Drive      Fly      Stay      Login    Signup

San Diego

General Travel

Advice or words of comfort on quitting your job to travel full time?

My boyfriend and I are quitting our jobs to travel full time for a few years, but it's scary to leave our comfort zone and decent paying jobs. We have a strong desire to break out of our 9am-5pm routines and travel, but I was hoping for any advice or words of comfort. Any regrets you've had? We are both in our 20's and feel like this is a risk we should take before settling down, but still.. it's a little scary to leave everything we know. We just can't fight the feeling of needing to get out there and see the world. I would love to hear your story to inspire us. 

23 Answers

top answer by
Carolann from Around The World

First, let me congratulate you because it is not easy and it is definitely a scary thing to do.

We quit our jobs in August of 2014, sold pretty much everything we had and flew out to SE Asia in September with no plans on a return date.

It was beyond scary, we were torn between doing what we thought was best for us and what was the status quo for the people and society around us (working 9-5, saving for a house, etc etc) but it was the BEST thing we've ever done and there have been absolutely no regrets.

I don't know if there's anything we could say that will completely calm the disquiet about doing something that seems so contrary to what the vast majority of people are doing. Leaving a comfort zone is scary no matter what. It won't go away until you get to that first destination.

But the one thing we repeated over to ourselves frequently and got us through handing in our resignations, our notice to our landlord, both of our garage sales and sorting out to donate the rest of our stuff, was this:

The worst thing that can happen is that we end up back where we started - at home, with a 9-5 job - and that's a pretty darn good worst thing to happen! 

There is a world of opportunity out there and you'll see it more and more as you travel. You don't have to worry about what you are leaving behind because a. it will be there when you get back and b. there's an innumerable amount of experiences, opportunities and memories ahead.

We also grew as a couple - something we didn't think we could do anymore of! We were already best friends and spent pretty much all our time together outside of work. Travel with someone, 24/7, is a completely different situation. It isn't always easy and it takes patience and time but we've learned more about each other, how each other thinks and our idiosyncrasies. We really do understand each other better than we could have thought or expected.

You'll learn quick each others' travel styles. For example, we now know that we get pretty grumpy if we're hungry for too long and if you add tiredness and hot weather, it's a nasty combination - especially for Macrae. :) We keep some snacks on hand for that reason but we also can joke about our "hangry-ness" now.

Some things we learned during the process:

1. Some people will support you but some will be upset that you are leaving and most will not understand why - it's okay. Remember it is about the two of you and what's going to make you happy. There are lots of us out there who have done exactly what you want to do - some for a year, some for longer - I've never heard of a single regret yet.

2. Communicate. It's a rule for all relationships but when you spend so much time with someone, the good, the bad and the ugly definitely come out and communication becomes more important than ever. We've worked at understanding each others' feelings and needs during this and keeping communication open and honest. We are really all each other has while travelling which, while it sounds scary, can be an amazing feeling.

3. Be open. Like I mentioned, there's a world of opportunity out there. New people to meet, new things to see and a lot of the best experiences happen unexpectedly. Be open and be open together.

4. It's not always going to be easy. Don't get me wrong, i wouldn't change it for the world and i've never looked back, but that doesn't mean it's all sunshine and roses. But we find the hard times here don't even come close to comparing to the hard times at work or back home. Now they are little bumps in the road we have to work through together. We do miss people back home, financial worries can pop up sometimes (I think it's a vestige of life back home where finances are a focus), we've gotten miserably sick together, etc. But like I said, the worst times now aren't really that bad and the good times far outnumber the bad. (note: when we got sick, we were in Thailand, able to work out our illness lying on a beach with 30 degree weather and amazing sunsets ..... poor us, huh?)

5. The skills you learn through this process of leaving home and travelling abroad are skills that will help you throughout life AND they can translate to skills you can use on a resume ;) 

We sometimes still can't believe what we are doing. It seems so surreal and amazing and we are loving every moment of our lives.

If you have any questions at all - anything you'd like to ask, or any suggestions, travel or otherwise, you'd like us to make please feel free to contact us! We would be happy to answer any and all questions - no matter how big or small they seem! 

Good luck to you! You're starting on an amazing journey and an unforgettable experience!!

31 thankscomments (1)

answered first by
Christopher from Melbourne

I've been a digital nomad for a couple of years now in one form or another and can say without a doubt that it changed me for the better.

Was it scary? Yes. Sometimes it still is. But life isn't supposed to be perfect and I'd rather be freaked out in the middle of nowhere with no plan of escape than be sitting on the couch watching late night TV whilst my ass expands on sugary treats.

Any regrets? One. I should have done this 10 or even 15 years earlier. I'm 35 and I'm not ready to stop.

The fear of leaving everything behind will haunt you till the day you leave. So you'd better leave sooner to lessen that fear.

