“Maybe all one can do is hope to end up with the right regrets” -Arthur Miller

In life, I try to live with as little regrets as possible. My motto Live Gnarly stems directly from this practice — To wake each day and embrace the possibilities, to take every opportunity presented to do something epic, and to overall lead an awesome existence.

But it doesn’t always pan out that way; especially with travel, and especially when you are a complete travel noob.

Trust me, mis-adventures made up the majority of my trip. But that’s what makes it exciting right?

Inevitably after traveling to New Zealand and stepping foot in my first foreign country, living the backpacker lifestyle, and being forced to return home early, I find my self left with some regrets.

And a few far more blaring than my regret of trying Vegemite…

So below you will find a list of my top 5 Travel Regrets, a nifty and reflective blogger game I was tagged in by Rexy Edventures Blog!


Not Scoring a Job In Wellington.

Windy Welly: The capital of New Zealand and by far my favorite city in New Zealand (okay, tied with Napier) also held the biggest roller-coaster of emotions and experiences for me.

Like a mashup of Marilyn Monroe and Beyoncé, I fell in love with the city’s architectural curves and class. Every wall was splashed with gnarly street-art, every corner had a musician playing, a lane called Cuba Street was filled with nifty cafés (bloggers drink your hearts out), and it was always active.


Wellington City


They even had bean-bag chairs in the grass by the harbor to drink beer in the sun.


Chilling in Wellington


Yeah, freakin’ sweet.

This was the city I wanted to work in. To live in.

Except there was one problem. I waited way too damn long to look for a job. It turns out, my first time traveling abroad can be used as an example how NOT to budget correctly.

I suddenly found myself with less than $25 in the city (watch this funny video confessional). For two weeks I illegally guerrilla camped in the woods above the city to survive, and after failed attempts to find work, I took a kiwi fruit packing job hours away that saved my ass.

Regretfully, I was never again to see the city I so dreamed of working in before I left…


Not Exploring more of The South Island.

The South Island is a nearly untouched jewel of New Zealand. With most of the country’s population living in the larger business cities of the North Island, the South Island is left to nature’s ravishing beauty.

Sure, you do have large cities like Christchurch (which was unfortunately ravaged by earthquakes). But the main expanse is covered by rolling hills, awe-inspiring fiords, Milford and Doubtless Sound which are said to be one of the most magical places on the planet, and glistening antarctic glaciers.

(Photo Credit Trey Ratcliff)
(Photo Credit Trey Ratcliff of Stuck in Customs)

Anytime you hear fiords, it’s worth seeing. And there are probably some cute penguins at the glaciers.

Enough said.

Due to a trip doomed from the start, I ended up missing out on the best of the South Island.

After a horribly botched attempt at hitch-hiking, I made it down to Christchurch to pick up a girl from the airport that was coming to see me from the US. We had plans to make it to one of the two famous Sounds, but instead we found ourselves stuck in the city wrestling with our schedules.

By the end of the first week together, the girl that I was quite infatuated with had a sudden change of heart about our relationship. What followed was a month of bickering, arguments, and frustration instead of adventure and exploration.

It was miserable.

Luckily, we did make a quick trip to Queenstown and had a chance to relax in it’s lakeside and mountainous beauty and had a chance to bungie jump again!


Lake Tanake New Zealand.


But after two quick trips to Queenstown and Christchurch, we were back on a bus to the North Island leaving behind what most backpackers raved was a lush and soul changing landscape to be experienced.

I will erase this regret someday and explore it…


Not Hiking the Tongariro Crossing

 “In the East there was a dull red glare under the lowering cloud: it was not the red of dawn. Across the tumbled lands between, the mountains of the Ephel Dúath frowned at them, black and shapeless below where night lay thick and did not pass away, above with jagged tops and edges outlined hard and menacing against the fiery glow.” – J. R. R. Tolkien

The Tongariro Alpine crossing is home to the volcano Tongariro, one of three active volcanoes in New Zealand, and also the range Perter Jackson chose to star as Mordor.


Mount Doom


You can literally hike to Mordor, pretty wicked huh?

And you would think if I passed through this area three times and also had the chance to hike the crossing twice I would have.

The first time I was in Tongariro National Park was on a sponsored Stray Bus Tour around the North Island. Everyone was jabbering about hiking the crossing and passing their Lonely Planet guides around to show everyone who didn’t know just how awesome the place we were headed to was.

Well, when we pulled up and our bus driver chimed over the loudspeaker, “Alright everyone, there is a big chance you cannot hike the crossing today because of the rain” we were all up in arms and looking to chop off heads.

It’s just a little rain right?

Turns out our guide wouldn’t take us. Even when enticed with a bus load of eager travelers willing to dish out $65 each, the guide said the weather conditions change so fast on the crossing that it was too dangerous for even him to hike.

