9 Things to Consider Before Quitting Your 9-to-5 Job to Travel

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It may seem like everyone and their hipster neighbor are quitting their jobs to work remotely and travel the world. Amiright? So is it the answer for you? We’re delving into what it’s really like to quit your job in pursuit of freedom. And I’m going to give it to you honest and straight – no bullshit.

Iceland Airplane wreck

You’ve probably seen at least a handful of articles with titles like, “How to Quit Your 9-to-5 and Travel the World”. 

You know the ones I’m talking about?

They are cluttering my Facebook newsfeed, and even though I know they’re clickbait, I click. Every. Time.

I like to call these “glossy articles” because they are beautiful and shiny and inspiring. But often times, they don’t talk about the not so pretty things. They gloss over truths that don’t sound good, and they leave the reader with an unbalanced and, frankly, unrealistic view.

There are blog posts, webinars and even paid courses devoted to this fad of quitting the so-called “grind”. And I have a feeling this trend isn’t going away any time soon. In fact, it seems like it will only grow.

The American Dream is changing and Millennials are leaving leaving traditional offices in droves to pursue remote jobs, freelance work or even their own entrepreneurial pursuits.

And I suppose I am one of those people.

So is quitting the 9-to-5 life everything it’s built up to be? Does it give you endless freedom and exponential amounts of happiness?

Yes and no.

There’s a lot that people don’t understand about all the stuff that comes along with quitting.

Coming from someone who left the traditional workforce, I can tell you that it’s not all beaches, daiquiris and rainbows.


There’s nothing wrong with those “glossy articles” I mentioned above. But between wanderlust-inducing photos and quotes about how much better life is after the 9-to-5, there are some big things that they’re leaving out.

I’m about to get real and talk about what those “glossy articles” aren’t saying, and let you in on what it’s really like to work remotely.

If you’ve ever thought about leaving your job or find yourself feeling envious of those who have, this article is for you.

Are you interested in living the digital nomad lifestyle? Take a look at our Ultimate Digital Nomad Guide for all the resources on working remotely while traveling the world.

1. 9-to-5 work can be rewarding

I’m not trying to trash talk “glossy articles”, because some of them are seriously inspiring. But I think many of them also perpetuate a notion that if you have a “9-to-5 job” you are somehow not living fully. 

That is complete bullshit.

There are plenty of people who work “traditional jobs” who are happy and live very fulfilling and meaningful lives. And to trivialize this by implying that 9-to-5-ers are somehow stuck in a “lesser” life is, frankly, a completely unfounded claim.

It’s wonderful that society is starting to recognize the benefits to remote work and that working for yourself is an attainable goal, but stigmatizing people who aren’t following this trend is unfair. And while quitting a 9-to-5 might be the path to happiness for some, it’s not for everyone.

Recently, I’ve been getting messages from readers who slip in the fact that they work a 9-to-5 as if revealing an embarrassing birthmark:

“I love traveling and seeing different parts of the world. But unfortunately, I have a 9-to-5…”

Others feel the need to explain:

“I’m still working a 9-to-5 job to save up for my wedding, though I know that’s not an excuse.”

Nobody should feel ashamed of the work they do because a series of hashtags is trending. #laptoplifestyle 

If your job makes you happy and allows you to lead a life that you love, that’s all that matters. It’s not important whether you punch in at 9 a.m. or you work from your laptop in the coffee shop of your choice. 

2. Quitting doesn’t necessarily equal freedom


There’s something romantic about quitting the grind and forging the way on your own. And those glossy articles capitalize on the idealistic mindset that work can be done anywhere in the world – even beachside with a cocktail in hand.

This notion isn’t entirely false. Many of those leaving the traditional workforce are successful. Overwhelmingly so. And yes, the whole working by the pool with a mojito at your side can be possible.

Sunsets and beaches and cocktails help sell those “glossy articles”, so of course that’s the image those authors will try to paint.

But it isn’t the norm. It isn’t every day.

I recently listened to a podcast where the speaker was really talking up working for yourself. And he’s not wrong: it can be great. But he went on to say that working for yourself means no longer waking up to an alarm clock and it means you can work less than 10 hours a week.

Slow down there, buddy.

Most successful entrepreneurs or freelancers are successful because they work their butts off. They don’t lounge around in their pajamas until noon. And they also work well over 10 hours a week. At least in the beginning.

Freedom is the goal of leaving a 9-to-5 job for many, but correlating quitting with beaches and cocktails is unrealistic, to say the least. 

The bottom line is: Quitting will bring you more work before it brings you freedom. Be sure you’re okay with that.

Prime Example: Here are 16 things no one tells you about being a travel blogger, the no bullshit rundown.