Hey, even if this lifestyle turns out to be incompatible with you, no major loss. You're on this planet for 100 or so years. Spending a year doing something different and failing is going to be a lot shorter than spending a decade or two wondering what it would have been like if you did it.

13 thankscomments (1)

answered by
Courtney from Los Angeles

Hey, Nina,

Wow, do I remember that feeling and boy do I understand it. I moved to Paris for a while when I was 22. This was way before the Internet really existed for most of us so the process of figuring how to do this was a giant hornet's nest. It was really, really tough back then to make arrangements or even get advice so I really went in blind so-to-speak.  

I arrived in the city on June 26th,19I'mnottelling on a one-way ticket with a place to stay for just four days, mediocre classroom French and not nearly enough money to sustain me for as long as I was staying (I didn't even have the sense to bring a map or an umbrella). I was literally shaking when I got on the plane and it turned out to be, absolutely, 100%, without a doubt, the single smartest thing I've ever done in my life. 

I think the key to doing this is knowing that while many, many people have given it all up to travel, not a single solitary one of them ever did it mistake-free. If I had a dollar for every mistake I made, especially in my first month or two, I'd be filthy rich. I got lost, I got ripped off, I misread train schedules, I didn't anticipate how much things would cost, I didn't bring the right clothes, etc., etc., etc. But after a while, you just get kind of...better. And gutsier. And much, much more forgiving of yourself. You stop thinking about the adventure you planned to have and start focusing on the adventure you are having

I don't know what you and your boyfriend do or how you feel about your jobs, but I can tell you this:

At no point in your life--not in your 30s, not in your 40s, not in your 90s--will you ever once say to yourselves, "Wow, we were so stupid to give up those replaceable jobs during the one time of our lives when we really had the time and freedom to have an adventure and experience and learn things we couldn't possibly have experienced or learned otherwise. If only we'd stayed right where we were we could still be there." 

You'll screw up, get frustrated with each other, want to give up...all kinds of things will happen if you go but that is one thing that won't.

So GO! Have a blast!!!! And make sure you tell us all about it!!!!!

8 thanks

answered by
Spencer from Los Angeles

I did the same nearly five years ago. It was following the loss of my father, followed by the loss of my dream job, and then the final trick, a divorce. Set off on a life of living and working somewhat nomadically and I've been doing so ever since. 

Mind you, I now call Los Angeles home and absolutely love it, but it was by far the best thing I've ever done. But that does it mean it wasn't scary as hell. It's still scary as hell, but I've always said that the greatest risk in life is to risk nothing at all. I'd rather be sitting at the end of my life saying that I risked, adventured, and packed too much into this life, then say that I wish I would stayed in an office longer. 

I really don't have any regrets. Some people say that traveling and living abroad for a year like I did would have inhibited my future work and relationships, when I say it actually accelerated it. I've had opportunities and done work that I don't think I would've had if it wasn't for the drive and ambition that resulted from traveling like I did. 

In the words of Kerouac, "Live, travel, adventure, bless, and don't be sorry.....and climb that damn mountain."

8 thanks

answered by

You only live once! I used to work in PR in Atlanta and went on a trip to Croatia for my 30th birthday that changed my life. While I was there, I realized I didn't like my job/career and wasn't happy with the path I was in. I took a seven month trip backing through Europe and blogged about it. Then, when I returned, I moved back to a place I had previously lived, Las Vegas, and started to work part-time in PR. I knew when I was there, it wasn't my resting spot. I took another trip, this time to Chiang Mai to volunteer with elephants at Elephant Nature Park, and ended up going back there to do their PR and social media. Now, I live in Madrid and am getting my TEFL so I can work anywhere in the world. You never know what opportunities exist for you outside of your comfort zone. You just have to actually get out of your comfort zone ... then the whole world and opportunities open up to you. 

I've written a lot about my work and my travels on my blog, if you want to check it out and get some more inspiration! Here's a post I think you will like to motivate you to go!

5 thanks

answered by
Brenda from Long Beach

I can only express to you the disappointment of being on the other end not having gone and tried it. My greatest regret in life is that I did not begin to travel when I was young. That I didn't literally take the road less travelled before I was too entrenched in a mortgage and possessions to explore the world. Now I am locked in, 10 years away from retirement, and saving like a fiend so I can go out by that date and see the world unfettered by other commitments. 


Right now, I get one month a year to go and see and be free. Had I taken the leap when I was younger, I would probably have children and be living in Spain. Instead, I went to law school and now work as a prosecutor, doing the government shuffle. At a certain point you become like a zoo animal, watered and fed every two weeks. I agree with what everyone has said. There is so much more to life and living and the opportunities that you will create will only be limited by your imagination and experiences

4 thankscomments (3)

answered by
Björn from Munich

Best decision! Haven`t done it myself (yet) but can recommend you two very nice books which will support your idea and might give some inspiration:

Henry David Thoreau - Walden

Rolf Potts - Vagabonding

Cheers from Munich


3 thanks

answered by
Bryan from Raleigh

When my girlfriend (now wife) and I traveled long-term for the first time, we too were a little scared. Our only regret in the end was that our trip was too short. We never should have come home! Many more trips followed....

