Choosing Location Independence: 21 Inspiring Stories.

Choosing Freedom Over Fear, Overcoming Adversity and Staying Location Independent

Table of Contents

When you decide to live life on your terms it is inevitable you will come up against roadblocks.

It is during these challenging times when we often feel most alone, doubt ourselves, or question giving up. However brief they may be, how we handle these moments shapes our entire existence.

When we look at others we tend to see either struggle or success; we don’t often see an honest “before and after” of their journey. Today we see both sides.

Recently I reached out to dozens of successful location independent entrepreneurs and asked them this question:

“What was one moment you doubted yourself, questioned your ability to live the life you do now, or came closest to giving up? Why, or how, did you keep going?”

The variety of answers surprised me. Some share details of their struggle while others focus on how they overcame it, the lessons they took from it, or the belief that kept them moving forward. If you read between the lines, you’ll discover that each answer contains a powerful insight into the personalities and beliefs behind these successful location independent entrepreneurs.

Below are their answers. You can follow all the contributors on twitter here.


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“One moment? Man, I wish there was only one moment, but honestly, it happens all the time. Self doubt is an entrepreneur’s toughest challenge, but can also be their greatest strength, because once you push through that cloud of doubt, or have that first success, its total euphoria!

The one time that really sticks with me is one year in to building my website. I had built a site that was gaining major traction in my niche. Email sign ups were pouring in, readers were engaging with myself and each other, and everything was good. Even the money.

I had built my site on a win-win situation with affiliate sales. I was promoting products that I used, genuinely believed in and helped my readers achieve their dreams of free travel.

I was finally making it on my own, doing what I wanted to do, making decent money in the process, and helping others.

And then, in one day, my affiliates pulled out. Completely. My income went to $0 in one fell swoop, and even though I still had all my readers and my site, I was now forced with a decision.

Either give up on my dream and go back to a regular job or change course, figure out another way to monetize my site, and keep plugging along.

After a few days of punching pillows and being pretty pissed off, I decided that, while I was pretty bummed about how things had played out, I’d be even more bummed if I went back a “normal lifestyle”.

I’d had a taste of what I wanted, an fully mobile, entrepreneur lifestyle, and I’d do anything to get that back.

I asked readers what they wanted to learn, looked at what I could offer that wasn’t already out there, and built a product that would be MY OWN, and that no one could take away from me.

It wasn’t easy, it wasn’t always glamorous, but I scratched and clawed to make it work, and slowly but surely, that product gained traction, and brought me back to the level I was once at.

And now, guess who wants to work with me again? That same affiliate company! Now it’s me in the driver’s seat, steering my own destiny. And isn’t that what we all want?


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London is an expensive city to live in, money was always tight, especially in the first couple of years of my business. With a bank at my overdraft limit, I decided I could write a book, self-publish and invest the money in an idea I’d had for an app.

I predicted I’d make around $6000 from book sales, which would be plenty to invest in the app, that would make me more money. My route to riches was assured. Except of course it wasn’t! The book sold around $2000 so I couldn’t invest in my app.

I considered giving up. I cursed my planning, my audience for not buying, my idea. However, I had a deep belief people would love the app, so I cut back my expenses further, hustled, waited and got it done.



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“There was a moment after I’d lived in Christchurch, New Zealand for a few weeks when I realized that I wouldn’t be able to continue running my branding business — the business that was funding my travels — while living there. The internet was just too slow and expensive, and I couldn’t send the big files I needed to send, or reliably Skype with my clients. The result was a massive change-up in my business model (you might even say my career), but for months I just sat on my hands, unsure which way to turn or how I would continue to make a living. It was a scary moment, and though I knew I’d make it work somehow, tendrils of doubt were definitely creeping into my decision-making process for several months as a result.

