Not Young, Not Done: Sherry Finkel Murphy’s Blueprint for Midlife Reinvention

Sherry Finkel Murphy CFP®, RICP®, ChFC® is on a mission to redefine what it means to thrive in midlife and beyond. As the Founder and CEO of Madrina Molly™, she blends decades of financial expertise with a passion for storytelling to help women navigate the complexities of extended life expectancy, encore careers, and financial freedom. Known for her fresh takes—like creating a “F*CK You Fund” and balancing life in the “Triple-Decker Club Sandwich Generation”—Sherry’s insights are both practical and inspiring. With her relatable wit and actionable advice, Sherry is transforming the conversation around ageing, proving that this chapter of life is not the end—it’s just the beginning. She reminds women everywhere: you’re not young, but you’re not done.

Can you share the story behind Madrina Molly™? What inspired you to create this platform? 

One of the things that was clear to me from my financial planning practice is how underserved and invisible “women of a certain age(ncy),” as I call them, are. Only 16% of the cohort has financial education. And yet we will control $30T by the decade’s end. So, we need to get smart fast. 

At the same time, only 24,000 CFP® Professionals are women. Thus, if a woman is looking for a qualified planner, she may have a tough time finding one. And since planners need to run profitable practices, they may not be available for the cohort that is high cash flow trying to understand how to become wealthy. They may be working only with the already wealthy. 

I was the only planner in my practice who did fee-only planning for this HENRY (High Earner  Not Rich Yet) group—offering a flat-fee financial planning engagement with no expectation of implementation of any financial products/solutions until I had earned it. As a result, I was able to spend time with my prospective clients without feeling the need to sell them anything until and unless they were ready. This group includes a lot of first-generation wealth—women who never expected to earn as much as they do and who need cash flow planning before they take any other steps.  

Then, when life came at me fast, and I discovered that I needed to be in two places at once, I  completed my portfolio succession plan and spent 2023 preparing to go virtual. I now describe myself as a woman with an extra walker in the boot and an extra child seat in the back of the same SUV. I am a grandmother when I’m in Ohio. And I’m a daughter to a soon-to-be 97-year-old mother in NY.  

I think I am being disruptive by using a membership model to democratize financial planning information. Women don’t need to know everything that I know. But they need to have a place to ask questions, share their experiences with peers, and learn some important concepts at their own pace. I can then refer them to credentialed professionals if they do not work with one already. Pardon the hubris, but most women planners are young. My life experience is useful in engaging the BoomX cohort. 

The concept of the “Triple-Decker Club Sandwich Generation” is so relatable. Please explain it—and how do you see this phenomenon impacting women’s financial and emotional well-being? 

This is the first time in history that 4 and 5 generations are living contemporaneously. We are  seeing a huge increase in caregiving needs at both ends of the age spectrum, housing needs due to shortages and failure of builders to build what Boomers and BoomX need, and an increase in multigenerational living due to financial considerations and to cultural influences of the Global South. 

For our cohort, it means that the window of freedom—between launching children and caring for elderly parents—is closing fast. And it’s a problem that money does not solve. You can have all the money in the world; but if you’ve waited until you’re 65 and the kids are launched to take that month-long trip to Europe, you might have it curtailed by worrying about an 85-year-old Mom who is still living in her own home. A generation ago, she would have already passed on.  

As a result, I am encouraging women to take their ‘big’ vacation or sabbatical in their 50s and exchange a year of retirement savings for a promise to avoid spending down assets for one year longer. This kind of math works. I call it “The Year of Not Saving.” And it can help us make the last big push—the last decade of work—a little easier, before calling it quits. 

On the other end, people tell me all the time that they want to retire early; let’s say 60. I point out that, if they had children in their late 30’s, are they sure they want to pay for the last two years of college out of savings and not cashflow? Ouch. And what if they have ‘emerging adults’ who are slower than we were to launch?  

Third, much as we hate to admit it, if we are planning to climb Machu Picchu or walk on Eastern  Europe’s cobblestones, we have to do it while our knees and hips cooperate, so to speak.  Sooner is better. 

