Rethinking Career Choices at Midlife

By Robin Madell (San Francisco)

As we get older, the way we think about work and contribution changes. Many women of a certain age are reconsidering earlier paths. After years of paying dues to become a senior executive, partner, or board member in their respective industries, an increasing number are deciding that it’s not what they really want after all. Some are opting to take extended time off for soul-searching, or leaving prestigious jobs to seek something more closely aligned with their current interests and passions.

What’s behind this shift, and why are so many women doing it? As we progress in our careers and encounter political situations, difficult people, and issues we can’t control, our perspectives change. But there’s more to it than that. Clearly part of the issue is that we made our career decisions when we were much younger, before we had solidified our true preferences. Once decades of our career are behind us, we know much better who we are and what we want. Armed with that self-knowledge, many women are asking, now what?

Research has shown that women tend to find an increased sense of personal identity and more clearly define their values in midlife. In doing so, a common value that often emerges is the desire to give back or contribute to a greater good, which is often behind the internal drive to make a midlife career change, says Keith Weber, author of Rethinking Retirement. “This need to give back tends to stay with the individual until it is satisfied, meaning that those who fail to act on it often experience regrets, whereas those who do act on it tend to show fewer regrets and subsequently greater well-being later in life,” explains Weber.

But making such sweeping alterations in your life is not easy. Career coach Dorothy Tannahill Moran explains that with career change, you can’t expect to just grit your teeth and push through your fears. “Most careers you work 40 hours a week or more and if you make a mistake, you’re living the mistake almost daily,” says Moran. “Your career is not a tidy compartment that has no effect on the rest of your life. It’s a huge part of your life and has implications with almost every other part, including financial impact.”

Change also breeds anxiety because we face so many unknowns. We can’t always imagine that a new situation will be better than the one we’re in, says Patti DeNucci, author of  The Intentional Networker. “No matter what the circumstances of change, the same basic fears surface,” says DeNucci. “What will my days be like? Will I enjoy it? Will I be able to attract business and clients I enjoy? Will I be able to make a good living? Will people respect me and will I make a difference? What if no one is interested in what I have to say? The possibility of having to ‘go back’ to something you’ve left behind because you outgrew it or no longer love it is scary.”

To address these questions and more, The Glass Hammer profiled a number of women whose careers began in finance, law, technology, and other industries, but who made a midlife career gear-shift. These women share what they’ve learned firsthand about deciding if you’re ready to switch, overcoming fear of change, and transitioning to a work-life that fits better with age.

From CEO to Realtor

Susan Phillips Bari was the founding president of the Women’s Business Enterprise National Council (WBENC), which she led for a decade. She spent the majority of her career in the nonprofit sector, but after resigning as president and CEO of the Leader to Leader Institute in 2010, she decided to make a big change. “I was ready to take control of my time and income,” says Bari. “Frankly, I was tired of having employees.” At heart a marketer, Bari selected real estate. “I figured that if I could raise more than $300 million for nonprofits and political candidates over my career, I could certainly sell something tangible.”

Bari says the hardest thing about the transition has been adjusting to the scale of what she does every day. When she worked at the White House earlier in her career, her actions had a potential impact on millions of people. When she ran WBENC, her actions impacted thousands. Now, her sphere is limited to her clients. “In my current position, I can be a role model but not a leader,” says Bari. “It has been an adjustment.” Bari notes, however, that she has enjoyed the lowered stress of her revised career. “I worry about my own well-being and that of my family, not that of employees,” she says. “My time is my own and while I work hard, frequently putting in long hours and weekends, it is flexible.”

The most important enabler for Bari’s career change was fully understanding the economics of the move. Going from an income of $200K+ to zero, with future income based solely on her own performance, she was prepared to tap savings. She also resolved to stop shopping and trim the home budget until money started flowing.

“Frequently the golden handcuffs of salary, benefits, and perks keep us tied too long to careers that have stopped being fulfilling,” says Bari. “If the finances are not yet in line, make a plan with a timeline and budget that will allow you to research your next career move.”

From Employee to Entrepreneur

Sara Fell’s journey to her current position as founder and CEO of career website FlexJobs has taken her full circle back to doing what she loves. After founding her first company JobDirect at age 21, she later sold the company and joined the traditional workforce as a full-time employee, serving at the director level in two different organizations. But in 2007, she was ready to return to her entrepreneurial roots. She founded FlexJobs while pregnant in response to a frustrating search to find flexible work that would fit with her life and growing family.