Why or how did you keep going?
Honestly, I was certain I could figure out a way around the problem because entrepreneurs, by nature, are problem solvers. It wouldn’t be the first time I’d come against adversity. I’d failed (sometimes epicly) enough in the past to know that even if the worst happened and I somehow had to put my travel plans on hold, it wouldn’t be long before I was back out in the world, enjoying it even more than the first time. Acknowledging — and even embracing — the potential for failure as part of the process is incredibly empowering, and defining that floor makes it much easier to jump higher than you’d be able to otherwise.”


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For about a year before I started Uncaged, I knew I had to create it, but it sounded like a pipe dream. No one I told really understood my vision, and even I doubted if I could really make it work. I’d always lived a life of travel and adventure, but could I really keep that up AND make some good money doing it? I’d never really had a real job, and I was always hustling to make enough money to buy the next plane ticket.

It eventually got to the point where I had no choice but to make it happen. I couldn’t handle the thought of getting another job, and I knew it was now or never. I immersed myself in the work of other people who were doing similar things to what I wanted to be doing. I learned everything I could, and I went for it.

And it actually worked. Holy crap. I still wake up sometimes and it doesn’t feel real that I work for myself, that I can pick up and go to another country tomorrow and it will be business as usual. And it happened way faster than I thought it would when I finally committed to going all-in.



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To be perfectly honest, I have moments where I question myself even now. I think no matter it is you are doing with your life there will be moments where you wonder what it would be like to be doing something else. I’ve often felt the most doubt and fear over what I’m doing as a nomadic digital nomad when I’ve hit rock bottom. For instance, there have been times when I’m barely able to make it out bed after getting food poisoning in developing country. Other times, I’ve struggled with monthly earnings online and wondered if this nearly slavish obsession I have with trying to make this self-employed gig stay afloat is even worth my effort. I keep going because I’m passionate about travel, photography, writing and making videos.

Even though I work longer hours than I have in any other job, I get a real sense of satisfaction from what I’m doing now with my life. It can be a struggle at times but I wouldn’t have it any other way. Right now I feel as though I’m pursuing my dreams, and even though I have moments of doubt, I feel confident in the direction I’m heading.


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A few months after I emptied my bank account to pay off my college loans, quit my job, and moved to Austin, I came home one night to find my apartment building engulfed in a 30 foot wall of flames. I lost everything… But I knew I wanted to do something great with my life. Instead of focusing on the pain of loss, I promised myself to move forward by improving myself, serving the world, and doing something truly great.


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I had my sink or swim moment very early on in my business. I set it up a few days before I got on a plane to travel the world. 

Three months into my trip, my savings had nearly run out and despite a good education and work experience, I couldn’t find employment abroad.

Do I head home? Do I borrow money from my parents? Do I give up? Maybe it was pride or just tenacious self belief but the answer to these questions was no.

I stayed in a cheap hostel, ate bread with what was effectively plastic cheese and powered through, working late into the night annoying my fellow dorm mates with my laptop light.

Then it finally happened… I started making money online. I didn’t go home. I didn’t need help, and four years on, I’m still travelling the world and have just released my first book.  

The road is paved with entrepreneurs who gave up. Figure out how much you want it, hustle, achieve and then pour a little out for your fallen homies.


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When I first left Canada after university to move to Japan, the decision was easy because I didn’t have a career, house, family or anything holding me back. I still had fears of the unknown, but they were largely overblown. Even before the Internet, it wasn’t that difficult to relocate to the other side of the world.

Years later, when I was making the plan to leave Japan and embark on a new career, I was married and had a great lifestyle. There was much more to lose.

It was very difficult to sell our business, house and car, as well as, get rid of all of our possessions. My wife and I had a great lifestyle and good income so giving it all up for something unknown and risky wasn’t easy. In fact, it took us several years to finally commit to the decision to leave Japan and begin a life of travel. We weren’t feeling challenged by our business, so we often talked about doing something new, but it took a long time to get the courage to act.