Now there’s a multi-generational solution to this that is very elegant. And that’s to involve the grown children in a little extra caregiving for our parents before they launch their careers and families. This is not a chore; rather, this is love and empathy. I think we disregard how powerful it is that Zillennials have known their grandparents all their lives. And, unlike our experience, they are using their exposure to design a future that is less ageist and gendered than the roles we inhabit today. The media doesn’t want to pick up on this. I want to discuss almost nothing else. Kids today think their grandparents are cool.  

Last, we should expect to have 100-year lives. That means that our tri-part expectations  (education-work-retirement) will be replaced by flex-ordered phases with breaks and recursive loops back and forth. We should develop flexibility early, before we need consultancy or a part-time role. We should be prepared to be in and out of the workforce several times between 50  and 70 or 75. 

You champion the idea that “we have more runway than we think.” How do you help women reframe their perspectives on longevity and retirement? 

This is a favourite of mine. When we think of chronological age, we do ourselves a disservice.  First, this is because we are far younger at each age than our parents and previous generations were. Second, this is because if we view ourselves as a deteriorating asset, it becomes a self-fulfilling prophecy. While the 19th and 20th Centuries made leaps of progress in reducing child mortality, the second half of the 20th Century added 20 years to the end of our lives. Unfortunately, it’s only now that we’re thinking we should do something productive with them. 

I recommend that we think “thanatologically.” When you realize at 50 that you likely have 32-39  more years to live, only the last 5 of which might be old age, you realize that there’s a lot you can do and it’s only too late if you don’t start doing it right now! 

Storytelling plays a big role in Madrina Molly™’s educational approach. Why do you think storytelling is so effective in financial and longevity planning? 

The problem of the financial planning domain, like the health domain, is that it is built on data and anecdotes from 20th-century white men. Women and minorities do not see their lived experiences in the data. I think it’s important that we include our anecdotal experience. 

I also think it’s important for women, who bring me their financial shame along with their financial questions, to hear that things are likely to work out just fine. Like the Scarecrow in Oz, we don’t need more brains. We just need the reaffirmation that we’re travelling on the right path.  

By the way, perfection in financial planning doesn’t exist. There are many ways to be successful and only a few ways to doom a financial plan. Don’t do the incredibly dumb stuff and you’ll likely be fine. But women need to hear this instead of hearing someone lecture them that they can improve their portfolio performance with the X model.  

Think of it: Advisors don’t get paid to say, “Stay the course, I can’t improve anything here.”  They get paid to scare you into giving them your money to manage. I remind women that they are speaking to me because of all the other pieces of planning that are, frankly, more critical than portfolio performance, like addressing tax-smart distribution or planning to mitigate frailty. 

You’re an expert in financial, retirement and longevity planning. Please share how planning for each of these differs from the others. 

If I were creating a diagram, longevity planning would be a superset of financial planning,  financial planning is a superset of retirement planning.  

Longevity planning includes financial management, health and frailty management, social factors like community and meaning; and geography, home and services. 

Financial planning is a comprehensive look at managing savings and growth to achieve goals;  addressing a Plan B and C if life throws a curveball. (Life always throws a curveball.) And solid estate and distribution planning, which requires lots of un-sexy thinking about taxes, rules, and beneficiaries. 

The retirement planning part is distribution and tax planning to understand how to decumulate a portfolio. As an aside, most advisors aren’t very good at it, having only concentrated on growing wealth, not spending it. And yet, it’s really important to get this right. Retirement planning answers a specific question: Based on your savings, your savings rate, and the tax treatment of the accounts, here’s how much you can spend monthly and live to 100. Do we like the answer or not? Then we talk about how to improve the number, how to reduce the risk of the unexpected happening, and how to secure gifts, estate, and intangible goals. 

You’ve chosen to mentor the next generation of financial advisors. What advice do you give them about connecting with midlife clients? 

I share what has worked for me. And that is that women do not want to be sold financial products. They want an education in what they need and why they need it. Some of them will want more details about what a particular product does. But, at the end of the day, BoomX women want to know the answer to one question: Will I have enough to do what I want to do for the rest of my life?  

That’s it. The goal isn’t $1 or $5 or $10MM. It’s “will I have enough?”  

