Want or need a second (or third) career? 50-Plus-Year-Olds are Reimagining Themselves

Amy E. Gerwitz

At a time when many of her contemporaries are winding down, Amy E. Gewirtz, 62, felt that some of her most interesting, fulfilling days were still ahead.

From the time she was a teen, she was drawn to theater. After receiving a law degree, Gewirtz practiced entertainment law. However, after her first daughter was born, she segued into law school administration, initially joining Cardozo Law School as a career counselor and admissions counselor for 10 years. Subsequently, she went to work at Pace Law School, where she started as a career counselor, and then created and directed a program to assist attorneys with their reentry to law practice or an alternative legal career.

When her younger daughter, a musical theatre actor, began performing with a community theatre in New Jersey, Amy realized she was beginning to miss the theatre world. She was also starting to burn out in her job.

“My work was very gratifying and a true labor of love, but it was also labor intensive. I was starting to realize that participants in my program weren’t getting the best of me and that wasn’t fair to them”, she says. Thinking she wanted to be a Broadway producer, she gave six months’ notice at work. While still at Pace, she invested in her first Broadway show and took some general commercial theatre producing classes to see if this was what she really wanted to do.

After taking almost every class the Commercial Theatre Institute (CTI) offered, she applied, and was accepted to CTI’s 14-week advanced class in commercial producing. In 2017, she co-founded and became executive director of Liquid Theatre Collective, Inc. 

Gewirtz is not an anomaly in starting a second and third career. Many of us have worked for years, getting up almost every weekday to get dressed, grab a cup of joe, and head to a job we don’t necessarily enjoy. And then one day we think, “Enough is enough.”

But too many people end up unsure of what they want to do next. Hours of golf, bridge, cooking classes and more all sound divine to those keen on those pursuits but after a while they might not be. Some decide to confer with a financial professional who gives a green light to retire and travel endlessly. But then what?

At first you might love the freedom of nothingness. No reason to get up early in the morning and what a luxury to lounge around in your PJs sipping rather than gulping down your coffee and slowly reading your favorite newspapers. But then slowly boredom creeps in. Or, your expenses mount—perhaps, your house needs massive repairs-- and you simply need greater income than your investments provide. What now?

One man we spoke to was sound financially to retire but wanted to fill the time. So, he became the family chauffer, picking up the grandkids and taking them to all their afterschool lessons and friends’ houses. It wasn’t enough, however, for someone who had been in the fast-paced financial world. He got involved with a nonprofit, offered his leadership skills pro-bono and took the organization to a new enhanced level. This kind of work has made him happy as he feels he’s contributing to the community.

If you’re not worried about money, then volunteer. If you are concerned about funds, consider flipping houses, baking cookies and cakes to sell at farmers’ markets, fixing bikes, becoming a Tai Chi instructor, or bottling your fabulous barbecue sauce. Maybe you’re a high school history teacher but enjoy working with numbers. You do all the finances and investing for your aging mother. You know also that you have a lot to learn. It could be fun to hone those skills by taking a few business and finance classes to become an accountant or financial professional.

We know of a hard-charging lawyer who wasn’t passionate about deal making but was about her Judaic studies. She went back to school for her master’s degree and now is an adult-ed teacher. And there’s a woman whose husband died of cancer. She had been a strategic marketing and communications consultant but suddenly found herself CEO of her late husband’s wholesale distributing business. She loves it, and the company has never been more successful.

Turning 50-plus is a good time to consider doing something you love that also taps is into your core values, suggests Astrid Baumgardner, a certified professional coach who specializes in career and leadership development coaching and teaches career entrepreneurship at the Yale School of Music. She also penned the book, Creative Success Now (Indie Books International 2019) that will be available soon (www.astridbaumgardner.com).

So, how do you begin a new career? If you’re uncertain, one approach is to hire a career counselor who administers client assessments and other tests and then based on results suggests a few career options. However, in Baumgardner’s experience, those tests might not be enough.

If you need to dig deeper and want a personalized approach, a career coach can be the ticket. The person will help you tap into your experience, talents and passions to figure out who you now are. “The process starts with personal development work to help point you in a new direction for a second career that you might enjoy and then figure out what is involved in getting it off the ground,” Baumgardner says. Since 2008, she has helped hundreds of students and clients figure out new career paths and assist them with their career and business development.

For those who want to recharge their lives with a new career, here are some tips on how to start and what path to take.

Dream big. Now’s not the time to hold back. Read about others’ careers in newspaper and magazine articles or TV shows. Or movies can become another route. The all-female crew of the sailing boat, the Maiden, now a movie, were well under 50 but their inspirational tale might inspire you even when others pooh-pooh your ideas.

Align with your values, strengths, passion and purpose. Baumgardner suggests digging down for elements of personal authenticity—people are happiest when doing what aligns with who they are. What are your personal core values, strengths, passions, talents and life purpose? What aren’t, which can help, too. Focus on subjects you like and where you shine.

Set inspiring goals. Baumgardner helps clients set inspiring goals that are continually reviewed and refined as the client acquires more knowledge and experience. She also guides them through the process and provides accountability as they make the transition.

Have the right mindset. Don’t be scared that you might not earn as much money entering a new role. Baumgardner says a client might say, “I was a lawyer so I should be making lots of money.” Here is where a career coach helps you get through the process to get to what you really want. Baumgardner cautions that a career transition requires a lot of energy, and there is no rule book on how to do this. It starts with the right mindset: “Be positive and proactive. Persevere through challenges and be resilient,” she suggests. And get in the flow, the highly-focused psychological state of optimal performance developed by Mihaly Csikszentmihalyi, the noted Hungarian-American psychologist.  This mindset, Baumgardner points out, aligns with positive psychology, the study of human flourishing. Humans are entitled to be happy and enjoy what we’re doing.

Take a series of action steps. Doing so enables you to achieve your goal, says Baumgardner. If you can, treat this transition to a second or third career as an experiment. Set an exploration goal: I’m going to explore my options to find out what works. I’ll give it a year. This will help you to move forward and use this time as learning experience.

Analyze obstacles to success. Identify what might be getting in the way of accomplishing your goals and then come up with strategies to overcome those obstacles.

Research careers that are hot right now. Also, make your own lists, perhaps, on a spreadsheet. Add the likely income.

Network. Attend career fairs. Meet people and chat with them. Go for information interviews, take classes and online ed-- many are free such as itunes University.

Come up with a profile of what your next phase will look like. Explore what’s interesting to you and keep track of what you like and don’t like. Also, consider from your old job what you liked, loved and what you didn’t like at all. Do on the job shadowing and gather information about what resonated and what did not. Take notes, journal and keep it as informational input. Try not to put pressure on yourself when deciding what to do. If you need to make money, it’s a different story. Examine your skills and experience, how can you translate them to another career and explore what is the best outlet to use those skills.

Check out organizations that can help such as Encore.com. This group assists executives to transition to new careers in the “do-gooders” space. If you want to work for a nonprofit, get some experience by volunteering and take a grant writing course. Or, if you have already donated your time to raising funds for a nonprofit, have developed contacts, and like it, parlay this into a paid position in development for either the same nonprofit or another.  Or set up your own nonprofit. Go online for help: foundation center, marketplace.foundationcenter.org/training or the National Council of Nonprofits, councilofnonprofits.org.

Go to job interviews when you hit on something you like. While doing all the transition work, it’s a good idea to fine-tune your resume and curriculum vitae as needed. Write your experience in terms of skills and results and do not be so hung up on job titles, says Baumgardner. Look for bosses and organizations that value skills sets rather than job titles. Have a professional look over your resume.

Try an internship or get a part-time job. This won’t add to your income but might give you a better understanding of what career might work for you. If you want to sell baked goods, consider working in a bakery, which will give you a good idea of how many you need to make daily, how to handle dough in a professional mixer, roll out mounds and mounds of flaky pastry and even how early you might have to rise to make enough for those wanting croissants with their coffee.

Volunteer. If money is no object, volunteering is great. You can make a world of difference in people’s lives and really give back to your community. Caveat: If you become such a great volunteer, you might be surprised that you could be offered a paid job. Now, you’ve got a conundrum. Do you want to go back to regular hours? What a nice decision to have to make!  

Baumgardner encourages those who are burned out at work and seeking second and third careers to take a plunge after doing their personal development work and information-gathering. “Instead of designing the ‘perfect’ career profile, go out into the world to experiment with different roles to find the one that is the best fit,” she says.

That’s what Gewirtz did. She says the theater world is offering her a very fulfilling career. “I feel blessed to be working in both the commercial and non-profit areas; each offers a chance to change and inspire the world through theatre. I’ve been lucky to be involved in several Broadway shows as an investor and am currently a co-producer on a show hopefully coming to Broadway in 2020. My non-profit theatre company has an ongoing mission, which appeals to me as well. We’re thrilled to be developing an original musical about an iconic woman in American history—stay tuned! I’ve been really lucky to have enjoyed each of my career chapters,” she says. “It has made my life more interesting, I believe, to have had a second and now a third career.”

What is the Liquid Theatre Collective?

This is a not-for-profit theatre company that combines a passion for theatre arts with a vision to benefit humanity, according to its website. Liquid’s goal is to develop and incubate projects with a social justice issue at their core through the initial development process and then for a commercial producer, or larger not-for-profit theatre company, to take the production to the next level. http://www.liquidtheatrecollective.org/

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