Considering an Encore Career in Retirement? Here’s How to Make the Most of Your Second Act

by Glenn DiBenedetto | Aug 8, 2019

There is one question every child is asked when they are young: “What do you want to be when you grow up?” A heavy ask for those still learning their ABCs, and yet common answers are nothing short of aspirational. However idealistic the career path, whether it entails becoming an astronaut, veterinarian or even president, there is something to be learned from these ambitions as you enter your golden years.

I know this because I experienced it firsthand. After a 30-plus year career as a CPA firm owner, I sold my practice and completed an employment agreement. I entered retirement looking to stay active using the experience and skills I acquired over the years, specifically by working with clients who were involved in business ownership transfers, including business mergers, sales, and acquisitions. As a client of NEIRG, when I discussed the potential for a second act with Brian and Nick, they mentioned they had just added exit planning to their offerings as a firm. Given my extensive experience in the space, and desire to continue working with closely held business owners, conversations progressed, and we soon joined forces to form Business Succession Advisers.

For retirees who yearn for the mental stimulation of their previous career but are now looking to explore professional passions on a full or part-time basis, an encore career may be a rewarding alternative. Below, I outline two key questions those intent on pursuing a second act should consider as they enter the traditional retirement years.

What do you want to do?

After a lifelong career, you have wisdom and experience. You also enjoy freedom from prior commitments and can now utilize the wealth of knowledge you’ve accumulated during your various jobs or prior business ownership. It’s time to take a step back and assess what you really enjoy doing the most.

While many people, like myself, capitalize on transferable skills, some retirees go a completely different direction. For example, a former client of mine, after 25 years as an educator, was approached by a cousin to help fund, own and manage what grew to be seven branded restaurants. As he neared his 70s, he then sold them to two key employees and other investors. Although a professional 180 like this is less common, my client ultimately wrote two acts in his career: one as a schoolteacher and one as a successful restaurateur.

Identifying your next career path doesn’t come without its share of challenges, however. People sometimes commit to things they’re not really interested in or don’t enjoy doing. Working for other people, after having been a business owner, might be a unique adjustment. It requires relinquishing control, which can be difficult. Therefore, it’s critical that you don’t settle when deciding on your second act. Your choice should be intentional, and an endeavor you are keen on pursuing.

What is the incentive?

Now that you’ve identified your second act, what is your motivation for doing it? Is it economic, or activity-driven? For many, the answer here is twofold: to generate additional income and stay intellectually active. An encore career offers you the opportunity to address life goals that you couldn’t accomplish in a standard retirement — perhaps helping kids or grandkids with tuition, or other financial considerations. Additionally, with longer life expectancies, retirees have greater needs and potentially more significant medical expenses. An encore career can provide funds to supplement existing retirement accounts.

It also provides you with the luxury of staying mentally active and challenged. American actress Helen Hayes, whose career spanned nearly 80 years, once said, “When you rest, you rust.” For anyone, the ability to continue to learn new things is a stimulating and enjoyable experience. A professional second act offers an invaluable opportunity to find renewed joie de vivre and add meaning to your golden years.