Orleans, Louisiana. More great food and sights to see!

Pictures of this trip will be added later on tonight.

Other Thoughts

  • Planning on writing about working from home and the equipment that's been of great use.

  • On the way here I saw an extremely large flag pole in Pennsylvania where a Confederate flag was mounted. Wow. I've only seen the flag on the news. To see it in my face was just really unnerving. I couldn't get my mind off of it for a while.

    On another instance when we explored downtown Asheville, some random dude drove past us, proudly showing off the Confederate flag attached to the side.

    Growing up in the melting pot of cultures and people that make up my hometown of Lowell, MA, I'm really naive to this kind of hate.

    Tiffany was wise in pointing out that everyone hates everywhere, that maybe around here people just seem to be more accepting of it. Sure, that may be true, but still. Fuck you, guy. Hope that we won't run into this kind of bullshit for the remainder of our travels... Actually, fuck him and fuck all of the people who think that it's okay. It's not okay.

  • If you buy freeze dried kale chips, you can put it in your mouth and then let your saliva rehydrate it. It's like a salad, but the bowl is in your mouth, and since it's already in your mouth you can just chew. #genius #yourewelcome