Anyone doing something new is going to have doubts and fears. Expect that going in. Whether you are thinking of starting your own business, changing careers, running a marathon, or going on a round-the-world trip, you are going to have uncertainty and doubt. That is the very nature of doing something new and challenging. You can’t predict the final outcome in advance.

To make matters worse, your friends and family are unlikely to support or believe in your goals. They will often think you are crazy for trying to do something new and out of the ordinary. This is completely normal. You can’t expect support and encouragement from people who haven’t done what you are planning. They are more afraid than you are. That’s precisely why they don’t act on their dreams and goals.

The remedy is to surround yourself with people who have done what you want to do. With the Internet and millions of blogs, it’s easier than ever to find communities of adventurers that have done exactly what you are planning. Finding and connecting with those people will give you the courage and advice to move forward.

Personally, blogging was absolutely essential for my journey. Beginning my JetSetCitizen.com website connected me with dozens, and now hundreds, of like-mined travellers and digital nomads that were living the life that I wanted.

I think we all know what we need to do to accomplish our goals, the problem is that we are not 100% certain it will work, so we hesitate. Knowing that hundreds, or even thousands of others have overcome the exact same obstacles, provides the confidence to do the necessary work towards our own dreams.

In my case, it ultimately took a public declaration on my website that I was going to change countries and careers within one year to really force me to take action. After that post, back in 2009, I finally started the preparations to leave Japan.

I don’t think blogging is a very good way to make money online, however, it’s a fantastic tool to connect with others that are pursuing the same goals and it helps to keep you accountable.

I think it’s important to remember that it’s easier than ever to do anything you want, anywhere you want. Our grandparent’s didn’t have anywhere near these options. Whether you want to film a movie, write a book, record a CD, start a business or travel the world, there are no barriers. With a laptop computer and an Internet connection, you can do anything you can imagine.

We have one life to live. We can either challenge our misguided fears now, or we can build up a lifetime of regrets. There is not a single day that goes by when I’m not thankful for the life I now have. We live in amazing times. Don’t waste this opportunity because of unfounded fears or self-doubt.

Follow John on Twitter or learn more at Jet Set Citizen


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If you’re aiming to do anything worthwhile, count on it being bloody difficult. Actually, hope that it is difficult. How ungratifying would it be if it was easy? Where is the growth in easy? The biggest growth comes from the most challenge. There is a fine line between those that give up when it appears the hardest, and those that continue on. Fact of the matter is that, nobody who ever ‘made it’ gave up. If they gave up, we never would have heard of them. And its been proven countless times that on the path to success, in any endeavour, the hardest part comes just before the biggest breakthrough.

For me, reading the book ‘The Slight Edge’ helped me with that a lot. And Seth Godin’s ‘The Dip’.


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I’m not sure if I’ve really doubted myself too much with the goals that I’ve had. There’s been times when what I was doing wasn’t working and I simply decided to change my approach. I’m not sure if you’d consider that “giving up”, but rather making an intelligent decision to shift gears and pursue other opportunities that have greater potential.

I can remember getting crushed by Google last year with some of their updates that affected some of my sites. I was down about it and tried many things to attempt to recover my sites back to where they were. Some of it worked, some didn’t, but that experience taught me an important lesson: diversify your income streams. I also learned how the internet is always adapting and changing, which means I need to adapt also. It ultimately forced me to look in different directions and try something new. I learned better ways to do SEO and other ways to make money online, which has made me more successful today.


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There have been many many moments when I’ve been down… And nearly out. Times where I feel like selling it all off cheap, giving up on the dream. This is usually driven by a feeling that I can’t make it over a major challenge the company is facing, usually financially related. The biggest tool that gets me through these times is strategic planning and positive self talk. I find that without clarity on your long term goals, and understanding on how your daily tasks are in alignment, big challenges can feel like too much. Secondly, I find the negative self talk can creep in, and you have to shut that out quickly. I simply give myself a mental pep talk over and over, until the negative self thoughts are gone. Nobody but you ever hears this internal dialogue (fortunately), because even though it is true, it sounds pretty stupid to tell yourself you are money and can do anything you set your mind too.


