8 Reasons to Quit Your Job and Travel the World Before You Are Ready


I made the jump to location independence before it made sense. My business wasn’t ready, neither were my friends, family, or business partners. Hell, I wasn’t even sure if I was ready. There are a lot of reasons why I was brought to finally take the plunge– but by living this lifestyle for two years now I’ve realized that a lot of my initial worries (and the warnings of just about everyone) weren’t that helpful or predictive of how things played out. Further, I’ve found a lot of reasons to go location independent before you feel you are “ready.”

This isn’t a step by step guide to this stuff. Some of it is anecdotal and it won’t apply to everyone. In general, if you are deciding between starting a cash flow “freedom” business vs. jumping quickly into a location independent lifestyle via a half measure like teaching English, consulting, digging into your piggy bank, remote working arrangement, or other radical maneuver, I recommend starting with location Independence. I’m assuming you are passionate about owning your time and mobility (so much so that you are willing to act a little crazy to earn them back). Here are the reasons:

  1. If you wait for a sustainable source of income, you might be waiting a long time. Its difficult to get a company to the point where its generating enough cash to support your lifestyle, or get you to the point where you would feel comfortable jumping ship and replacing yourself. I’ve seen many entrepreneurs inadvertently build themselves into their businesses, even if they had other intentions. It hurts your wallet big time to “leave” your business, mid-start up phase, and go for a more flexible arrangement. If having location independence is something that is valuable to you, its worth going for it right now. It doesn’t get easier once you have a business on your hands.
  2. Very few distractions. No family, established group of friends, commute, arbitrary 9-5 desk time, in-laws, “stuff”, community obligations, I could go on forever. Its all gone, and it makes a big difference.
  3. Easy access to top talent. Selling to a western market? You’ll be able to afford top assistants, programmers, and administrative personal in countries like the Philippines. You’ll have the flexibility to meet their requirements and give them a great experience growing a global, results-oriented, earth-shatteringly cool business that allows all its employees the opportunity to live a great life and contribute to something great. Feeling crazy? Try in-sourcing some talent from the west. Found somebody good via twitter? Go visit them. Even crazier? Try renting a budget resort and flying in creative, talented people who want to learn your business and earn back their time, freedom, or just blow off some steam in a tropical paradise. Hmm. That does sound good. Who’s going to beat me to it? You have a few months… I’ve interviewed several resort operators here in the Philippines and annual burn rate for a fully functioning resort with restaurant starts at about 35,000K a year. YEAOH! Why aren’t software development shops taking advantage of this?
  4. Easy access to top investors. There are TONS of medium level, very liquid investors in “lifestyle destination” foreign countries (especially the Philippines), and they are easy to find and access. I can’t speak for other parts of the world, but I can say this, the guys and gals “at the top” are much easier to access in foreign countries. Often expats are older, successful individuals (of course these a big clump of the opposite case) who are sitting on a lot of cash because its difficult to manage investments back in their home countries. Many of these folks are former and current entrepreneurs as well, and the same drive that brought them to build companies and wealth brought them to new lands for adventure. There is also oftentimes a generation gap– and am assuming here that most of my readers are under 45 years of age. Even if that’s not the case the very fact that you are reading blogs will often make you much more tech savvy than potential investors, giving you instant edge and leverage for an excellent equity stake. This issue is big in scope, worth a better look in another article.
  5. Less of a cash burden on the company during start-up phase. I can afford to draw a much lower salary than I would be comfortable with if I was living in California with all the trappings of my old yuppie life (man, I used to have an Italian shirt, ew!). Now I can still pull a decent salary, put it in the bank, and keep cash flow in the company for hiring and investing in new product lines.
  6. Get used to being off the path. That’s where the value (and incidentally, the fun) is. When I left my real world trajectory, “the path,” I thought, we’ll hey, I’m not gonna be big time rich for a while, but its worth it. My time and freedom is worth the sacrifice. But of course, successful entrepreneurs do exactly that. They leave the path. They get used to it, and they become adept at creating value where others couldn’t see it, or weren’t brave enough to go for it.
  7. Nothing to Lose. When I quit my job and took up a backpack, I was prepared for the worst. I still have a million scenarios in my mind that allow me to keep the “nothing to lose” mindset. I tell myself: everything could blow up and I could still keep this thing going. I love Dave Ramsey’s quote: “you’re only as secure as your ability to go out there and drag it home.” We’ll I believe that, and its worth ensuring now you’ve got the skills now to go and drag it home. To turn the phrase: if you don’t learn how to drag it home, you are probably getting drug, to the tune of 40+ hours a week.
  8. You’re already rich. I try not to gloat too much about my lifestyle, especially when some of my employees still work in an office (although its not required!). But its difficult not to. The bottom line, is that in countries like the Philippines, you can live like a real rock star for next to nothing.

Hope everyone is off to happy new year. Pop your email in the box below if you want to be on our alert list.

Published on 01.11.10
  • Hey mate,

    I eagerly await the updates! I couldn’t agree more with your life choice and hope that as soon as I finish my masters I can get back on the road again! inspiring stuff! What line of work are you in though?

  • Totally agreed Dan. So many people I’ve met throughout my travels are always and have always been planning for the day that they’ll be ABLE to work location independently. A big part of the experience for me has been jumping off the edge, so to speak, and having faith in my own abilities to make it all work out. Not only do you get to enjoy the benefits you mention, but it’s a lot more exciting that way!

