10 Lessons Learned from My First Year as a Suitcase Entrepreneur

Posted on / by Natalie Sisson / in Guest Contributor Post, Mindset / 1 comment
This is a guest post by Michael Burns, the founder of Baydream Creative.

So you’ve read Natalie’s book The Suitcase Entrepreneur, taken The Freedom Plan program, and hashed out your scheme to finally escape the 9 to 5 grind.

You’re ready to live life as a Suitcase Entrepreneur or digital nomad.

You’ve figured out a service or business, maybe set up a website or quit your job, and are ready to take the leap. Soon it will be all Instagram photos of your toes and laptop next to the beach as you conquer the online world.

But we all know it’s not that easy, right?

Wouldn’t it be great if you had some insight into what you were about to get into? The problems you would face, the dilemmas you would encounter, the mistakes you would make – and how to avoid them?

Well, you’re in luck.

I’ve just completed my first year as a Suitcase Entrepreneur (and/or Digital Nomad), and along the way I’ve managed to learn a few things that could be useful as you begin your journey into the world of working from anywhere.

First, a brief bit about me: I’m a copy and content writer originally from the USA. I left Los Angeles on November 7, 2016 and returned on November 3, 2017 – 361 days later.

Places I lived on my sojourn included Ubud, Bali, Indonesia; Singapore; Koh Phangan, Thailand; Chiang Mai, Thailand; Sydney, Australia; and Wellington, New Zealand.

I brought two suitcases on my journey, and one sadly did not survive the experience.

It was the best year of my life – and also the most complicated. To quote one Jeffrey Lebowski, “You know, a lotta ins, lotta outs, lotta what-have-you’s.

I began working and writing full time just eight months before leaving the USA, and was building my business on the fly – literally, sometimes working while flying.

Here’s what I learned on the way that may help you as you begin the Suitcase Entrepreneur journey.

1. Expect the Unexpected

During the course of my life,  I’ve been through my share of unusual disasters both natural (hurricanes, earthquakes, etc) and man-made (car accidents, illness, etc); but never did I expect to leave the place where I lived because of an active volcano.

But that’s exactly what happened when Bali’s Mount Agung, which I could see clearly from my balcony, came to life this fall.

With the threat of an imminent eruption of uncertain outcome, and an expiring travel insurance policy that was non-renewable for volcano-related coverage, I was forced to leave Bali for safer harbor elsewhere – and at great personal and business expense.

The point of this is, have a backup plan if where you are living doesn’t work out for a variety of reasons, and have financial resources stashed away to fund your travels in case the unexpected arises.

2. Know Where You Are Going

I’ll be honest, I like to wing it. It’s fun to figure things out on the way, or once you get to a place. Often you have unexpected and memorable adventures.

But when I’m leaving, there’s often a few things that make me say, “Oh man, I can’t believe I didn’t go there”, or “I wish I had known about that.”

There’s really no excuse for this. Thanks to a little thing called the internet, there’s no shortage of travel guides, blogs, apps, and Top 10 lists to read up on before you go someplace.

Make a bucket list if there are too many choices in one location.

Be sure to read up on local laws, cultural norms, and foods too – ending up in jail and hungry because you decided to watch a cat video rather than prep properly for travelling is not the story you want to tell the grandkids.

3. Keep a Record of Everything

Make some time every day to record your adventures. It’s tough, because immersion in a new culture can be overwhelming. I’m still processing everything that happened and all that I learned. Having a record of this is invaluable for continued growth – and to preserve your most cherished memories.

Some easy ways to do this are writing a blog, recording daily vlogs, writing down highlights of the day in bullet points, or becoming a social media machine by posting photos or videos with stories.

Take lots of photos and back them up in the cloud. You won’t want to forget a minute of your adventures. As a bonus, your family and friends will enjoy sharing your travels vicariously.

On the business side, make sure to keep records of expenses, clients, jobs, contacts, and all the things you need to keep your business running smoothly.

4. Have a Budget (and Stick With It)

I tend to keep my budget in my head. As it turns out, this is a poor location to keep important financial information.

There were a few times while traveling that I suddenly came up a bit short and had to forego fun activities because there was no cash available.

When you’ve finally made it to a new country, this is not the problem you want to have. In order to get the most out your journey, keep a close eye on your financial situation using an app, website, or spreadsheet.

Always know where your money is going – and budget enough to do the things that are important to you.

5. Keep the Money Train Going

It’s vitally important to know how money is going to continue coming in the door while you’re on the road.

If you have a regular paycheck, you are one step ahead. If you’re freelancer, have a plan on how you are going to continue to acquire new business over the weeks and months ahead.

It’s best if you already know that the plan works, and you don’t find out that your plan stinks with your bank account at zero while 17,000 km from home in a strange country.

