Skip to content

Lisa Benton figured if she could explain multiplication to special-needs third graders, she’d have no problem explaining retirement investing plans to advisory clients.

After 10 years of teaching, she wasn’t tired of students or of education, but she did wonder if her aptitude for explaining complex concepts in simple terms could position her for success in the advisory profession.

“Individual education plans and financial plans are very similar,” Benton said. “They both depend on knowing what you can do with what you have. Relating to people, that’s embedded, as a teacher. Learning the ins and outs of finances, I had to grasp.”

She found a side door into the financial planning profession through a Morgan Stanley program designed for midlife women who want to shift career direction without losing much momentum. Cracking through the qualifications for licensing and certifications wasn’t enough: Benton pressed on to pursue a master’s degree in financial planning and counseling.

Now, she’s a financial adviser and retirement plan consultant with the Abeyta Bueche & Sanders Group at Morgan Stanley.

And she didn’t have to sacrifice the camaraderie of the teachers’ lounge, either, finding an equivalent in the firm’s women’s advisory council.

“It’s a safe place where you can get sound advice from someone you trust, and who will keep your question confidential,” Benton said.

The financial advisory and investment professions say they want more women like Benton but do precious little to recruit them. In the past two years, midlife American women have had a collective epiphany: They want to trade in their current careers for something different and better. They want to make the most of their experience and skills, make more money and center it all sustainably around their personal responsibilities.

Gender Gaps Go Unfilled

The financial advisory profession offers what midlife women want — but midlife women don’t know that. Worse, the advisory profession and adjacent investing ecosystem largely are not rising to the opportunity to expand their ranks with experienced, motivated women, though doing so would fill much-lamented talent and gender gaps.

“Nobody’s talking yet about the fact that for midcareer women, this is a great opportunity,“ said Barry Mulholland, founder of Diversitas, an annual symposium and quarterly forum hosted by the University of Akron College of Business to foster greater diversity in the advisory profession. Diversitas is just starting to expand its outreach from its initial target of high school and college students to midlife career changers, who currently make up only about 10% of its attendees, he said.

The post-Covid-19 economy sets the stage for an influx of midlife women into advisory and investing, said Greg Sloan, who sold his wealth management practice (while maintaining his CFP license) and now runs talent development software and consulting firm Go Beyond.

The shared trauma of the pandemic shook women into a wholesale awareness of their strengths, he said. Professionally, their prowess with communication, collaboration and consensus kept organizations functioning through wrenching, forced change. Personally, millions of women were thrust into roles as health care case managers, family finance coaches, estate planners and grief counselors.

“People are looking for meaningful work that is aligned with their personal purpose,”’ Sloan said. “They’re looking for a sense of belonging, and the flexible work schedule and appropriate compensation. Those two things are coming into alignment.”

Midlife women are especially suited to be financial advisers, said Luke Dean, associate professor at Utah Valley University and self-appointed industry ambassador. Having weathered child-rearing, loss and family growth, midlife women make no apologies for focusing on both their own financial longevity and clients’ financial well-being.

“A financial planner helps people sort out their goals and priorities,” Dean said. “These are deep personal conversations, and you need people with emotional intelligence. Males are traditionally not as good at that.”

Defining Success

Critical elements of a midlife career transition into advisory and investing are compatible with how women define success. The industry offers numerous career paths and opportunities for daily autonomy for workload, schedule and flexibility. Earning professional credentials is an investment, but one that’s in line with women’s ingrained definition of career accomplishment: Copious research indicates that women put more stock in credentials than men do.

And midlife women’s determination to build their own financial security has snapped into focus in the past three years. Covid-induced workplace turmoil has merged with a dawning realization for Gen X and older millennial women that they must work longer to stoke their lifelong financial security.

Data provided exclusively to InvestmentNews by AARP from its 2022 Financial Trends Survey found that 58% of women age 50 and over expect to continue working past the traditional retirement age, compared to 53% of men. Expectations for those aged 30 and up reflect similar sentiments. And across both age groups, women cite financial motivations more than men for continuing to work. (The AARP research included only those who have not already retired.) Overall, 63% of non-retirees assume that they will have to continue working in retirement, ongoing AARP research found.

The pandemic only accelerated women’s realization that they must find careers that carry through retirement. In 2019, even before the pandemic upended career expectations, 38% of women expected to work into and through retirement, according to a report by the Federal Reserve Bank of New York. A 2020 Federal Reserve report delineated personal health, family caregiving and forced retirement as key timing triggers for 47% of retirees.

All are factors that could be mitigated by flexible work schedules and self-directed career paths — the very characteristics that many advisory and investing positions offer. The Covid-19 pandemic famously sparked a national game of career musical chairs, with disaffected staff taking new jobs in pursuit of better work-life balance and more money, according to a mid-2022 LinkedIn report. And now, inflation and market fluctuations have further upended retirement expectations.

Midlife women occupy the four-way intersection of these trends. They want to find careers that can sustain their financial, family and personal goals past the traditional retirement age, and they aren’t afraid to invest in new skills.

But many of them don’t know that the financial advisory and investing sectors offer a career bull’s-eye — and the advisory and investing sector isn’t doing much to come in their direction.

Dean finds himself continually making the case for advisory and investing careers to two categories of midlife women: those who come to UVU in search of career guidance and the mothers of undergrads who are picking their majors. “They don’t know this exists,” he said.