Ultimately, you will not just learn about the places you visit and the diversity of the world, but you will also learn so much about yourself. You will learn how to accomplish your goals. You will learn how to handle stress and pressure. You will learn that you can live in many different ways without the luxuries we are familiar with. You will learn that there are other life goals and career opportunities out there other than the path that our society tells you to follow.

In the end, the only thing you are really risking is money, but you can always earn money later.

Do it!

3 thanks

answered by
Cassandra from Long Island (New York)

HI Nina,

It seems you have some great advice below! Some extra added advice: write about your travels & document everything through Instagram!

There is a such a connection on the social media world to others just like you--it would be awesome for you to have that support!

Good luck :)

3 thanks

answered by
Will from On The Road

Hi Nina,

I am re-posting an answer I wrote in another discussion thread on Trippy, because I think it is very relevant to your question:

For me working online has been key. Much of the last ten years I have been able to see the world while also keeping a steady income through remote work. With such a set up there are really no limits to how far or how long one can travel for.

I think the most suitable jobs for full-time travellers (regardless of whether they work for others or for themselves) are those that offer the maximum flexibility and require only a laptop and an internet connection point – where deliverables and paychecks can all be submitted online. Examples include the creation of website content, editing reports, handling graphic design assignments, computer programming, selling products on eBay, stock trading, translations, digital film editing, and freelance and/or journalistic writing.

Other ideas on how to fund one's travels can be found at and

I hope that helps! :-)

3 thanks

answered by
Gina from Minneapolis

Nina, I haven't done it, but based on my experiences, I have to urge you to go do it. At this point, my husband and I can't pick up and go, as much as we would like to (really, it's just the fact that we have older dogs and it would kill us to leave them). 

Remember that it's going to be hard sometimes, because literally everything is. Even the things you love are hard. As Mark Manson said, you have to find your favorite flavor of s*$% sandwich—you're going to have to eat s*$% at some point, so make it something you can tolerate. If you can stomach a travel s*$% sandwich, then that's your answer.

The thing is this: if travel is your passion, this urge is not going to leave you. It only intensifies and making it happen only becomes more complicated as you get older and entrenched in work and so on. You've got an extraordinary opportunity—go!

3 thankscomments (1)

answered by
Anna from Los Angeles

If things go well, you won't have regrets. If things don't go well, you may have regrets. But the risk is worth taking.

Traveling, besides being fun, will help with your creative problem solving skills. You'll see new ways of solving familiar problems. And that drives innovation. Getting away from your day to day will remove you from the details of your life in the comfort zone and give you distance to see your life differently. With the details gone, you'll get a better overview / be able to think more abstractly about issues/life at "home". --These things have been studied and proven. So note that travel will improve how you navigate the world.

But the world won't wait for you to get back. It'll keep on moving along. So I recommend making something out of your travels that could help your job search later on. Write a blog. Share insights. Use it to market your dream selves. Think (and feel free to think big) about what you want to get out of your travels and write with that intent when blogging about it. This could create a new career path or elevate the one you're on. You'll definitely stand out as people who take action to grow and pursue dreams.

3 thanks

answered by
Rocio from Costa Rica

After reading Carolann Hughes advices...not much to add but to wish you the best. Enjoy the ride!!!

3 thanks

answered by
Vit from Marrakech

You know what Nina!? The level of your commitment to long term travel is determined by what you really do! 

I was f*cking scared but I did it anyway. You will also if you really want it!

Wish you good luck !!!!!!

2 thanks

answered by
Hazel from Port St. Lucie

My son traveled the world at 23-27. He was working 16 hour days. On the phone late and early to manage time zones to meet customer needs. Made all his travel arrangements. So if you feel so strongly choose a career that involves travel. People are leaving out the expenses. Plus the dangers. You are not planning for problems you may encounter. I always read the FBI travel problems websites. You have to carry your own pharmacy.