Instead, we did a hike around the base. Beautiful, but nothing compared to the crossing.

Tongariro Fail


The second chance I missed was while I was packing kiwi fruit the small town of Te Puke. A bunch of friends from the factory decided they were going to leave at 4am to drive 3 hours and hike the crossing. By this time it was in deep winter, and I hate the cold, so I decided not to take them up on the offer.

Plus the trip was put together at midnight while they were drunk.

Yes, they returned having seen the beautiful emerald lakes resting in the crater, but they also returned miserable. It was one chilling cold and they were all exhausted and frigid.

(Photo Credit: Aron Teo)
(Photo Credit: Aron Teo)

Oh, and one of their cars broke down and they sat in the freezing cold for 4 hours waiting for a tow, and being in the middle of nowhere, they were forced to pull the car along by a rope attached to the other.

Still, I regret not hiking Mount Doom one of those times…


Not Skydiving in New Zealand.

Slap me in the face; I know I’m a fool.

New Zealand is a country that oozes adrenaline out of every pore; offering up heart-pounding adventure and tonsil rupturing extreme sports even in the most remote areas.

Throughout my trip I found myself shooting over the highest legally raft-able waterfall in the world, absailing into caverns hundreds of feet below ground, and leaping off bridges with a bungie cord strapped to my ankles (twice.)

Bungy Jumping Taupo

So how the hell did I miss my chance to jump out of the plane over one of the most stunning skydive destinations in the world?!

Idiocy. Well, mainly a busted budget. But that’s linked to idiocy.

I was even hired to write an article pretending to be a hostel’s camel mascot that went skydiving. Yes, I got to take photographs of a plastic camel in a plane, but never got to go myself.

Camels can Fly


In the middle of my trip I was suddenly hit with a brick in the face, which is a fitting analogy for completely running out money. This led me to working in a kiwi packing factory for 3 months instead.

I was even in talks with a guy I became good friends with that ran Auckland Skydive and said he wanted to toss me out of a plane REALLY bad, and I was totally down, but it never panned out.

This is one I may regret forever…


Not Staying the Full Year.

You only get a year-long Visa in New Zealand once in a lifetime.

I left at a mere 8 months in, cutting that once in a lifetime chance by a third.

After 8 months of being in the country, I realized travel was definitely the lifestyle I want to live. The last three months of that time had been spent packing kiwi fruit in a factory and had given me plenty of time to reflect.

I want to travel longterm. But I was not ready yet.

Sure, I had changed drastically as a person and realized this was my dream, but I was not yet the person that could do this long-term.

Before I sold all of my belongings, quit my job, and left for New Zealand, I had just ended a 2 1/2 year-long court case from a drunk driver that hit me. They crippled my car, crippled my credit, and I received barely any compensation for the destruction they had caused on my life.

Instead of paying off the debt from my medical bills, I used the winnings to buy my ticket to New Zealand without much forward planning.

Adventures that start like that are stellar, but I was still haunted by my debt. It was time to take care of that anchor that dragged me down once and for all so I could travel worry free. So I returned back to the United States and work two jobs currently to tackle this task before my big planned trip this May.

I can’t say I don’t regret leaving New Zealand, because I do, but it was what I needed to do at the time.

“There are no regrets in life, just lessons” – Jennifer Anniston

Wew, Jennifer Anniston isn’t just a hottie, but she nailed it on the head. As much as travelers and people chasing their dreams try to live a regret free life, it WILL happen.

You will have regrets. You will wish you had done something you missed out on. That’s life. But instead of dwelling on them, take them as life lessons learned.

And I learned PLENTY of lessons on my first adventure abroad.

One day I will return to the Land of the Long White Cloud to do what I regretfully missed, but until then I am tasked with crushing my debt, buying my mother her gravestone, and saving for an epic adventure in May!

Please, share your travel regrets and lessons learned below!

Now time to tag 3 of my favorite bloggers for the game!

Kathy at Live The Fine Life (view blog) (Twitter @LivetheFineLife)

Lyn at Lyn Midnight Blog (view blog) (Twitter @LynMidnight)

Taryn at Wanderista (view blog) (Twitter @Wanderista)


  1. Kenin Bassart January 10, 2013 at 2:38 pm

    Nicely done post! I didn’t realize you only get the chance to have a 1-YR visa once to NZ! That sounds crazy to me, I’ll have to remember that when we make plans for that corner of the earth.

    1. JustChuckinIt - Site Author January 11, 2013 at 1:24 am

      Definitely make sure it is the right time for you Kenin, a 1 year visa in NZ is not something you wold want to waste! You can always go for three months at a time, but if you really want to experience the culture and maybe work, save the year-long visa until you can stay the whole time!

