Dream Big and Often – Financial Samurai

Personal finance opens up a world of possibilities, allowing us to dream about what could be. When I was a freshman vying for a spot on the varsity tennis team, I used to dream about becoming a professional tennis player, signing autographs at Roland Garros. These days, whenever I attend a tournament, those childhood feelings rush back, and I’m a kid all over again.

As a college student strapped for cash, I would walk past business students glued to CNBC and dream about making it big on Wall Street. I imagined myself managing hundred-million-dollar trades and baffling traders on the opposite end. After a profitable day, the celebration would continue at Peter Luger’s Steak House, riding in a sleek black car, surrounded by clients and friends, all on the company’s dime.

After enduring several grueling years of long workdays in New York City, my dreams shifted towards freedom—setting my own hours and escaping the relentless grind. As someone who loves poker, I also fantasized about winning the WSOP’s multi-million dollar prize. While some might quit their jobs on the spot, I envisioned continuing to work, enjoying it far more when money wasn’t a necessity. After all, I’d be the WSOP champ!

Now, retired from the corporate grind, I still dream. It feels like I’m living a dream within a dream, having broken free from the corporate life earlier than I ever imagined. This freedom makes me wonder about the new opportunities that might unfold over the next 25 years.

A reader once expressed surprise at seeing “Live Free” as one of my goals. Ironically, freedom can be daunting when you’re faced with making all your own choices. But I’d always choose to have options rather than be stuck with none.

I dream of progress and adventure. The best thing about dreaming? It’s free and anyone can do it.

What are your dreams?