How to Become a Digital Nomad – 3 Simple Steps to Prepare

How to become a digital nomad? Prepare! Plan your work then work your plan.


Becoming digital nomads was not a decision Lisa and I took lightly.

Deciding to pursue our passion for full time affordable luxury travel was a process.

But once that decision was made we were determined to take the transition seriously.

We had both been successful corporate strategy and program management executives and consultants.

So we applied those skills and tools to our digital nomad project.

You can too!

Set a Launch Date!

The first thing you have to do is set a launch date. Not a soft time frame – an actual date!

Lisa convinced me to leave corporate America and adopt a full time affordable luxury travel lifestyle during a vacation in southeast Asia.

We gave ourselves about one year to prepare to be digital nomads.

A few months into that year we realized that ‘about one year’ was NOT actually setting a date.

And let’s face it: nothing ever gets accomplished if there is no hard deadline assigned to it!

Meanwhile the lack of clarity was actually causing us stress. We knew we had decided to go, but we weren’t taking any sort of strategic approach to make it happen.

So we set a date: January 20.

Create a Work-Back Plan

Simple Step two is to create a work-back plan to meet that deadline!

With a deadline in place we were forced to put a plan in place to achieve it.

Our plan was aggressive but achievable.

We had to:

  1. Get rid of most of our stuff.
  2. Decide exactly how light we would pack.
  3. Figure out what we would pack.
  4. Decide where to start our new affordable luxury full time lifestyle.

Implement the Plan

Simple Step 3 is to implement that plan.

With a plan in place it was time for implementation!

Here is how we did it.

1. Get Rid of the Stuff

The Condo and Furniture

One year before we made the decision to become digital nomads we had purchased our dream condo in the West End neighborhood of Washington, DC.

It was a posh two-level flat on the sixth and seventh floors of a high rise.

We loved it.

But it had to go. 

The condo went on the market in the Spring.

Lisa had furnished it in a fairly bespoke manner so, after some thought, we decided to include the furniture as part of the sale and it was all sold a few weeks later.

We signed a 5-month lease for a tiny furnished flat just off of Dupont Circle, walked out of our apartment with nothing but a couple suitcases and a few boxes of stuff!

The Cars

We are very much experience people as opposed to ‘things’ people. Obviously.

But we both always felt that driving a nice car is more of an experience than a thing. So we got into the habit of leasing BMW sedans. Affordable luxury!

As fate would have it, our 3-year car leases would expire in the Spring and the Fall leaving each of us car-less for part of the year. Lisa’s lease expired first, but she was easily able to become a subway commuter. 

My lease expired just around the time we moved in August, and I wasn’t able to take public transit to work.

So after some research and math I determined that my best bet was to subscribe to Zipcar for Commuter.  For $199/month plus 45 cents per mile I got a car from 5am Monday to 7pm Friday and that price included the car, parking, gas and insurance. And when it was time to go I simply ended the subscription!


We also spent a couple months scanning old photos and important papers and made hard decisions about knickknacks and other accumulated ‘stuff.’

I gave away a lot of stuff to co-workers. The rest to Goodwill, a local women’s shelter and various other charities. 

In the end we had three plastic bins of stuff we couldn’t bear to part with but couldn’t take with us: a couple of Lisa’s beloved purses, some high school and college yearbooks and diplomas. Those 3 bins now live in Lisa’s parents’ basement.

In the end, we shed so much. At first it was hard. Maybe we are weird, but ultimately it was cathartic.

It’s like Ryan Bingham said in the movie Up in the Air:

2. How Light to Pack

Speaking of what fits in your backpack…

Matt’s Osprey: a backpack with wheels!

Moving from our condo to a tiny furnished flat – going from 2 walk-in closets to one small closet – naturally forced us to downsize our wardrobes. 

Losing 30 pounds by adopting a keto diet also moved us from our ‘fat clothes’ back to our ‘skinny clothes.’

So all the ‘fat clothes’ went to Goodwill.

In the end our plan was to become digital nomads with just one Osprey Ozone 22 inch convertible wheeled backpack each.

That way we could carry on our luggage on just about any airline in the world.

Having traveled all over the world full time using it, we now think that the Osprey is the best long term travel bag on the market.

What to Pack for an Affordable Luxury Digital Nomad Lifestyle

So even though we had already downsized our wardrobes considerably, we still had a lot of paring down to do.

What actually fit in our bags was far less than we had imagined.

Ultimately we took our wardrobes down to about 30 to 35 pieces each….and that includes socks and underwear!

Here is our Long Term Travel Packing List.

4. Where to Start our Affordable Luxury Digital Nomad Lifestyle

The final tactic in our strategic plan was to figure out where to launch our new lifestyle of full time travel.

In August the fates spoke: a $585 business class fare from LA to many Asian cities on Hong Kong Airlines appeared on our radar.

We snapped up two tickets from LA to Bangkok, figuring we could pretty easily and inexpensively get anywhere in southeast Asia from there.

We were worried that these ‘mistake fare’ tickets would be rejected by the airline (they had left a zero off the fare it was supposed to be $5850, not $585), but a day later the airline agreed to honor them!

We took that flight…and we loved it!

Bottom Line – How to Become a Digital Nomad Preparation

Making the decision to become a digital nomad or full time traveler is easy.

Preparing for the reality of it is harder.

Unless you want to pay a ton of money for things you aren’t using and for storage storage then it means letting go of dwellings and possessions and clothes and all of the things that you have spent your life collecting.

But it is SO worth it!

The way to make it happen is to treat your digital nomad preparation just like any other major project: set a date for launch, make a plan so you can hit that date then implement your plan!

So what are you waiting for!?

SET A DATE TO LAUNCH and get started on the 3 simple steps to prepare for full time travel!

And be sure to check out our 5 Tips For How You Can Become a Full Time Affordable Luxury Traveler Too!

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