Dealing With Self-Doubt While Living Abroad (Or Building Your Online Business)

I felt the time was now right to write an article touching on this.

I feel this one is long overdue and is something almost every up-and-coming online entrepreneur (or Freelancer) deals with.

I know I certainly did.

I first experienced this years ago, when I was building up what you now know to be Calmandcollected.com.

Calm and Collected is now more than just a blog, it’s blossomed into something bigger. It’s finally turning into, what I always envisioned it to be: a brand.

I knew where I wanted to take it.

I dreamed about it.

I obsessed over it.

Every day I did this…for 8 YEARS.

Now in 2022, here we are after many accomplishments, meetups around the world, and thousands helped.

I knew there were men out there who needed my help. Men struggling with all the same self-doubts I used to.

You know, a funny thing starts to happen though when you start building what I’ve built (and am still building).

New doubts start to creep up. You start to question whether you’re the real deal or not. Even when it’s painfully obvious to others that you are, you still have those moments where you doubt things.

This is worse in the earlier years however, much worse.

Every now and then, even to this day, I still have random doubts. They’re much fewer and further between these days, but I’d be lying if I said they didn’t sneak up now and again.

Then when we talk about the subject of moving abroad, that’s a whole another experience that can mess with a lot of guy’s heads.

Below I will discuss the 4-5 most common forms of self-doubt, that people like you and me deal with.

Many of you may have experienced some, or even all of these already.

For others, this article may foreshadow some ugly thoughts that might pop up for you one day. I’ll cover the main ones here, and likely more in future posts.

Let’s begin…

1) Fear of Failure

Everyone has experienced this one at one point or another.

The fear of failure can be very intense when you’re building up your first business.

Any business, not just an online one.

When you reach the point where you’re starting a 2nd or a 3rd business, this fear goes away. There may still be moments that creep up, but they’re gone for the most part by the time you get to a 2nd or 3rd business.

This potential impending fate that’s poking you in your side every day.

You may worry for example, about all the time and money you’re investing, and whether or not it will pay off.

Often this threat will actually help you because it lights a fire under your ass.

It gets you out of bed in the morning and gets you moving.

Now, this fear of failure is even more threatening when we’re talking about uprooting your life and moving abroad. Moving overseas to start a new life is a daunting thought for a lot of guys. It can take a while to work up the inner gumption to say for certain you’re doing it (and mean it).

For me personally, it’s something that took years. It took me years of mapping out in my mind how I would pull it off.

Then, when I finally had the balls to decide I was doing it, I had to stick by my decision. I knew there would be objections from family and friends, especially my mother.

You may have people in your family or social circle that tell you you’re ”throwing it all away”. That everything you’ve built your life up to be back home will suddenly cease to exist.

I look at it differently. I look at life as having different phases, and I never saw myself as being tied to one location.

Not at this stage of my life anyway.

I wanted to travel and see the world, and that’s exactly what I’m doing. Still, you may worry that things won’t work out and you’ll have to go home and have the naysayers be right. That they’ll look at you and tell you “I told you so”.

At some point, however, you’ll realize that failure is ultimately a choice. If you truly are motivated to succeed, you will find a way to make it happen. You’ll find a way to succeed.

“But Dylan…what if I’m worried I may not be truly motivated?

I get guys that ask me this. My response is always the same, I tell them they will always know in their hearts if they don’t want success before it reaches the point where it matters.

Meaning a sort of ”point of no return” they worry about.

Let me give an example of why I say this. Let’s use an example here, of a guy who’s expatriated. By the time that guy has taken the initiative to uproot his life and move to another country, 8 times out of 10 it’s a pretty safe bet that guy is one who’s truly motivated.

He would never have gotten that far most likely if he wasn’t serious.

2) The Fear Of Success

This one is a bit different.

I noticed this is something that isn’t discussed very often on blogs. Often, we’ll become so preoccupied with the fear of failure, that we won’t realize the fear of success is going one at the same time.

The fear of success will manifest itself in strange ways. This never really happened with me, but it’s happened with several guys I know. Guys who pushed through it and are now very successful.

Based on the stories I’ve heard about this, it will usually occur right before one is about to have a big breakthrough.

Right before they are about to succeed and hit their goal. They will find ways to stall and sabotage themselves without even realizing they’re doing it.

They might manufacture some kind of problem in their lives out of nowhere.

They will essentially just stop working on whatever it is they’re about to have a breakthrough with.

There are a number of excuses or reasons why they’re doing this they’ll come up with. When you experience this, your fear is rooted in the idea that your life will never be the same again after you have your big breakthrough.

Your big breakthrough, by the way, could also be moving abroad finally. This is a tough one to deal with, and the main reason for this is because it’s often true.

