Drawing from my experience as a Community Leader with Remote Year let me give you the insider’s guide into RY and what you need to know to do a program and what makes this experience so transformative—both professionally and personally. Discover my top 3 RY destinations in my post: Remote Year: Working and Travelling The World and destinations you NEED to visit
Note: On 20th December, Remote Year announced the closure of their operations, a devastating blow to many in the global remote working community.
For those friends and former remotes now facing sudden uncertainty—disrupted travel plans, lost opportunities, and unexpected challenges—my thoughts are with you. While the organisation may be ending, the connections, memories, and transformative experiences of Remote Year will endure far beyond this moment.
The spirit of global adventure continues.
The Dream Job—And Then Some: My Journey as a Remote Year Community Leader
Working as a Remote Year Community Leader was truly my dream job. Travelling to incredible countries alongside inspiring individuals while being supported by a dedicated team was nothing short of amazing. But it was far from a holiday.
The job required navigating a unique dynamic where your customers were also your travel companions and, over time, your friends. You’re “on” 24/7—supporting, guiding, and managing logistics—while constantly adapting to new environments, cultures, and team dynamics. From resolving personal conflicts within the group to handling logistical hiccups in foreign countries, no two days were alike.
Recommended reading: learn how I got started as a community leader and how you can travel the world within 3 months
Remote Year: The Challenges That Shape You
Leading a community on Remote Year pushed me outside my comfort zone. I learned to be a cultural bridge, an empathetic listener, and a logistical mastermind—all while maintaining a sense of adventure and fun. The role demanded constant adaptability, problem-solving, and emotional intelligence.
The city teams on the ground were invaluable. Their local expertise and unwavering support ensured smooth transitions and helped navigate cultural nuances, making each destination feel welcoming and accessible. They quickly became more than colleagues—they became family.
The Personal Growth
Despite the intensity—or perhaps because of it—the experience was profoundly rewarding. Through this journey as a Remote Year Community Leader, my patience was tested again and again, but it grew stronger with each challenge. I learned to pause, reflect, and hold my tongue when tensions ran high, understanding that pressure often reveals people’s vulnerabilities rather than their true intentions.
One of the most liberating lessons I discovered was the realisation that it’s okay not to be liked by everyone. Letting go of the need for universal approval freed me to focus on being authentic rather than striving for perfection. In doing so, I found a new sense of self-love and acceptance, recognising that my imperfections are as important as my strengths.
Equally crucial was learning the value of self-care and setting boundaries. In a role that demanded so much emotionally and physically, I realised that taking care of myself wasn’t selfish—it was essential. I became better at recognising when to step back, recharge, and set limits to protect my well-being.
Looking Back
I’m leaving this experience feeling like a better, stronger version of myself. I’ve grown in ways I never anticipated, and for that, I wouldn’t trade this journey for anything. Remote Year is much more than a job or a travel program—it’s a life-changing experience that reshapes how you see the world and yourself.
The relationships formed, the skills gained, and the memories created were worth every challenge. From solving unexpected issues (like breaking a remote out of airport jail in Japan) to facilitating meaningful connections within the group, the role of a Remote Year Community Leader was as much about building community as it was about managing logistics.
The challenges, triumphs, and personal growth have been life-changing, and the memories will stay with me forever.
So, what is Remote Year?
It’s a program that allows you to work remotely while exploring the world. They handle the logistics, so you can focus on your job and adventures. You choose your program, pack your bags, and immerse yourself in new cultures while building a global network. Remote Year provides a framework for a year of adventure and professional growth.
Ready to Go? Here’s How It Works
Choose Your Adventure
Remote Year offers several options to suit your wanderlust. Their flagship program, The Original Remote Year, is a 12-month journey across 12 countries (this is the one I led). It includes accommodation, access to a workspace, flights between countries, and a built-in community, both within your travel group and globally.
If you’re not ready for a full year, the 4-month program explores a specific region, visiting four countries. Or, dip your toes in with a 1-month program starting at $549, which gives you access to the community and platform. Be mindful that with all Remote Year programs, your flights to and from the first and last destinations are not included, so you’ll need to budget for this.
Prepare for Take-Off
Once you’ve picked your program, secure your spot and start packing! Invest in a sturdy, lightweight suitcase (hard-shell is the way to go). Pack light, but don’t stress—you’ll be surprised what treasures you’ll find along the way (my trinket of choice was jewellery!). Sort out any visas and ensure your remote work setup is ready to roll. Oh, and check out my packing list to avoid those dreaded overweight baggage fees, especially in Asia!
Embrace the Unknown
Get ready to be amazed—and perhaps a little bewildered at times. Culture shock is part of the adventure, but don’t let it hold you back. One key lesson I learned during Remote Year is about the growth zone. This is when you step outside your comfort zone, open yourself to new experiences, and begin to grow. Embrace the experience of living and working in new cities, building connections, and exploring different cultures.
