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Going from 9-5 Job to Traveling the World

Going from 9-5 Job to Traveling the World

Essentials for the Everyday Traveler. Ethically made in Canada with sustainable and eco friendly materials.

This is a guest post from Leah Davis of

Location independence--that is, the freedom to work from wherever you want, whether it be your home office, your favorite European city, or a beachfront hut in the Caribbean--is likely well within your reach, and you don’t even know it.  Since saying sayonara to the 9-5 grind nearly three years ago, it’s been my goal to prove this to as many people as possible.

If you have a laptop computer, an uncanny ability to sniff out strong WiFi connections, and an unrelenting work ethic, you’re already a prime candidate.  If you’re a pro at adapting to changing circumstances and adept at weathering emotional ups and downs, even better.  Those last two will come in particularly handy.

This lifestyle choice is especially popular among millennials but is rapidly gaining traction across generations, and whether you work remotely for just one company, become a freelancer and work for many, or start your very own online business, this type of lifestyle can provide freedoms unmatched by any office-bound job.

I can’t stress this enough: The road to location independence is not easy.  The faint of heart need not apply.  But if you’re willing to put in the extra time and effort now, it can have big payoffs down the road.

Payoffs like the ability to work when you feel most alert, creative, and motivated; the freedom to travel whenever and wherever you please; the luxury of waking up when your body feels rested and not when an alarm clock forcibly tells you to.

While this may all sound wonderful in theory, it’s an intimidating prospect if you aren’t sure where to start.  Do you simply up and quit your current job, buy a one-way flight to Southeast Asia and rent a $5 per night bungalow while you “figure it out?”  This might work for a few certain daredevils, but most savvy working women would prefer to have a plan of attack in place rather than just winging it.

If you’re considering transitioning from your 9-5 job to a location independent lifestyle, here are three smart ways to go about it.

Essentials for the Everyday Traveler. Ethically made in Canada with sustainable and eco friendly materials.

Take your current job remote.

Remote work is a good option for those who are interested in location independence but are not ready, willing, or able to take on all of the risks associated with it.  Remote work is also a great option for those who love the role they’re currently in but desire a little more flexibility (so long as your duties can be fulfilled remotely).  

If remote work sounds like the right path for you, do one of these two things:

  1. Get your current employer to agree to let you work remotely
  2. Get a new job with a company that hires remote workers

In order to take your current job remote, you'll need to draft a proposal that, above all else, addresses your manager's concerns about sending you out into the great unknown. They don't care why you want to work more flexibly; all they really want to know is how the change will affect them.

Provide them with a detailed plan that includes what days you plan to work, how your working remotely will benefit the company (will it save money or increase your productivity?), a thorough description of your new working conditions (will you be at home or in a different time zone?), how you plan to communicate with your team and superiors, and how often.

If your goal is to work remotely 100% of the time, it may help to ease into it by working from home a few days per week and slowly building up to full-time.

Highlighting the benefits to the company while alleviating fears will give you the best chance of getting the green light from your employer.

If your current job isn’t one you’re crazy about or can’t be done remotely, there are plenty of other jobs out there.  I recommend browsing the listings on sites like Flexjobs, We Work Remotely, or


Leverage your current skills and become a freelancer.

Freelancing comes with its own set of challenges, but can also offer more flexibility than working remotely for an employer.  You’ll need to be motivated enough to market your services, secure new clients and track down invoices, and weather the financial instability that may result from slow months or people who refuse to pay you on-time.

This is a great option for those who have strong computer-based skills like web or graphic design or writing and editing.  If you don’t yet have a strong skill set that could translate into online freelance work, choose something that excites you and start learning with online courses.

Udemy and Skillshare are two great places to find affordable online courses on just about any topic.  Polish your new skills by providing services at reduced cost to friends and acquaintances before actively pursuing your first real clients.  Nothing beats good old-fashioned experience.

No matter what service you’re offering, you’ll need a web portfolio.  Create a simple website where you can show off your best work and clients can learn more about you and find your contact information.  This will be many clients’ first point of contact with you--make it memorable, professional, and true to your own personal brand.

You may find that once you have your first client, word-of-mouth will go a long way in helping you get more, but don’t rely on on that alone.  Be proactive by marketing yourself through social media and networking as much as possible with others in your field, both in-person and in online forums.  It’s also a good idea to list your freelance services in online marketplaces such as Upwork and

I recommend keeping your 9-5 as you begin building up your client base (avoiding direct competition with your employer, of course) and only take the leap into full-time freelancing when you’re making the minimum you could comfortably live on.  This may require you to put in hours on nights and weekends for a few months.  Having some money in a savings account will allow you to make the leap even sooner.

Essentials for the Everyday Traveler. Ethically made in Canada with sustainable and eco friendly materials.
Essentials for the Everyday Traveler. Ethically made in Canada with sustainable and eco friendly materials.

Start your own online business.

Starting an online business is by far the path of most resistance, but it also stands to bring you the greatest rewards in terms of freedom and control over your lifestyle.  Entrepreneurship will require the greatest amount of time and effort up-front, but I believe it is the best option for those who value autonomy and flexibility in their work above all else.

Just as with freelancing, you’ll need to put in hours on nights and weekends in order to begin building up your new business, unless you have ample enough savings to leave your day job and live comfortably until you begin making a profit.  The good news is, online businesses can be started with fairly little money, and often have few overhead costs.  Starting a blog is a great example of this.

There are limitless possibilities when it comes to online businesses, so you’ll have to assess your skill set, cross reference it with what you’re most passionate about, and then determine how you can help people solve their problems.  Consulting agencies are always in demand, or you could create and sell your own information products such as ebooks and online courses.

Don’t be afraid to get creative, here--your unique value proposition is what will allow you to stand out from the crowd.  Finally, make sure you know exactly who your target demographic is and where you can reach them.

The web is overflowing with online business ideas; here’s a comprehensive list to get you started.  Once you’ve narrowed down your idea, get to work building your online empire.

At the end of the day, the possibilities for creating a life of freedom, flexibility, and travel are only limited by your imagination.  Transitioning from your 9-5 to a location independent lifestyle doesn’t have to be a scary proposition if you go about it with purpose and direction.  Get started today and you, too, can take your life back into your own hands.

Photos (c) Leah Davis, the Published with permission.


Essentials for the Everyday Traveler. Ethically made in Canada with sustainable and eco friendly materials.About Leah

Leah Davis is an avid traveler, location independent blogger, and author of the eBook Take Your Life Back: Finding Freedom Through Location Independence. Find more inspiration and practical advice for becoming location independent on her blog, Facebook, and Instagram.




Essentials for the Everyday Traveler. Ethically made in Canada with sustainable and eco friendly materials.

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