When you’re single, retirement planning comes with a different kind of freedom. There’s no spouse’s career timeline to coordinate with, no debate about whether we’re ready, and no compromising over what retirement is supposed to look like.
Great! You get to make all the decisions.
Also: You have to make all the decisions.
And one of the biggest may be when to stop working.
On paper, retiring at 65 instead of 60 can look like the financially responsible choice. Five more years to earn. Five more years to save. Five fewer years your portfolio needs to support you.
But there’s another side to that equation: Those are also five years of your life.
Five More Years Can Make a Big Financial Difference
There’s no getting around the math. Working longer can strengthen a retirement plan in several ways.
- You have more time to contribute to retirement accounts.
- Your investments have more time to potentially grow.
- You delay the point when you begin withdrawing from your portfolio.
- You may be able to wait longer to claim Social Security.
- And if your employer provides health insurance, you can avoid having to bridge as many years before Medicare eligibility at 65.
For a single woman who is solely responsible for funding her retirement, those advantages can be significant. But financial planning isn’t only about maximizing the amount of money you have.
It’s about deciding what you want that money to make possible.
But…What Else Could You Do with Those Five Years?
Imagine yourself at 60.
Maybe you’re healthy, energetic, and ready to travel. Your parents may still be around. Your kids, nieces, nephews, or friends may have more flexibility than they will later. You might want to hike through Italy, spend a month at the beach, volunteer, take classes, move somewhere new, or just discover what Tuesday morning feels like when nobody owns your calendar.
Now imagine yourself at 65. You may be able to do every one of those things. But you also may not.
Health changes. Family responsibilities change. Friends and family members age. Energy changes. Life has a mildly irritating habit of refusing to follow the spreadsheet. That doesn’t automatically mean you should retire at 60. It means time deserves a place in the calculation alongside money.
There’s Also a Third Option: Stop Treating Retirement Like a Light Switch
Retirement doesn’t have to be full-time career until Friday, completely retired by Monday.
Maybe the choice is working full-time until 60 and consulting until 63. Maybe it’s moving to four days a week. Maybe it’s taking a lower-paying job you actually enjoy. Maybe you negotiate more vacation, work remotely, or take a sabbatical.
You might even decide you want to keep working, not because you need the paycheck, but because you like what work adds to your life.
The goal isn’t necessarily to stop working as early as humanly possible; the goal is to have enough financial flexibility that you get to decide.
Ask a Better Question Than “When Can I Retire?”
Instead of focusing on one magic retirement age, ask yourself:
- What would working five additional years give me financially?
- What could retiring five years earlier give me personally?
- What experiences are especially important to me while I’m healthy and active?
- Would working part-time or differently give me some of both?
- How much additional financial security would I actually gain by waiting?
- Am I working longer because the numbers require it, or because retiring earlier feels scary?
That last question can be especially important.
There’s a difference between needing more money and wanting more certainty. And when you’re the only person responsible for your financial future, it can be tempting to keep moving the finish line because another year of income always feels safer.
At some point, however, you have to ask what all that careful saving was for.
These questions are a big reason why I wrote You Can Go Your Own Way: The Single Gen X Woman’s Guide to Money, Midlife, and Meaning. I love helping women make financial decisions without relying on the traditional roadmap built around marriage, shared finances, and someone else’s timeline. For many single women, the goal is to have the financial flexibility to make choices based on what you want your next chapter to look like.
And sometimes, going your own way is exactly the point.



