The Retirement Freedom Paradox: Why Most of Us Are Planning to Keep Working

Ask future retirees what they want in retirement, and you'll hear one word over and over: "freedom."
But here's the twist. When you ask those same people what they're actually planning to do in retirement, more than half say they'll keep working.
Not because they're passionate about their current roles. Not because they love the commute. Because "freedom" turns out to be more complicated than we thought.
The Split That Tells the Real Story
According to a recent survey of over 1,000 education workers approaching retirement, about a third are considering retiring sooner than planned. Their top reasons? Working conditions and health concerns. They're being pushed out.
Another quarter are considering delaying retirement. Their top reason? The economy and inflation. They're being held in.
This isn't about people freely choosing when to stop. It's about external forces making the decision for them.
The people who talk about working in retirement aren't planning to stay in their current full-time roles. They're imagining something different. Part-time work on their terms. Consulting gigs. Passion projects that actually pay. A gradual transition instead of a hard stop.
One respondent put it clearly: "I plan to continue contributing, would be a better way to put it, or perhaps working on my own terms with a reduced load."
That's the dream. But having the choice to work on your terms requires something most people don't talk about: enough financial security to say no.
The Hidden Barrier to Working on Your Terms
Here's a detail from the survey that deserves more attention: nearly a quarter of respondents reported experiencing ageism in the workplace.
Think about what that means for someone who wants to transition into part-time or consulting work. If you're already hitting invisible ceilings in your 50s and early 60s, finding flexible work on your terms gets harder. One respondent noted: "There's an unspoken culture for advancement that means you hit the ceiling at some point as you get older."
So even if you have the financial means to step back, the workplace might not give you the option to work on your terms. You're either in or you're out.
This is the gap between the retirement people want and the retirement they're likely to get.
What Actually Creates Freedom
The respondents who felt most confident weren't necessarily the ones with the biggest savings accounts. They were the ones with plans.
But not just any plan. A plan they understood well enough to model different scenarios. What happens if I retire at 60 instead of 65? What if I work part-time for three years first? What if the market dips the year I retire?
Freedom isn't just about having money saved. It's about knowing what your money can actually do. Can it support you working part-time? Can it handle an early exit if working conditions become unbearable? Can it stretch if you need to delay retirement by a year?
The difference between anxious and confident isn't optimism. It's information.
The Choice That Matters Most
The new retirement isn't binary—work or don't work. It's about control. Can you work on your terms, or are external forces deciding for you?
Some people will be forced out early by conditions they can't change. Others will be forced to stay longer than they wanted because they can't afford to leave. Both groups lose the thing they said they wanted most: freedom.
The only way to know which group you're in is to see your numbers clearly. Not vague hopes or rough guesses. Actual scenarios that show what's possible at 60, 62, 65, or 67. What happens if you work part-time for two years first. What CPP looks like at different start dates. Whether your savings can handle the transition you're imagining.
Because "freedom" isn't just about stopping work. It's about having enough clarity to choose—whether that means working less, working differently, or not working at all.
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