How do you deal with the fear of leaving for the first time?

It sounds like you’re in a good situation, having transitioned slowly and with a 2-year-old business already.

Once you start - and especially once you do connect with commnunities of people who have the same mindset, and who will inspire you to go even further - I think those fears will dissipate; the people who you surround yourself with will become the “new normal.”

About the fear of failing to sustain, it’s possible for location-independent entrepreneurs to fall into one of two traps:

A) Getting so distracted by travel and the delights of the place you’re staying that you fail to give your business sufficient focus and energy;

or B) Being so uptight about maintaining your business that you overwork and fail to enjoy the lifestyle.

Which one you’ll tend towards depends on your personality (I’m a “B” myself) but the remedy to both is balance and clearly defined work/fun separation. Some examples of various schedules you could adopt…

  • buckle down and work HARD for 4-5 hours, then go out and have fun the
    rest of the day
  • work 3 hr in the early AM, go out during the day, then do a couple more hours in the evening
  • do an intense “sprint” of 8-10 hr-days for a work week, followed by a week off

I’ve used all of the above at various times, depending on my business and travel situation. So to sum up, the best bet for following through or sustaining this lifestyle is two-fold - to surround yourself with likeminded people, and to have the self-discipline to establish a good work/life balance (whatever that might look like for you).

Good luck, congrats on booking the ticket, and make sure to update this thread after you’ve taken off!


Thanks for the thoughtful reply @Shayna I appreciate it :smile:

You’re right, I think once I can surround myself with more like-minded people I will feel more comfortable and it will help me grow and learn things that I could never of imagined. I love learning, so connecting with other similar people is one of the big reasons why I’m looking forward to the trip.

Work/live balance may take some time to really figure as you mentioned and is something that I’ve been thinking about. My current plan is to enjoy my mornings: get up around 9 and have breakfast, go for a walk/work out/do any small tasks, have lunch, work for a solid 4-5 hours, and then have dinner. Then either work, read, or enjoy something else in the evening for a few hours (depending on my workload). Then for weekends, I want to explore the area and do some other activities. Just a rough idea which may change

Well Eddie, Thailand could be a bit much for a first timer. Culture and language shock could initially discourage you from a rewarding thing you’re going to do for life otherwise. I left home (Australia) when I was 20-21 and in part it was being able to research and do most of it on the internet first that made it easier. Mind you this was Dotcom 1.0 era too so it had much more of a feeling of adventure to it.

If you’re American, try something a bit closer to home. For example Montreal/Quebec in general is “France on training wheels at a fraction of the price” that I think all North Americans should try . It’ll be sufficiently foreign enough to feel like you’ve gone somewhere but at the same time you can fall back onto English if you need to, even though it would be to the disgruntlement of many locals :wink:

By the way, much respect to building up to this point over the years. I feel much less frustrated at the few months of no luck and slow progress I’ve had so far. I’ll send you a msg :slight_smile:

Thanks for your thoughts. By all means, I’m not new to traveling. I’ve traveled to Canada a few years ago (Toronto & Montreal) and also spent a few weeks in Europe (Germany, France, Switzerland, Austria, Liechtenstein) but this will be my first trip alone.

One reason I chose Chiang Mai is because it’s a bit slower pace, it’s cheap, and has a highly developed network of Digital Nomads (who can maybe teach me a thing or two about traveling too). I know it will be a bit of a culture shook but that’s what I’m looking for. Canada isn’t really that cheap and one thing I want to do is baseline my living costs so that I can pump more dollars back into my business.

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haha fair enough. Dont ever come to Australia if you think Canadian costs are high :wink: I’m aiming to use Panama to approximate something like US costs or less since Australia is easily 2-3x (and in some cases 10x) what an equivalent would be in the US.

Just pull the trigger. It’ll all work out.

Honestly - you could board that plane with nothing but your debit card, passport, and the clothes on your back. You’d figure it out when you got there. You’ll still be alive when you disembark. Society still exists.

Have fun!

“More scared of not going” – I can totally relate to that, and to your fear. Sometimes it’s hard to separate a true “danger signal” fear from the a bad case of the jitters. But you’re probably suffering more from not having anyone around who gets it! “Vagabonding” is definitely a book that helped me (“if you’re not enjoying it, you can always go home” – it’s true), as did “Tales of a Female Nomad.” I had traveled abroad alone several times before, but never to Asia-Pacific which felt so far to me – so I also broke my flight into chunks (PHL to LA, LA to Hawaii, Hawaii to Fiji, Fiji to NZ, NZ to Bali, etc)… I hate long flights anyway and I think that helped me a lot with making a transition, rather than just dropping myself into Asia. It also sort of symbolized something that helps me with my fear of heights, especially when hiking on steep, somewhat dangerous terrain as I did in New Zealand: be aware, generally, of where you’re going, but in this moment, only focus on the next step you need to take… and definitely don’t look down or back! I swear it’s the only reason I’m alive because I nearly had a melt-down on that icy mountain! :smile:

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Hi Eddie,
When I had to deal with this situation, the thing that helped me the most was asking myself what’s the worse that can happen? The answer was pretty much the same every time- “I won’t like it and i’ll go back home”, not so crazy hey? To be honest, the other option was much scarier- not going and forever wondering “what if”. Going is probably the best choice whether you’d like being a nomad or not (which is okay too), just to get it out of the system.