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My vision and dreams were more powerful than my fears.


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The closest I came to giving up my initial travel dream, which was to circle the globe without getting on a single airplane, was about halfway through.

I was at the Kenya/Ethiopia border and on bad information from the US Embassy, I didn’t have a visa, as I was told I could get one at the border. I got there via a grueling two-day cargo truck hitchhiking effort and the only way back to Nairobi was the same way, or getting on a small plane to do it. Luck and fate ended up conspiring to help me out, in the form of a group of South African and British motorcyclists, one of which was in the same situation as me.

I’m not sure what I would have done without their help, but I certainly thought long and hard about my failure at that point. Fortunately, I made it into Ethiopia in the end, and eventually around the world.


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One time it happened was several months after quitting my job. It was the middle of a recession and my grand plans for the ‘can’t fail to get hordes of interest’ ideas were, in fact, failing to get hordes of interest.

I was in a cafe and I literally could not think of a single thing I could do to make money come in. Like, nada. I’d created the website, tweaked it a billion times and (surprise surprise) sticking up flyers wasn’t getting anywhere. Honestly, if I’d had a job offer there and then I’d have taken it (luckily the job offers came before and after that time, and I turned them down!).

How did it turn around? Because I was so stubborn (aka persistent) I kept putting myself out there in unusual ways to get work in my old field as well as my new one, and focused on what I could do to help other people and organisations make things work for them, how I could contribute to them (rather than hack away at building a platform one client at a time by shouting into the void!). That approach wasn’t an overnight thing but honestly it was much faster than tweaking my logo and sticking up flyers for another 2 months! Making those connections (focusing on helping others) was a key turn around. The other thing I did differently was focus on the two things I loved the most: speaking and writing. Instead of just doing conventional marketing I looked at ways to do more of those two, and a lot of my growth came from there. Within a year I was earning as much as I had been back in that ‘good job’.

But back at that table in that cafe I didn’t know any of that was coming: I felt helpless, stupid for having quit a ‘good job’ where I knew what I was doing for something where I had no idea where to turn.Now I look back on those days and wish I could go back and give old-me a good dose of marketing advice… but more than that I wish I’d known this is just a part of the journey: in my book I warn readers that soon after the high of leaving your job, you will start wondering if this is a crazy dream whether you should quit; as I say in there, “some people call this a reason to give up. I call it your first three months.”

It’s not just you, and if what you’ve been doing hasn’t worked, look at your existing skills and strengths and see how you can use them to help others rather than relying on the same old things everyone is doing.


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That would be now.

I am watching the clock count down. About 3 weeks ago I quit my day job to work for myself on my own software projects. The plan is to give up the paycheck and try to support myself with consulting while my new site, BloggerBridge.com, ramps up. Walking away from a real paycheck at a company that you think will be successful can give you a few sleepless nights. I am trying to change my lifestyle to have some more location independence to be able to say “yes” more often when people offer me free trips to Poland, New Zealand, the Canada Rockies, or the Caribbean (all of which I have turned down this year).

There is a better than even chance that this will fail and that I will fall on my face but I have failed before and it is not a permanent situation. As I recently wrote about on my chris2x.com blog, I have spent 18 years at Silicon Valley startups. One failed so badly (went from so much promise to out of money) that we made it onto a list of 30 biggest failures in the (now defunct) Byte magazine. That failed startup led to 7 job offers.

So… once more into the breach


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For me, I think the scariest moments or the ones filled with the most doubt were actually before I’d even started this lifestyle. For months I questioned whether or not I should leave my job and start my own business. All the uncertainty terrified me.

However once it happened and I started the path towards entrepreneurship, while there are absolutely difficult days, my life was so much better. I was traveling, having adventures, but most importantly, I was making progress on the business. Because I had so much more time, it was easier to feel like I was making forward progress – and as long as you’re making forward progress (or at least feeling like you are) it’s easier to have faith you’re doing what is right.


