Confessions of a Digital Nomad, Part 1

Category: Uncategorized

“So where is your home base going to be?”

As I sorted, packed, donated, and gifted away nearly all the material trappings of my life in the summer of 2019, I kept getting this question again and again from people. Somehow, the fact that I was going to be voluntarily homeless, wandering the globe with no permanent address just wasn’t something they could wrap their minds around.

But then again, I’ve never been someone that’s run with the pack.

Becoming a digital nomad has been rattling around in my brain for a long time. Ever since I got my first taste of international travel and lived overseas in Saudi Arabia. Up until now, I was rooted in place, raising my kids and building businesses and community in Hawaii. I’d never trade in these years, the friendships I’ve made and the experiences I’ve had living on the Big Island. They are precious to me.

But then, suddenly, I looked up and my kids were grown, living lives of their own. I had my own coaching business with Asentiv, which I realized I could do from anywhere with an internet connection and a laptop. I looked around at the big three-bedroom home with the ocean view I’d been living in for the last nine years, the beautiful art from around the world I’d collected, my kitchen full of gadgets for hosting parties and cook-outs, and I realized that all this space and all this stuff didn’t make sense for me anymore. It was now, or never to finally let go and become a digital nomad.

Then came the hard part. Getting rid of all my sh#$!

For those of you who know me, you know I’m a methodical organizer. You also know how much I Iove my paper calendars. I had nine years of old paper calendars in my house! Nine years of meetings, notes, and to-do lists. This is just one example of what I had to let go of. Let’s just say, I’m all electronic now.

I realized I would need a system to prevent me from getting emotionally hijacked when it came to all my stuff. I also realized that I wasn’t a monk and that I was not going to rid myself of all my possessions. There were some things I wanted to keep and save for my kids. I found it helpful to ask myself one simple question as I started to go through my things: “Is this something I want my kids to inherit?”

With this question in mind, I made three piles as I went through each room in my house. Items to keep, items to gift or sell, and an uncertain pile which I would revisit. I did not spend time on each item, I simply picked it up and whatever came to mind is the pile it went into. Emotionally I could not afford to get into the memories that the item triggered. I recognized that the memory was NOT the item, that the memory lived within me. Just because I got rid of something doesn’t mean the memory went with it.  This realization prevented me from going too deep into the emotional side when I needed to be methodical and decisive.

I went through this process in less than three months. I started in May 2019 and had two garage sales that month where I got rid of a ton of non-essentials, 50% of my wardrobe and accessories, and many larger household items. I secured buyers for major things like the couch, the TV, and beds, who would wait to pick them up until right before I moved out at the end of July. I made the garage sales fun by inviting friends to participate and sell things they wanted to get rid of alongside me. The night before the first garage sale, I had a special preview for close friends – who were stoked to make off with a bunch of my jewelry, clothes, and other accessories. It felt easier selling and getting rid of things I loved when it was going to people I cared about. I was even able to let some treasured pieces be loved by strangers.

One thing I worried about was my car. I didn’t know what to do with it. I didn’t want to deal with the expense of shipping it to the mainland to my kids (or two of the three being pissed they didn’t get it), or the hassle of storing it on the island, as some friends offered. In perfect timing, my friend’s nephew was looking to buy a car and could wait to take ownership until I left the island. The remaining things I wanted to save for my kids and a few items for myself that I couldn’t travel with were boxed up and put in storage. I rented a storage unit on the mainland near where one of my kids lives with her family.

The entire process was intense, but extremely cleansing. It felt good to let go of all that stuff and to realize that I carry the memories inside me that are attached to all those things. Just like that, I was down to a few boxes for storage and two large suitcases and a carry-on.

Since leaving the Big Island in August 2019, I’ve been to the mainland, Europe, Vietnam, India, and now I am in Thailand for a month (I was in four countries within 8 days). The first trip to the mainland was to see my kids and grandkids, get the storage unit situated, and tie up some loose ends. The universe threw me a major curveball two days after landing in Las Vegas when I got into a car accident. A van hit me, pushing us into a spin and sending my family’s vehicle across traffic and up onto the curb. Luckily, no one was seriously hurt, but it was a jarring experience and was definitely unexpected.

Then, I was on to Switzerland for a month for our Asentiv Global Team meeting and to help train new franchise owners from around the globe. It was a whirlwind several weeks, pulling 12 + hour days working on Asentiv stuff and then meeting virtually with my private clients on top of that. Did I mention I was also in the midst of negotiating the sale of my other business back in Hawaii?

During this time I learned that it can be a challenge working by remote when you don’t have your own home or office and need to rely on a coffee shop. One thing became immediately clear: not all coffee shops are created equal for zoom coaching calls! I had to scout out locations and pay attention to things like privacy and background noise. In certain countries, like Thailand, I was able to find a great AirBnb with wifi to work from. Scheduling work calls as I hopped time zones was a whole different animal. I’ve had to get creative with my calendar and pay close attention, especially with set call times.

For the next month, I’ll be in Thailand where I can take a deep breath and relax after a hectic couple of months, of course between 4 am work calls…Phew! I’ll be continuing to blog about my experience as a digital nomad and entrepreneur and post photos and videos to my Instagram account @lynnh808 and @asentivhawaii. I invite you to follow along. I’m hopeful that by sharing my experiences, maybe someone out there will be motivated to take the leap and go for it – whether that’s becoming a digital nomad, or realizing another big fish sized dream.


Until next time, I’ll leave you with this poem “Fear” by Khalil Gibran that I love. It reminds me very much of what it feels like starting this new chapter in my life and business.

It is said that before entering the sea

a river trembles with fear.

She looks back at the path she has traveled,

from the peaks of the mountains,

the long winding road crossing forests and villages.

And in front of her,

she sees an ocean so vast,

that to enter

there seems nothing more than to disappear forever.

But there is no other way.

The river can not go back.

Nobody can go back.

To go back is impossible in existence.

The river needs to take the risk

of entering the ocean

because only then will fear disappear,

because that’s where the river will know

it’s not about disappearing into the ocean,

but of becoming the ocean.


About Lynn

People and possibilities. These are the two words that motivate Lynn Howard, owner of Asentiv Hawaii. She lives by the motto “No excuses, only solutions.” As a business coach, her passion is to inspire others to achieve their own success by believing in themselves and

taking action to overcome adversity. She is blessed with a delightfully snarky sense of humor, which provides comic relief when doing difficult ECC work with clients. An adventurous spirit, she loves to travel and has visited Indonesia, Bahrain, Thailand, Peru, and Columbia. She is based in Kailua-Kona, Hawaii.