Encore Careers: Helping Executives Achieve Freedom, Flexibility, and Fulfillment

“What’s next” is a question that you and many other successful people are currently contemplating.

The COVID-19 pandemic triggered the Great Resignation, as millions of people reflected on their life and work and decided to step away from what they were doing. This trend is intersecting with the rising number of baby boomers — many of whom are healthy and financially secure — who have experience, energy, and interests, and don’t desire a traditional “retirement” (at least not right now).

But while choosing to step away from what you have done for many years may be a relatively easy decision, deciding exactly what to do next and how to go about it is often much harder.

Crenshaw’s Encore Career Planning

In working with our transition clients, we realized that many had trouble defining what that career transition looked like and how to achieve it. As a Transition Advisor and Executive Coach, I worked with Crenshaw Associates to develop the Encore Career Planning program to help executives navigate this important and often difficult process.

Our proprietary Encore Career program is an in-depth, personalized approach with one goal: helping you identify and plan the next phase of your life, one that focuses on achieving more than just a paycheck, but a heightened sense of fulfillment.

Taking into account a “portfolio model,” Crenshaw’s Encore Career Planning program uses multiple tools and weaves together a series of revealing activities that are purposeful, enjoyable, and at times demanding in a way that is motivating and ultimately extremely satisfying. The outcome is a personalized Encore Plan for your career and life with greater clarity about what’s next and an action plan for how to proceed.

Encore Career Planning in Action

Lisa Marks had worked in various sales and marketing leadership roles for multiple companies for more than 30 years. For the past 27 years, Lisa had been at American Express, where most recently she was a senior vice president overseeing a multi-billion-dollar global sales organization.

When considering early retirement from Amex, Lisa — who was almost 55 — decided it was time to move on. “While I loved the company and the people, I had gotten tired of the intense roles, the global travel, 12-hour days, 7 a.m. meetings, and lack of work-life balance.”

But Lisa was unsure about what to do next, who could help her think through her future, and how to go about developing a plan. Lisa explained, “I didn’t need an outplacement service, because I didn’t want to be placed.” When learning about Crenshaw Associates’ Encore Career Planning program, she saw it as different. “It’s not about how to find your next job or change industries or careers, it was about reimagining what my future could be like. This goes across both my personal and professional life,” said Lisa.

Crenshaw's Encore Career Planning process

Crenshaw’s goal is to help executives, like Lisa, in the middle of their lives, explore what’s next in the second half of life. Our robust program, which focuses on developing a personalized Encore Career Plan, consists of four critical processes:

1. Identifying your drivers.

   Having a general sense of your motivators, stressors, and other personality traits is one thing. Seeing it on paper opens up a much deeper conversation on what truly drives you. We take each Encore Career client through a rigorous battery of assessments using various tools, leading to an in-depth, personal, highly revealing interview with their advisor and a psychologist to understand their unique motivators and demotivators. Lisa, who was initially skeptical of the assessment and interview, ended up thoroughly enjoying the process because it dealt with topics such as values and focused on her as a whole person.

2. Allocating your time in a portfolio.

   To achieve the freedom and flexibility our Encore clients want, we focus on allocation of time. This step involves listing and analyzing how you currently allocate your time and envisioning an ideal future time allocation where the main priorities are those activities you are looking forward to. Lisa found it extremely valuable to think through “How do I want to spend my time moving forward?”

3. Designing your Encore Plan. This process then turns to the work of developing your individualized Encore Plan. Based on your motivators and demotivators, the plan consists of commitments, passions, dreams, and curiosities. An Encore Plan can take several forms depending on how you best envision that plan. The goals also vary by client. Some individuals seek to hone new skills, leverage their experience through board work, or take a proactive approach to focus on family and personal passions.

   In creating her Encore Plan, Lisa thought through the steps of starting a part-time consulting practice that leveraged areas of interest and expertise from her previous career. We collaborated closely with Lisa, offering practical advice on how to get her practice up and running, established clear parameters for her consulting practice — such as not working more than 15 hours per week — and helped Lisa articulate and become comfortable with personal dreams outside of her professional career.

4. Discovering, Culling, Committing, Going forward, and Launching. Once your plan is created, the focus shifts to putting the ideas into action. Throughout the program, we take you through a cycle of discovering the activities you want to pursue, cull ideas that don’t fit, and commit to activities that do, until you have a finalized plan, ready for launch.

   The “go forward and launch” portion of the program is built to be flexible based on your personal needs. Some clients want a thought partner and choose to leverage their Crenshaw advisor for their knowledge and experience. Others simply need an accountability partner to make sure they make progress on their plan. As Lisa moved through her Encore Planning program, our experience shifted from a collaborative process as we developed her plan to a supportive role where we could catch up on how she was doing and celebrate early wins of her burgeoning consulting practice.

The Encore Career Planning program combines the expertise of our highly experienced coaches with Crenshaw’s proprietary tools and processes. The magic of the program is that it is personalized to each person’s unique situation, personality, motivations, and dreams.

In reflecting on working with Lisa, the greatest benefit I provided was enabling a structured yet flexible process to explore possibilities for Lisa, serve as a sounding board, and provide Lisa with greater confidence on embarking in the next chapter of her life and career.

Lisa — who is now implementing her Encore Plan — observed, “One of the best parts about working with Crenshaw on my Encore Plan is that it wasn’t a static program. It followed a set of steps but was a truly customized partnership to help me get to the life that I want to be leading.”

Lisa’s experience working with us illustrates the value of getting expert assistance to help answer the “what’s next?” question and to develop a personalized, actionable Encore Plan.

To learn more about developing your Encore Plan, visit www.crenshawassociates.com