Hi, it’s Melissa, and welcome to “your founder next door”, a bi-weekly column with relatable stories of my journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up truth bombs on what it’s like to build a company without an abundance of resources or friends in high places.
In my last newsletter, “Where you wake up determines your success,” I shared how leaving Vancouver for New York changed the trajectory of my life. This is the sequel…
The Big Aha! 💡
I left New York for Amsterdam to trade chaos for balance. The city gave me the community my soul craved, but it also softened the hunger that once drove my ambition. It took a solo trip to London recently to realize the thing I’ve been missing in my life is the big city energy that made me feel alive a decade ago.
Leaving New York 👋
Over time, the things that drew me to New York became the things that exhausted me. Cue someone saying, “Be careful what you wish for.”
As my company started doing better, work stopped being my only priority and the transactional nature of the events and friendships I once flocked to no longer excited me. I still appreciated the city for the reasons that drew me there, but it wasn’t what I needed anymore.
Eventually, David and I left New York to nomad full time for 3 years. Because of him, I got to experience the world, reinvent myself, and build a life around who I am today. We got tired of traveling, discovered Amsterdam, and decided to make it home in 2019. Ironically, we wanted a home base to travel less, and because of 2020, we ended up being on the road for 1.5 years in search of places with less restrictions. 😂
Complacency: The enemy of success? 👀
We ended up in Amsterdam because the parties were amazing. This is not a joke!
For years, life was just David and I. We had friends in NYC, but never had a community where we felt like we belonged. We discovered house music together and searched for parties by following DJs we liked. We found Amsterdam that way and because we kept going back for the parties, we met more friends there than we’d had anywhere else. Friends who had fun the same way we did, friends who felt like home.
A quick Google search will tell you why Amsterdam is one of the greatest, most livable cities on Earth. For me, it was the much needed break I needed from the bustle of NYC.
In Amsterdam, nobody used “what do you do” as their icebreaker. In fact, we didn’t know what most of our friends did for a living because it didn’t come up. People were happy getting to know each other as people and spending time together. It wasn’t business driven, and I loved it because it gave me refuge from talking about my startup.
Most importantly, it gave me what my soul needed most: Community.
When I was struggling to make ends meet, work was my number priority because it had to be. Hitting profitability freed up mindshare for me to start asking myself what I needed, and tip the work/life balance scale the other way. I realized there was so much more to life than work…which might seem obvious to most people but not from the culture I grew up in (Hong Kong), where money and status took precedence.
In the last few years, our newfound friends and community gave us more fun than I ever thought possible in one lifetime. I can honestly say that we live a richer life than most people who are financially better off. But, here also lies a problem…
As I wrote earlier: The city you live in determines who you are and how you live; it’s the environment and people you surround yourself with. Your friends, your community, your social life, everything contributes to the person you become. This city is not just the physical place where you chose to call home -- it’s the vibe, energy, and ambition you absorb by simply existing within it.
Because the community I surrounded myself with prioritized fun over most things, I became that way too by osmosis and tipped the scale all the way to the other end. Turns out, work/life imbalance can be caused by too much life.
Over time, it got harder and harder for me to focus on work and spend time building my business. It happened gradually, but because I had gotten a taste of the other side, I just wanted to have fun and not work. Sadly, retirement was not an option. I was back to self-motivation and pushing the boulder uphill alone again.
Last summer, I decided to take a step back because I was feeling guilty when having fun but also unable to be productive at work. Since I was failing at both, I gave myself permission to take it easy for a couple months so I could come back to work stronger. Unfortunately, my inspiration didn’t return to the level it once was and my ambition never fully recovered. (I wrote about this period in this article, How losing purpose led me to rediscovering it.)
I left New York a few years ago to be away from the energy that lit my entrepreneur fire, but in the process, I became complacent because life was pretty good. I lost the hunger I once had because I sold my last company and my current one did well enough to pay me a salary. I believe that desperation breeds creativity, which means the opposite is also true. I convinced myself that I didn’t need that much to live a great life and renegotiated my dreams of becoming somebody.
