Lately, at the age of 34, retirement has been on my mind more than ever. It's a distant milestone, but one that resonates strongly with my generation. We're known for hopping between jobs and often don't have the cushion of traditional pensions. As an expat, I'm faced with unique challenges, like being unable to contribute to a 401K. Planning for retirement, therefore, becomes a complex puzzle, peppered with uncertainties about lifespan, financial needs, and the ever-changing global economy.

A recent Twitter discussion brought to light a crucial comparison: the potential financial benefits of investing in the stock market throughout one’s working life versus relying solely on Social Security. The stark contrast was eye-opening. Those who invested independently seemed to be in a better financial position. This throws a spotlight on the reliability of Social Security, a system with no contractual obligation, often deemed an unstable safety net. Even economists like Milton Friedman have critiqued it as The Biggest Ponzi Scheme on Earth.

For me, retirement planning means making a singular, irreversible decision. I'm set on avoiding a return to work post-retirement. Therefore, generating passive income is key in my strategy. Property investment is my current focus. I own a condo in Chiang Mai and am planning another purchase in 2025, contingent on how my savings stack up in 2024. Despite its risks, real estate offers a tangible path towards financial security for someone without royalties or product sales.

It's intriguing how we perceive money. Way back when, trading was pretty much like a swap meet. You have a wheel of cheese, your neighbor has a chicken, and you'd strike a deal – no middleman, no fuss. But then, enter the big game changer: money. Imagine the look on someone's face when they're told, 'Hey, forget the cheese. How about this shiny coin with the king's mug on it?' It must have been a real head-scratcher. We went from bartering with stuff you can eat or use, to trading pieces of metal and paper that are, frankly, useless in a desert island scenario. It’s like someone waved a magic wand and said, 'This piece of paper? Yeah, it's now worth 10 chickens or a small goat.' It's kind of bizarre when you think about it – the whole concept of money relies on us all buying into this big idea that these coins and notes mean something. It’s like the ultimate trust fall exercise, but with the economy.

While the prospect of achieving what's often referred to as "Fuck you money" — the level of wealth that allows absolute financial freedom and power — might be out of my reach, my goal is more about comfort than command. This desire for comfort, I believe, resonates with many. 'Comfortable' is a subjective term, and its definition varies widely. For me, it means living without financial worry. I envision a life where I can freely choose what I want from a restaurant menu without a second glance at the prices, where I can generously give gifts to my loved ones during Christmas, and where an unexpected medical emergency won't threaten my financial stability. What that means in terms of annual salary, for me, would be around $100,000, which would also allow me to save a significant amount.

That being said, I'm embracing the art of spending money judiciously while also honing my saving skills. My spending is directed towards things that add genuine value and joy to my life – be it travel, the latest tech, or cherished signed jerseys. This approach stems from a fundamental belief: what is the point of all our hard work if we don’t allow ourselves to enjoy its rewards? Life, after all, is about finding that delicate balance between diligent saving and rewarding oneself for the efforts put in.

Navigating the financial aspects of life, especially planning for retirement, is a journey of balancing aspirations with practicalities. But again, easier said than done.