Becoming a Digital Nomad: Why You SHOULDN’T Do It

By Sean Ogle •  Updated: 09/27/19 •  10 min read

Becoming a digital nomad and working for yourself  always like a combination of unicorns, glitter, and mint chocolate chip ice cream – don’t believe anyone that tells you otherwise.

Ok. That’s a lie.

I’ll be totally honest, sometimes being a digital nomad and solopreneur totally sucks.  I mean, usually it doesn’t, but nothing is ever all glitter and rainbows.

With that in mind, today I want to highlight some of the aspects of this lifestyle that often get overlooked amidst the instagram photos of first class flights, lavish hotels, and laptops on the beach.

So if you’re considering becoming a digital nomad, but you want a little dose of reality for what it’s really like? And what some of the downsides are? Then today’s post is for you.

We’re going to dive into not just the realities of traveling and the downsides that come along with that, but also the business aspect of being a digital nomad.

Because let’s face it, you have to have a business to earn the title. Otherwise you’re just on vacation.

Becoming a Digital Nomad: The Pros and Cons (VIDEO)

If video is more your thing, here’s a YouTube video we shot in Vancouver, BC all about the pros and cons of work and travel.

1) There’s only one way things get done: you.

When you’re first starting your business as a digital nomad there’s going to be one giant roadblock in your way: yourself.

If you don’t get work done, work doesn’t get done, and you’re eating ramen for the next month.

As your business gets bigger you can hire people to help (and even then, it can be a difficult transition to make), but in order to be successful you need to be disciplined and have productive routines in place or risk death by sodium induced pasta.

Here’s my secret for getting stuff done.

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2) Separating Business and Personal Finances is Next to Impossible

Sure I have a separate business bank account, but as a single member LLC, my business and personal finances are largely intertwined.

So when I pay someone a grand to say, fix my website that got hacked, it feels like that money is coming right out of my pocket, rather than the business.

10 years in and this is still a difficult thing to get past, especially for someone who tends to be cheap, ahem, frugal, like me.

It can also be made even worse if you hit a period of time with slow sales or a lack of new clients. The lack of a steady paycheck can wreak havoc on the business/personal life balance.

3) The “So What Do You Do” Question

Go ahead, do it. Ask me what I do.

Depending on who you are, the day you ask me, and my mood, you might receive one of the following answers:

Anyone of those could come out of my mouth, and most of them are true. I still don’t have a good answer for what I do!

Which I suppose is great, because it means I do a lot of things and keep it interesting. But trying to give an answer to this question is a very difficult proposition, and many people still won’t get it.

Hint: Don’t say you’re an “entrepreneur”. You’ll get a collective eyeroll as the person will most likely move onto someone else thinking that’s code for “I’m unemployed.”

Second Hint: Don’t call yourself a “digital nomad” – you’ll get an even bigger eyeroll. Live the lifestyle, but don’t give yourself the title.

I’ve been struggling with answers to this question for awhile…

4) The 7 Day Workweek for a Digital Nomad

Don’t get me wrong, I take a lot of vacations.

Well, kind of.

I go a lot of places, and do a lot of fun things.

But no matter where I am and what I’m doing, bubbling just below the surface is the feeling of “I should be doing ______”.

There will always be something you could or should be doing in your business.


That will never go away, and working early mornings, late nights, and on weekends will all be a part of your journey.

Sure, this allows you to golf on a Tuesday if you want, or go work from a nice cafe on the banks of the Song Saigon – but while you’re out on the course, or exploring a new city, you’ll always have modicum of stress about work.

My "Office" earlier this year on the banks of the Saigon River in Vietnam.

My “Office” recently on the banks of the Saigon River in Vietnam.

5) The Inability to Take Business Risks

So this is totally counter-intuitive, and maybe it’s just me. But it’s my post, and I’m including it anyway.

I once I wrote about the importance of risk taking. This week at risk of sounding like a hypocrite (see what I did there), I’m going to talk about the difficult part of risk taking as a digital nomad.

And I’m not talking about “eating the mushroom milk shake at the Full Moon Party” kind of risk.

Once you’ve got a system that works, changing it is scary. I can roughly predict how many Location Rebel Acadeny sales I’ll get in a month, how many people will open an email, how many people will read a post etc. on any given day.

Everything works. Could it be better? Could I make major changes and grow the business more?


Would that involve making some changes, and taking a big risk that has the potential to make it all go to zero?


And as a solopreneur and digital nomad that’s all on me, and that’s one risk I’ve found to be difficult to make.

6) You’re the One Who is Expected to Be Flexible

Yeah, I get it, I have a flexible schedule. But I’m still running a business and working more than a 40 hour workweek (ok, usually).

