How to Quit Your Job & Travel the World in Your 50’s & Beyond

What are you going to do if it all fails?’, said one of my closest friends at the time over the kitchen table.

The company won’t rehire you. You’ll be out on your ear and broke. I think you’re making a big mistake‘.

I still remember this conversation as clear as day some 20 years ago now. My friends, so fearful of change, did their utmost to talk me out of quitting my reasonably well paid job to start my own business.

I was on an upward trajectory and as one of my friends was a director of the company he was certain there were ‘big things’ ahead.

There certainly were big things ahead!

3 months later I walked free to start my own business and 20 years later I’ve lived in and travelled to 40+ countries.

In just a few weeks from the time of writing this, my daughter finishes the amazing International School we’ve been able to put her through here in Phuket, Thailand for the last 8 years, and my husband & I will set off and become the perpetual travellers we’ve always wanted to be!

Big things indeed!

aerial view of a wide school surrounded by green grass field and trees
British International School – Phuket

The Era of Uncertainty

My life changing decision was made 20 years ago when job security was still a thing.

As it stands now the world we live in is changing at an unprecedented rate, and if you’re questioning whether your employer is as loyal to you as you are to them, you’re right to do so.

The recent spate of massive layoffs in companies like Meta, Google & Amazon is a stark reminder that when the shit hits the fan, companies prioritise their bottom line above all else.

screenshot of CNBC news shwoing layoff on employees

I’m not saying that every company is a heartless entity, devoid of any consideration for its workforce. But when push comes to shove, and financial pressures mount, or technology creates efficiency, even businesses which strive to create positive work environments and invest in their people, may be forced to make tough decisions that can leave loyal employees out in the cold.

So if the companies we work for can take advantage of the great technological revolution, why can’t we?

The opportunities right now, to generate life changing income without the overheads and risks of a traditional business, are unparalleled and you, my friend, deserve to live life on your own terms.

How We’ve Funded World Travel

Over the last 14 years, my husband and I have built fully remote online businesses that have given us the income and the freedom to live & work from anywhere in the world.

Including selling digital courses, coaching, affiliate marketing, email marketing, e-commerce, blogging, and more, we’ve run the gambit of online business models.

This has afforded us the opportunity to design our life how we want to and to give our daughter an incredible start in life.

But I still feel as if I’m only just beginning!

Technological advances mean it’s becoming easier than ever for anyone no matter their skill level (or their age!) to create life changing income. In fact I believe we’re on the precipice of the greatest transference of wealth in our lifetime.

I’ll save my sensationalist opinions for another post, but suffice it to say the best time to start is right now!

Embracing Fear

It is scary though. There’s no doubt about it.

You’re considering making huge changes to your life which means moving significantly out of your comfort zone.

  • What if it goes wrong?
  • What if you can’t keep up with the young kids?
  • What if technology moves too fast?
  • What if you don’t enjoy travelling like you thought you would?
  • What if you up sticks, make a huge change only to come back with your tail between your legs?

What if you die never having tried to fulfil your dreams?

What a waste that would be.

quote image showing man on top of a mountain

You will undoubtedly make mistakes. I’ve made more mistakes than I’ve got things right. But each mistake has given me more experience, more resilience, and more tools to create success.

Maybe things will go wrong, maybe you will have to stop and regroup and try another approach.

Maybe some friends will tell you you’re having a mid life crisis and say ‘I told you so’, when it doesn’t go as planned.

I was convinced I was going to be the next Richard Branson when I stepped out on my own. In fact my first business spectacularly failed, as did my second.

It took me quite a few years to make any ‘real’ money and as a result, I maxed out credit cards, and even lived in the basement of my husband’s parents house for a while, which as an independent family with my daughter in tow was not ideal!

But we persevered because the alternative – returning home, becoming a corporate slave, and not chasing our dreams – was unacceptable.

My fear of a life I didn’t want to live drove me forward and continues to do so to this very day.

Breaking Free!

So how can you use your fear as a lever to spur you into action?

By channelling it into strategic planning and preparation.