The Remote Year Perks
Stress-Free Travel
Remote Year takes care of all the details so you can fully immerse yourself in the experience. From securing accommodation and organising co-working spaces to planning group travel between destinations, everything is seamlessly arranged. No more worrying about finding reliable Wi-Fi, researching the best places to stay, or navigating unfamiliar transit systems—Remote Year’s team has it covered. This allows you to focus entirely on your work, exploration, and personal growth without the usual travel stress.
Instant Community
One of the most unique and rewarding aspects of Remote Year is the built-in community. You’ll be travelling with a diverse group of like-minded adventurers from various professional backgrounds, all sharing a passion for travel and self-discovery. These connections often go beyond casual acquaintances—participants frequently form lifelong friendships, professional collaborations, and an unparalleled global support network. Whether it’s brainstorming over coffee, sharing a meal, or embarking on a weekend adventure, the sense of camaraderie is second to none.
Work-Life Balance Harmony
Striking the perfect balance between work and play can be challenging, but Remote Year creates an environment that makes it easy. With reliable co-working spaces equipped with high-speed internet, you can stay productive and meet your deadlines while enjoying the flexibility to explore each destination in your downtime. This harmony between professional life and personal adventure fosters creativity, improves well-being, and helps you feel fulfilled in all aspects of your life.
Cultural Immersion
Remote Year isn’t about ticking off tourist attractions—it’s about truly experiencing each destination as a local. Through curated activities, workshops, and opportunities to engage with the local community, you’ll gain a deeper understanding of the cultures you visit. Imagine participating in a cooking class in Thailand, learning tango in Argentina, or volunteering with a community project in South Africa. These immersive experiences help you connect with people, traditions, and customs in meaningful ways, leaving you with memories and insights that last a lifetime.
Remote Year offers more than just travel; it’s a transformative experience that blends adventure, personal growth, and professional development. Imagine living in a new city every month while staying connected to your career, supported by a global community of like-minded individuals. Whether you’re seeking lifelong friendships, professional inspiration, or a fresh perspective on the world, Remote Year delivers a transformative experience.
Is it all good though?
While Remote Year offers an incredible and transformative experience, it’s not without its challenges and areas for improvement. Understanding these nuances is crucial for anyone considering participating or working with the organisation.
Cost vs. Value
One of the biggest critiques I heard about Remote Year was the cost. The program comes with a premium price tag that can be a significant hurdle, especially for those early in their career. While the cost covers accommodation, logistics, and co-working spaces, not everyone felt it represented true value. The quality of accommodations varied considerably between cities, sometimes falling short of expectations given the price point. Many participants noted they could potentially organise similar experiences independently at a fraction of the cost.
Group Dynamics
Travelling with a group for an extended period is both a blessing and a challenge. The sense of community—one of Remote Year’s strongest selling points—can simultaneously be a source of tension. Personality clashes, differing expectations, and individual personal challenges often create complex group interactions. As a Community Leader, I frequently found myself mediating these delicate situations, recognising that while these moments were valuable learning experiences, they could detract from the overall program enjoyment.
Work-Life Balance?
Remote Year emphasises work-life balance, but the reality is far more complex. Significant time zone differences—particularly with Asian destinations being 11 to 16 hours ahead of the US—create substantial scheduling challenges for those working with American companies. Throw in the shaky internet in some locations and the constant adjustment to a new environment every month, and it’s easy to see how maintaining productivity can be tough.
Some participants expressed feeling burnt out from constant travel and the lack of routine, which can significantly impact the overall experience. The romantic notion of working from anywhere meets the practical challenges of actually doing so.
Support Structures
Having worked behind the scenes, I witnessed the immense effort required to make Remote Year run smoothly. The city teams (the literal RY backbone) were exceptional, often going above and beyond to support participants. However, the broader organisational support occasionally felt disconnected from day-to-day realities. The intention was always present, but there’s room for more seamless integration between different support levels.
So is it still worth it?
Remote Year is more than just a travel program—it’s a life-changing experience that redefines how you live and work. It’s designed for individuals ready to embrace a global lifestyle without compromising career progression or personal growth.
The opportunity to live and work across 12 countries in a year, building meaningful connections with like-minded professionals while exploring diverse cultures, remains truly unique. The personal growth is unparalleled: learning to adapt to new environments, becoming more self-aware and discovering hidden strengths.
Despite the challenges—balancing work, travel, and group dynamics—the rewards far outweigh the obstacles. Professional connections, acquired skills, and extraordinary adventures make every challenge worthwhile.
Remote Year offers far more than just a job abroad. It’s a chance to change the way you see the world and yourself. The professional connections you’ll make, the skills you’ll acquire, and the adventures you’ll have are worth every challenge. So, what are you waiting for?
