I am not going to die wondering

It’s 2pm on a Saturday afternoon.

The sun is shining.

I’m slightly hungover, with a case of brain fog that even strong caffeinated beverages won’t remove.

Ten minutes ago I gazed out the open window at people walking past below, pausing for a moment of reflection that became an extended daydream, and now I can’t wipe the smile off my face.

My whole life lies before me.  And you know what?  I rather like the look of it.

Yesterday I took what is probably the biggest leap of my life.  I booked a ticket to Thailand.

Is that exciting?  Well no, not really.  But what that ticket represents is possibly the most exciting thing I’ve ever done.

That ticket represents freedom.

For the last thirteen years, every time I’ve started a trip there has always been an end date in mind.  It might have been a week later, it might have been six months, but there was always a point at which I knew I was going to stop.  A point at which the fun was going to end and I was going to have to grudgingly find a job and head back into an office.

This time it’s different.

Several weeks ago I wrote about the wonderful session at the World Domination Summit that resulted in me writing a single powerful word on my arm.

One of the best exercises that we did as a group was to tell a stranger of a time when we felt the most alive, with the goal of coming up with the one word that defines us more than any other.  We then had to take an indelible marker and write that word somewhere on our body.

The word that I wrote on the inside of my left wrist was FREEDOM.

That session – and that word – has played on my mind ever since.  If I want to be truly happy, I need to be truly free.  And like it or not, I’ve finally realised that isn’t going to happen if I keep having to return to the cubicle every few months.

So I’m not going to.

It’s time to try to make a location independent living, to try to at least cover my expenses while living wherever I choose.  I’ve made a start, and while the income levels are still very low and very uncertain, it’s given me the strength to believe that this crazy idea might just be possible.  There’s only one way to find out, I guess.  So come early November, that’s just exactly what I’ll be doing.

I don’t know what the future holds.  I don’t know when I’ll next be back in this part of the world.  Other than a few vague plans, next year looks like one big blank canvas.  There’s a dozen different ideas.  I may do all of them.  I may do none.

I do know, though, that I regularly tell people that my biggest fear is lying on my death bed saying ‘if only’.  As a result, I guess I don’t really have a choice in the matter.  I have to give this a go.  I refuse to die wondering.

I’m quitting the status quo.  More importantly, I’m quitting my status quo.  It’s going to be a lot of hard work with zero guarantee of success, and to be honest that scares the shit out of me in many ways.  At the same time, though, it makes me tingle with excitement even just thinking about it.  Life is funny like that.

It’s time for a change.

See you on the road.

64 Responses to “I am not going to die wondering

  • Woohoo! In all honesty…you already know the worst that can happen. Why the heck not try for the best?! You know you’re going to miss the fab coffee and sunny skies of Melbs though…coffee date before you go!

    • Exactly right! I *do* know the worst that can happen, and if I have to return to it, well, the world will still keep turning I guess. So on that basis, it’s time to aim for the best.

      And you know, I will miss this place. I always do!

      Coffee date for sure… 🙂

  • Congratulations Dave!!! You know we’re pulling for you…let me know if there is anything I can do to help. Cheers!!!

  • Congratulations. Exciting! Just remember on thing: don’t pack any weed into your boogie board bag. Otherwise, you’re set! Melbourne—in all her cold, psychotic glory—will miss you.

    • Damn, there goes my plan on how to finance my travels. Smuggling weed into SE Asia. Because I hear that’s what the smart kids do…

      Hey, congrats on the book launch by the way! 😀

  • Yay! Congrats! I’m reading this post at a small brewery about 45 minutes outside of Portland wearing my WDS t-shirt on my way home from starting my day at yet another small brewery and then some stand up paddle boarding in Hood River. I’ve been extremely antsy lately so I did the only thing I know how to do when I get in a rut…pretend I’m traveling! Explore…find a scenic place, a cold beer and just do what feels right at that moment. In other words…when’s that double decker bus trip starting? 🙂

    • Well that sounds rather awesome to me, I have to say.

      Damn I miss those Portland microbrews….