Here are four key steps to get you ready for the leap from quitting your job to embarking on your travel adventures:

1. Designing Your Path

I don’t necessarily recommend my strategy of burning your bridges, jumping off the cliff, and seeing if a net will catch you.

This worked for me as I’m not a half measures kind of woman. If I’m going to commit to something I’m all in. Plus, at the time I hated my job and was desperate to go out on my own.

You need to do what suits your personality, and if you’re in a job you’ve quite enjoyed over the years, have a house, ageing parents, financial commitments, and a life you’ve built, then the planning stage will be crucial for you.

Just like planning a trip, start with the destination you have in mind. And I don’t necessarily mean a place, but the lifestyle you ideally want.

Whether you see yourself backpacking across Asia, driving an RV across Canada, or slow travelling across Europe for 10 years. It’s handy to know what your travelling lifestyle looks like for you.

Knowing what you want to do and how you want to live and travel helps with determining the budget and operational strategy required.

When my husband and I decided to leave our lives behind 14 years ago and jump on a plane to Cyprus with our four-year-old under our arms, we had no idea what our future was going to look like.

We were simply looking ahead to the next six weeks and the house sitting opportunity we’d secured from some friends of ours.

arrow showing  a white building near the ocean

While this is certainly a spontaneous way to live life, a lack of planning can cost time, and money, and seriously elevate cortisol levels.

As we look ahead now, we have a good idea of how we want to live and travel and can therefore plan with confidence, visas, budgets, packing requirements, etc.

But that’s not all, you need to pick a date when you want to go, how much notice you have to give, how you intend to sustain yourself on the road, and what you’re going to do with your house, possessions, etc.

That’s step 2.

2. Streamlining

You likely have a lot of ‘stuff’ lying about your house, plus you’ll be paying for memberships and unnecessary extras.

Your first step is to streamline and minimize your life from where you are now. Minimalism means freedom, flexibility, and valuing experiences over possessions.

Your goal is to emotionally disassociate with all the crap that you’ve gathered over the years. And as you clear out your clutter, you’ll discover a newfound freedom to chase your dreams without being weighed down.

Back in 2021 my dear old Mum (god rest her soul) fell and broke both her hips. I returned to the UK for the summer to clear out and sell her house as she was unable to care for herself any longer.

I boxed up beloved possessions she’d had for years, including holiday photos and souvenirs, gifts, keepsakes, ornaments, family heirlooms, etc, and asked Mum what she wanted to see/keep.

She wanted nothing. I mean absolutely nothing. Not the photos of her and Dad on safari, not the gold ring her Mum had passed down, not even the old coin (sentimental value only) given to her by her oldest friend.

All she wanted was to spend time with us, her family. All she wanted was time. There wasn’t a single possession she owned that gave her just us, being with her as often as possible until she passed peacefully in 2022.

selfie picture of daughter and mother
Love you Mum xx

So whatever you think you own that you emotionally hold dear, will mean very little when the time comes.

Consider as you go through your home, room by room, evaluating your ‘stuff’ and asking yourself, “When was the last time I used this?” and “Does this item bring me joy or serve a purpose in my future life of exploration?

If it’s not a ‘Hell Yeah’, sell, donate, give away, dump!

Once you’ve decluttered your house, analyse your financial commitments. What can you reduce or eliminate? Forget keeping up with the Joneses, maybe it’s time to sell your house to free up equity, or trade your car for something smaller.

Also get rid of subscriptions, memberships, and any unnecessary extras. The goal is to reduce your financial burdens and increase your flexibility.

Beyond possessions and finances, think about your time commitments. Which of these add value to your life, and which feel more like obligations? It’s time to prioritise activities and commitments that align with your aspirations and bring you joy.

If you have ageing parents or family commitments, is there a way to share the burden? Can you make alternative arrangements or think more creatively about your responsibilities?

These days with technology you’re a Facetime or WhatsApp call away, so try to think out of the box.

3. Funding World Travel

Once you’ve streamlined your life you’ll need to look forward and begin to plan how you’ll fund your adventures.

Travelling the world doesn’t have to be as expensive as it sounds.

