Reimagining, Planning and Affording What’s Next

5 minute read

Joanne Lipman, former Editor-in-Chief of USA Today and the first female Deputy Managing Editor of The Wall Street Journal, awoke one morning in mid-April 2020 with a stark realization: “We don’t know if life is getting back to normal. We don’t know if work is getting back to normal. All of us are going to have to figure out what the new normal looks like.” She quickly scribbled a note to her publisher. “There is no guidebook to get us there, to tell us how we rethink living and working.” The best-selling author of “That’s What She Said” had found her next project.

“Next! The Power of Reinvention in Life and Work” hit shelves in March of this year.  For the members of the Peak 65™ generation – the 12,000 people a day who will turn 65 in 2024 – and millions of additional pre-retirees facing similar issues, it couldn’t come soon enough. “I don’t think we are on the other side of this crisis,” Lipman says. “We are still in a moment of transition.” And that transition takes on different forms for different people. It might be a new way of spending our days, a new locale in which to spend them, a new way of earning money (or making the money that you’ve already earned and invested last as long as you do), or many other things.

And a transition of this scope is not easy. That anyone says that it is, or even that it should be, is a big part of the problem. “We skip over the struggle part in the stories we tell,” Lipman says. “As a result, when you are in the struggle, it seems like only your problem. You feel stuck. And when you finally start to talk about it? That’s the moment of reappraisal.”

In her research, Lipman has come up with dozens of strategies and tactics to help you get from where you are today to your next iteration. She unpacked a few of them in the latest Your Money Map with Alliance Education Fellow and HerMoney CEO Jean Chatzky.

But somehow, along the road to adulthood, we lose the power to reimagine different futures.

-Joanne Lipman, Next!

WATCH Your Money Map: Reimagining, Planning and Affording What’s Next

On May 3, 2023, Joanne Lipman, author and former editor-in-chief of USA, joined Jean Chatzky for an episode of Your Money Map titled, Peak 65: What a Retirement Surge Means for Your Future. In 2024, more Americans will turn 65 than ever before. This represents a major demographic shift — our population is growing older, which means it’s even more crucial for us to plan ahead for retirement. How does a higher number of retirees impact older Americans? What effect does it have on our retirement income streams? With longer lifespans and increasing economic uncertainty, how should we be rethinking the traditional retirement age and lifestyle?

See It To Be It

It might sound obvious, but in order to get where you’re going, it really helps to have some idea of where you want to go. It doesn’t have to be exact. In fact, keeping some optionality in the picture – an open mind – is important.  But you also want to start seeing yourself as a version of the next you, or as Lipman puts it, your “future selves.” This is the first step in motivating yourself to evolve.  But then you have to move past the visualizing into a place where you’re doing something that will help you become that next you. “You have to take action on it,” she says. “Shadow someone. Take a course. Take it up as a hobby.  [Do something that entails moving] on the idea.”

Seek Out An “Expert Companion”

What if you’re one of those people who doesn’t know – really doesn’t know – what your next move looks like? Don’t panic, Lipman says. You’re not all that unusual. “So many of us have talents and skills that are so innate to us that we either don’t recognize them at all or we discount them.” The presence of an expert companion – a title she borrowed from trauma psychologists – can help. In the study of trauma, it’s a person who acts as a sounding board for your story to help you get into a phase of post-traumatic growth. In reinvention, it’s someone who knows you really well. “Their job is not to give advice, but to reflect you back to you,” says Lipman. “It allows you to see yourself with far more perspective.  And it’s helpful in seeing the progress that you’ve already made.”

Create a CV of Failure

A CV of failure, for the record, is just as it sounds. It’s a resume – or if you’d prefer, a laundry list – of every job you didn’t get, every interviewer who ghosted you, and every promotion you were denied. Lipman learned this trick from, among others, a scientist with an amazing career who told her: “Yes, I got into Harvard, but in fact I applied to 16 other programs [that I didn’t get into.]” Detailing the disappointments of her working life brought her to the realization that all of her failures were related to scientific work done in a laboratory setting. It made her realize her strengths were in computational biology – so she pursued positions in that area, and that’s where she started to thrive. “Your failures provide you with data,” Lipman notes – and the data can be illuminating.

Don’t Quit Your Day Job

Finally, as you go through all of these steps – and potentially many more – it’s important to keep an eye on another important set of data as well: your balance sheet. “Financial security is a real thing,” Lipman says. Seeking out expert advice as you transition about how to be sure that the money you’ve accumulated for retirement or your next chapter will go the distance, when to tap Social Security, and how much you need to keep earning (and for how long) is an equally important part of the discovery process. That’s why a visit with a financial advisor at least 10 years prior to retirement is a must on the list of to-dos. But don’t let the list itself become so daunting that you hold yourself back, Lipman notes. And as you’re going through the process, keep an open mind – or one as open as possible. “Not having an end goal allows you to pivot. [For many of the people I spoke to,] it allowed them to go to more fulfilling places that they didn’t expect.”


For more tips on preparing for retirement or your next chapter of life, and making sure that your income lasts a lifetime, visit the Tools and Guide section of The Alliance website.

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