There’s a Chinese saying that marriage is like a fence—those inside want out, and those outside want in. Personally, I think that’s a bit dramatic. Plenty of people are perfectly happy inside the fence, and plenty are happily lounging outside with a cocktail.
And the same goes for work. The grass isn’t always greener on the other side of the work vs. retirement fence—it’s just cut differently. Some people work well past retirement age, not because they have to, but because they genuinely love it. Others retire early and find fulfillment in hobbies, travel, or perfecting the art of doing absolutely nothing.
Life isn’t about escaping or breaking in. It’s about making wherever you are feel like exactly where you’re meant to be—fence or no fence. And how do people do that? By designing a life that actually fits them. By knowing what energizes them and doing more of it, whether that’s meaningful work, creative pursuits, or just having an afternoon coffee in peace. By focusing on what they have instead of what they think they’re missing. And by realizing that happiness isn’t about being on the “right” side of some imaginary fence—it’s about planting the kind of grass you actually want to stand on.
Related Post: What is Your Freedom?
[Written by Claude]
The Reluctant Retiree
Meet Eleanor, 72, a former corporate executive who views retirement like a mandatory vacation she never asked for. While her peers are collecting seashells and perfecting their golf swing, Eleanor is consulting, mentoring startup founders, and terrorizing local business networking groups with her unretired energy.
“Retirement?” she scoffs, adjusting her designer blazer. “That’s just another word for irrelevance.”
Her calendar is more packed than most 35-year-old professionals. Speaking engagements, board memberships, strategic advisory roles—Eleanor hasn’t just retired; she’s reimagined what retirement could mean. The corporate fence she once wanted to escape now looks like a playground she’s reluctant to leave completely.
The Fence-Hopper
Then there’s Michael, 45, stuck in a corporate job that feels like wearing a suit made of sandpaper. Every Monday morning is a battle, every meeting a test of his sanity. He stares out the window, dreaming of the other side—retirement, freedom, escape.
“Just ten more years,” he mutters, marking another day off his secret retirement countdown calendar. His colleagues have learned to avoid him during coffee breaks, lest they trigger another monologue about beaches, woodworking, and the mythical land of “doing whatever I want.”
The FIRE Starter
Then there’s Zoe, 28, a walking spreadsheet with dreams bigger than her current salary. FIRE (Financial Independence, Retire Early) isn’t just a concept for her—it’s a lifestyle religion. While her peers are upgrading their smartphones, Zoe is optimizing her investment portfolio down to the decimal point.
Her apartment is a masterclass in minimalism—not because she’s trendy, but because every unspent dollar is a soldier in her early retirement army. Ramen isn’t just a meal; it’s a strategic financial decision. Vacation? That’s what YouTube travel vlogs are for. Her idea of luxury is a perfectly balanced index fund and a side hustle that generates passive income.
“I’m not living to work,” Zoe declares, showing her meticulously color-coded budget spreadsheet. “I’m working to live—specifically, to live freely by 35.”
Her colleagues look at her like she’s speaking a foreign language when she talks about geographic arbitrage, passive income streams, and the magic of compound interest. But Zoe sees the corporate fence not as a career path, but as a temporary pit stop on her journey to complete life autonomy.
The Unexpected Middle Ground
But here’s where the story gets interesting. Not everyone sees work as a prison or retirement as the ultimate liberation. Some find their sweet spot right in the middle—dancing along the fence, one foot in, one foot out.
Like Sarah, who negotiated a flexible consulting role after “retiring” from her tech leadership position. Or David, who transformed his passion for teaching into a part-time university role after leaving his full-time engineering career. They’ve discovered that the fence isn’t a barrier—it’s a vantage point.
The Illusion of Boundaries
The truth is, the fence between work and retirement is more of a suggestion than a wall. Some leap over eagerly, some cling to it desperately, and some find the most joy in straddling both sides.
It’s not about escaping or entering—it’s about choice. About creating a life where work isn’t a cage, but a canvas. Where retirement isn’t an endpoint, but another beginning.
The Real Pension Plan
What if the most valuable currency isn’t money, but options? The ability to pivot, to reinvent, to find meaning whether you’re wearing a corporate badge or a “retired” label?
Some will always want what’s on the other side. The corporate warrior will dream of lazy mornings. The retiree will miss the structure of work. The fence will always have its appeal—but the magic happens when you realize the fence is of your own making.
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