When you’re the one with a flexible schedule, people can expect you to be the one to work around them – which can at times definitely be inconvenient.

This is especially true when everyone around you is essentially on vacation. If you’re with travelers and backpackers who aren’t concerned about getting stuff done, it’s going to be up to you to be disciplined enough to say no and prioritize work when necessary.

You’re also the one who can be available to hang out at odd times. Does a friend have a day off and want to hit the mountain? You’re the guy! Someone else want to go to a gym class at 10am? Sure, I’ll go!

This flexibility is great, but it can be difficult being the one who is always expected to be available. And based on my strategy of almost always choosing play over work, there are times where my desire to have fun wins and I find myself being much less productive than I should be.

Check out this post on Digital Nomad Productivity for some help with this aspect of the lifestyle.

7) Permanent Travel is a Great Dream with a Frustrating Reality

Ah the dream of traveling around the world while making thousands of dollars each month from your laptop.

This dream is absolutely a reality for many people, myself included.

However it isn’t as easy as you’d like it to be.

When I’m constantly on the move, it’s nearly impossible to do work that will grow my business. I can maintain it, but growth is hard.

I learned this during my 2 month digital nomad sabbatical.

So when people set out on a backpacking trip and expect to build their business, they often find themselves overwhelmed and frustrated because getting stuff done can be hard.

My advice? Travel slowly and build routines.

Stay in places for at least a week at a time, and during the first day of each location decide where your “office” is going to be and what your “office hours” will be.

Make that the most rigid thing in your schedule.

If you’re in a new hostel every day or two, you’ll prioritize adventure over work, and never get much done.

READ: 6 Things No One Tells You About Running a Business Full Time

8) You’ll Face A Significant Lack of Respect as an Entrepreneur

Lifestyle entrepreneurs, digital nomads, or solopreneurs are often compared to startups. What I’ve found though, is that many people in startups could care less about what I’m doing as a solopreneur.

Last year I wrote an article for Forbes talking about this called “What Startups Could Stand to Learn from Lifestyle Entrepreneurs.”

Regardless of the fact I make good money, directly help a lot of people, and have a great work/life balance – many people in the startup world simply aren’t interested.

And that’s fine, but it’s also something I was pretty unprepared for.

I think what I and thousands of other Location Rebels are doing is pretty cool, but that’s not always the sentiment.

9) The Benefits (or Lack Thereof)

One question I get asked frequently is related to the idea of benefits, or in my case lack thereof.

“How do you pay for health insurance?”

“What do you do about saving for retirement?”

The reality? I pay for my health insurance out of pocket, and make annual contributions to my SEP.

No employee matching, no subsidized insurance costs – it’s simply one of the downsides to being a solopreneur.

10) It Can Be Lonely

As a digital nomad, there’s no watercooler. You don’t get to gossip about what happened over the weekend, or go out for company picnics.

Most days, I sit in a coffee shop all day. By myself. Sure I talk to a lot of people online, have frequent in person meetings, and I travel a lot – so it’s not like I’m living in a black hole of loneliness – but there are definitely times I wish there were someone working right next to me.

And often many of the relationships you do build are fleeting. When I lived in Bangkok I still remember two girls who lived near me that in 100% seriousness almost refused to be friends with me since they knew I’d be leaving within a few months.

That’s a real thing.

Yes, These Things Can Suck, But…

Still reading?

Still want to work for yourself?

While yes, all of these are realities of becoming a digital nomad, I can definitively say the benefits far outweigh these downsides.

Over the past 10 years I’ve done all kinds of things I never in a million years thought would be possible, and if it weren’t for the freedom and flexibility that comes with working myself – they probably wouldn’t have been.

What kinds of things? Well for starters here are 14 Things Location Rebels Can Do, that Employees Can’t.

So, ready to become a digital nomad for yourself? Awesome, we’re here to help. Start with our free 6 day email course that walks you through exactly how to get going on your own.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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15 comments on "Becoming a Digital Nomad: Why You SHOULDN’T Do It"

  1. This is the underbelly of the beast!

    Working for yourself has definite downsides, and they don’t get talked about very much. But that’s the trick: we can’t! I don’t think we can give dire warnings to people who are about to break out of a cubicle, because it already takes so much courage to make that transition, it’s not good to deflate their ambitions by warning them against it; maybe online entrepreneurs just have to find these difficulties out for themselves.

    In addition to all of these downsides, I had additional frustrations with being a father, and traveling with my kids.

    There’s no such thing as a ‘vacation’ when you travel with kids. It’s a ‘trip,’ and it’s work.