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When I started out learning to make a living online I had doubts all the time. One day I would be super excited about a new idea I had and the next day things get overwhelming and I would feel like giving up again. In retrospective what kept me going were all the small successes along the way. Take one step at a time, but always keep the big picture and your goals in mind.


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In February of 2011, I had one of the worst nights of my life. I remember tossing and turning all night, battling panic attacks and gasping for air, because the doubting voice in my head told me that I was going to fail at my first product launch. I was two weeks away from releasing my first big product, and the voice in my head had me convinced that I would fail, and that I’d always be a failure.

I thought about packing it in. In fact, I thought about closing my entire business because I was so scared. However, at the advice of my friends and those closest to me, I carried it through to completion.

The result? Hundreds of thousands in revenue, happy affiliates and customers, and world-wide recognition as the expert on my topic. It was then that I realized that fear is a muscle – you have to face it and defeat it over and over again until you develop the skill set to let it drive you.


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I’ve had many of these moments and have overcome them different ways each time. This story comes from a few years back.

I was working as a freelancer and still struggling. It’s Saturday evening and the weather is just miserable. Dark clouds, drizzling rain, cold enough to be uncomfortable yet not like a romantic Christmas cold you get bundled up for and almost enjoy.

I was at home thinking about my situation and suddenly was overcome with emotions. Where was the light at the end of the tunnel? Something has to change or I’m not going to make it.

I knew I needed to make a serious change in my life because I couldn’t handle the stress much longer. The clear decision was to “Call It Quits” and move back home for a bit while I look for a job.

Lucky for me I was a few glasses of wine into the evening and wasn’t seeing “clear”. So instead of calling it quits I decided to up the ante and booked a one-way ticket for Costa Rica. 

When I took off I had less than a month’s living expenses…I was going to sink or swim. It was a huge risk…and it paid off.

When things got hard I had plenty of opportunities to raise the white flag. To retreat. To turn my back on the life I really wanted. I’m sure you’ll have the same opportunities. Ignore them.

Don’t ever, ever think going for it, going after what you really want, will be easy. But it will always, always be worth it.


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In April 2012, a few months into trying to turn my blog into a business, I got pretty discouraged. It was WAY harder than I had imagined, and I just wasn’t seeing results as fast as I’d hoped.

I never really thought of giving up to be honest though. My whole journey online has been based on the idea that the only way I’m going to fail is if I give up… and early on I committed to NEVER giving up, no matter how hard it was.

The biggest way I got myself out of this funk is that I learned to be more in the present (after reading The Power of Now by Eckhart Tolle) and moved to Boulder to be in a community of entrepreneurs. Close support of people who really understand what we’re going through is key… especially in those tough times!


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Self doubt, which mere mortals like myself have certainly experienced, stems often from the story we tell ourselves. This story of why we are not good enough or why we shouldn’t do something, is often an illusory inferiority reinforced by society and trapped by our own minds.

If they judge you, it’s because they don’t want to judge themselves. They laugh, because they know your balls are bigger than theirs, and you failing would make them feel better about themselves.

After all, you tried, and they didn’t. Otherwise, they’d understand. Anyone who has walked the path knows that pain is progress. Surround yourself with the right people. They will encourage you to embrace your fear and to grow and push your comfort zone. Most importantly, just do something. Anything. Make that leap, and fail more often. Believe in yourself. Good luck.



In sharing your stories, you demonstrated an incredible level of trust, openness and wisdom. You have given us the insights and inspiration to shed self-doubt and work through our challenges.

Readers, now it’s your turn. Please share at least one comment below. Every word you share adds to our community.

Share This Resource. Did any of the stories above provide inside, inspire you, or spark new ideas? If so, please take 2 seconds and share this with others so they can feel the same. Just use the Facebook and Twitter share links to the left or below. 

