Starting our Digital Nomad Lifestyle: The Adventure Begins!

After a year of planning, launch day finally arrived. We had quit our jobs and said tearful goodbyes. Our teeny tiny little backpacks were packed. After a Goodwill run to donate the last of our meager possessions, our tiny little rental flat was empty of what few belongings we had remaining. It was time to start our digital nomad lifestyle. This is the story of how we decided where and when to go first and how we got there.

Where and When to Begin!? Let the Fates Decide!

Having made the decision to become digital nomads a year earlier, we had decided to keep an eye out for cheap international airline tickets and let the fates of airline pricing algorithms help guide us to our first destination. After all, the whole point of our adopting this lifestyle was to be flexible and go with the flow as opportunities present themselves.


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 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!


A few days later we decided to start our adventure by returning to the place where Lisa talked me into this crazy adventure a year earlier: this island of Koh Samui, Thailand for some R&R on lovely Chaweng Beach from the hectic launch. Destination sorted!


The launch date was set by another act of fate: the random day that our dear friend Martin was born. Many of our travel friends have a tradition of doing a Napa wine tasting weekend for Martin’s birthday over the Martin Luther King Day long weekend in mid-January (Martin! Martin! Martin!).

Martin and his wife Ashley had a baby girl this fall, so the wine tasting was moved to their hometown in Southern California. Guess what else is in SoCal!? Yep: LAX airport, where our cheap flight to Bangkok would originate!!! The fates were smiling. We bought those cheap tickets to depart LAX January 22!


So we had a fantastic long weekend with friends in SoCal:

Happy Birthday, Martin!

Then jumped on the 15-hour Hong Kong Airlines flight to Hong Kong. And I have to say: Hong Kong Airlines was terrific! Every other row has 2 seats right next to each other. Lisa and I could literally cuddle when the seats were laid flat! Not sure how I’d feel about having a stranger for a seatmate in that configuration, but it worked out great for us!

hong kong airlines business class seats
Hong Kong Airlines has Awesome ‘Cuddle Seats’ in Business Class

For AvGeeks like me, here is our literal launch seen from both external cameras on the Hong Kong Air A350!

We spent the long flight eating, drinking, watching movies and sleeping. Then we spent a 5-hour layover at HKG airport catching up on emails, working on the business, posting to this blog and trying to stay away, then took the much shorter 3-hour flight to Bangkok.

We overnighted at the Bangkok Airport Novotel hotel which has a great ’24 hour’ policy. Because flights arrive and depart BKK at all sorts of crazy hours, a hotel reservation there lasts 24 hours from when you check in. In our case, we checked in around 2:30am, which meant we didn’t have to worry about normal 11am check-out times.

Based on that policy, we had decided to sleep in the next day and had booked an afternoon flight on Bangkok Airlines from Bangkok to Koh Samui. We had a 3:30pm flight so we were able to check out and walk over to to the airport around 2pm.

An hour later we had finally arrived ready to unwind, relax and start our lives as digital nomads!


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