109: How I Built a Life I don't Need a Vacation From

👋 Managing Tech Millions 📈 your go-to source for building wealth with tech equity and managing the money that comes with it.

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For years, I chased the dream that everyone told me would bring happiness—big title, high salary, working at the top of my industry in New York City. In 2016, I had it all: I was the Chief Information Officer, working on Madison Avenue, climbing toward an IPO with equity and prestige. But deep down, it felt like hell.

I remember the breaking point clearly—another phone call to my wife, telling her I wouldn’t make it home for dinner. Again. I had three young kids at home, a beautiful family I barely saw, and despite all the money and success, I felt exhausted, frustrated, and empty.

This video is the start of my journey to build something radically different: a life I didn’t need a vacation from.

I dive into the painful realization that chasing traditional success was costing me everything that really mattered. I share how I began to redesign my life, step by step—rethinking what work meant, redefining success on my own terms, and learning to prioritize freedom, presence, and purpose over status.

This isn’t a get-rich-quick story. It’s about alignment. It’s about creating a sustainable lifestyle where your values match your calendar. In this episode, I open up honestly about what pushed me to make a change and the early steps I took to get out of the rat race.

If you've ever felt stuck in a career that looks good on paper but drains you daily, this story is for you. I hope it inspires you to ask better questions and start building a version of success that actually feels like your own.

* Discover why chasing titles and high salaries doesn't guarantee happiness—and what actually does.

* Learn how redefining success can help you align your life with your true values and priorities.

* Get mindset shifts to help you start living intentionally.

* See how small, courageous steps can lead to a more fulfilling, balanced, and sustainable life.

* Learn why building a life you don’t need to escape from is not only possible—but necessary.

⏱️ Timestamps

* [00:00] Introduction to building a life without needing a vacation

* [02:30] Living the corporate dream—but feeling empty

* [05:15] The family sacrifices and emotional cost

* [08:00] The moment I knew something had to change

* [10:45] Redefining success and starting over

* [13:20] Learning to live with intention

* [15:40] Lessons from stepping away from the rat race

* [18:30] First steps toward a freedom-based lifestyle

* [21:00] Key takeaways and what’s coming next

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