The Reality of Organizing Community Events:
Lessons from a Digital Nomad
Introduction
Organizing events across different cities while living a location-independent lifestyle has been one of the most rewarding yet challenging aspects of my journey with Break Outwards. As the founder of a community dedicated to empowering individuals to embrace freedom, exploration, and personal growth, I’ve experienced the full spectrum of victories and setbacks that come with building community events from scratch in unfamiliar territories.
In this article, I want to share an honest perspective on what it truly takes to organize meaningful events in different cities around the world. Whether you’re a digital nomad looking to create community wherever you go, an entrepreneur aiming to expand your reach through events, or simply someone passionate about bringing people together, these insights from my personal experience might help you navigate your own event organization journey with more resilience and wisdom.
The Emotional Journey of Event Organization
When No One Shows Up
There’s a special kind of disappointment that comes from pouring your heart into planning an event, securing a venue, preparing materials, and then… waiting in an empty room. I’ve been there more times than I’d like to admit. The first time it happened in Hoi An, Vietnam, I had spent weeks promoting a digital nomad meetup, coordinating with a local café, and preparing an interactive workshop. When only two people showed up (one being the café owner), the feeling of failure was overwhelming.
But here’s what I’ve learned: sometimes, no one will come, and that is completely okay. This isn’t necessarily a reflection of your worth or even your event’s value. Cities have different rhythms, communities take time to build, and sometimes the timing just isn’t right. Each “failed” event became a stepping stone to better understanding the local community and refining my approach.
Understanding Your Motivation
When facing setbacks, I’ve found it essential to return to the fundamental question: Why am I doing this? Is it for community building, making friends, generating profit, or something else entirely? Your answer will dictate how you measure success and whether you have the resilience to continue.
For me, Break Outwards events began as a way to connect with like-minded individuals while traveling. The motivation was primarily personal—to combat the isolation that sometimes comes with a nomadic lifestyle. As the vision evolved, so did my motivation, expanding to include empowering others to embrace location independence and personal transformation.
Understanding your true motivation helps you weather the inevitable disappointments. If your sole metric is attendance or profit, you’ll likely burn out quickly. But if your motivation includes personal growth, community building, and the joy of creation, you’ll find value even in sparsely attended events.
Maintaining Focus on Vision
When organizing events across different cities, it’s easy to get distracted by what others are doing or trying to please everyone. I’ve learned that maintaining a laser focus on your community vision is crucial. For Break Outwards, our vision centers on creating transformative experiences that help people break free from traditional constraints and embrace a life of freedom and fulfillment.
This vision became my north star when making decisions about event formats, venues, pricing, and content. It helped me resist the temptation to dilute the concept just to boost numbers. By staying true to our community values of exploration, transformation, and authenticity, we gradually attracted people who resonated deeply with our mission—even if that meant smaller gatherings initially.
Embracing Failure as Part of the Process
The Art of Iteration
One of the most valuable lessons I’ve learned is that few event concepts work perfectly the first time. If one idea doesn’t work, that’s okay. The key is to try it a few times, gather feedback, and be willing to tweak the concept until it resonates.
When our skill-sharing workshops failed to gain traction in Chiang Mai, instead of abandoning the concept entirely, we experimented with different formats. We tried evening versus morning sessions, varied the venue from coworking spaces to cafés, adjusted the structure from formal presentations to casual roundtable discussions, and explored different promotional channels. After several iterations, we discovered that casual skill-sharing breakfasts in outdoor cafés attracted our ideal participants and created the relaxed, collaborative atmosphere we were aiming for.
Iteration requires patience and humility. Each “failure” provides valuable data that brings you closer to finding what works for your specific community and context.
Knowing When to Let Go
While persistence is important, equally valuable is knowing when to let go of ideas that aren’t serving your mission. We often become emotionally attached to event concepts because we’ve invested time, energy, and sometimes money into them. This sunk cost fallacy can lead us to continue with formats that consistently underdeliver.