      And as for the bus trip? Watch this space… 😉

  • Congrats, Dave! I think WDS really changed us all in lots of ways. Here’s to never saying “if only”!

    Wishing you crazy success, happiness and nothing but freedom!

    • Hey Peggy!

      Yeah WDS certainly changed me … or at least reaffirmed the direction I wanted to head and gave me the strength to do it. If there’s 500 other amazing people out there doing what they love, then I can do it too…

      Thanks, you too!

  • You’re the man Dave. Hoping to buy my ticket this week…

  • Woohoo! Congratulations Dave! 18 months into our location independent life we still don’t know how things are going to turn out but certainty is boring isn’t it? You won’t regret it. Looking forward to seeing you in Thailand.

    • Certainty is *highly* over-rated. I’ll take an uncertain awesomeness over certain mediocrity any day! And can’t wait to see you guys again 🙂

  • couldn’t have said it any better. from someone about to try the digital nomad life as well, congrats for taking the leap! we may not get the results we want at the end of all this, but it sure is satisfying to know that we will be giving it a go. 😉

    • Good luck Paul! The satisfaction is beyond compare, and I haven’t even started yet!

  • Congratulations. I will be following your blog with even more interest! I can promise you that the old saying about regretting what you didn’t do as opposed to what you did do, as you get older, is totally right. The cubicle will always be there (or the equivalent!) your youth won’t be.

    • Brilliant, thanks Linda! And you’re damn right about the cubicle always being there … it ain’t going away. Great point!

  • Congratulations mate! That is a huge step and I’m sure you’re feeling an array of emotions; you’re acting on what so many only think about – brilliant. Wishing you all the best!

    • Thanks mate! My emotions are all over the place even now, two months out … but I know that’s normal for me. So excited already….

  • You now OWN the word “Freedom”! Congrats!

  • Yaaaay! I’m so happy for you Dave! I know from reading your blog and getting to know you a bit that this is a huge deal for you and I’m so glad that you’ve finally taken the step!

    I am a little sad you are leaving Melbourne when I just got to Sydney but that just means we’ll have to plan something sooner than later… or I can just come to Thailand!

    • Yeah you’re right Annie, it really is a big deal for me … and I think my time in Portland and Vancouver in June really bought that home.

      Hope we can catch up again before I head away … but you’re right, you just need to come to Thailand anyway! 🙂

  • Well done mate, you’ll no doubt have a blast.

  • All I can say is best of luck, man! This is an amazing lifestyle you’re chasing after and I wish you all the success in the world. It sounds like you’ve figured what you want from life, so just go after it all guns blazing and never look back. Not even once.

    • Hey cheers Rob! I’ve just gotta give it a go really … so much more to gain than I have to lose…

  • Congrats, Dave!! You’ll do smashingly, I promise.

  • Julie Robertson @thefairytrails
    6 years ago

    Congrats! I’m going on my first trip overseas in the beginning of October, open-ended as well. It’s terrifying to have no plan, but everything that’s good is scary, right?!?

    I’ll be in SE Asia around December, maybe we’ll cross paths 🙂

    • Everything that is good is *absolutely* scary. That’s how you know it’s good! 🙂

      I’ll be there for sure … kicking around somewhere in Thailand. Most likely Chiang Mai at that point. Stop by and say hi!

  • I’m so excited for you! Here’s hoping everything works out as planned and when it does, please let the rest of us know how to get hold of some freedom as well 🙂

  • It’s so incredibly rewarding – congratulations for taking the leap! My girlfriend and I took the same leap 7 months ago and started living a remote lifestyle. We traveled the world for those 7 months and started our business – a website and marketing company focused on companies that do good in the world. If you’d like to check out our site, it’s Start Somewhere – http://www.start-somewhere.com.

    Best of luck!!

  • Awesome! A ballsy move indeed but I agree that wondering what would have happened is far worse than any outcome that may come from giving it a shot. Best of luck in all your future ventures!

  • Now that’s the freedom based adventurer I wanted to see. You will not regret this day Dave. apart from Thailand being absolutely awesome (Laos is better though) it’s a journey and you are now on it so it’s yours to choose what to do with.