Here are some tips on how to travel without breaking the bank;

House Sitting

When we leave Phuket we’re returning to the UK for 3 months to see family and get some affairs in order. We’ve secured house-sits for the entirety of our stay.

All we have to do is take care of the houses and the pets, which is, of course, our pleasure to do, and we get to stay in the houses rent-free!

The UK is notoriously expensive to stay short term so what could have potentially cost us over £2k – £3k a month in accommodation fees, we now get for free!

House sitting is available the world over, simply sign up to a site like trustedhousesitters.com and look for house sits in the areas you want to visit.

You’ll likely have to look after a dog, cat, or as in our case some chickens, but that’s part of the fun!

screenshot of trusted housesitters website

Volunteering

Volunteering is exactly that! Offering your time and skills to help out where it’s needed, often in exchange for accommodation and sometimes meals.

It’s a practical way to immerse yourself in new cultures while keeping travel costs down.

The variety of volunteering opportunities is vast. You could be teaching English, participating in wildlife conservation, or working on organic farms. Websites like Workaway.info and WWOOF list these opportunities worldwide, making it easy to find something that matches your interests and abilities.

screenshot of workaway.info homepaage

While volunteering, expect to get involved in the local community, which might mean getting your hands dirty in a garden or leading a small project. It’s rewarding work that connects you with people from all walks of life, offering a deeper travel experience.

Besides saving on accommodation, volunteering opens the door to new friendships and enriching experiences, making it a valuable part of any travel plan.

Live in Asia (and Other Affordable Destinations)

Asia, along with numerous other spots around the globe, is a prime example of where your dollar stretches a lot further, and living costs are surprisingly low.

Places like Vietnam, Thailand, and Cambodia, or even parts of Eastern Europe and Latin America, also offer an incredible quality of life without the hefty price tag.

In these destinations, not only can accommodation be found at a fraction of what you’d pay back home, but day-to-day expenses like food, transportation, and entertainment are also much more affordable.

In a place like Chiang Mai in Thailand, for example, you could rent a beautiful pool villa for less than the cost of your monthly utility bills back home.

Also eating out doesn’t have to be a splurge when a delicious local meal can cost just a couple of dollars. Plus, public transport and local markets make living and exploring these areas both easy and economical.

Add to that the rich experiences these countries offer. From the bustling street markets and serene temples of Southeast Asia to the historic cities and stunning landscapes of Eastern Europe, there’s a wealth of culture and adventure to be had without breaking the bank.

body of water surrounded by green rock formation and green field

Earning as You Go

Alongside travelling cheaply I highly recommend you start a side hustle or remote business doing something you’re great at or love to do and earn as you go.

Here are some ideas to get you started;

  1. Freelancing: A popular choice among nomads, with over 50% taking this route. It involves offering your professional services, such as writing, graphic design, or web development, on a project basis. Websites like Upwork and Freelancer act as marketplaces where you can connect with clients. The flexibility of freelancing allows you to work according to your travel schedule.
  2. Blogging: Transform your travel experiences or any other passions you have into engaging stories and valuable tips for your readers. Blogging can evolve into a revenue stream through methods like affiliate marketing, sponsored posts, and ads. It’s a way to build a community while sharing your journey.
  3. Digital Courses: Put your knowledge and skills to good use by creating and selling online courses. Whether it’s a language, a craft, or professional expertise, platforms like Teachable and Udemy can help you reach students worldwide, allowing you to earn while imparting valuable skills.
  4. Ecommerce: Running an online store can be a fitting venture for travellers, especially with options like dropshipping, which eliminates the need to manage inventory. Platforms such as Shopify and Etsy simplify the process of setting up and running your store, making it a viable option for those constantly on the move.
  5. Coaching: If you have a knack for guiding others, consider remote coaching. This can range from life coaching to specialised areas like fitness or business. It involves working one-on-one with clients to help them achieve their personal or professional goals, offering a fulfilling way to earn an income while you travel.
  6. Subscription Newsletter: Capitalise on your niche interests or expertise by launching a subscription-based newsletter. Platforms like Substack or Beehiiv make it easy to start. Share exclusive insights, deep dives, and personal stories with your subscribers. It’s a more intimate way to connect with your audience and a sustainable model to earn through their support.