‘A Perfect Fit’

When Kelly Mould left a corporate customer service management job in her 40s to earn a law degree, she never envisioned that she’d end up at age 50 as senior vice president and wealth sales team lead at Johnson Financial Group.

As a brand-new, middle-aged lawyer, she quickly realized it would take time and dogged effort to build an estate planning practice. So she took on public defender cases to build her reputation and revenue. She found herself in the dim courthouse corridors tending to people who were traumatized and terrified.

Colleagues helped Mould see that her intuitive ability to guide distressed people through complicated, opaque processes comprised a powerful career skill. One professional friend told her that she had the “kind of personality that can wrap around a family and their experiences,” said Mould, now 58. A few days later, another woman attorney observed that Mould’s aptitudes were a “perfect fit for financial advisory.”

That was news to Mould.

“I’d never have thought I’d have been good at it,” Mould said. “But two people told me I might.” She started researching what was involved and quickly realized that advisory rolled her experience into a career that was just as fulfilling and lucrative as law but more flexible.

The latest report from McKinsey and indicates that Mould’s intuitive rationale for shifting into advisory now is widely shared by women corporate leaders: 49% of them, compared to 34% of their male colleagues, prioritize flexibility as a key factor when deciding whether or not to leave their current jobs. The study also found that women want to work where their contribution to organizational success is recognized and rewarded — especially often-unheralded work in diversity and investing in others.

That a woman as experienced as Mould was surprised to discover advisory proves a point made repeatedly both by women who’ve made midcareer shifts and by career advisers: The industry claims it wants women but does little to reach midlife women where they are.

Teachers, nurses and other professional women are actively looking for fresh options that let them shift gears, not start over. But a complacent advisory and investing industry does little to bring its message directly to them, instead expecting potential career shifters to discover the industry on their own.

Flipping The Script

Jen Pritchard sees the recruiting gap as a rich opportunity. Pritchard, an adviser, and business partner Alex Hopkin, a military spouse who had to fashion a mobile career, co-founded Simply Paraplanner, an online career transition and training platform that provides a steppingstone into the industry. The duo started the company in 2016 and now has more than 100 people — mainly women — progressing through the program at any given time.

“Covid has sped everything up,” Pritchard said. “We have people come from the clergy, from hospitality, health care, education. A lot of them are in helping fields. These are people applying for jobs with the understanding that it’s a people business, and they have those skills.”

Mould believes that the advisory and investment industry will immediately discover multitudes of qualified, motivated midcareer women candidates if it just flips the recruiting script.

“This industry needs to reevaluate what qualifications it’s looking for,” she said. “What brings in business? If it’s interpersonal skills, you have to look at résumés differently and examine what your training does for people who are already good with people.”

But for many women of all ages, business development remains the most daunting aspect of a potential shift. Almost by definition, said Sloan, the consultant and former adviser, helping professions eschew the profit motive. “Women who are good at helping people may not be good at business development,” he said.

And the industry fails itself by refusing to clarify “financial adviser” business models, thus confusing and repelling midlife women who are loathe to wade into commission-driven occupations, Dean said.

“If they think this is a sales job, we can’t recruit. If they think this is a job about helping families, we get the stars,” he said.

Industry employers are starting to catch on.

Mike LaMena, CEO of Wealthspire Advisors, has a bit of insight into career changers, having started his own professional life as a high school teacher.

Retooling the business development model is job one, LaMena said, for building new paths into the industry for otherwise qualified women.

“We’re not going to drop midcareer women in and say, ‘Build a book of business from the ground up, and if you haven’t done that in six months, we’ll cut our losses,’” he said. “We want to be more deliberate about it. This is an amazing industry where women can thrive, where they can have autonomy. We need to provide information, access and pave the path for them to explore it.”

Wealthspire is analyzing how its recently arrived career shifters found the industry, and the firm, with an eye to proactively connecting with others like them. A clear starting point, LaMena added, is to mine the insights of advisers who are adept at working with midlife clients and who can detect overlooked ways to reach those who don’t realize the industry is looking for them.

“It’s a massive opportunity,” he said. “That is a big question — how do we get in front of people with a better narrative around what our career is about and about the diverse backgrounds that contribute to success in it? People need to get a sense that this industry is as much about reading people as it is about reading spreadsheets. That’s how people in parallel careers see a path of transition for themselves.” A

Success Story

Back in 2005, Laura Steckler, then 32, was getting restless in her psychotherapist job. It was interesting, but she wanted more flexibility and fewer constraints on her earning potential. And she couldn’t shake her entrepreneurial urges. Over dinner, a friend who worked in financial services commented that Steckler had the makings for success as a financial adviser.

“I was taken aback by that,” Steckler said. “She saw something in me in terms of transferable skills. So I told her that I got a C in macroeconomics in college.”

Still, the possibility pulled her in. The more Steckler looked into the financial advisory profession, the more sense it made. “Strong active listening, identifying people’s goals and fears — there’s so much psychology in money,” she said.

She scouted the landscape and found that Raymond James offered a training program that would systematically equip her with credentials, confidence and clients. Now she’s managing director of the Steckler Wealth Management Group of Raymond James.

Her path shows the way, Steckler said, and now is the moment.

“We have to reach people and pose the question and see if they are open to a change,” she said. “And especially in a post-Covid environment, people are open to possibilities that they weren’t before. This is the opportunity of a generation to attract midcareer women into financial services.”

As seen on