    The Universe will always back you up no matter what. And so will I.
    See you somewhere around the world very soon!

    Congrats

    • I *love* Laos, but it didn’t seem to be the best place to try to knuckle down and do some serious web based work for a few months due to internet speeds in particular. Be sure that I’ll be doing a few border runs there though!

      See you somewhere! 🙂

  • Fantastic, Dave! I completely agree with everything you wrote here, and have no doubts that you’re making the right move. I’ve been location independent since 2004 and I’ll never go back. See you on the road! 🙂

  • You are very brave. Seeking freedom is what made me travel thousand miles from one continent to to anther 15 years ago. The most valuable freedom comes from inside. Hope you find it in your trip.

  • Samanta
    6 years ago

    I just love your life philosophy! This is how everybody should live – in order not to die wondering…

  • I think location independence beats the cubicle any day. BUT you have to be careful that that office on the Mekong(?) doesn’t become a prison of its own…

    Juggling work and travel is something that not a lot of people write about, and it can be challenging, as well as wonderful. That said, I’d not go back.

    • Very true … a prison with a nice view and cheap drinks is still a prison. 😉

      Still, it’s a problem I’d be happy to have right now…

  • Terry Lee
    6 years ago

    Don’t die wondering why…a buddy of mine did this about a year and a half ago. Let’s just say he’s a lot happier now than he was ever at his cube. Met a beautiful girl from Denmark and the rest is almost history. The trek is yours and yours alone. Enjoy the ride!

    Terry

  • Woohoo! Cheers to early November.

  • How amazing for you! I don’t think you’ll ever miss the cubicle! My husband and I and our children made that leap with no income certainty at all 5 years ago to Latin America and after 5 years we realized we were just as stuck as we were in the US. Not under the same things but stuck all the same, stagnant! So be careful this doesn’t happen in Thailand because anyplace you allow yourself to become stagnant is the same as that cubicle more or less:) I will be in Thailand in less then 2 months, hope to see you there!

    • Brave move to take the leap in the first place, and brave move to then realise you were still trapped a few years later. Congrats on figuring it out and doing something about it. See you in Thailand!

  • Hey Dave! We’ll be in Melb Sept 24th and 25th and the wife is sticking around for a conference for a few days after. I probably won’t get a chance to meet up with you then but maybe here in Thailand 🙂 Cheers, Ray (and Nok)

    • Ahh that’s a shame we prob won’t get to meet up … but yeah, as you say, Thailand sounds good instead! Not long to go now … eeek! 🙂

  • Awesome, good on you!! Look forward to following the adventures!

  • Dave,

    This is awesome!

    You have done something many people are afraid to do.

    Cheers,
    Timo

  • I love this post. Actually, I love the story about the marker. I love that you wrote “freedom” on your left wrist. I have a tattoo on my left wrist which symbolizes a bit what freedom would be to me.
    I don’t travel full time and I don’t think a nomadic life with moving around all the time would be for me. However, every trip I take makes me more aware of the fact that I don’t want a “regular” life either. Yes, I want some stability, but I somehow want to create it for myself and not just have it by following the expected path.
    I’m still figuring out what exactly it is that I want to do (and then I still have to convince Boyfriend to do it with me:p), but I’ve got a feeling that I’ll know soon.

    All the best.

    • Full-time travel definitely isn’t the only way to have the freedom that a lot of us crave, that’s for sure. To be honest, for the vast majority of people, it’s not particularly sustainable after a few years — I know that I’m slowing down the longer I do this, and wouldn’t be surprised if I ended up moving towards having a few bases around the world in the future.

      I’ve discovered that what I really needed was the freedom to make choices about where I was, who I was spending time with and what I did for money — but that doesn’t have to mean moving every few days. The things I listed above aren’t all compatible with moving all the time, in any case.

      • “the freedom to make choices about where I was, who I was spending time with and what I did for money” – I think that’s what freedom means for a lot of people. Great way of summing it up.

        Having a few ‘home’ bases around the world sounds pretty good. I also think it’s much more sustainable.

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