  2. Natalia January 10, 2013 at 3:39 pm

    I would have been miserable camping on the woods!!! Well, all these experiences make for a good story. I am sure your next trip will be perfect. I enjoyed reading about New Zealand…. on my bucket list now!

    1. JustChuckinIt - Site Author January 11, 2013 at 1:26 am

      Natalia, glad I helped add another items to be knocked off! New Zealand should be on everyone’s bucket list. And as much as running out of money sucked, the part about living in the woods as a last ditch survival tactic was actually quite amazing. One of my fondest memories actually 🙂

      Welcome to my blog and thanks for the comment!

  3. Kate - CanuckiwiKate January 10, 2013 at 4:12 pm

    I can completely sympathize with the Tongariro Crossing – I got up and left Taupo by 6am to do it in July ’09, on a stunning cloudless sunny morning. I forget just how far along we were, when the weather turned so quickly, suddenly visibility was limited to a mere few feet in front of us and the guide made us turn around (thank goodness because I was hating scaling the side of a snowing mountain!) we had to slide down the newly icy slopes to get back home, and we didn’t get to see the famous emerald lakes. Alas, the Crossing is still on my list. If I’m back in NZ when you return, we should make a mission together!

    1. JustChuckinIt - Site Author January 11, 2013 at 9:32 pm

      Ah Kate, what a tease that must have been! I always hear it changes so fast there, and with the loose soot and dangerous drops, I guess weather must be perfect. Yes, I agree, when I return to New Zealand we should definitely hike the crossing together!

  4. Lyn Midnight January 10, 2013 at 4:13 pm

    1. Where are you going in May? 2. Thanks for tagging me! 3. OMG, Wellington sounds like the place for me! I can never stay away from artsy places and I dream of living in a place like this one day. 4. Ah, I’m such a lousy traveler, I’ve yet to bunjee jump. I’m not very sporty, so no hiking or cave-diving, BUT I do like adrenaline rushes. I’m alive, aren’t I? 😀

    And wow, can I say that your decision to use the court money to just jump on a plane and go to NZ is like the most kick-ass thing I ever heard. And I’ve heard a lot of kick-ass things. Well done. Keep chucking!

    1. JustChuckinIt - Site Author January 11, 2013 at 1:30 am

      In May I should be headed out on an epic bicycle trip across the USA Lyn! Well, depending on if I go to TBEX this year (which I plan to) it may be pushed back two weeks, but it is a definite thing that will happen!

      I was happy to tag you, I can’t wait to read some, you were one of the first to come to mind. I know you and I are all about the good mojo and vibes, but I feel everyone has some sort of interesting travel regrets.

      And thank you for the rad compliment! I was pretty proud of my rebellious act, and I would NEVER go back and change my decision. But it was the cause of my trip being shortened, so just another lesson learned!

  5. Kristin of Be My Travel Mues January 11, 2013 at 11:47 am

    It’s cool, just find a Kiwi to marry and the whole year-visa thing is a non-issue! BOOM I’m a genius… and so modest.

    1. JustChuckinIt - Site Author January 11, 2013 at 8:34 pm

      Boom! you are Kristen. Now to set up my grand plan of finding a kiwi lass.

  6. Lilian January 12, 2013 at 8:48 am

    I can relate to this so much – I also ended up broke in Australia, left earlier than I could have, but while there I realised that travelling was what I wanted to do. Don’t worry we all have regrets and things we wished we could have done differently. I know I do! The most important thing is to learn from them and as you said tat’s life 🙂

    1. JustChuckinIt - Site Author January 13, 2013 at 8:46 am

      Good outlook Lillian, so are you working toward another trip or are you already back to traveling? I wanted to make it to Australia as well…I’m thinking I’ll make it in the next few years.

    2. Lilian January 22, 2013 at 6:53 pm

      This week I will be applying for a working holiday visa to Canada – just waiting for the visa program to open. As soon as it’s apporved I’ll be on a plane to Canada! If for some reason it doesn’t get approved I’ll head back down under, but to New Zealand. It’s all a bit up in the air at the minute, but I hope to get back travelling very soon.
      If you get a chance to go to Australia go, it’s beautiful, expensive, but beautiful 🙂

      1. JustChuckinIt - Site Author February 6, 2013 at 12:53 pm

        Totally awesome Lilian! So excited for you and I hope you get accepted to Canada! Either way, your fall back to New Zealand ain’t too shabby either 🙂 And if I am in Australia at the same time we’ll definitely need to catch up!

  7. Koren @ City Gal January 13, 2013 at 10:18 pm

    The new site looks great! And I try never to have regrets 😉 Life is too short!