3. It’s not a quick path to happiness

Seeing those glossy articles may make it seem that leaving the world of cubicles will make your life so much better. All your worries will be gone and you’ll finally be content.

But to think that quitting your job is suddenly going to bring you happiness would be foolish. Sometimes in the midst of a struggle, we can be vulnerable and latch onto the idea that there is one thing standing between us and happiness. In this case, your job.

More often than not, it’s more complicated than that. Just like quitting your job won’t magically bring you freedom (see #2), it won’t bring instant happiness.

And for some, it might not even bring happiness at all.

Consider the following: What is it about your job that is making you unhappy? Is it the long hours? Or is it the actual work you’re doing? Do you crave more opportunities to be creative? Or would you like to interact with people more than you look at a computer screen?

Just because you are unhappy at your current job doesn’t mean that you can’t find happiness at another job. And it certainly doesn’t mean that working remotely is the key to a happy life. 

4. Being your own boss is harder than it sounds


Those “glossy articles” I was talking about often neglect to mention the growing pains of working remotely or for yourself. And I don’t blame them. It’s a lot sexier to focus on the good parts of working remotely – like the fact that you can spend your day in a bikini instead of a pantsuit. 

But in order to work for yourself, you have to be equal amounts passionate and disciplined. Trust me when I say that it’s easier to stick to someone else’s deadlines than your own. I mean, who’s going to yell at you when you don’t complete your own deadlines? That voice in your head?

And perhaps even more importantly, working for someone else means that if you do your work, you’ll be paid. When you work for yourself, sometimes you do the work without getting paid. It’s not a sure thing; at least not at first. 

It can take time – frustrating amounts of time – for your efforts to pay off. Working remotely can feel isolating at times. And if you’re working for yourself, there will be times you feel as if you are trying to keep afloat in a raging sea that’s trying to drown you. Heck, there might even be times you long to be back in that cubicle. 

But the beautiful thing is that when you’re the boss, the benefits can be greater. When you work hard, it’s not for someone else’s benefit. You are the one that reaps the rewards.

5. You’ll be giving up a lot (and gaining some, too!)

Before even mustering the 4-letter word to your boss, consider what you will be giving up. (The 4-letter word I’m talking about is Q-U-I-T, folks. I’m not encouraging cursing at your boss!)

If your current job comes with benefits, that is one giant tick on the “con” list for quitting your 9-to-5. Yes, I’m talking health and dental insurance, but don’t forget all the other little “perks” your job may come with: networking opportunities, a workout facility, industry discounts, childcare, professional development, happy hours, retirement funds, furthering your education… Factor in all the benefits you’ll be giving up if you quit.

This isn’t to say that you can’t find these benefits on your own, but it should be part of the equation.

And once you’ve factored in all the things you’ll have to give up when you quit, think about everything you’ll gain. Like potentially more flexible hours, or the opportunity to focus on something that you care about.

Weigh it out with a good ol’ pro and con list to get a visual of what quitting will actually look like for you – with the good and the bad all out on the table.

Everyone’s pro and con list will be different. That’s why it’s so important not to follow someone else’s footsteps without considering if it is actually the best path for you.

6. Be ready to take risks


If you are thinking about starting your own business, it often takes a monetary investment. And if you’re thinking about freelancing, the first few months can be spent seeking out work before getting anything solid. Or you could get lucky… 

Quitting is a risk. A huge one. It could be great, or it could be an absolute failure.

I’m saying this not to scare you, but instead, to make sure your expectations are realistic.

I am a huge proponent of taking risks, because I believe some of the best things in life come from getting out of your comfort zone and putting everything on the line. But for some people, quitting is a bigger risk than they’re willing to take.

Each person’s journey is unique, and no path is more worthy than another.

Related: Check out this huge list of digital nomad jobs, packed full of advice from female nomads.

7. Travel doesn’t have to be part of the equation

Those “glossy articles” almost always seem to have a huge focus on travel: “Quit Your Job and Travel the World” seems to always be the thesis statement.

While many people crave more flexibility and perhaps more frequent vacations, the nomadic life isn’t for everyone. Leaving a traditional job doesn’t mean you are required to leave your “traditional” lifestyle.

I’ve shared before how travel isn’t all hammocks and palm trees. There are sometimes when travel can straight up suck. But those glossy articles fail to mention this. Don’t let them convince you that holding down a job makes it impossible to have adventures.

Even if seeing the world is your passion, it doesn’t necessarily mean you have to quit your job to make your travel dreams come true. Our friend, Amanda, shares how she rocks a 9-to-5 while still making time for travel.