  • Matt

    Great post. A month and a half until I quit my job and start traveling. Am I ready? No way. My business makes $0 currently. I have the money to live/travel for roughly 6 months and if I can’t make any money by then I have an apartment and a job to come back to. ‘Throwing my life under the bus’ as I say has always worked for me before so why not now. I work much better when consequences are real.

  • Dan

    @ Johnny, thanks for the shout. I made a quick little video while taking a break the other day where I talk a little bit about my business: http://www.youtube.com/watch?v=qnhcX9zzS8k

    @Matt – Your comment just gets me excited. Thats a killer challenge and putting yourself to it is bound to create a lot of awesome stories and opportunities. Where are you going to start?

    @Steve – Totally. I remember being amazed at how many people around me where doing the same thing. Its difficult to really have that perspective until you just take the plunge. (blogs are making it easier though!)

  • Wow, this does put things into perspective. I should go to Thailand for at least a vacation. This might be my first comment here :) I have some catching up to do!

  • Dan

    Thanks for dropping by Moon, I would recommend Koh Phi Phi island for world class snorkeling, beaches, and fun. Hope you’ll stick around and share your insights on passive income. I know we are all looking for a little more of that.

  • Stephhthinks

    Just so you know, some of us reading are older than 45, and are still benefitting from your words and thoughts. Our minds think alike…hopefully soon we’ll be working and living alike (meaning we’ll, not you’ll, be making a change!).

  • Dan

    Hey! Great to hear it. That was probably a silly point for me to bring up, my 2 best friends here in Manila are both over 50 years old. Part of me thinks that the internet and living overseas opens up the doors for more “age diverse” relationships where in San Diego I seem to spend most of my social time with people within a few years of my age. I’m glad you’ve stopped by, hope you’ll share your big change when it happens….

  • Lately I’ve been reading career tips from the Penelope Trunk and many times in her posts did she mention about quitting your job right after 2 weeks (you’ve read it right, 2 weeks man!) and do yourself and the company a favor by doing so. Then I get to see people quitting their jobs and doing what they like and it’s funny how these people are more productive and successful. Why? Because they do what they’re good at and loving it. Man, you seem to be having a great time here in the Philippines. It’s the people like yourself that makes the future of internet marketing really bright.

    Sometimes when we want to get somewhere or do something better, we need to leave that which is good. As we look back, we will realize that we only emptied our hands just in time to receive more. Cheers!


  • Dan

    Hey Jonha, thanks for the nice comment. And yeah, I’m really happy to be here in the Philippines. Like your site!

  • No worries, I love to blog hop and bookmark interesting ones. :) Where are you in the Phils? Hey thanks, which site?

  • Dan

    Manila. The one you linked up!

  • Very good post, I came across this issue in my first post on my blog. I understand that having your back against the wall can produce exceptional results, however if by delaying your departure by, in my case 12-18 months, so that I can save lots of money and learn the ropes, wouldn’t that be a much better situation to be in?

  • Dan

    Hey Adam, great first post. Its inspiring to see more freedom fighters joining the ranks! Its really tough to give an opinion on this but that won’t stop me from trying :) The best way to approach this is to start approaching your life and current job like a business. What exactly do you need this money for? What kinds of ropes are you looking to learn? In my view, there is only one rope that matters. Customers.

    What you really need are customers that don’t care/don’t know about your lifestyle aspirations. You current customer, you boss, cares about how and where you spend your time. Start looking for customers who don’t and things will probably be clearer. My general sense is that 20K and 18 months feels a little arbitrary. If for example I said, great work on the blog Adam I’ll pay you 1,500K a month to run my blog! Would you quit tomorrow? Those are the kinds of questions I’d start to ask. Customers are the key to this lifestyle. Working from a beach is the easy part :)

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  • nayar ali

    great post Dan. i think your correct in saying start before your ready.
    i have found by speaking to many people in the past and currently and including myself, we are stuck in lifestyles which we are taught from an early age are the norm! regardless of whether that’s the lifestyle we want. so much so that when a conversation about ‘starting before being prepared’ comes up, a sense op panic descends and people quite literally start to panic. sometimes its just best to let go and do something without preparation and then when your there you are more inclined to make it work as you have made the first step and don’t want to go back as a failure. been reading your posts and finding them very informative, they are helping me fashion my brain to quits the norms and venture forward to start the journey to becoming location independent. many thanks for this

  • thanks Nayar, best of luck on your journey!

  • Lola Azb

    L feel like um not good in english and l need to learn it as fast as l can to find job any one here advice me

  • Number 2 is crucial, I think.
    Most people barely even realize the distractions they live with and how that affects their performance, the things they get done and the outcome.

    Great post! Thanks.

  • you got it!

  • Austin

    Vey true. I just came across your guys website as someone who is 19 and already taken the leap. 3 months ago I dropped out of college to start traveling south american with $300 in savings and an $800 per month income stream. Back then I was scared shitless, now I have found ways to make it work, have more than doubled my income and have done some of the coolest shit I can imagine and this is just the beginning. Thanks for the great content guys. Keep it up, maybe we can have some drinks when I make it over to SE Asia ;)

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