What I Have Learned in 6 Months as a Digital Nomad

Deuce Thevenow
5 min readAug 17, 2021

When I finally talked my wife into selling almost everything we owned and moving out of our apartment in Los Angeles in the middle of a pandemic, I didn’t really know what the future would hold. What I did know was that being holed up in our apartment for the last year in one of the most expensive cities in the world with all of our nice amenities banned was not enjoyable. So, we packed our bags, bought a one-way ticket to Costa Rica, stopped for a month-long stay at each of our parents’, and haven’t looked back since.

Quepos, Costa Rica
Quepos, Costa Rica

Living as a digital nomad has certainly instilled a new spark in our lives, we have grown a stronger zest for adventure, and I certainly feel like a happier person living out a lifelong dream. Each day is a new opportunity for us. To wander around stumbling into hidden coffee shops, bars, farmers' markets, and exploring different cultures and scenes has been a dream. Nearly every weekend is like going on a mini-vacation. My batteries feel recharged and I feel like I have gained a new perspective on life.

After spending nearly six months as a digital nomad and living on the road I wanted to share what I have learned and hopefully inspire other people to take a chance and do this at least once in their lifetime.

Do not overpack

Plan for enough clothes for seven days and keep it to a minimum. You don’t need four swimsuits, four pairs of shoes, and three winter jackets. My new rule after learning the hard way is to keep it to a (1) medium suitcase minimum.

Try to stay at each location for at least 2–3 weeks

One of the most draining parts of living as a digital nomad can be the constant traveling, feeling like you are always on the run, and not having enough time to truly enjoy the place you are in. We have found that by staying in each location for a minimum of two/preferably three weeks you will avoid burnout.

Planning out the logistics can take much more time and can be stressful at times, especially trying to plan during a pandemic

Planning out your next spot can take some time. There is part of it that is fun and exciting and part of it that can be mentally draining. For us, finding the perfect spot to work and enjoy can be a challenge as not every place, especially in Costa Rica, has fast wifi. We set our limit at 100mbps.

We typically try to have 45–60 days planned in advance and finding the perfect Airbnb/place to stay can actually take a lot of time, especially when you have to message each location to check their wifi speed.

Trying to plan this during a pandemic can be even harder. We had an entire leg of our trip planned to Canada based on an expected border reopening only to find that it got extended by another month and had to come up with a plan B (Park City, UT). Ultimately, our plan B worked out amazing and we now are rebooking our Canadian adventure to Banff as well.

You can negotiate with Airbnbs to get better rates

Prior to being a digital nomad, I had stayed in a lot of Airbnb’s. I much prefer staying in an Airbnb than a hotel and trying to immerse myself into what it feels like to live in each city. I had never really tried to message Airbnb hosts and negotiate prices, now we do it every time especially when staying for an entire month and having really good reviews. I would say probably 60% of the time we are successful in getting some reduction in the rate and average 10–20% price reduction from the listing price.

It doesn’t have to be more expensive

A big barrier to most people becoming nomadic is the fear of increased living expenses. Depending on what your current living situation is I would argue you can do it for the same price or less as long as you choose the right times to be in each location. As I write this we are staying in an Airbnb in Breckenridge, Colorado in August. For the most part, it’s pretty quiet and a lot of restaurants/shops are on the summer hours as it is not the busy season. We are paying $140/night but in the busy season, it is $1000+/night.

The other key tip is to make sure your place has a kitchen, cook at home as much as possible and buy from the local farmer's markets. Visiting the local farmer's markets is both a fun experience and a cost saver. In Costa Rica, we discovered so many delicious local and new foods this way.

One noticeable area that I have spent considerably less on is Amazon and online shopping. I didn’t realize just how bad my addiction to online shopping became during the pandemic until we went to Costa Rica and stopped being able to order Tony’s chocolate bars online on a whim and have them delivered the next day.

The best way to explore a new city is biking, walking, and running

One of my favorite ways to explore a new city is by morning walks, runs, and long bike rides. This is a great way to discover all of the local off-the-beaten-path places.

Dillon Reservoir, Frisco Colorado

If you are working, get a travel office setup

Personally, I can’t stand not having a second monitor when I work, and having an easy traveling office setup has made working from anywhere a breeze.

At the beginning of the trip, I was lugging around a 24” monitor in my suitcase until it broke. Now my entire office setup can fit in my Knackpack backpack (which has been amazing for traveling). We currently are driving and have two small desks and a computer chair with us as well since we have some extra space but not something everyone else might be able to accommodate. Links to my work setup are below.

Mobile Office Set Up

Follow me on my journey

So far our journey has taken us to some amazing locations and I don’t regret any of them. You can follow the adventure along on my Instagram and DM me if you are looking for recommendations in any of these areas.

  • Quepos/Manuel Antonio, Costa Rica
  • La Fortuna, Costa Rica
  • Monteverde, Costa Rica
  • Santa Teresa, Costa Rica
  • Playa Hermosa, Costa Rica
  • Park City, Utah
  • Winter Park, Colorado
  • Breckenridge Colorado

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Deuce Thevenow

I am the Co-Founder of @RECESS. A life-longe entrepreneur, foodie, outdoor adventurer, and curious tinkerer. Husband and proud #hoosier