2 thankscomments (3)

answered by

Well, I've travelled a few times over the years (mainly Europe). I lived in Germany & UK for periods of time. From My experience in extended travel-living there. It has been my experience that there are always good and bad people, Mainly good. I have found it has always been helpful to learn a bit of the language of where I plan to go. I speak broken German and My S/O speaks broken Italian. It can be more problematic with multiple countries involved. I once found myself in Poland speaking German to a Polish man at a festival we wandered a crossed in Our travels. I usually make a goal of learning at least 12-15 words for each country I go to. Like someone said earlier. With cellphones & internet, this is much easier. I once found myself in Lvov, Ukraine with a friend from Kiev. Proublem was. In Kiev they speak Russian, Lvov they speak Ukrainian. The cafe had internet, so I used a translator app. Quick, fairly inexpensive (price of a coffee & tasty borsch) and easy. I found that blending in with the locals. I find inexpensive places to stay, eat or see. Eastern Europe was by far less expensive than Western Europe, Northern Europe-Scandinavia were most expensive. When I was in Budapest, a Friend recommended a buffet. For $5 I got all the tasty food I could eat. In Prague I ran into a Gentleman who owned a taxi service. He gave Me His card and anytime I wanted a taxi. I called and He had one sent. I had a shop owner give Me clothing discounts, CD's as gifts. I think also part of it is attitude. I am always super stoked to be there. I like to talk to and interact with locals. Do what they do. I've made Friends sometimes before I left with people in places I plan to go to. My Friend in Kiev I made before over a common love of similar music. I made my friends in Budapest over love of motorcycles. My Friends in Canada over passion about Reptiles. I look for things in common and go from there. I don't worry to much about tomorrow, if I'm alright today. Everything up to this point had always worked out:)

2 thanks

answered by
Suzanne from Tarifa

"If you think adventure is dangerous, try routine. It is lethal."- Paolo Coelho

Go do it! What's the worse that can happen? Maybe that you have to go back to you 'comfort' life. 

I've been slow travelling around the world for 10 years now and I cannot imagine 'going back' to conventional life, whatever that is these days... The number 1 most asked question I receive, is how do I finance all this? First of all, my lifestyle is at a considerable lower cost than the average person who asks me this question. I choose to live with little to gain more freedom to explore. I value time way more than money. This requires some creativity, proactivity, and adaptation efforts. But it's soo worth it!

I wrote a blogpost exactly about this. Maybe it helps you to go on that road/flight/boat/canoe:) Check it out and let me know which destination is gonna be the first:) Dreams are meant to be pursued, not postponed.

Have a great adventure!

2 thanks

answered by

I know your worries too well. I thought about quitting my job for over a year but finally did it and haven't regretted it since. I wrote about finding courage and following my heart here: Maybe this gives you some motivation. After six months on the road, I haven't regretted one day and wrote something about my life and learnings here: If you need any tips on long-term travel, you find a lot of advice about preparation and potential problems on my blog as well.

I can only recommend you to get out of your comfort zone. You won't regret it, even though you won't like it, you will learn a lot and simply will know that this life isn't for you. And if it is for you: Lucky you. Then you made it. Because it's always better to try something and fail than dreaming about it, not doing it and in the end regretting it all your life. 

2 thanks

answered by
Elissa from Pittsburgh

Not much to add on my end.... But as a 54year old I would say DO IT now!  I wish I had the nerve to have done it when I was your age.  Life is too short and looking back you may regret it. 

1 thanks

answered by

I left a job I was miserable at to do the same thing. It changed my life and my way of looking at what I "need" to live. I once thought I needed money, but that experience, when I was back, showed me that freedom and flexibility were more valuable to me.

I've never gone back to the 9 to 5 job, and I'm much, much happier than I was. You may realize that you need stability more than flexibility, and that's fine, too. Whatever happens, you will learn a lot about yourself and about the world, and those are very worthy lessons.

The one piece of advice I would give is to have a plan for how you will account for the blank in your work history if you do decide to return to full time work afterward. Can you research something you'd like to write a book about? Gather cultural information? Learn languages? All these are good reasons to stop working in the traditional sense.

1 thanks

answered by
Edna from Paris

I've been living and working abroad for seven years -- I left home at 18 to move across the world -- and last month I quit my well-paying, career-building job to travel full time.

I wrote about my decision here:

Carolann's answers are spot on, I'd just have to add that ultimately it came down to taking advantage of my youth while I had it, and the lack of responsbilities (e.g. a car, mortgage, kids, etc), not to mention the possible career opportunities that may come from this while I'm still in my 20s.

I've never for a single moment regretted moving abroad at 18, and I don't think I'll regret this either. Besides, isn't it better to know and experience than to look back and wonder, what if?

answered by
Pawan from Delhi

Nothing much to say, but just this that if you find adventure risky than routine is lethal. As far as regret is concerned, i think you will regret more if you wont do it.

answered by

Dont quit, be practical, you dont know what will come ahead in life. make 3-4 small holidays every year and find a more fulfilling careers. rest is up to u.

© 2018   ·   View: Full | Mobile

Follow us:        
Questions   ·   Destinations   ·   Drive   ·   Fly   ·   Airports   ·   Stay   ·   Search

Login   ·   FAQ   ·   About   ·   Feedback   ·   Privacy   ·   Terms