8. There will be other jobs

One of the biggest myths we’re told when we graduate high school or college is that a “gap” in a resume is a death sentence for our career goals. While that may have been true a couple decades ago, this notion is no longer relevant in many workforces.

Americans seem to be more hesitant to take time off to get to know themselves compared to young people from many other developed nations. Whether it’s taking a mid-career sabbatical or a gap year between university and the so-called “real world”, time to explore your passions can truly impact the course of your life.

Much the same, you may be feeling nervous to quit your job to pursue a dream or start working for yourself.

What happens if working for myself is a failure? Will I end up being unemployable?

Those questions that tug on the corners of your mind late at night can be showstoppers, and may be the reason you never give your dreams a shot.

Next time those thoughts creep into your mind, push them aside and remember this:

As long as you can articulate how a gap in work benefited you, many employers will see this as a valuable asset rather than a fault. They’ll see your ingenuity, drive and fearlessness rather than a “gap”.

9. It is possible. Yes, even for you.

If quitting your “traditional” job and transitioning into a lifestyle that allows you to work remotely truly is your dream (and not just because you’ve read a handful of articles that convince you it’s an easy escape), I will be the first one to tell you to go for it.

There are many people out there sharing a glimpse into their digital nomad lifestyle and how they were able to make it work. 

Perhaps you have more obstacles than some of the authors of those inspiring articles, and you think, “It sounds great, but I can’t do it.”

I’m here to tell you that for every “excuse” or obstacle, there are people who have created their dream lifestyle. That’s not to say it was easy. But it can be possible.

Whether you have a disability or a family to feed or debt, there is somebody out there who has reached their goals in spite of adversity.

If you’re going to do it, my biggest piece of advice would be to go all in. Don’t let naysayers get you down. Don’t doubt yourself. Take control and plan it out.

It is possible, and with a little dedication and a lot of hard work and patience, anyone can figure it out.

If traveling the world while working remotely is something you’re interested in, we’ve put together a detailed step-by-step guide on how to become a digital nomad. From figuring our your income stream and saving money for your travel budget, to planning your next destination and preparing for life on the road, this guide covers it all in 10 easy to follow steps.

Final thoughts

Now that you know some of the not so fun parts about quitting the 9-to-5 life, does it still appeal to you? I hope so. It can be so rewarding if your expectations are realistic and not too “glossy”.

Are you interested in living the digital nomad lifestyle?

We have TONS of resources on working remotely and traveling as a digital nomad. Check out our Ultimate Digital Nomad Guide for all the answers to your most burning questions, or read some of our favorite articles below.

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What Nobody Tells You About Quitting Your 9 to 5
Want to quit your 9 to 5 job to travel? Read this first.

We want to hear from you!

What are your thoughts? Can you relate? Have you ever considered quitting a job? Do you work remotely? We’d love to hear from you in the comments below!

Comments (3) on “9 Things to Consider Before Quitting Your 9-to-5 Job to Travel

  1. iloenchen@hotmail.com says:

    Thank you so much for this article! There are so many articles about quitting your job that only describe how great it is and nobody ever describes the downsides.

    That said, I like the idea of remote work. It’s nice, being able to work from anywhere. Right now, it’s not for me but it’s something I could imagine doing in the future. I’m lucky and my company allows me to work from home one day a week if I want to, so once I have passed my probation period, that’s something I would like to try. But I can already see one downside: I’m going to miss those short chats with my co-workers. Having other people around me and working in a team where everyone gives their input is something I value a lot and that I might miss if I go completely remote.

    On a completely different note, it might be nice to work from everywhere but after having travelled for a year, I can say for sure that I wouldn’t like to work on a beach. Those photos look so amazing, with people in a hammock, a laptop on their lap. But I’ve used electronics at the beach and I find it very inconvenient. There’s all this sand. There’s so much light that I can’t really see the screen and that it just hurts my eyes. And it’s warm so my hands get sweaty and everything gets very sticky.

  2. hello@somtoseeks.com says:

    I quit my job in December to become a travel writer, and I definitely agree that being your own boss is harder than it sounds. While I enjoy the autonomy of setting my own schedule, I have to be more disciplined than I was at my 9-5. I’m entirely responsible for every dollar that comes into my bank account so if I slack off I don’t get paid. Simple. At a 9-5, I could coast for a bit and still get my salary at the end of the month. That said, I think becoming my own boss is the best decision I’ve ever made. Becoming an entrepreneur is a risk, but there is nothing more satisfying than doing something you wholeheartedly believe in.

    • hello@twowanderingsoles.com says:

      Thanks so much for the thoughtful comment, Somto. I can completely relate to you. It as the best decision we made too, but harder than it sounds! Wishing you all the best on your journey!

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