By Shelby Deering | Photographed by Hillary Schave

Robert Frost once famously wrote, “Two roads diverged in a wood, and I—I took the one less traveled by, and that has made all the difference.” When you wake up each morning to get ready for work, what road are you taking? The one that’s free of obstacles, and that you know like the back of your hand, but presents little excitement or passion? Or one marked by heart-centered values, fulfillment and self-discovery?

Work is an undeniable, and sizeable, portion of our lives. Although it offers financial security and a feeling of stability, a career can also serve as a source of joy in one’s life. Work and happiness can  go hand-in-hand.

So, what does the road to a career change look like? If you are considering taking the leap, plan for some soul searching, big questions and personal challenges. They’re standard checkpoints on any path that leads to a rich, thriving life.

Luckily, sage local experts—both coaches and women who have made the leap—are here to offer their wise words around the process, the roadblocks, the merits of making a career change and how to make that change less daunting.

Darcy Luoma, president and owner of Darcy Luoma Coaching & Consulting, who coaches individuals and groups to intentionally craft their futures, went through a career reinvention of her own. For over a decade, she served as the director of U.S. Sen. Herb Kohl’s office. When he chose not to seek re-election, Luoma was at a crossroads.

She says, “I hired a coach and she helped me figure out how my values had shifted and changed.” The coach asked a series of “really powerful questions,” says Luoma. “I realized that if I kept playing it safe and only focused on my retirement and savings accounts, I would have regrets.”

Luoma says that she decided to “step into” her passion, a major shift from the risk-averse career she had pursued for over 20 years.

Today, Luoma is a professional speaker, life coach and leadership expert, carrying out a value she calls “aliveness.”

As to where to start, Luoma says, “I think it comes down to giving yourself the time and the faith and the permission to ask powerful questions and be very present and open to the answers.”

In addition to books, seminars and quizzes that pose these tough questions, Luoma also recommends speaking to a close friend, family member or confidante who can “hold up the mirror and reflect back.”

Deborah Biddle, a consultant and coach through her business High Performance Development Solutions, acts as one of those “mirrors” as she guides people through career transitions.

“Clients typically begin the process concerned and sometimes confused about what the future holds,” she says. Biddle helps her clients evaluate their options before jumping into a job search and uses techniques to nudge them toward uncovering their true talents and ideals.

Biddle says, “When considering a career change, avoid making decisions based on what is urgent, practical, logical or lucrative without consciously considering how your interests, skills, passions and values contribute to your overall job satisfaction and success.”

She notes that although some people know their purpose when they’re young, others don’t have that straight and narrow path. In that case, Biddle recommends trying “as many things as you can until you find the career that gives you joy, pays the salary you want and engages your mind, talents and abilities.”

Although finances need to be considered when making a career shift—Biddle recommends saving enough money to live on for three to six months— Sybil Pressprich, senior counselor at the University of  Wisconsin–Madison’s Adult Career and Special Student Services, is a proponent of taking action.

As she leads people through self-assessments and identifying pathways to achieve goals, she shares her No. 1 tip, which is, “Don’t wait until you are 100 percent clear on what you want to do before taking action. Often we think we can figure out this problem if we just wait and think about it long and hard. But that’s not how you will get clarity.”

Instead, she suggests reading about career fields, participating in informational interviews, doing job shadows and finding volunteer positions.

Pressprich believes that a person’s purpose gets clearer as one “experiences more.”

But going out into the world and exploring a dream can be unnerving at times.

“Remember that action is the enemy of fear,” she says.

In that vein, Pressprich asserts, “Take action toward that faint light that is of interest. Don’t wait. Be open to discovering your purpose by serendipity and stick to the process of self-assessment and reflection, exploration, goal-setting and taking action toward those goals.”

The following women have done just that. They’ve already traveled the road toward career reinvention and realized their dreams, serving as examples that it can be done.