Adjusting to a New Financial Reality

You’re going to need to recalibrate your financial expectations and budgeting to align with a more nomadic lifestyle.

Your income might fluctuate more than in a traditional 9-to-5 job, so building a robust financial buffer and adopting a flexible budgeting approach is crucial.

Tools and apps for financial management can help you keep track of your income streams and expenses, ensuring you stay on top of your finances no matter where your travels take you.

Here’s a budget sheet I highly recommend you take the time to complete. Start investigating exactly how much it will cost to live/stay where you want to go, how much flights and transport are, food, entertainment, etc.

You’ll likely find you don’t need anything like as much as you think you do to live your ideal life!

image of a notebook showing expenses in different column you can fill out

4. Make It Happen

You’ve embraced your fears, designed your path, streamlined your life, and planned your budgets.

What next?

It’s time for action my friend!

Years ago I attended a Tony Robbins UPW event in New Jersey. After a massive build up, lots of chanting, and what can only be described as mass hysteria, I found myself in a queue in a dark parking lot about to walk over steaming hot coals.

As I repeated ‘cool moss’ over and over in my head, I felt the excruciating pain as the fire burnt my foot.

At the time I thought I must have done it wrong. Gone in with the wrong mindset or something. But my foot healed quickly (it was only a minor burn) and not long after I commended myself for taking the action required to face my fears and take a leap into the unknown.

This experience, as intense and somewhat bizarre as it was, is a powerful metaphor for the journey you’re about to embark on. Taking that first step towards a life of travel and adventure might not involve walking over hot coals, but it requires the same courage and commitment.

You will have doubts and fears, even feeling the ‘heat’ as you prepare to step out of your comfort zone. The important thing is that you’re ready to take action, to move beyond planning and dreaming into doing.

Taking action might mean booking that first ticket, saying goodbye to a steady but unfulfilling job, or stepping onto foreign soil for the first time with no return ticket in hand.

Whatever your ‘firewalk’ is, remember that the discomfort is temporary, but the growth and experiences you gain will shape you for a lifetime.

If however, you’re not quite ready to run across the pyre as yet, here are some transitional steps you can take to make the journey easier;

  1. Short Breaks: Start with weekend getaways or mini-breaks to different destinations. This is a great way to dip your toes into travel and discover what kind of experiences resonate with you. Whether it’s city explorations, countryside retreats, or beach holidays, these short trips can help you gauge your passion for travel and identify the style that suits you best.
  2. Remote Work Agreement with Your Employer: If you’re employed, initiating a conversation with your employer about remote work could be a game-changer. Many organisations are open to flexible working arrangements, especially if you’ve proven your ability to manage your responsibilities effectively. This step offers the security of a regular income while you start to venture into new locations, providing a safety net as you explore the possibilities of working from anywhere.
  3. Starting a Side Hustle: Launching a side project while still employed is a prudent way to build an additional income stream. Whether it’s freelance work, an online business, or any endeavour that aligns with your skills and interests, this approach allows you to gradually build financial stability. However, it’s important to be mindful of the potential pitfalls, such as lack of time or the comfort of a steady paycheck, which can lead to inaction. Committing to your side hustle and setting clear goals can help you navigate these challenges and make meaningful progress toward your dream of a nomadic lifestyle.

You’re Worth It

Loreal was onto something with their advertising campaign. You are worth it!

  • You are worth living the life you dream about.
  • You are worth being happy and fulfilled.
  • You are worth being a master of your own destiny.

And the fears and uncertainties you’re feeling now are part of your journey, pushing you towards personal growth and proving your resilience.

Travelling the world isn’t just about the places you go. It’s really about pushing your own boundaries, learning about yourself and the world, and seeing life from new angles.

When thinking over the pros and cons, try to see beyond the travel logistics. Ask yourself what you really want out of life. Is it adventure, new skills, meeting people, freedom, or all of the above?

You’re worth the leap. Every bit of worry, every challenge, it’s all part of the process. Facing your fear is where the magic happens.

So, what’s holding you back? If not now, when?

Good luck!


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About the author

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