Invest Retirement

Retire On Your Own Terms With Anne Lester

Haley Paskalides  |  March 13, 2024

Anne Lester shares how she socked away enough to retire early (even though she didn’t start saving until her mid-30s).

We’ve been thinking a lot about “Peak 65” over here at HerMoney HQ. If you haven’t heard about it,  it’s the fact that more people are turning 65 starting this year than at any other point in history. That’s important because this age shift is going to have a huge impact on everything, including our economy, Social Security, the upcoming election, and especially on retirement.

If you’re starting to think about retirement planning (or perhaps you’re in the midst of it!) you may be feeling surprisingly disempowered — despite the endless commercials showing golf courses, grandkids, sailboats, and long walks off into the sunset with our partners. That’s because there’s so much bad information out there on how to truly have enough to make it through our golden years. 

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Anne Lester, former head of retirement solutions for J.P. Morgan Asset Management Solution Group, wants everyone to know that planning for retirement doesn’t have to be so scary — it can be empowering, and yes, even fun.

Despite her job title, Anne says she’s never been good at saving — she didn’t save for retirement until her second son was born. “I was 37 and I’d signed up for the 401(k) plan, but I hadn’t actually paid any attention to it. I remember thinking, ‘Well, okay, I’ve got two kids. I really have to get serious about this adult stuff,’ but trying to figure out what to do was so stressful,” Lester says. 

“What unlocked everything for me was when I started learning about behavioral economics and brain wiring. And that was such a powerful thing for me to go, ‘Oh, I’m not stupid. I’m actually not even irresponsible. This is just the way I’m wired.’”

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In Lester’s new book: “Your Best Financial Life: Save Smart Now for the Future You Want,” she talks about how she was finally able to stop living paycheck-to-paycheck and was able to retire early on her terms. She also breaks down how much we really need to save to retire comfortably if we’re 20 or 30 years away from our retirement date. 

While there are many ways to calculate this, Lester says one rule of thumb she likes to go by is to have ten times your annual income saved. “So if you’re earning 100,000 a year, that means you should have saved $1 million dollars,” Lester says. “And that means the money you can generate from that million dollars, whether it’s using lifetime income opportunities, whether it’s combining that with maybe some withdrawal strategies, plus social security, should give you 80% of what you were living on before.” 

Lester also wants people to know that retirement looks different for everyone, and that embracing part-time work well past your retirement date can be a great option — both socially and economically. 

For folks in their 50s, Lester recommends starting to envision what you want your retirement to look like, and putting plans in place to get there. “Try to imagine what that next decade looks like that might lead you to an off-ramp that helps you embrace all the benefits that come with working, and develop a roadmap that will get you there.”

In Mailbag, we hear from a listener who is wondering if they should stay at a job they don’t love for the excellent retirement benefits. In our money tip of the week, with Mint shutting down in less than two weeks, here are the other budgeting apps we recommend.


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All advisory services offered through Financial Engines Advisors L.L.C. (FEA), a federally registered investment advisor. Results are not guaranteed. AM1969416

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