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

Hey everyone!

I’m getting ready for my first trip abroad alone (this Oct). I decided on Chiang Mai because I feel like it might be the best place to get my feet wet. Plus I’ve been planning on going to Thailand now for about 3 years. Dream started 3 years ago, started my business 2 years ago, finished college/moved out of my parents 1 year ago, left my part-time crutch job a few months ago and now I make enough online to be location independent.

But now that my dream is becoming a reality, I’m actually kinda scared. Just thinking about boarding a plane with only a backpack in my possession is liberating but also frightening. Probably the craziest thing I’ve done in my life and I’ve worked so hard to get to this point.

I’m sure that most people here had to deal with the fear of leaving for the first time, the uncertainty of what will happen, and maybe even some resistance from your family. I’m just wondering how you dealt with it? Maybe I just need to re-read some of the books (4 hour workweek, vagabonding, The $100 startup, etc…) that gave me the motivation and courage to start in the first place. What motivates you to keep going?



You’re lucky. I’m $90k in debt and I’m going off on the same journey as you this Fall. But then again, I like to live life on the edge. Here’s the thing: as long as I’m alive, I’m living proof that someone with less than you can survive.

Hope that helps.


Hi Eddie,

As you keep going, the fear will fade. As with anything risky in life, it feels a bit crazy at first. But as soon as you start you’ll realize it isn’t as impossible, crazy, or terrifying as it may seem.


I was always a wanderer so i never had the whole fear thing. but keep this in mind: you can only control what you can control. the rest you will just deal with when it happens and worrying about it is a waste of your energy. what’s the worst that can happen? you die? well, you went out doing something you dreamed about so that’s not a bad way to go. anything other than death can be dealt with so really no point in worrying about it, IMO.


Maybe I can help. I got on a plate at 15:40 yesterday on Portland, Oregon, and I’m currently five hours into being a digital nomad in London, UK. Scary? Yes. Worth it? FUCK YES JUST DO IT.

PSA: take everything I say with a grain of salt. Almost everyone else on this forum is more experienced than me. :pray:

As with most scary things, the only way to conquer your fear is to do it. You prepare as well as you can (which will never be close to enough), and then you dive into the deep end and learn how to swim.

What’s currently holding you back from booking your plane ticket today, and what are you doing to resolve that?

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I had that fear at my first time when I left my comfort zone, but the comfort zone was too boring for me so I had to make a decision, go or not. I opened the booking page of an airline, selected a flight and filled all the info, then I stopped at the checkout button. I gave myself 5 seconds to decide, so I started to count from 1 to 5, and I made it at the last second, I booked the ticket without thinking anymore. I had one month until my flight departed, so I tried to prepare as much as I could. At this moment I’m asking myself why I needed to prepare that much? huh!! because it was the first time, and we always feel stupid when we recall what we did in the past. That one month was damn long, I felt like 1 year, I counted every single day to wait for it, so if you haven’t booked a ticket, make sure you have a flight that departs as soon as possible, time may make you change your mind. Once you’re out of it you will realize that it’s not that difficult to be scared a lot. There might be a culture shock if this is your first time going to Asia, try to watch some videos on youtube first to see how Chiang Mai looks like so you know what you should expect to see better. Those books are bullshit, only the office men want to read them and dream in the day, get out of your house, the life will teach you how to survive and work better for free.

Thanks for input! One thing that has really helped is that I’ve reached the point where I’m more scared of not going. I’m so tired of just living day to day in the same city and apartment. I’ve felt more alone than ever because I’m surrounded by people who have bought into the status quo, are materialistic, aren’t doing anything with their lives, or get caught up in petty drama or arguments over the stupidest things.

After college, a lot of my friends have essentially “disappeared.” Some have moved away, others got jobs that consume their life, or are now too busy with their significant other.

I’m just hoping that I can meet more people who believe in the same life values, who want to explore, live life in the moment, and are working on building their own business and wealth. I never felt like I belonged anywhere while growing up, and for the first time (well 3 years ago) I finally felt like I found a lifestyle that fits my personality and life goals. That other people have the same thinking and that for once…I wasn’t alone.

So, maybe it’s not the fear of leaving I’m feeling, but the fear of not following through or failing to sustain the lifestyle that I want. How sad it makes me feel when older people tell me their regrets of not following through with their dreams, how they lost sight of what was important, or how they were led to the belief that traveling is “only for the rich.” How they lived their whole life chained to the system because that’s what they were told to do and couldn’t break out.

But I have my plane ticket and leave in the fall, so I’m ready to do whatever it takes to make this possible and I’m excited for the next chapter of my life.

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hey man, if you didn’t feel fear, you wouldn’t be doing the right thing. It wouldn’t be an adventure, it would never be the time of your life. It would be just another routine.

Actually, you shouldn’t expect fear before a big hungry lion is running after you.
I like to think “fear” is a misnomer that you didn’t choose yourself: let’s pretend it’s excitement, or the urge to do something!

I’ve never regretted all the crazy choices I made. It’s the “reasonable” ones I’ve regretted.

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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.