“The older you get, the more you understand what you want, and don’t want, out of your career,” says Fell. “As I’ve gotten older, the sense of adventure that I had in my early career has given way to more of a sense of purpose.” Fell is now committed to doing work she feels passionate about, rather than targeting a higher title or paycheck. “Work-life balance has become profoundly more important now that I have a family, whereas in my younger years I didn’t mind having work occasionally dominate my life,” she says.

Though as an employee she had generally positive experiences, Fell admits that several “less than ideal situations” helped to relieve her of rose-colored glasses about working for others, including a married superior making sexual advances toward her, condescension about her age, an extremely difficult boss, and defensive competition from colleagues. Fell’s biggest take-home from these experiences was to rise above them, and find the best and fastest solution possible.

Part of that solution meant becoming her own boss again, despite the fact that she was just starting a family. “I definitely had concerns about whether I’d still be able to be as dedicated as you need to be when starting a company,” says Fell. “There’s always management as my company needs me more or my family needs me more.”

From General Counsel to Community Design—and Back

Not everyone’s career-change leap of faith results in a final destination. Some women we spoke with discovered that they missed the essence of their original path, and hope to return to it.

Henriette Nielsen spent most of her career practicing international law, most recently as General Counsel and EVP at Actavis Group,  where she spent six years with overall legal responsibility for worldwide operations for more than 10,000 employees in over 40 countries. Although she loved her job, she felt a strong sense of wanting to do something “more” and “different,” and resigned her position in early 2011. “I wanted time to think about what I wanted to do with the rest of my life, but I had no real sense of what such a future would bring,” explains Nielsen.

She started her journey by exploring a business idea with a friend and fellow lawyer, but the pair abandoned the plan six months later. After considering various alternatives, they decided to partner with a third friend on a community design website called OurDesignStories, with a goal of creating products connected to worthy causes where the community is directly involved in the design.

While Nielsen is enjoying the project and feels that it was the right decision to shift gears when she did, she wants to explore a return to international law once the site is successfully up and running. “I would like to get another GC job or similar position, as I miss the challenges of legal work,” she says. She was also surprised to discover during her corporate hiatus that her workplace happiness depends largely on social connection. “I’ve felt a sense of loneliness and isolation following my departure from the bustling activity and constant peer interaction of the big company,” she says. “I just needed to make sure I would not have any regrets later on, and now I know I will not.”

From Financial Analyst to Hair Stylist

After spending nearly 15 years as an analyst at Wells Fargo Bank and on the verge of turning 50, Sarah Kelly decided to do a complete 180. She decided to open a hair salon. “I fell out of love with spreadsheets, so I resigned and went to beauty school,” explains Kelly, who has a degree in economics. Newly armed with a cosmetology license, Kelly opened P3 Hair Design at the start of 2011, financing renovations to an existing salon through savings. With a year in business now under her belt, she is starting to breathe easier about her decision. “I knew I was alright when customers were calling and my website was on the first page of Google,” says Kelly.

Her path has not been without its difficulties. When she started at Wells Fargo, it was before a divorce, and the decision was based largely on needing a steady gig to pay her bills and provide health insurance for her son. But as she moved through the ranks, she discovered that the increased responsibility came hand-in-hand with office politics. “I had reached several impasses with management—I was an outside-the-box thinker in a highly regulated, conservative industry,” says Kelly. “Not a good fit for me.”

She found herself anxious and miserable, and with her son now a teen, wanted to set a better work-life example for him. “I didn’t want him to think that work was something that needed to be endured,” she says. “I wanted him to find his calling, and mine certainly wasn’t banking.” But leaving to start something different had challenges of its own. “Sometimes the hell you know is better than the hell you don’t know,” says Kelly. “Could I really cut hair, could I run a business? I was scared witless about marketing.”

Rather than get discouraged, Kelly used referrals from friends and family, and started learning about social media marketing and SEO to promote her business. She recommends that women who are not in their dream jobs see change as a beginning, not an ending. “If you see yourself at a dead end, you are at a dead end,” says Kelly. “If you can reframe your situation, you can see how you’re benefiting yourself, company, community, or whatever motivates you.”

From Tech Sales to Company Leadership

Prior to launching Impact Instruction Group in 2007, Amy Franko managed a $12 million sales territory for IBM and Lenovo. She says she will never forget the day she resigned from tech sales, walking away from a six-figure income in order to create the new career and life she wanted as a business owner.