It’s ideal to have multiple ways of client acquisition and if possible, multiple income streams, to cover you in the event of rough patches.

Say, if you have to leave an island due to a volcano, and your clients on that island suddenly can’t afford you because there are no tourists and thus no money to pay the copywriter. Yep, lesson learned.

6. Self-care Is Number One

At one point, I worked 28 days straight. Then I noticed that I was exhausted and had begun to break out in an odd rash.

I took two days off, then worked another 14 days straight. Then I went to the hospital, where I discovered that I had contracted a potentially lethal infection.

Fortunately it was caught in time, and I survived to write this blog.

As it turns out, you literally can work yourself to death. Lesson learned – take time every day for self-care, both mental and physical, and pay attention to your health.

Get ample rest, and adopt a healthy lifestyle and diet – you’ll live longer and be happier. Don’t work so hard that you burnout – as Wyatt Jozwowski discussed in his guest post Why Entreprenuers Constantly Burnout And How You Can Prevent It.

Remember, it’s Suitcase Entrepreneur, not Coffin Entrepreneur.

7. It’s A Balancing Act

The corollary to #6 is making sure you have work/life balance. Now, sometimes you have to put in the hours to finish a project or close a deal. I get it.

But what’s the point of living somewhere fun and exotic like, say, Thailand or Bali, when all you ever see is a laptop screen and the inside of a coworking space, and the only local person you meet is the barista pumping you full of double espressos so you can keep “crushing it”?

Calendar out your days and weeks, and be sure to make the best use of your time when working – so that you have time to live.

There are ancient ruins to explore, forests and mountains to trek, beaches to lounge on, and so much more. Make time to enjoy it before you blink and that time is gone.

8. Too Much Change Can Be Too Much

As you embark on this journey, you’re going to simultaneously be experiencing personal, professional, cultural, and environmental change – all at the same time.

As Natalie found out and explained in her podcast When Too Much Change is Dangerous.

When there’s a lot of change to process at once, how do you manage it without curling up into a fetal position on the floor whimpering “Mommy”?

My advice is to take things slow, especially at first.

If you make too many dramatic changes too fast, you’re setting yourself up for failure. Make changes in small increments, gradually.

Incorporate positive systems to relieve stress and anxiety into your daily life such as meditation, yoga, and exercise.

Get a coach or mentor or therapist (or all of the above) to talk to and help you stay on track.

Maintain healthy relationships with friends and family back home, and make new friends on the road so that you always have someone to share and talk with.


As with many things on this list, being proactive and making a plan will make your life so much eas



9. Make the Right New Friends

The old aphorism that you are the sum of the 5 people you spend the most time with is never more true than when traveling the world by yourself.

In order to continue being successful and – more importantly – stave off the inevitable loneliness that comes with long-term travel, you need to put a solid network around you.

This can be challenging because while many people you encounter at a location are there on holiday, you are there to live and work.

This means your priorities will be very different. In order to find friends more in alignment with your life and goals, I’d suggest trying coworking spaces.

They are a gold mine of cool people doing cool things, social events, informational seminars, and like-minded peers.

Another idea is to use Facebook groups to find nearby people with common interests (for example, Chiang Mai Digital Nomads).

These groups are not only great for making friends, but also for business networking, finding events, and obtaining crucial pieces of information (such as “Where is the best local laptop repair shop?”).

10. Have Fun Where You Are

As I said before, you don’t want your only memory of a location to be the splinters in your butt from a chair where you sat working the whole time.

Make time daily to explore the area a bit, try new things (like food!), and immerse yourself into some local culture.

You don’t have to learn an entire language, but learning the words for yes, no, hello, bathroom, thank you, and delicious will open doors to all sorts of things in a foreign country.

Take time away from work for fun activities that will recharge your mind and soul, and remind you of why you decided to undertake this journey in the first place.

As Natalie says, the goal is freedom in business and adventure in life – don’t just remember it, remember to live it, and you’ll stay on the right track towards getting the most out of your experiences.

Bonus Tips

I sincerely hope you found this helpful and inspirational, and I wish you all the best on your journey as a digital nomad and Suitcase Entrepreneur.

Here are two final bonus bits of advice: #11, when you are taking those Instagram snaps on the beach, no one wants to see your toes.

#12, when in doubt, always remember the immortal words of Dr. Seuss in Oh, The Places You’ll Go!:

Out there things can happen

and frequently do

to people as brainy

and footsy as you.

And then things start to happen,

don’t worry. Don’t stew.

Just go right along.

You’ll start happening too.

Michael Burns is a Storyteller, Copywriter, and Content Consultant who helps entrepreneurs and businesses grow by crafting engaging, creative words that tell their story with purpose. Whether you need copy, content, or website content consulting, Michael and Baydream Creative have a story for everything.

“Oh, The Places You’ll Go!” © 1990 Random House and Dr. Seuss