Will I Regret Quitting My Job to Travel?

Last Updated on February 29, 2024 by Eric Cantu

Have you ever asked yourself, “Will I regret quitting my job to travel?” Is it even possible? Will I be able to make it without that safety net? Is it possible to work and travel at the same time?

Let’s consider everything necessary so that you can make the best decision to satisfy your thirst for travel.

Will I Regret Quitting My Job to Travel?

The answer very well may be yes and no. Will you lose some of the comforts of home? Yes. Will you lose that security blanket you’re so used to living under? Yes. But, if you’ve prepared yourself, could you have the adventure of a lifetime? I say yes!

How prepared are you to drop everything? Have you considered the types of jobs (yes JOBS) you’d have to land? How easy would they be to find? And finally, WILL YOU BE HAPPY?

Facing Your Fears

Let’s face it. Quitting your job to travel is a scary proposition. It’s extremely important to consider the pros and cons of quitting your job to travel. Justfaceingsunsets.com listed the following factors to consider when quitting your job to travel:

• Home ownership
• Finances
• Retirement accounts
• Health Insurance
• Pets

If you own a home are you prepared to sell it? How about renting it out?

Obviously, you need to be in a comfortable space with your finances if you’re thinking about quitting your job. But remember, when you travel, you still need to be responsible and save money for when things go wrong.

What about your retirement accounts? What happens to them when you quit? Will you get some or all of it back? Will you need to keep paying into them to collect later? Will your health insurance premiums go up when you quit your job? Will you be able to keep it?

And if you have pets like I do, you REALLY NEED TO STOP AND CONSIDER WHAT’S GOING TO HAPPEN WITH THEM. Can you take them with you? Do you have a loved one who can take them?

Workaway.info also shares the importance of setting a realistic budget (no, you can’t survive on $2/day), making sure you have travel insurance to protect all your stuff, and HAVING ENOUGH MONEY FOR A RETURN TICKET!

How’s that for a slap in the face of reality? We romanticize the idea of living a carefree, endlessly fulfilling life seeing the most amazing sights and experiencing each day to its fullest, but you need to consider if it’s realistic for you.

Have people dropped everything before and survived, and even thrived doing it? Yes. But have people also tried and failed miserably and thought to themself, “What was I THINKING?” afterward? Yes.

And while it’s possible that you’re considering quitting your job to travel with a partner, chances are that more than likely this is a solo mission. Solo travel isn’t for everyone. Some get anxious even thinking about it.

Do you have kids? A family? A significant other who would laugh if you threw this question out there? Or are you living a life that you can cut free from at any moment, with nothing tying you down?

How old are you? It’s one thing to quit your job and travel in your 20s, but what about if you’re older? True, the older you get the more stubborn you become, but you have to face reality that traveling the world long term is much easier for someone in their prime than for someone in their late 30s.

Would it be possible to maybe quit your job and travel for 3 months? How about quitting your job to travel for 6 months? These are the kinds of realities you have to first consider.

You don’t want to make a huge decision like this without considering the consequences of your actions. It’s all about weighing the feelings of “can I actually do this” against the feelings of “how will I feel if I don’t at least try”.

Are You Happy? Is Traveling the Answer?

And now for maybe what I feel is the most important question: “Are you happy?” A user on Quora.com in the thread “Does Anyone Regret Leaving Their Job For Traveling” related the following with regards to dropping everything to travel:

My take is, life is a journey. Travel is a journey. It’s all about choices. If you make a choice you better stand by that choice and hope that choice is the one that made you happy. I’ve seen too many people making the safe choice (security) over the riskier choice (happy one) and be miserable later.

Adonis Villanueva via Quora.com “Does Anyone Regret Leaving Their Job For Traveling”

How true is that! Sometimes we just want to escape, try something new, get busy doing something we’ve never done before.

I can tell you first hand as someone who got busy traveling and went to 24 countries in 3 years prior to covid hitting, traveling is INCREDIBLE! Check out my adventures on instagram! But if you’re not happy with yourself, at your core, traveling won’t magically solve all your problems.

Trisha from psimonmyway.com actually shares how she regrets quitting her job to travel. She even took the time to take back advice she had given to her readers.

So if you’re someone who is considering leaving your job and everything behind to travel long term, it needs to be because of a passion inside you, an undeniable urge you have to explore, see this world, live freely, feel alive… not to just escape a bad situation.

