Navigating the Messy Middle: Debunking Midlife Money Myths

This month, we celebrate both International Women’s Day and Women’s History Month. In her new book, Navigating the Messy Middle: A Fiercely Honest and Wildly Encouraging Guide for Midlife Women, author Ann Douglas opens with the idea that midlife “requires a radical imagination: a willingness to tell ourselves new and better stories about our lives.” We asked Ann what women had to say about money, how they feel about their financial lives and what living well means to them in midlife.

Inspired Investor: Can you tell us what about the current environment inspired you to write the book?

Ann Douglas (Ann): The past few years have been a really challenging time. We have been living through a series of interconnected crises: climate change, political and social upheaval, economic shifts and, of course, a global pandemic.

I wrote this book to offer encouragement and to validate what midlife women have been thinking and feeling about journeying through midlife right now. But, above all, I wanted to offer an alternative to the cultural messages that tell women like me that midlife is either completely magical or completely miserable when, in fact, the truth falls somewhere in the middle. The messy middle.

Inspired Investor: You interviewed more than 100 women for the book about a wide range of topics. How often did the topic of finances come up?

Ann: Given that I didn’t explicitly ask any questions about money, I was surprised how often the women I interviewed spoke about that, especially given the longstanding cultural taboo about being open and honest about your finances. The fact that so many of them broached the topic of money themselves indicates how anxious many of them were feeling as they reflected on their finances moving forward. Many find themselves circling around the same, worrisome question time and time again: “Will this actually be enough?”

Inspired Investor: You outline a number of common myths about midlife. Let’s talk about a few of them.

Inspired Investor: When many women reach midlife and this vision is not their reality, how does it impact them?

Ann: Some of them feel angry—like they were sold a bill of goods about an aspirational lifestyle that is only a possibility for a privileged few. Others pivot to a place of self-blame, feeling that they must have made a lot of bad mistakes along the way when, really, they were bumping up against structural factors. And still others are working on finding enjoyment and satisfaction by ignoring the myth that travel or expensive spa days are the measure of a life well lived.

One 48-year-old businesswoman told me, “I’ve learned to embrace who I am. For so long, I tried to tamp down who I was to accommodate the wishes of others,” she said. “I’m not everybody’s cup of tea and it’s taken me almost fifty years to realize that’s quite okay.” Maybe that’s the real “me time.”

Inspired Investor: When it comes to women’s financial lives, what did you learn about this generational shift and how it applies to women creating the future they want?

Ann: While not all are on solid ground financially, women who are moving through midlife today are more likely to have had full-time jobs outside the home than their mothers or grandmothers did.

A 2021 article from the journal American Psychologist warned about the impact of growing financial pressures, a shrinking social safety net, and increased mental and physical health challenges. To put it bluntly: this is not your parents’ or grandparents’ midlife experience. It’s a whole lot messier. But one thing that many women told me is that midlife teaches us that “we can do hard things”. By looking back at some of the tough experiences in their past, many women told me they are able to look to the future from a place of strength, knowing they are better equipped to deal with whatever life throws at them in the decades ahead than they might have been when they were younger.

Inspired Investor: When many women are busy with some combination of work, home, elderly parents, kids and more, the idea of “finding a passion” can be just another pressure added to the list. What are midlife women are really focused on?

Ann: Most of the women I interviewed are juggling multiple roles and responsibilities while also daring to imagine what it is they actually want for themselves. Here’s something interesting I learned. Our time perception flips when we arrive at midlife. Instead of focusing on how many years we’ve lived through, we start thinking about how many years we have left. The question then becomes: “How do I want to spend that time?”

This realization can be incredibly clarifying for midlife women. This new-found sense of urgency can encourage them to zero in on things that matter most to them. It doesn’t have to be expensive or time-consuming or life changing. It can be as simple as daring to acknowledge what it is they really want—and to start looking for opportunities to get more of that good stuff in their lives, both today and moving forward. Financially, this means focusing available resources in an intentional way and tuning out the persistent noise about cruises or golf.

Inspired Investor: This is a persistent myth. What are today’s women saying about finding their own path to midlife joy?

Ann: Many of the women I interviewed told me that the path to midlife joy involves self-knowledge, self-acceptance, and self-love. It’s about understanding the person you’ve been, celebrating the person you are, and loving the person you are becoming. It’s about understanding that life is always about change—and that change isn’t necessarily something to be dreaded. It can also be something really beautiful.

Inspired Investor: For the parents out there, when it comes to the empty nest, does it tend to have a positive or negative effect on how women view their financial life? Does it provide some measure of financial relief?

Ann: Not always, unfortunately. Sure, you don’t have to fill the fridge with quite as many groceries if your young adult children are no longer living under the same roof, but that doesn’t necessarily mean that you’re off the hook financially. As I note in my book, while the teen years used to be the years requiring the greatest financial investment from parents, over the past few decades that’s changed. Parents are most likely to feel the most financial pressure at two separate points in the parenting life cycle: when their kids are very young (under the age of six) and during the young adult years. Some scholars have even suggested that over one-third of the financial costs of parenting are now being incurred in the years after children turn 18!

But when kids are starting to become financially independent and parents are no longer having to cover their day-to-day living expenses, that can provide a bit of financial breathing room (and fewer lineups for the bathroom!). It’s also an opportunity to be the kind of family that has frank and honest conversations about money—to break the silence that can lead to so much needless anxiety and self-blame.

Inspired Investor: We’re all unique. Your interviews for the book included women with a wide variety of different backgrounds and experiences. Were there universal themes that emerged despite all these differences?

Ann: A couple of key themes come to mind. The fact that midlife can be a time of tremendous learning and growth as well as increased self-knowledge and self-acceptance. The fact that midlife women have a tremendous amount to contribute, as a result of all our decades of life experience, and that society would do well to treat us as a powerful resource. And the fact that relationships mean everything as we travel through this messy middle chapter of our lives.

It’s important to look for opportunities to forge friendships with other women—and to do so across generations. As midlife women, we can journey through the remainder of our lives “with one arm stretched out to those who are older than ourselves, and the other reaching back to those who will follow in our footsteps,” in the words of narrative psychologist Molly Andrews. We were never meant to journey through this life stage—or any life stage—on our own.

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