“I had plenty of fears—from wondering if I could make it work, to wondering where my next paycheck would come from, to wondering if in a year I’d want my old job back,” she says. “But none of those fears could overshadow the fear that I would look back in 10 years and wish I had taken the chance on myself.”

A key mental shift that Franko made over the course of her career change was to evolve from a “worker bee” into an “executive bee.” “I had to get crystal clear on the executive-level activities that I needed to be doing, versus those activities best suited for a team member or outsourced,” says Franko. “That shift alone has helped me to value my time and become more discerning in what I choose to take on.”

Lisa Adams, founder of Fresh Air Careers, made a similar switch, having spent much of the past two decades in software sales, and later strategic partnerships, for tech companies. She left corporate two years ago to launch her own coaching business. “I work from home, see my kids more, am out of the corporate political structure, and am doing what I love,” says Adams.

Earlier in her career, Adams was driven by money and recognition. But as she moved into her 30s, her priorities began to shift toward more flexibility, less travel, and learning new skills. By her 40s, she felt her career decisions had led her further away from any “sweet spot” in her skills or interests. “I wanted to have a business of my own and looked to the future with a bit of anguish,” Adams says. “My stress was driven by my new desire to find that perfect fit for me.”

As part of her quest, she began working with a career coach, and through the process determined that coaching was what she wanted to do herself. Though the outcome has been to her liking, Adams recommends that women who may be thinking of a career change do a full evaluation of what is spurring it. “Is it really the career or are there other factors involved?” she asks. “I have seen clients blame their career when really it is a lack of balance in all areas of their life.”

Like Franko, Niki Pfeiffer had a background in sales for IBM (as well as IDS Scheer and SAP) before a trio of events led her to leave the tech industry after 12 years to launch her own company, Niki Pfeiffer Designs LLC. The first was having children and wanting a more flexible work schedule; the second was a political situation at work; and the third was the economic downturn, which made her realize that she was vulnerable to a layoff in her current situation. “I did not want to find myself in my 50s and have a layoff happen at a time in my life when it would be much harder to reinvent myself,” says Pfeiffer.

Pfeiffer was anxious about whether her family would be able to live on one income, and about starting a business at the same time as being pregnant with her second child. But she was more afraid of finding herself 10 years down the road, having dedicated so much time to work and away from her family only to get laid off. This realization put into perspective that she had to take control of her life if she wanted to achieve her own version of success.

“The experiences we gain at work can help bring to light what we are good at, what fulfills us, and what drains us,” says Pfeiffer. “Once I truly understood this, it was amazing how it simplified the decisions I had to make about the direction of my career.”

From Corporate to Small Business Owner

After being downsized out of her third human resources job, Lynn Sudlow was ready for a change. “I became disenchanted with the focus on needs of management over needs of staff,” says Sudlow. In one example, she was horrified to have a COO state that her ideas were too focused on the “little guy” rather than on the management team. She also grew weary of endless meetings and tiptoeing around difficult managers. “There always seemed to be at least one in every workplace, and somehow they escaped repercussions,” she says.

With a huge leap of faith, Sudlow decided to start her own business. Today she is a certified concierge specialist at the company she founded 12 years ago, The Complete Errand. It took her just over a year to build to full-time income levels, and she says she was fortunate that her husband was employed during this time to provide health benefits.

“I don’t expect to ‘have it all’ now that I no longer have the challenge of balancing children at home with a career,” says Sudlow. “I’m not compelled to meet others’ expectations or ideals unless they’re my clients.”

In her 40s, Marty Stanley also experienced a layoff that opened the door to her current sole proprietorship as owner of Dynamic Dialog. “I’d had it with the corporate world,” she confesses. “I was a vice president at a prominent company, in the position I always wanted, but after a while I thought, ‘This is it? It must be the company.’ So I left and went to a larger international company as a VP in a different industry.”

But changing industries didn’t solve the problem. When Stanley’s position was eliminated in a restructuring at age 49, she was free to start her own business. Now 60, Stanley is an author, speaker, facilitator, and executive coach, and was recently certified to facilitate a program for people over 50 about how to discover and pursue what you want in the next stage of life.

Stanley recommends that women who hope to chart a similar course ensure that they have sufficient financial resources to carry them through for 9 to 12 months.  “Sometimes it’s better to quit a job before you have another if you’re miserable,” says Stanley. “Most people who leave an unfulfilling job wish they’d done it sooner. Even if they don’t have another job, they feel freer and more at peace with themselves.”