Remember that letting go of a specific event format doesn’t mean abandoning your overall mission. Sometimes it’s the necessary step to make space for something that aligns more authentically with your goals and the needs of your community.
Practical Organization Tips
Effective Promotion Strategies
Getting the word out effectively is one of the biggest challenges of organizing events in new cities. Here are some approaches that have worked for me:
- Consistent social media presence: Establish a posting schedule at least two weeks before your event. Use location-specific hashtags and tag relevant local accounts.
- Leverage existing communities: Rather than building from zero, connect with established communities that share similar values. In most cities, I search for Facebook groups, Meetup groups, and Telegram channels related to digital nomads, expats, or specific interests aligned with our event.
- Collaborative promotion: Partner with local businesses or other event organizers to cross-promote. This significantly expands your reach and adds credibility.
- Personal outreach: Never underestimate the power of direct invitations. When starting in a new city, I spend time in coworking spaces and cafés popular among digital nomads, making personal connections and inviting people individually.
- Create shareable assets: Design eye-catching graphics with all essential information that attendees can easily share with their networks.
Remember that promotion isn’t just about quantity but quality of connections. Five deeply interested participants will create a better event than 20 people who don’t align with your vision.
Building Collaborative Networks
One of the most sustainable approaches to growing events across different cities is connecting with others who share similar growth ambitions. I’ve found tremendous value in building relationships with:
- Local event organizers who already understand the community landscape
- Venue owners looking to attract specific clientele
- Content creators seeking collaborative opportunities
- Community leaders who can provide insights and introductions
These collaborations create win-win scenarios where you can leverage each other’s strengths, share resources, and combine audiences. In Kuala Lumpur, partnering with a local coworking space owner who wanted to increase community engagement allowed us to host regular events with minimal venue costs while providing them with increased visibility and potential members.
Sharing Ownership
Perhaps the most transformative organizational principle I’ve embraced is being willing to share ownership to advance larger goals. Initially, I wanted to control every aspect of Break Outwards events, from conception to execution. This limited our growth and led to burnout.
By empowering local community members to take leadership roles—becoming city ambassadors who co-create and sometimes independently run events—we’ve been able to establish more sustainable presence in multiple cities. These ambassadors bring local knowledge, networks, and fresh perspectives that enrich our community.
Sharing ownership might mean adapting your original vision, but the collective intelligence and distributed responsibility create something far more resilient and impactful than what any individual could achieve alone.
Finding Joy in the Journey
Through all the challenges of organizing events across different cities, I’ve come to believe that the most important element is finding personal enjoyment in the process. If you don’t find joy in what you’re doing, no amount of attendance or financial success will sustain your motivation long-term.
I’ve learned to appreciate the small victories: meaningful conversations with individual participants, witnessing connections form between attendees, personal growth through overcoming challenges, and the privilege of exploring diverse cultures while building community.
Some of my most treasured memories come from events that would be considered “unsuccessful” by conventional metrics—like the “failed” workshop in Hoi An that led to a four-hour conversation with the café owner about community building, which eventually resulted in a lasting friendship and a permanent venue partner for future events.
Final Thoughts
Organizing events across different cities as a digital nomad or location-independent entrepreneur is not for the faint of heart. It requires resilience, adaptability, and a genuine commitment to your mission. There will be empty rooms, logistical nightmares, and moments of doubt.
But for those willing to embrace the journey—with all its unpredictability—it offers incomparable rewards: genuine human connection across cultures, the satisfaction of creating spaces for transformation, and the continual growth that comes from pushing beyond comfort zones.
At Break Outwards, our journey of community building through events continues to evolve. Each city teaches us something new about ourselves and the beautiful diversity of human connection. If you’re embarking on a similar path, remember that the most meaningful communities aren’t built overnight. They grow gradually through authentic engagement, consistent presence, and a willingness to learn and adapt along the way.
The world is indeed our office, and curiosity our currency—especially when it comes to discovering the infinite ways we can come together to create meaning and connection wherever we find ourselves.