If you like this article you will also enjoy Why We Want To Be Part Of Your Life, The Rulesand The Dream Big Manifesto.


25 thoughts on “Choosing Location Independence: 21 Inspiring Stories.”

    1. I’m really not sure from a statistics point of view. In terms of the article, it’s more a reflection of the people I know plus a much lower response rate from the girls than the guys.

      I do know one thing, there are a lot of very eligible bachelors very keen to meet nice location independent women!

      1. Guess being a young, single, child free guy might make location independence a tad easier than most other demographic groups (or way easier), however, I’m on my way back to that world in a couple of months as a 51 year old woman with my partner and two teenaged kids 🙂 As part of the international homeschooling/unschooling community, I’m aware of a number of women out there raising their kids location independently. It’s got a different vibe than most of these guys you know, but it’s a great, free range family life.

        1. That’s great Heather! I totally agree that my demographic, and that of many of those featured in the article, has the “easiest” route to location independence but that doesn’t mean it is the only route. The message I want to spread is that anyone can life the life they want. This article is about overcoming the challenges that will come with that. I look forward to hearing more about your story.

  1. hi dan! i loved your post…i am a newbie on this..i am from the Philippines, i have been a cruise line crew for the past 13 years…and i have been thinking of staying home for good…i have been reading and have been a fan of ryan moran for the past year since i have been looking for ways to earn a living in the internet world…i came across you through ryan’s post on facebook just today…ryan has been giving advise on turning passion into profits and i was thinking of just sharing my experiences onboard the cruiseship as a crewmember…i know it will be from a different point of view but i am not sure if i will gain anything from it…these are doubts, i know, i just wanted your honest opinion on this…thank you and more power

    1. Hi Helen, Thanks for your comment. I believe it is possible to make money in almost anything. I also believe that it is much easier (aka less stressful) to make money in some areas than others. I imagine there is a market, I do know a lot of people who dream of working on board cruise ships, and of course millions travel on them as well. I don’t know enough about the cruiseship industry or your experience to give a concrete answer. If you haven’t already, opt in to my email box that says “Want to be location independent”. There are a few lessons around value and the nature of getting paid that I think will be valuable for you.

    2. Helen, why don’t you start a “Who Done It” murder mystery on the ship, get people to pay you each night to participate. I would pay $50.00 to do that, possibly more.

  2. Hey Dan,

    I was led to your amazing blog by my friend Colin Wright. I found this posting to be wonderfully inspirational and have nominated you for my “Very Inspirational Blogger Award” featured on my site. I know it would be very time consuming to undergo the rules of the award but I just wanted to let you know that you have inspired me and I have subscribed to your blog and look forward to your updates.



  3. A wonderfully thoughtful post, so many perspectives to appreciate. I especially enjoyed JET SET CITIZEN’s sober view on Blogging’s power to connect people and the realities of making a solid income with it.
    So much of storytelling is about facades, Its nice to be reminded that we’re all living the dream in some respects but might not always realise or appreciate it because we focus on what’s missing instead of what we’ve already achieved or even began with. Great post.

  4. Pingback: How To Set Effective New Year Resolutions and Achieve Your Goals

  5. It’s great so many young people are location independent, but it would also be nice to hear from older ones. There are MANY people in their 40s, 50s, 60s, and older who are full-time wanderers and entrepreneurs. And, yes, more women, too.

    1. I totally agree! Actually, my second or third coaching client ever was a wonderfully adventurous woman in her 60s. Do you have a story of full time travel to share?

  6. Dan, I love your focus and contribution to the many ways humans can choose to live life. I continue to grapple with all of the societal conditioning that is put on us as we go through life. I have to tell myself that it’s still possible to break free of the golden handcuffs – and MUST treat my ideal passion as just as or MORE important than how I am currently making money. I feel like the further you stray off course of your passion the more difficult the road back to our Truth. Keep Up the Awesome Work and Inspiration.

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