Jordan Rosenfeld

Thu, Jun 26, 2025, 10:03 AM3 min read

When retirement is still ahead of you, it often looms with mythic power as an ideal, easy time when you no longer have to work or carry as much stress as during your working years.

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The closer you get, however, the more danger you’re in for making financial mistakes (typically through a lack of planning), according to finance expert Emily Guy Birken, author of the book “The 5 Years Before You Retire” and many others.

“Before you retire is the best time to think about retirement,” Birkin said on a podcast with CFP Jeremy Keil of Keil Financial. For a lot of people, retirement doesn’t become real until this time window, if you’re lucky, and for many others, not until after they already retire and discover their plans aren’t foolproof.

These five years before you retire are a crucial time because they allow you to “road-test ideas” for retirement, Birkin told Keil. This is when you can actually practice living as you might after retirement, focusing on how you want to spend your time (in small doses), explore places where you want to live, lean into areas of interest and, of course, start to dial in your financial plans. The importance of these five years is that you still have time to pivot, she pointed out.

“It can be affirming to do this but people put it off because it feels overwhelming,” she said.

If your plans don’t seem like they’ll be ideal, you can change them before the actual end date.

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Birkin said in these five years prior to retirement you should be not just running on common assumptions about how much you need in retirement but actually crunching hard numbers so you don’t come up surprised or short.

It’s important to be looking concretely at your typical “day, week, month and year” expenditures and then being able to point to where you’re saving money concretely, she said.

It’s also a time to start reducing expenses, or planning to reduce them by the time you retire, and thinking about how to enjoy life in different, or more affordable, ways.

It’s also important in this five-year window to figure out a “Plan B,” she said. That means that if the first plan you strategize for is out of reach financially, you should ask yourself “What is the least you need to be satisfied?” Once you know what that is, by adjusting your expectations, you can still feel like you’ve succeeded in retirement.