Dear Risk Takers, your stories of taking chances and diving into the unknown really bring a smile to my face. While I usually advocate for having a financial cushion, there’s something genuinely exhilarating about your bold moves. It’s a reminder that sometimes, we don’t need much to make a significant change, especially in a place as resource-rich as America.

You are truly fortunate, unburdened by what you could lose, which might not be much to begin with. This freedom to risk it all without the weight of heavy losses is truly liberating. I first pondered these thoughts back in 2010 when I was 32, questioning the true value of my routine life in finance.

Thoughts on Breaking Free

For many of us, the reality is much different. We’re anchored by mortgages and car payments, tethered to jobs that pay just enough to keep us from leaving. We chart our lives in spreadsheets, counting down years and dollars to eventual freedom, dreaming of the day we can travel the world without financial worries. Until then, we live vicariously through each of you who has taken the leap.

Remember the fresh excitement of freshman year in college? That sense of endless possibilities and new connections felt like a whole new world opening up. Yet, as time passes, we often find ourselves conforming to societal expectations, losing that spark of curiosity and adventure.

Two Choices Post-College

When I graduated, my choices were stark: venture abroad to manage a widget factory or dive into a coveted corporate job that every ambitious graduate desired. I chose the corporate path, reasoning that there must be merit in what everyone else was striving for.

That decision led me to a grueling routine that I eventually broke free from to start anew in San Francisco. Here, the refreshing environment and accessible recreation made life vibrant again. But I often wonder, what if I had chosen differently? Perhaps I would have been a tri-lingual millionaire, or maybe I would have been worse off if the factory had failed. It’s a fun thought, not one of regret but of curiosity.

You Are the Lucky Ones

People don’t upend their lives when they are content. They do it because something is gnawing at them, demanding change. Maybe it’s an insufferable boss, a soul-crushing job, or a sudden realization that life is slipping by. These catalysts provoke change, leading to the inspiring stories I cherish.

It’s a pity we can’t live multiple lives or be in two places at once. Each choice leads us down a unique path, so choose wisely and live without regrets.

Thank you for sharing your adventures. They inspire those of us not quite ready to make the jump ourselves. Maybe in a decade, when my career has wound down, I’ll be ready to join you. Until then, I appreciate living through your experiences, and perhaps, just maybe, you’ll find that some are envious of your freedom to chase your dreams.