    Taking these intensive trips, when I had to manage the luggage and logistics for five people, AND make sure everyone was fed and watered, AND deal with any behavior difficulties as they cropped up, meant that working while traveling just didn’t happen very easily for me.

    I like your tip above about staying in one place for at least a week, and deciding on your office location and office hours on the first day. I find that the momentum of having a steady work environment means I don’t have to spend so much time on figuring out how to work, and I can spend more time actually working.

  2. You hit the nail on the head with this one. Being a solopreneur is definitely not all sunshine and rainbows, but at the end of the day these challenges are worth it to have a business I enjoy working on and the flexibility to do what I want to do. Great post, Sean!

    1. Jessica – you hit the nail on the head. Flexibility is all important to many of us.

  3. Timo Fischer says:

    Oh god Number 3 hit the spot haha. Everytime somebody asks me that question I say something different because as you said it depends I do many things next time I’m just going to say I do online porn just to see the look in their faces. And yet I love being my own boss sometimes it’s hard but I still love it. Great post I really enjoyed it.

  4. Great stuff as always Sean. I always appreciate your words of wisdom and honesty. Being a solopreneur may not be as glamorous as many may think and that’s fine (grass is always greener). I’d have it no other way though. Loved the section and your answer to “So what do you do” – awesome. Thanks again man – cheers!

  5. I totally feel you when people ask, “What do you do?”

    I normally respond, I’m a “business owner” (a little more professional than “entrepreneur” haha) or a “Whale Hunter” (in the mood to be funny).

    That’s my gauge to see how interested they really are… to see if they ask “What do you own?”

  6. Nanci Casson says:

    With the exception of nos. 8 and 10. I am actually doing mostly everything on this list. While I am still working full time, it is encouraging that I am doing the exact same things as you. While I still work full time, I am hoping in the very near future I can eventually earn a sustainable income.

    Each day I see more sales and signups with gives me motivation beyond belief. Eveyday for a few hours a day, I am constantly doing something to work on my business and I can see that it is really starting to payoff. One of the greatest feelings in the world is waking up and checking your stats to find out that you have made money in your sleep… really is a beautiful feeling. While I am not quite making enough to quit my job, I do believe without a doubt that my long term sustainable lifestyle business will allow me to live the life that I long for.

    Great post as always Sean

    1. Sean says:

      Great to hear about your success Nanci, and thanks for the kind words!

  7. Tom Lekhanya says:

    ‘Don’t say you’re an “entrepreneur”. You’ll get a collective eyeroll as the person will most likely move onto someone else thinking that’s code for “I’m unemployed.” ‘

    Haha I thought that was just Johannesburg thing. ‘yeah I’m an entrepreneur’, usually drug dealers or unemployed folks say that here.

    In month 2 in Location Rebel, and after getting my first gig in writing, I’d say I’ve felt that thing of you’re the biggest thing in the way. Getting some progress now though – in terms of self-confidence -, what a nice view of Vietnam there.

    Looking forward to enjoying my own nice views globally in the coming years.

  8. Ahh, but being a solopreneur is so much fun!

    It s important to BUILD real assets with the income though. I know tons of people who make money but end up having nothing to show for years of work.

    As a result, they gotta keep on working!

    Hope all is well. Fly by Saigon last week from Cambodia.



    1. TOM LEKHANYA says:

      Hey Samurai, what do you mean by build ‘real’ assets?

      And can you give examples of what situations you meant of people working making good cash and nothing to show. (IM people/graphic design or what?)

      These assets do you mean skills or like products created that flow in income?


  9. Kim McFayden says:

    Totally hearing you! Most of my close friends don’t “get it”. I set my business up with a view to working from anywhere but find myself feeling guilty unless I’m working practically every minute. Duh! Don’t even get me started on the elevator pitch. Feel like a douche bag saying anything other than “I’ve got this website….”. I definitely need to get more like-minded people in my life otherwise I’ll go insane. Thanks for this article. Nice to feel less alone 🙂

  10. I use the porn line way too often as a way to avoid prying by hair stylist.

    All of these are accurate and it’s nice to read someone else write about it. Feels less lonely.

  11. Roland says:

    My biggest problem in #1. Not only that but also WHO do you blame when something is done wrong?

  12. Great post Sean.

    #10 stands out to me as I am in the rollout phase of a second business that was really spawned from a consequence of this very item. Alone is alone, but it also a limits scale. #10 forces you to think about the process around the mundane things; like even getting a proposal or contract that you want physically in someone’s hand. So much can be re-imagined and I guess that is why we are soloprenuers – Enjoy

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