    1. JustChuckinIt - Site Author January 15, 2013 at 2:55 pm

      Cheers for the compliment Koren, glad you dig it! And I try to with without regret as much as possible.

  8. Adventurous Andrea January 13, 2013 at 11:03 pm

    No joke, your photos have made me want to visit New Zealand. Well, I’ve always wanted to visit, but now it’s up among my top countries!

    I’m curious as to why you chose it.

    1. JustChuckinIt - Site Author January 15, 2013 at 2:58 pm

      Glad to build the interest in such an amazing country. I chose New Zealand for a few reason that I’ll be writing a post about, but here are a couple:
      -Easy acquiring a Visa
      -A fresh young country to symbolize my fresh start
      -Friends had been and described just how beautiful it was, and I got hooked.

      Thanks for the compliment!

  9. Taryn January 14, 2013 at 2:33 am

    Awesome post; I have so much respect for your dedication to do it the right way this time–it will all be worth it soon!

    And I’m psyched to be tagged in this post–thank you. I’m totally struck by the Arthur Miller quote as I work on my own regrets. I’m also amazed at how scared I am of potential future regret (the idea of, if I don’t do this *will* I regret it?) in comparison to how little I actually ever do regret.

    Anyways, thanks for sharing! xxo

    1. JustChuckinIt - Site Author January 15, 2013 at 3:00 pm

      Oh trust me Taryn, I am ALWAYS thinking about “what if” and I think it is programmed into us to worry. But you just have to learn to turn that off or ignore it and fillies your heart.

  10. Scarlett January 16, 2013 at 9:09 am

    Ryan I absolutely LOVE the new site – it looks amazing. Travel regrets suck… but at least you have a reason to return to places xx

    1. JustChuckinIt - Site Author January 21, 2013 at 11:12 pm

      Thanks Scarlett! And that is an awesome way to view the regrets as well, I’ll definitely be back someday.

  11. Si January 17, 2013 at 9:24 pm

    I’m so stoked that the little blogging game I started back in December has made it this far! I mean I was – and still am – a big fan of your blog when I was just getting into the travel blogging game a year ago, and now you’re participating in something that I started! Haha. It’s a proud moment. As for your regrets, I was born-and-raised in NZ and still I’ve never hiked the Tongariro Crossing. I am hugely regretful of that fact!

    1. JustChuckinIt - Site Author January 21, 2013 at 11:14 pm

      Yikes mate! Born and raised there and have never done it?? Gotta’ get in that like me! I’m glad you still dig my blog and I’m hoping to really ramp up the writing as well, so wild that this is a game you started!

  12. Annie January 30, 2013 at 12:29 am

    Hi Ryan, I didn’t wish you a happy new year, full of dreams and expectations leading to adventures, as yet unimagined.
    I’ll be following you quietly, maybe even stalking you (to the uninitiated) and wishing you all that is good.
    Be safe, Annie

    1. JustChuckinIt - Site Author February 6, 2013 at 12:50 pm

      Thank you so much Annie!

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  14. The Nomadi Nepali June 2, 2013 at 9:07 am

    Nice to go through this wonderful article. All nice things remember and plan your trip wisely.
    Happy Travellig..:)

    1. JustChuckinIt - Site Author June 8, 2013 at 12:16 pm

      Yeah, I learned a few things about not planning enough. It’s always good to be open, but to plan accordingly as well.

  15. eemusings August 21, 2013 at 4:45 am

    Hey now, 8 months is not a shoddy amount of time in NZ!

    Wellington is fab, and everywhere in the South is stunning (if it weren’t so expensive, I wouldn’t mind living in Q-town for a little while). Shame you missed out on skydiving, especially as it’s fairly cheap in NZ. I did it once and while I wouldn’t do it again, it was definitely a once in a lifetime thing.

    The Tongariro crossing is something I kinda want to do – maybe I’ll eventually get around to it. The problem with tramping in NZ is the weather is so temperamental.

    I’m almost homesick now 🙂

    1. JustChuckinIt - Site Author August 21, 2013 at 10:44 pm

      Haha, sorry to make you Homesick! I have Farsickness for New Zealand right now. Yeah, 8 months was stellar, trust me, but there was just much more I want led to do. Oh well, next time!

  16. lena yim December 27, 2013 at 2:25 pm

    Hi! Your site is great! I backpacked New Zealand with a kiwi friend last summer as well and I’d love to go back. How did you get your year visa/what kind of visa was it?

    1. JustChuckinIt - Site Author December 28, 2013 at 5:19 am

      Hey Lena,
      So stoked to read you got to explore NZ! Loved my time there as well. You can apply at the New Zealand Embassy, or I went through a company called BUNAC which took care of everything and helped with Job placement. Good luck!


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