Light a Spark

Jesse Skaltizky loves children. The mom of three started a family with her husband, Paul, right out of college. “But the thought of never being pregnant again was devastating to me,” she says. With a degree in cellular biology from UW-Madison and a background as a student embryologist, her mind turned to surrogacy. She delivered three healthy babies to grateful families while staying home full-time with her kids. She was content—but she couldn’t shake her dream of helping even more families grow.

She explains, “I remember the moment. It was during my second surrogacy, and my intended parents were visiting. They told me, ‘You have this gift that you can share. Now is the perfect time in your life to just take the leap.’ Within a week, my husband and I put together a business plan and filed for an LLC.”

The result was Pink & Blue Surrogacy and Fertility. As the owner and program coordinator, Skaltizky specializes in finding and matching intended parents and surrogates throughout the country and as far away as Europe, Asia and Australia.

Going from a career as a stay-at-home-mom to a mompreneur was “scary” at first, but Skaltizky says that shortly after launching the business, “things fell into place very quickly and easily.”

The ease can undoubtedly be credited to Skaltizky’s background and knowledge, but it can also be attributed to the fact that she is helping people make meaningful, impactful change in their lives.

“It’s fulfilling for me emotionally to be able to do something I love and support my family, but also grow families on a daily basis,” she says.

When Skaltizky thinks of others making the leap, she recommends that they seek out “support and encouragement from their people.” She also believes in finding personal fulfillment through a career.

“I think when you find something that makes you feel fulfilled, you’re better at everything you do in life. You’re happier at home, you’re happier with what you do, you’re happier in your community and maybe you’re more willing to volunteer. It lights a spark.”

Skaltizky isn’t promising that when you do make the transition, things will be perfect. In fact, there will be difficult times amid the joy. But she believes that the struggle is worth it.  “It’s not all sunshine and rainbows. But at the end of the day, no matter how bad a day it’s been, I go to bed happy knowing that there are a lot of babies in this world and a lot of new parents and growing families because of what I’m able to help do. And that’s very fulfilling.”

Be Yourself

A career as a lawyer is certainly an investment— time, finances, effort. So, when a person decides to forgo all of that to do a career 180, it points to a decision that required substantial introspection.

That’s Diane Krause-Stetson’s story. She graduated in 1982 from UW-Madison’s Law School and jumped in as a labor lawyer at a midsized firm. Krause-Stetson spent years building her career, was recruited by Fortune 100 and multinational corporations and eventually worked as a vice president of human resources for a private company.

“Sometimes I was used as an example of being able to aim high,” says Krause-Stetson.

There is a connecting fiber among those who make a major career change—a pivotal experience. For Krause-Stetson, it was losing her 48-year-old cousin to breast cancer in 1999. When she was asked to give the eulogy, she began to examine her own life.

She made the decision to retire from her law career. And in a cottage on Elkhart Lake, KrauseStetson began to think back on the past decades.

“I have since understood that I was driven as much, if not more, by not feeling good enough and my fear of failure as I was by a desire to succeed.”

Krause-Stetson’s path to self-discovery led to a coaching business and a role as the owner of retail locations Style Encore Madison and Plato’s Closet Madison East and West.

Specializing in gently used, name-brand clothing, these are the places where Krause-Stetson finds “personal satisfaction” through creating a “family atmosphere” and developing close relationships with her young employees.

“Everyone knows that my husband and I are more than employers. My love of connection and mentoring is a part of that.”

For others who are considering a new career, Krause-Stetson shares three steps to take, based on her own experiences and know-how as a coach.

First, she advises that it’s important to dig deeply into why you are considering making a career change.

“Whether someone is not content with where they are in their career, it is important for them to know more about who they are now. They may think they are unhappy with their career, but it may be just their current working environment. Perhaps the culture is incompatible with their way of working or even their values.”

The second step is to talk about the things that are important.

As a start, Krause-Stetson says to consider whether you want to work “independently or collaboratively” or “require freedom or prefer structure.”

Krause-Stetson recommends wrapping up the process by talking through making the decision with someone and acting on what matters most to you now.

“In this stage, you examine the desires and goals and create the plan of action to achieve them,” she says.