From Partner to Trainer

After practicing law for 30 years—24 of them as a partner—Betsy Munnell decided to start her own consulting business, Elizabeth Munnell & Associates, to train law firm associates and law students preparing for practice. The reason? After practicing full-time for decades while raising three children, she could no longer offer the 24/7 responsiveness essential in firms, even after adopting a flex-time schedule and reducing the number of deals she normally managed. As her hours and availability declined, so did Munnell’s access to the most juicy assignments.

“I knew I could never tolerate a permanent role change to counsel or contract attorney, with the inevitable resulting loss of credibility and opportunity,” says Munnell. “Neither flex-time nor part-time work is easy to sustain in a large firm.” Though she knew some type of career change was essential to her future, she had no idea what it should be.

It was Munnell’s investment in her firm’s diversity efforts that ended up holding the key to her next stage of life. Her work promoting the firm’s commitment to the recruitment, retention, and advancement of women and minority lawyers began to grow legs of its own. In the year before she withdrew from the firm, she conceived and implemented a curriculum offering practical skills training for women associates. Her firm’s professional development director asked her why she didn’t just jump ship and start her own business advising associates and young partners. Within the next few months, she left her firm to do just that.

“Like many lawyers, I believed for years that I lacked the skills to be successful doing anything else professionally, at least nothing I might enjoy as much,” says Munnell. “It hasn’t been easy, but I have been blissfully engaged, challenged, and entertained in my new career. And I am giving back to my profession at a level that was impossible in private practice.”

From VP to “Boss of Me”

Kim Box had managed every aspect of information technology during her nearly three decades at HP. But two years ago, Box went from being a VP at HP in charge of a global operation with over 10,000 employees and 5,000 contractors in more than 100 locations, to president of her own company, Kim Box Inspires. “I had a very rewarding and successful career at HP,” says Box. “But as I was approaching 50, I gave a lot of thought to what I was doing in my life, and decided I was ready to make a change.”

Some of those changes include writing the book Woven Leadership: The Power of Diversity in Transforming Your Organization for Success, doing keynote speaking and workshops, and leading two start-up corporations. Box also serves on a number of boards, including her regional chapter of the American Red Cross, and became a triathlete.

Box admits that this eclectic mix of businesses and activities has at times been difficult to define. She struggled initially with answering the question, What do you do? “Having a long career in the IT industry, it can sometimes define who you are,” says Box. “I had to comes to terms with letting go of being the ‘executive in charge’ and know that experience will always be a part of me, but it is not who I am.”

Box says it takes some soul searching to unearth what you want to do. She recommends that women take the time to determine the source of their current dissatisfaction before restructuring their lives, to avoid moving from one situation to another only to find that nothing improves. “I got some great advice from a mentor which was, ‘What’s the worst thing that can happen to you? You might have to go back and get a job in your field!’ says Box. “That helped me take the leap.”

Stephanie Corey also used to be an HP executive. She was chief of staff to the general counsel of HP’s legal department at the end of 2010 when she left to start her own home-based business. “When I was in corporate, I was working 65 to 70 hours per week, until a family tragedy made me rethink my priorities,” says Corey. “Going into the office each day became more and more of a chore.”

When Corey first started her career, she wanted to climb the corporate ladder as quickly as possible. She set goals—to make six figures by the time she was 30, to make director by 35—and beat them. But in her mid-30s, her brother-in-law died from cancer, leaving her sister alone with three small children. Corey didn’t realize how much this had affected her until a year or so later.

“I found myself wanting to downsize and be able to spend more time with my family. I just didn’t want to spend my life in a cubicle.” After spending months researching careers that would give her more flexibility, an opportunity presented itself from an unlikely place. Her youngest son had developed a fear of monsters. After weeks of trying to coax him to bed unsuccessfully, she slapped a “Zombie Repellent” label on a bottle of lavender spray and gave it to him, and Miss Stephanie’s Potions was born. Six months later, she left HP to begin product development full-time.

Corey’s initial euphoria at the move turned to panic a few months later, as her savings started to dwindle. “I didn’t realize how much comfort I was getting from having a regular paycheck,” she says. “I was having anxiety attacks that would last days.” Corey continued to plow forward, and is now considering seeking funding to take her business to the next level.

She advises women who are on the fence about whether to stay or go in their current position to consider the advice that she used to give her team at HP every year at review time. “If you want to be here, it has to be because you made the decision to be here—not because of your boss or the company,” she says. “The happiness has to come from you, not what someone else is giving you.”