That being said, if the regret of failing isn’t nearly as harsh as the regret of not trying, then it’s time to start considering how you’re going to survive on this adventure.

How Will You Survive Once You Quit?

While you travel, you’re going to have to put food on the table. And let’s not fool ourselves, it’s inevitable that feelings of “Oh my god what have I done?!” are going to sink in.

Practicalwanderlust.com put it this way:

The minute your plane actually lands, excitement will give way to immediate terror and regret.

Quitting Your Job to Go Travel

So let’s be practical, shall we? Let’s put our daydreams aside for 2 seconds and consider how to make money while you travel.

This list contains some of the most popular jobs that allow you to travel the world.

Some on this list are more long term than others, and you may think to yourself, “Why would I trade my current job just to land into another one?” But remember, we live in REALITY right? You need to make MONEY!

Let’s start with jobs that are more conservative and work our way to living a life with nothing to tie you down.

1. English Teacher Abroad

Ease of attaining: Not difficult, but may take time for some
Pay: $2000 – $3000 per month

One of the most popular and sought after jobs that you can travel with is being a professional English teacher. English teachers are very sought after all over the world.

And you don’t have to be a Shakespearean expert in the language either. A basic knowledge and understanding plus a couple of credentials along with a college degree can be all you need.

You speaky the English? Yes? You’re hired!

You think I’m joking? Surprisingly, as related by one of my readers in the comments section below this article, his interview basically took as long as that sentence took to type:

You speaky the English was more or less all I had to listen to at an interview with Thai school staff. Being presentably dressed and well mannered also help a great deal. They’re not keen on teachers with tattoos here, so if you have any, keep them covered up.”

– (read the original comment left by James in the comments section below the post).

As I mentioned, you do need a college degree and a TEFL certification (Teaching English as a Foreign Language). But if you can acquire those and are ready to travel, the pay isn’t bad.

You normally even get your accommodations taken care of, too. While the TEFL isn’t too hard to get, the degree will take time if you don’t have one already. Hit the books for a couple of years and enjoy very rewarding career and the travel that comes with it.

2. Flight Attendant

Ease of attaining: Training & lots of patience needed
Pay: $1000 – $4000 per month

I’ve been on many, many flights and witnessed many, many passengers doing things that irritated me beyond all belief. Customer service isn’t always fun.

But you know what is? Constantly flying around the world, checking out the nightlife in seemingly limitless cities, taking in all the different cultures, free travel for you and your family, and of course, the view out the window from working above the clouds!

Did I mention the free travel? I did? Ok good.

All those perks are needed because customer service in a confined space with cranky passengers can be VERY difficult. The training can be grueling, the hours are sometimes long (16 hour flight to australia anyone?), and you’ll have to get used to skyping your loved ones.

But hey, the perks that come with this job are hard to beat and may just outweigh dealing with the woman throwing a childlike tantrum in seat 16C because you’re all out of ginger ale.

3. Au Pair

Ease of attaining: Not too hard, must love kids
Pay: $400 – $1000 per month

This is another very popular one, especially among young, female wanderlusters. An au pair is a live-in babysitter. To be an au pair you’ll probably need mastery of a second language since you’ll be communicating with your host family and their kids constantly.

You should probably really love children too.

Being an au pair has a dash of English teacher sprinkled in with it. Besides your basic household chores, you’ll also be helping teach the kids a new language. Kids are sponges when it comes to language, so try not to cuss around them. If they start sharing their newly learned English cuss words with their parents, you’ll have some explaining to do.

In return for your duties, you get room, board, and a modest income. Also, you get to live in a foreign country and truly experience a new culture up close and personal.

Can you say “total immersion”?

Don’t expect to have too much free time though. Kids need lots and lots and lots of attention. But this also makes for a very rewarding job.

4. Bartender

Ease of attaining: Pretty easy
Pay: $1000 – $4000 per month

Now we’re talking.

You know what’s one of the best things about working in the bar industry? The job description is just about the same everywhere you go! Bars, restaurants, and nightclubs all have a proven formula when it comes to bartending. Be attentive, be social, and most importantly make really good drinks!

I’m always partial to a bartender who smiles, but I’ll take a stone faced bartender who knows what they’re doing and never leaves me waiting without a drink in a heartbeat.