Krause-Stetson is living out her plan of action— and dreams—through her newfound career, using a saying from coach Thomas Leonard as her guide: “I don’t want to change anymore. I just want to be more of myself.”

Ask What’s Next

There are those of us who choose a second act for our lives. Or a third act. Or perhaps a fourth. Mary Helen Conroy is one of those people.

Conroy has worked as a public librarian on the South Side of Chicago, a library building consultant, and while she completed her doctoral program in adult education at UW-Madison, she took a job as a sales consultant at the publication Women in Higher Education, and that’s where she stayed for over 18 years.

But then the publication was sold in 2014, leaving a 62-year-old Conroy without a job.

“I can still see myself locking the door for the last time and walking off that stoop saying, ‘Now what?’ I had no idea what I was going to do,” she says.

But she knew that she wasn’t going to just “sit on a couch.” So, she set a goal for herself in her first year that she was no longer working at the publication—a “50 Cups of Coffee Challenge” through which she would meet 50 new people.

That’s how she met Carol Larson, a one-time broadcast journalist and producer for Wisconsin Public Radio and Television. They found themselves in similar life stages. And they both wanted to take action. So, they founded RetireeRebels.com, an online destination tailored to the newly retired featuring encouraging content and four podcast categories through which “Rebel” retirees are interviewed and enlightening observations are shared.

She says, “[Carol and I] both knew that there was a demographic there that needed to know not about the money about retirement, but about the life issues of retirement. People tell us that you need so much money, but it doesn’t matter when the first month of retirement is lonely and scary and rocky and you’re having panic attacks when your alarm clock doesn’t go off. That’s why we started RetireeRebels.com.”

Conroy says she’s excited about the lives they’ve touched, particularly when they hold events at senior centers and speak with retirees face-to-face. Her experiences have even inspired her to write a book: “Your Amazing Itty Bitty Retirement Book: 15 Essential Tips for You, the Nearly and Newly Retired.”

“It warms the cockles of my heart and gives my life purpose,” she says.

Conroy is also a reinvention life coach and CEO of her business Life’s a Daring Adventure, supporting people as they make transitions. For those thinking of leaping to another career, she uses the three R’s: review, retreat and reinvent.

First, she suggests making a timeline of your life—what gave you pleasure? Angst? What was left undone? Then give yourself time to be alone and reflect. Lastly, she urges pondering the question “How do you want your life to be?” with the help of a journal, dream board or life coach.

The inspiration for Conroy’s business name is a beloved Helen Keller quote: “Life is either a daring adventure or nothing at all.” But Conroy always adds her personal mark to the end of it: “…And I’m not done yet.

The Next Step

If you’ve just started thinking about making a change, there are plenty of resources that can put you on the road toward your authentic purpose and a brand-new career.

StrengthsFinder 2.0 is a popular book and online resource that provides an all-encompassing self-assessment through which you’ll determine your top five talents. strengthsfinder.com

The classic Myers-Briggs Type Indicator is a go-to for consultants, counselors and coaches. Once you discover your personality type, it may be easier to land on a career that fits your unique characteristics. It can be taken online or through a trained professional. myersbriggs.org

UW-Madison’s Adult Career and Special Student Services offers career-planning workshops, like Tools for Purposeful Career Change, an intensive two-day workshop, and Career Change 101, a two-hour session that gives participants tools to get them started. continuingstudies.wisc.edu /advisin

The U.S. Department of Labor has resources available to those switching careers, like its website O*NET OnLine where you can take an “Interest Profiler” quiz. onetonline.org

“What Color is Your Parachute?” has become a quintessential book for career-changers since its release in 1970. The new edition holds practical advice for navigating the job market. jobhuntersbible.com

Attend the April 28 BRAVA THRIVE Conference to focus on and explore your career and personal possibilities. Sign up for laser life and career coaching sessions with Darcy Luoma Coaching & Consulting as well as professional head shots and networking sessions. For details and to register: thrivewithbrava.com

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