All of this led me to what I would call my “first mid-life crisis”, which I’ve been untangling in the last few months by working on myself. I went to two self-development retreats, The Hoffman Process where I learned about the importance of self-love and Rise Higher where I realized I lost the delusional self-belief I once had, which prevented me from building my company from a place of trust, courage, and determination.
Finding New York again somewhere else 💂
A few weeks ago, I went to London for a solo trip and was reinvigorated by its chaos. I was ignited by random conversations with strangers; intelligent people doing amazing things. By sharing their ideas with me and showing me their power, they reminded me of mine. Every conversation I had was intellectually stimulating, and reminded me that I once moved to New York to feel exactly this way.
Being there showed me that the thing I’ve been missing in my life is energy.
I felt alive again!! 🔥
The short time I spent there lit up my mind by filling it with potential, possibilities, and curiosity.
Ten years ago, I moved from Canada to New York alone to be surrounded by people who were trying to build a life for themselves against all odds. Moving there was the Butterfly Effect that changed the trajectory of my life.
I have since nomaded for 3 years and settled in Amsterdam 5 years ago, where I currently "live" but travel 10 months of the year between warmer and funner places. Somewhere along that journey, I got comfortable and lost the spark that used to inspire me to create.
I went to London because I wanted time with myself. But in the end, life gave me what I needed instead: Time to rediscover myself.
Last year, at 41, I thought my career was over. I haven’t seen success the way I’ve wanted, and told myself that it was never going to happen. I lowered my expectations and tried to be grateful for what I already had. I shrunk myself because I didn’t think I could. I lost trust in myself because I thought everyone else was more capable and more qualified than me.
These were the lies I told myself because I was scared to fail. But, what I have been more scared of all my life was the pain of regret.
My career is not over, it has barely begun.
I found my New York again, this time in London. Just like I did a decade ago, I’m going to move there with no friends, say yes to everything, and see where it takes me.
Reflections 🪞
The key to finding success is to first figure out what your definition of success is, and that changes over the course of your life. Then, you need to manufacture the conditions to maximize your chances of achieving your dreams. Surround yourself with the right people in the right place that puts you in the mindset that propels you.
When I didn’t have professional success, financial stability was all I wanted. When I had that, I realized I was failing miserably at my social life and community.
Now, when I’m ready to take my company to the next level, I want a more balanced life, weighted towards personal and professional growth. I want to take everything I’ve learned and build the biggest company I can, so I can contribute more time and resources towards my community.
I wanted to end this piece with a note I wrote to my friends at the Vancouver airport the day I moved to New York:
If you are at all inspired, if even a small part of you wonder whether you too, can embark on a journey into the unknown, I would like to leave you with this: There exists within all of us a dreamer and an explorer. When we allow them to find each other, we are at our most powerful. Let your curiosity and quest for knowledge pave the way, and may that become the story we will one day share.
The biggest lesson I learned through all of this is:
The quickest way to unstuck yourself is to change where you wake up in the morning.
It’s always harder to move forward than stay where you are.
As someone who has done this a few times, I promise you, once you do it, you’ll realize you were ready way before you took the leap.
🗞️ Read the prequel to this piece: Where you wake up determines your success
Stuff mentioned in this article 👇
What losing delusional self-belief did to my startup
Thank you for reading!
— Melissa ✌️
Newsletters I follow (and think you should too) 🗞️
Dr. Julie Gurner: Ultra Successful - Insightful, easy to digest advice & executable strategies that makes you think by a badass performance coach.
Greg Head: PracticalFounders - Weekly interviews with founders who have built valuable software companies without big funding.
Kyle Poyar: Growth Unhinged - In-depth case studies and deep dives on pricing & packaging, go-to-market strategy, SaaS metrics, and product-led growth.
Enjoyed reading this? Help spread the love 💜
If you enjoyed this piece and found it valuable, please consider sharing it with friends who you think would also benefit from this column. They can also sign up at melissakwan.com.
The only way this grows is by word of mouth, so I’d really appreciate all the help you’re willing to give. 🙏