I encourage women advisors to network and teach prospective clients and use the laws of attraction to offer a relationship to them. That is how I built a loyal practice—by teaching women things they could not learn elsewhere. I would sit with anyone and have coffee, rather than try to  ‘sell’ them my advice. I also think the future of planning is behavioural finance and distribution.  Portfolio management by robo-advisor will become more and more popular. 

What’s your favourite piece of financial advice you’ve ever received? 

I purchased my first apartment at 24. But before anyone gets jealous, my mortgage rate was  11.85%! When I wanted to trade up to an apartment in NYC at 26, my mother said to go for it  and this: 

“If you wait for a man to bring you the good things in life, you’ll be waiting a long time.” 

I thought that was funny. But, far from disparaging men, I interpreted this to mean that my ambition and financial goals were up to me to achieve. My future husband would be a partner,  but I should not look for him to be my financial rescue. And that’s how I’ve treated my own goals. That’s what I tell clients and members. A man is not a plan. I end most social media posts  with #WeRescueOurselves 

What is the most important financial or retirement advice you’ve ever given? 

I can think of three ideas (probably five, but I’ll stop at three) that I want to impart to everyone: 

1. Invest in your health: Move every day. Walk. Stretch. Lift. Get down on the floor and stand back up until you can do it easily. Mind your glucose metabolism and your cardiovascular profile. There is nothing sadder than spending your retirement savings on out-of-pocket medical costs. You are living longer than you think. You want to do it under your own steam. 

2. Invest in your financial plan: Don’t take money out of a down market. This is a technique that good planners use, but anyone can deploy it with their money. Buffer your cash and create sources of liquidity so that you will have what you need to wait out a bear market. This implies that you know what it costs you to live monthly. That’s a critical number. Figure it out.

3. Invest in your skills. Embrace technology that will help you communicate with your health care provider (electronic medical charts), your banker (online and phone banking), and your grandchildren (who knows if it’s been invented yet!) when you are 80. You don’t have to be  

good at it. There will be help. You just have to be willing to learn and laugh at yourself while you do. 

Looking back on your career, what are you most proud of, and what’s next for you and  Madrina Molly™? 

I’m proudest of my resilience. I have a permanent lump on my head from the corporate glass ceiling. But when I wanted something, I persevered through the tears. And it means a lot to me to be a role model for women, both my peers and the younger generations. Don’t tell me that you’re not good at math. It’s irrelevant. A few simple rules and any woman can feel successful with money. I like that I’ve made my clients feel like they were superwomen.  #WeRescueOurselves 

I am proud of my continuous reinvention. I have changed careers. I have helped manage the slow decline of three out of four parents, two with dementia. I have been divorced and it cost me  60% of everything plus maintenance and health insurance for three years. I am part of a blended family now, with all of the complications that entails. I walk my talk here. I am a member of my cohort too. 

And, last, I’m proud that I’m not young and not done. I use that as a hashtag a lot. My mom is still going strong at 97 and her mother went to 96. That means I have, thanatologically, almost thirty years to grow Madrina Molly™ into the go-to for financial and longevity planning for a cohort that has been underserved. This year we will grow membership, and I will ensure we are visible as a resource. 

How do you envision the role of women financial advisors evolving in the future? 

I think the future of payment for financial planning is fee-only plus robo-advisors. Portfolio growth will be academic. I think the clients understand paying a fee for a specific service and then having the option to pay to deploy a financial product/solution. 

However, everyone’s lived experience is different. And when it comes to distribution and how you want to use your money, that will require the touch of a talented fiduciary woman planner.  We need advisors who ‘get’ us. They get our goals for ourselves, our families, and our values.  

They are willing to spend time talking about planning topics that don’t involve things they are explicitly paid for.  

We’re going to see a lot more elder care planning, planning for the season of frailty, and planning for joy. After all, if you die with a lot of money and your goal wasn’t explicitly to create a legacy, technically, you flunked retirement. We’re going to see women advisors teach their clients that it’s okay to spend on themselves. Certainly, I will encourage that.

How can our audience connect with you and become part of the Madrina Molly™ community? 

You can find me at www.madrinamolly.com, where you can sign up for the Community or take a free or paid mini-course. The community is divided into free shared wisdom chat rooms and a paid financial & longevity planning area that is organized by topic and includes bi-weekly member zooms and access to me in my planner capacity.