Your life WON’T be the same again in many cases.

It boils down to having a fear of the unknown really. Human beings take comfort in familiarity, even those of us that are more risk-averse.

It’s not a guarantee you’ll experience this one (some people don’t) but just in case you ever do, you’ll be glad you read this so that it’s something you can refer back to.

The fear of success is similar to the fear of failure in that: sooner or later just becomes something you realize you have no choice but to overcome.

Now, oftentimes there will be other parts of your life you’ll have to end up changing, to accommodate the changes the new success will bring.

Take Ed Latimore for example. Ed realized he had to quit drinking, in order to have the kind of life success he knew in his mind that he could achieve.

He had to make room in his life for success, in other words. This happens more often than people think, and can take different shapes (depending on the individual who needs to change, and their unique situation).

Perhaps Ed’s drinking had been a form of self-sabotage. Self-sabotage is common, and recognizing you’re doing it is the first sign you are making progress.

Success almost always requires sacrifices. Never forget this.

3) Comparing Yourself To Others.

When you compare apples to oranges, you’re always going to find yourself disappointed. Each of our lives are complex, in different ways and for different reasons.

This is mainly due to our upbringing, and what happens to us in the first 3 years of our lives. That itself, is a topic for another article, for now just realize our upbringings shape who we become.

Chris from the old Goodlookingloser blog talked about self-expectations in a few of his old articles. He said the main reason why some men give up on their dreams, and never reach their destinations, is because they start out having unrealistic expectations.

It’s very important to always understand what you’re getting into, and what you can realistically expect.

If you run an online freelancing business, and it’s to the point where it’s now earning you enough money to live on, then you already know what I’m talking about.

You already know how important it is to be able to reasonably predict certain things before they occur.

Having this ”6th sense” so to speak, will guide you in your ability to make decisions about your business. It will guide you in your ability to adjust and adapt as needed and to do so swiftly.

Now let’s talk about a moving abroad scenario for a moment.

When you move abroad, one of the tough things about it is this feeling of being no longer able to relate to most people. You have stepped out of your own and done something most people would never have the balls to do.

At the same time, there are also many people that have done this, but everyone’s story is different. You’ll drive yourself crazy trying to match your results abroad exactly to someone else’s.

No matter how similar the things the two of you are doing may seem, they aren’t.

The only person you should measure yourself by, is you. You only have to be a little better than you were yesterday (or even the same).

So whether we’re talking about freelancing, blogging, online business, or expatriating, comparing your experience to someone else’s is a fool’s errand.

4) 2nd-Guessing Or Questioning Your Decisions.

I believe this last one is more common to the moving abroad experience (than the business building one) though I’m sure there are those who experience it working online too.

Sooner or later, every successful freelancer who moves abroad, realizes they must learn to trust themselves.

Trust in themselves, as well as trust in the process.

They have to believe in themselves.

They’ll realize this because if they don’t, they’ll drive themselves crazy.

You simply cannot be successful online as a freelancer or live overseas as an ex-pat, if you don’t believe in and trust in yourself.

Now this one can be very tricky, because sometimes in business you will realize you actually DID make a mistake. When you realize it, you’ll have to be able to recognize it and pivot quickly.

The same can be said for moving overseas: sometimes you’ll realize you just picked the wrong place to live.

This is why it’s so very important to always do your due diligence and research before you make an important decision. Never just rush into something without thinking it through beforehand.

This is why they say: Hire slow, and fire fast.

That phrase has meaning beyond just the scope of bringing on an employee or a VA.

What it really means is what I’m trying to get at here: make important life and business decisions slowly, but once you realize you’ve made a mistake, once you know it in your gut, act on that realization FAST.

This last point here is tied in closely with the first two points: the fear of failure and the fear of success.


Self-doubt is a nasty thing we online Freelancers and Expats deal with. I wrote this article because I feel we deal with it on a more intense level. We are trying to accomplish great things. We’re trying to move the world forward, to do things that not many before us have ever done.

This can be a frightening idea. You are not alone.

Even a guy like me, has been there. I know how you feel.

Keep your mind active and healthy, keep your body active and healthy. Doing these will help you to have pure thoughts, which will allow you to do things clearly.

Leave any questions or comments you have down below.

Thanks for reading.

Until next time,

Your friend,

Dylan Madden

About Dylan Madden

My name is Dylan Madden. I've written over 300+ articles for those who want more out of life and are interested in traveling the world. I am from US city where most people work the same old job for their entire life. Now after traveling to 18 countries. I've set up a home in Dubai where I spend my days helping freelancers build successful businesses within The Real World and on the blog Calm and Collected. Within this website you will find the motivation and action steps to make your life better.

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