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1-Year Into Entrepreneurship: Was It All Worth It?

Sophie Vo

I’ve just returned from a two-week retreat in Japan, and while most people assumed I was on “holiday,” it wasn’t a vacation in the traditional sense.

Each year, I commit to travel somewhere new and engage in activities I’ve never done before. This isn’t just a break from routine—it’s a deliberate effort to remain curious and gain fresh perspectives on both my business and personal life.

When I was employed, I used to approach these trips as holidays, a time to disconnect. But now, as an entrepreneur, I see this time as a fundamental investment for myself and my soul.

During this trip, my partner James (also an entrepreneur in the podcast world) and I immersed ourselves in the beauty of Japanese nature—hiking, cycling through the rain, and island-hopping. But we were also partially working on our respective businesses and that’s a life I’m beginning to embrace.

As I mark my first year as a leadership coach and entrepreneur, I wanted to share a few key lessons I’ve learned—many of which came into sharp focus during this mind-expanding retreat in Japan.

I hope they will offer you perspectives and encouragement to invest time to step back too.

Lesson #1: One Step At A Time

As part of our journey, James and I embarked on a two-day cycling trip across the seven islands of Shimanami-Kaido. What we didn’t plan for was two days of intense rain! We had already committed, so we just pressed on, frequently taking breaks to let the rain pass before continuing our journey to hit the finish line. It was a humbling reminder that things will be beyond our control, and we can’t rush through them. We need to respect the process of life and learn how to flow with it.

Shimanami-Kaido

This is a perfect metaphor for business. As a former executive coming from the fast-paced world of game development—where features are launched and tested within days, getting one win after another—I had to adjust to the reality that growing a business takes time.

2024 has been all about testing different initiatives to see what grows my leadership coaching business and what turned out to be distractions.

While 2024 was the year of experimentation; 2025 will be the year of full-speed execution.

Lesson #2: My Inner Compass Is My Superpower

Long walks and endless cycling provided the perfect backdrop for reconnecting with my intuition. When my mind isn’t actively trying to solve problems or generate ideas, I find a sense of peace—and that’s where the magic happens ✨.

In those moments, I rediscover my inner compass—one that isn’t swayed by external validation like status or money, or by fears of what others think. This intuition fuels my creativity, enabling me to produce high-value, inspiring, and memorable experiences that elevate founders, executives, and entrepreneurs—whether through my coaching and workshops.

Zenpoji Temple (Tsuruoka)

A new big project I’ve been quietly developing from all my exploration is a leadership retreat for 2025. If that sparks your interest, DM for an inquiry.

Lesson #3: My Wealth Is My Time

One of the biggest reasons I ventured into entrepreneurship was to reclaim my time. Time, unlike money, is finite—we can’t get back our youth, health, or moments lost with loved ones. I couldn’t accept a future where my time was constantly traded for money (as in being employed), so I became determined to build a path where money would instead buy me free time, through assets and owning my business.

I wanted the freedom to work when and how I choose, without needing permission to take a day off, spend time with family and friends, or get off to retreat in Japan for a few weeks. I also want a future where I can be present as my children grow up. This freedom—freedom of time—is why I embrace the uncertainty of entrepreneurship every day. And I wouldn’t trade it for anything.

Lesson #4: Building A Business Is A Messy Process

I’ve struggled to commit fully to one business this year. It’s the kind of truth you can’t avoid when you take time to reflect and confront yourself.

Much like a startup testing different products to see what sticks, I have been exploring various ventures, between Kylan, Rise and Play, and Olivya. I guess this is my professional deformation as a former product leader—I’m used to iterating quickly and testing ideas. It was a painful process to close down projects I had invested in once I realized they weren’t the ventures I wanted to commit to fully.

Building a business is a non-linear process. Sometimes, the best way to find out what works is to do it, measure it, and then stop or continue.

Looking back, I hadn’t yet found clarity on my why, my fuel, as an entrepreneur. I initially thought I had found it with my passion for elevating leaders and expanding human consciousness through coaching.

But there was something deeper driving my decisions. That clarity came to me during my time in Japan, in a profound moment while attending a Buddhist prayer. I began to cry out of joy and relief when I realized that my why wasn’t about work only —it was about the family life with freedom I wanted to create.

A life in which I own my time as a woman, a mother, a partner, and a business owner.

Daishoin Buddhist Temple

Now that I’ve gained clarity on what makes me wake up every day, I am more determined than ever to commit to building my own business. I feel unstoppable.

Lesson #5: Letting go

This year has been about letting go of many things—shedding the habits and mindsets I carried as an employee, shifting from a saving mentality to one of investing in myself, and releasing the guilt of working on weekends or during “holidays.” I’ve learned to embrace the flexibility that entrepreneurship offers: sometimes working when others aren’t, and sometimes doing as I feel when everyone else is working.

I’ve also had to let go of past identities—like being a top executive at Corporation ABC, the comfort of a predictable monthly income, and even the act of building games directly—to make space for a new identity.

This process included letting go of businesses, such as Kylan, that no longer aligned with my vision while honoring the journey I shared with the partners involved.

I am very grateful for my business coach Matteo who has supported me in the process of throwing away all the playbooks and approaching this new chapter of my life with an open mind and intuition full-on.

⏯️ Retreat To Hit Pause And Reset

I encourage anyone—whether you’re taking a holiday, a few days off, or joining a retreat—to step back and reflect once in a while on your life choices. The benefits go far beyond work, offering a chance to evaluate where you’re heading and why.

When else will you take that step back if never? Do you want to be in the driver’s seat or passenger seat of your life?

Here are a few reflection questions I’d like to offer:

  • When was the last time you stepped back and took a broad look at your life choices?
  • What are you afraid to confront if you allow yourself that time for reflection?
  • What might be at stake if you don’t address these important questions soon?

📣 2025 C-Level & Founders Retreat

On that note, I’m thrilled to announce that our team will host a 3-day retreat in early 2025, exclusively for C-level executives and game founders. We’ll gather in a stunning villa nestled on a mountaintop close to the sea, with the exact location to be revealed later. If your busy schedule has kept you from taking a much-needed retreat, don’t worry—we’ve taken care of everything.

You’ll be joined by 11 curated game changers like you, sharing an intimate space to deeply connect, learn from one another, and elevate your thinking and business impact to the next level.

This is THE project I’ve been quietly working on all year, and I’m beyond excited to finally bring it to life 🌱

💌 If this resonates with you, DM me for more details. The retreat is exclusively reserved for Rise and Play members.

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