Yea I 100% agree. I don’t want to get older and have regrets of “what if.” Plus, I can always go home or try a different country.

However, I’m fairly confident that I’m going to love it. I never felt felt like I “belonged” and felt like I was living a lie. But, thinking of traveling and living the digital nomad lifestyle has grounded me. It’s given me a purpose to keep going, to start and grow my own business, and to expand my learning and thinking. It’s what I live for and has opened a whole new world of opportunities. It’s like I’m starting to see colors for the first time…


I am a little late into this conversation but if it helps, I left my job of 24 years to go travelling round the world. My RTW trip is coming to an end but I am going to be living in Penang for 90 days to see if I like the place, and could cope with working location independently. I do have some freelance work, that I can do remotely, and online, so that helps. When I first left my job I asked myself numerous times, “Are you doing the right thing?” and I came back with the same answer every time. It was the best decision that I have ever made and while I am exhausted from travelling continuously for six months, I can’t wait to settle down somewhere.

Go with your gut instinct, and think to yourself, what is the worst that can happen? You’ll find that there are solutions for any concerns that you have.


Just do it. I did it and bough a one way ticket to Bangkok in 2014. I remember taking the taxi from BKK to Bangkok everything around me was in Thai (the ads, the signs). I was pretty scared and in shock. I was in a different part of the world, I didn’t speak Thai, nobody could help me, I had no friends near me, no family, no car, nothing. It was only me, my backpack, and my computer. After a week or so I got used to it and the rest is history. I was forced to meet new people in hostels. I become much more independent and social. Now I’m not scared to go anywhere. I can pack my backpack tomorrow and fly to anywhere I want and I know that everything will be ok. Having this sort of feeling makes you feel almost like a super hero. It was the best decision I’ve ever made in my life and it also turned out to be the best year of my life.


Awesome! Thanks for the inspiration :smile:

Everybody afraid of something they didn’t experience before. Think that if you listen to your fear and doubts and won’t go, you’ll regret all your life, it is a bran new world for you and big amount of new opportunities.

I always tell myself that everything is for the best! And it’s always true :slight_smile:

Hello Eddie,

I am in a very similar boat , I am also leaving for Chang Mai for the month of Oct , lets connect and share tips, At this time all I have is a plan ticket to BKK and a backpack with a laptop and few clothes :slight_smile:

Any suggestion on anything will be very helpful.


I am in a similar position, with no business though, but with 2-3 years of runaway money and a complete distaste for my current job (corp finance) and city. I don’t know, the fear is real, especially if you don’t have technical skills to sell, because then you know you are pretty much giving up your carrier for the unknown.

So, I don’t know, yet. I think if you have a plan B and a good soft landing in case the house burns, you should go for it. If not, maybe it’s worth thinking about a plan B.

Said that, the more I stay in my current situation, the more I feel like going without a plan B…

By the way, it would be great to have some “carrier” advise from the community.

I bought a one-way ticket back in 1997, and the rest is history. Although I’ve never gone back, I’ve only been a ‘digital nomad’ for 3-4 years. In the early days, I would sometimes wake up disoriented in the night, but it wasn’t a big deal and with time it went away. What has always been most important is how I live my life, and by getting that ticket in 1997 I embarked on a life of my own choosing. It was absolutely the right choice and I have never, ever regretted it.

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Well if you don’t like your job, why don’t you leave? Life is too short to being doing something that you distaste.

Since you have some money saved up, why not learn a new skill or enter a new field? Could either go back to school, take some courses online, or find a mentor.

Not really sure what you mean by a plan B. My plan “A” is to travel, continue running my business, and to grow my new second business. If something doesn’t work, I’ll do what I always do, pivot and adapt. Don’t really have a plan B because this is something I have to do and I’m willing to do whatever it takes to make it happen.

I am leaving, I am working on a soft landing and a way to minimize risks, but I will leave. The main reason I am still here is because there are things I like about this job and I am working hard to find a way to either consult or train. It’s not easy, but maybe it works, maybe it doesn’t, then I have other ideas, too many actually. I am also decent developing in Flask/Django and RoR looks reasonably easy to learn.

So, I have got some plans and I am definitely leaving, I just think that living abruptly quitting on the whole field (in which I have 5 years of experience) may end up in missing good opportunities.

The mentor point is a great advice by the way, have you found any? I see many of the good people working on web stuff are usually too busy for newbies.

I’ve never heard about stoicism philosophy then i was leaving, but it appears that i practiced something similar. Before leaving i was practicing different ‘worse case’ scenarios -> eat only raw food for a month, sleep on a floor for a month, not drinking alcohol for a month and etc.

So then time came to move along, i didn’t had a single fear inside me. Just smile on my face. :slight_smile: