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Explore encore career ideas, stories, and tips

Amy Fontinelle

Posted on January 09, 2024

Amy Fontinelle is a personal finance writer focusing on budgeting, credit cards, mortgages, real estate, investing, and other topics.
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Relate how some people embark on encore or second act careers without more schooling.

Describe how others go back to school in order to fulfill a new career dream.

Point out the need to have a financial plan in place to make a career transition successful.

Second act. Third act. Encore career. Whatever you call it, it’s a metamorphosis from a career that no longer serves you into one that reenergizes you. The pursuit of a second act can be born of necessity after a layoff, the upheaval of trauma, or the slowly dawning realization that your current work is no longer satisfying.

What you decide to do in your second act — or third — will light you up every day if you focus on finding passion in your work and bringing harmony into your life, said María Tomás-Keegan, a certified career coach and transition expert who specializes in partnering with professional women through her business Transition & Thrive with María. Identifying what you’d like to do next means asking yourself questions like these: What do I value most? What skills do I have? What do I love to do? And, perhaps most importantly, what don’t I want to do anymore?

The tips and stories that follow may help you step into the next stage of your career when you’re ready for a major change.

Avoiding more schooling

You’ve already earned an informal second degree through your real-life experience, inside and outside of work. And you may not have the time, money, or desire to go back to school. That’s fine. Many second-act careers don’t always require you to attain new credentials. (Related: Other options besides college)

Take writing, for example. It’s a logical way to disseminate your hard-won knowledge. And pursuing a writing career as a freelancer offers you the opportunity to set your own schedule and choose the clients you want to work with. These freedoms can be a breath of fresh air after working as an employee.

Elizabeth Hanes, BSN, RN, founder of RN2writer, has experience with pulling off such a transformation. She leveraged her degrees in creative writing and nursing, as well as her clinical nursing experience, to start Hanes Healthcare Communications in 2011.

Hanes has become an authority on health care content marketing and freelance health journalism, producing content ranging from patient information to brand journalism for some of the biggest names in health care. She also trains nurses to become freelance health writers through her RN2writer coaching programs.

“I always tell them — and anyone else interested in doing this — that the very first thing to think about is getting work samples. Virtually no editor or client is going to take a chance on a writer who can’t show that they’ve had work previously published,” Hanes said. “I recommend reaching out to a local nonprofit to volunteer your writing skills. The charity receives the value of your talents, and you get lovely work samples to show off.”

As a bonus, you may develop an ongoing relationship with a nonprofit you’d like to be more involved with. Tomás-Keegan said that she has had clients who homed in on one activity for a full-time career and engaged in the other as a volunteer.

“As a result, they got the best of both worlds and didn’t have to choose one over the other,” she said.

If you do have time for a bit of job training, Hanes added that aspiring writers may find it useful to enroll in a course or coaching program that focuses on the business of freelancing.

“They need to understand basic marketing skills, how to write content for the web, copyright and plagiarism issues, and so on,” she said. Acquiring this skill set can accelerate success and reduce the frustration of trial-and-error.

As for the myth that writing doesn’t pay? As a freelancer, said Hanes, you can earn a full-time living in part-time hours. (Related: The freelancer’s benefit checklist)

Getting more schooling

After teaching high school English for nine years, Darrin Dennis felt that he had accomplished everything he could as an instructor. Over the next three years, while continuing to teach Advanced Placement classes and grade reams of essays on the weekends, he contemplated his next move.

Conversations with colleagues and former students helped Dennis crystalize what he most loved about teaching: building individual relationships with students and imparting knowledge. Not only that, but his students would come to him with their personal struggles, not just their academic ones. Dennis would often refer them to the school psychologist.

“I realized I wanted to be the person the kids were being referred to,” Dennis said.

He decided to make the transition as quickly as possible. His wife became the sole breadwinner; he quit teaching and took out student loans to work toward his degree full time. Less than two years later, he graduated at the top of his class in the online Master of Arts in Counseling program from the Family Institute at Northwestern University, a highly rated online program for clinical counseling. The entire process, from starting school to becoming licensed, will take him a little over six years, he said. (Related: 7 ways to pay for grad school)

Anyone contemplating a major career change should understand this: “People will generally look at you like you’re crazy, especially a lot of your peers,” Dennis said. “A handful of people will be really supportive, some will say you’re brave, and you’ll get a lot of ‘I could never do that.’ It’s a matter of knowing yourself and trusting yourself. I told myself, ‘this will either be the right decision, or if it’s the wrong decision, I can navigate my way back to the career I had before.’” (Related: Getting the most from a graduate degree)

Since graduation, he’s worked in several supervised roles and settings to accumulate the 3,000 hours he needs to earn his license. Working in different clinical environments with a wide range of patients has helped him identify what caseload he can manage, which populations he prefers working with, and where his gifts lie: working with young adults, individuals on the autism spectrum, and couples.

Were the degree, the debt, and the upheaval worth it?

“I’ve gotten more personal satisfaction than I ever expected to,” Dennis said. “I’m way happier as a therapist than I ever was as a teacher, even though I liked being a teacher. But I no longer deal with administrative tasks, grading papers, or managing 35 students at once.”

Having a financial plan

Can you find stories of people who told off their bosses, quit on the spot with no plan, and were running their own profitable business within months? Sure. But many of us would rather minimize the disruptions that change inevitably creates. A financial plan and a career transition timeline can help your second act succeed.

A financial plan. If your second act is beginning with a sudden change in employment status, you won’t have the luxury of planning your transition. But if you do, you can take steps to give yourself financial stability during the transition.

If possible, start your new career or business as a side hustle at first, said Cynthia Day, CFP® professional, managing director of wealth management and financial planning for BLS Wealth Management, a MassMutual firm in Fort Lauderdale, Florida. You want to make sure your new career or idea is viable before cutting off your primary source of income: namely, your current job, she said.

And if you’re starting a business, it’s a good idea to have some clients already established so you can hit the ground running. (Related: Looking to start a business? You need a market, means, and mindset)

Another way to help yourself get through the transition is by having at least two years’ worth of living expenses in cash or available in other liquid assets, Day said.

“Other sources that can be tapped for reserves are cash value in life insurance policies and home equity lines of credit,” she added.

Look into whether you will be able to continue your current employer benefits after leaving, such as health insurance through COBRA, disability income insurance, and life insurance. Figure out how you will secure and pay for any coverage that will run out (like COBRA) or that is not portable (life and disability insurance, potentially). You may also need to find new coverage for any partner, spouse, or child who receives your benefits. (Related: Creating a financial plan for your family)

Day further recommends paying off any pretax 401(k) or retirement plan loans you may have taken out through your current employer. “These outstanding loans will become a taxable distribution when you leave,” she said. (Learn more: Switched jobs? Consider consolidating your retirement savings)

A career transition plan. If you have the luxury of making a gradual shift to a second-act career, the road map and timeline depend on your commitment to making the transition, Tomás-Keegan said. To start, it requires reserving energy to discover who you are and what you want. Then, create the vision.

Transitions don’t always happen when we’ve got energy to spare. In fact, the opposite is often true. Tomás-Keegan recommends identifying ways you deplete your energy — spending time with negative people, not getting enough rest, always prioritizing others’ needs over your own, being a perfectionist, procrastinating — and stopping at least one of them to begin refilling your energy reserves. (Related: Making a career change: Understanding the cost implications)

“After that, you can carve out time for research, identifying opportunities, testing options, and making a strategic plan that puts the vision into motion,” she said. “Then you can set a timeline of three months or six months to make it happen — shorter or longer are also possible.”

Change is easier with support

“Surround yourself with a support system that gives you positive feedback and shares expertise in your areas of interest,” Tomás-Keegan said. “Find a mentor and role model so you can tweak their roadmap to create your own. The quickest and easiest way to start your second act is not to do it alone.”

Other resources you might find helpful include Andy Levine’s podcast, Second Act Stories; the book Second Acts by Stephen M. Pollan and Mark Levine; and this guide to creating an encore career transition group from Marci Alboher, author of The Encore Career Handbook.

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This article was originally published in November 2021. It has been updated.


The information provided is not written or intended as specific tax or legal advice. MassMutual, its employees and representatives are not authorized to give tax or legal advice. You are encouraged to seek advice from your own tax or legal counsel. Opinions expressed by those interviewed are their own and do not necessarily represent the views of MassMutual.