Downsizing to Become a Digital Entrepreneur

Empowering aspiring globetrotters to try global mobility

I’ve gone from being a full-time expat living and enjoying the comforts of home in one country to being on the ‘road’ in many countries. As such, my life has transformed significantly in the past three years.

When I started this journey, I left Singapore in June 2019 with 34 boxes that went into storage for an unknown final destination. Amidst the global shipping challenge of the pandemic, in June 2020, those 34 boxes shipped to Bangladesh a year later.

Later that year, I left Bangladesh with 13 boxes to head to Niger, West Africa. In late 2021, after completing a year in Niger, I opted to depart with 2 suitcases, a small duffel bag, a carry-on, and my purse.

This was no small feat, and even after downsizing this much, I still packed items I did not need. My mind will periodically go back to my philosophy, declutter, donate, sell, and keep if you are using it consistently.

I am now in the Dominican Republic and reassessing what in my suitcase is worth keeping and what I will then donate. This is my new journey of downsizing again as I continue to be on the road, on the go, and global. My new journey as a digital entrepreneur, international higher education consultant and job search coach has allowed me to pay attention to what is in my suitcase.

During this reassessment. I am consciously working towards my goal that wherever I land next, I will be down to two suitcases, my carry-on, and my purse. Of course, this does not mean that I may not buy things while I live in a place for three months, six months, one year or more, but whatever I buy will remain in the country that I buy it in unless it is small enough to fit in my suitcase. Otherwise, it will be donated before I board the plane for my next destination.

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Being a digital nomad, I had to rethink how I traveled and packed two suitcases. Part of my rethinking had to do with the fact that I love to cook and carry various kitchen gadgets with me in my suitcase that were small, took up less space, and allowed me to enjoy one of my favorite hobbies: cooking and eating.

The other thing I had to do was reexamine what I brought in my suitcase when I started this journey. I had lots of things like towels and sheets and things of this nature, but I realized long-term, those things were very bulky, and so I had to reevaluate the size of many of those items. As such, I had to travel with smaller or lighter items. This included a new beach towel as I’ve never traveled with a beach towel, but I found it more essential as I’m on the road, and I love the beach, so I want to be able to enjoy it whenever I’m near one.

I also traveled with regular towels. Although I love my IKEA towels- they’re great, lightweight, absorbent, plus they dried fast- they were too bulky and took up too much space in my suitcase, so it was time to switch to micro towels. I now have four towels that all roll up to equal the size of one; they are still absorbent, fast drying, and take up only 1/3 of the space my old towels would have in the suitcase, which is truly amazing and left me more room for things like my clothes.

Speaking of clothes, I also had to redesign my wardrobe and think about layering, so I started to think about what I could do! I had many sundresses and decided to get what I called blouse jackets- blouses that could be worn over dresses as jackets or as blouses or jackets- and were great in a very multi-purpose way. I went for mostly cotton, lightweight dresses that can be paired with a jacket or a blouse over them.

I love dresses and skirts, so these items became the majority of my wardrobe along with one or two pairs of pants, all the accessories, and so on. I am replacing more bulky clothing with the option for a layering method of lighter clothing pieces.

For my shoes, I opted to get a lightweight, casual pair of gym shoes that I can use for everyday travel, and I also have a pair of gym shoes that I use for gym and working out.

Then I switched to regular shoes, one pair for those evening gowns that I must travel with and will not give up even though they’re bulky.

I also switched to comfortable black and blue flats that go with most of my wardrobe. They are thin and pack easily. Gone are the heels and the chunky shoes as I am in a place of practicality from being on the road.

I still have my one, classy clutch for evening gowns. I still carry all my jewelry. I still even have a small case with all my necessary papers because those travel with me, but I also have to leave space for electronics. These days my electronics have become more important (laptop accessories, iPads, lots of cords, plus things like a selfie stick and so on), so my carry-on gets all these items.

I also travel with lots of what I call the basic ‘hanging around the house clothes. These are casual knit dresses for hanging out or running errands. I’ve also learned to adapt sarongs as skirts or tops for daily wear outside of using them for the beach. I have probably around half of a dozen sarongs that double as skirts and a couple of spaghetti strap camisoles that I used to wear with my sarongs, and I have a new outfit.

These adaptations in my wardrobe have allowed me to downsize. I still carry one business suit and two shelves of blouses just in case I need to do something that requires a suit. However, outside, my clothes are still business oriented but have a less formal feel to them. They now reflect the mood of who I am and why I am traveling across the world.

Now, I know two suitcases are still a lot, but that’s what I am comfortable with at the moment. There are people out there who travel the world with one suitcase or even better, some travel with just a carry-on, and that’s great.

I think it’s important that as you travel, whether you are a digital nomad, a digital entrepreneur or a slow traveler, you find the right level of packing and baggage that you’re willing to carry around. In my case, it’s two suitcases and a carry-on.

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To make it easier for you, some of the things I carried in adapting to my new digital nomad life can be found on my website. From there, you can grab a couple of these items by going to my favorite online store on my website, checking out these items and purchasing them for your journey, whether for your digital nomad journey or just plain traveling. I found these things helpful, lightweight, made it easier for me to travel, and allowed me to have more of what I liked in my suitcase.

While downsizing can be a chore, as a digital entrepreneur, you have a more serious task to consider along with your suitcase; it is immigration. When commencing a digital nomadic life, please ensure you have the appropriate visa for the country you plan to stay in or do any work.

With the number of digital nomad visa offerings increasing globally, everyone should aim to minimize risk while understanding that the immigration laws of the potential location are no joking matter. Breaking the laws can result in you being refused entry, fined, imprisoned or deported. Further, any of these could have a longer impact on future travel plans.

These two sources for quick blogs, NomadGirl or Traveling Lifestyle, seem to be updated regularly, but always check the official government website of the country or countries of interest. So, do your research, adhere to the immigration laws, and you will have a pleasurable journey, be it with one or two suitcases or even just a carry-on.

I am learning with each move to travel lighter, purchase locally, donate when I leave and only keep what is important to me, such as my traveling kitchen gadgets. I also hang on to hard-to-find items like my black hair care products, favorite seasonings, and plus-size items along my travel journey.

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Want to know how you could become a digital nomad? Click on my affiliate link below to check out this course by my colleague, Ashley.