Wherever you’re working, it’ll be helpful to know the basics in the native language. Although when I’ve partied abroad, I’ve found that everyone seems to magically understand each other when alcohol is in the mix.

Funny how that works.

But to avoid insulting your patrons, take a cram course in the native language. You’ll pick up the rest as you go. The more experience you gain bartending, the more opportunities will open up with a potential for higher pay.

And who wouldn’t love to say they bartended all across the globe? No matter what age you are, if you’re serious about working abroad and don’t mind working for someone else and working lots of crazy nights, bartending abroad may be for you.

5. Cruise Ship or Private Yacht

Ease of attaining: Not too hard, but patience is a must
Pay: $2000 – $3000 per month

Working on a large cruise ship or private yacht may seem like a spectacular way to see the world, but there’s definitely work involved. In general, to succeed in this field you’ll need to be fast, attentive, and always have a “the customer is always right” attitude. This is similar to the attitude needed if you’re a flight attendant.

Again, customer service isn’t easy. Some great perks are that your food, accommodation, transportation, and even insurance are covered while working on most cruise ships. Further, many also provide vacation time so you can travel on your own.

There are also a boatload (see what I did there?) of different types of positions available. As a result, you could work as a deck-hand, stewardess, chef, paramedic, entertainment manager, entertainment staff, engineer, and many more.

6. Work at a Hostel

Ease of attaining: Pretty easy, depends on availability
Pay: Varies, but can offer accommodation benefits

Now this could be fun.

If you’ve ever stayed at a hostel then you know how quickly the group dynamic can welcome you the second you walk in the door. In Rome I stumbled into a bar that was part of a hostel and within minutes everyone knew me and I was instantly part of the group.

Imagine working at one during your stay! You could work during the day, then enjoy the nightlife with fellow travelers!

You could even volunteer at one in exchange for free accommodations!

Duties would vary, and mostly include cleaning and helping with check ins, etc., so you’d need to be good with completing tasks and dealing with people.

7. Freelance Jobs (Artist, Writer…)

Easy of attaining: must have talent
Pay: varies

Do you have artistic talents? Play an instrument? Paint? Have the confidence to showcase your talents in front of others? I feel like if you have the talent this could be a bucket list type of experience.

Can you imagine being old and grey and being able to say, “Oh I remember backpacking across Europe, busking while I traveled…”

Don’t worry if you have stage fright. Not all art forms are performing arts. Just about any creative or artistic talent can find its audience and earn you money.

But don’t forget, unless you can book a regular gig your livelihood will depend on other people’s spare change. They don’t call them “starving artists” for nothing.

8. Build Your Own Affiliate Marketing Business

Ease of attaining: Must be self-driven with focus
Pay: With the right training there’s no ceiling to what you can earn

While working for someone else is the norm, being able to bring your business with you and transform your surroundings into your office just by opening your laptop can be a huge game changer when it comes to traveling.

This very well may be the ultimate option on the list.

Would you ever regret quitting your job to travel if the end result was being your own boss? Yeah, me neither!

Affiliate marketing is all about connecting people online with the products and services they’re already looking for. You don’t need products of your own, you just need to understand how Google works and how people go about buying the things they want.

How about becoming a blogger and sharing your travel adventures? Never built your own website? You can learn. It’s actually more straightforward than you think, it just takes time. You can build several niche websites, each bringing in consistent monthly revenue.

Whether you’re a photographer who’d love to sell your photos online, a freelance writer, travel blogger, fitness enthusiast, yoga instructor, chef, personal coach, video gamer, or anything really, this is a great option.

Want training that delivers? Check out my detailed review and full walkthrough of the affiliate marketing training platform I owe all my success to! The training is straightforward, affordable, and you can test drive it first to see if it’s a good fit. Click here to check out my full review!

Final Thoughts

It’s a common saying that people don’t regret the actions they took, they regret the actions they didn’t take. If you’re seriously considering quitting your job to travel, take a look inside yourself first.

If you’ve weighed out your options and are ready for adventure, dive in head first! Even if you try and fail, the fact will be that you tried and that’s more than many can say.

What’s holding you back from leaving your job to travel the world? Have you seriously considered this before? Let me know in the comments section below! I always reply and look forward to hearing from you!

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