How To Find Fulfilling Work in Retirement

Older man helping his younger colleagues
••• vm / Getty Images

Finding a successful r happens when you take the time to discover all the things about you that make you uniquely suited to a certain type of work. The path to the right second career starts with asking yourself the right questions. Start with the five ‘E’s’ below.


Think beyond traditional schooling. What certifications, classes, courses, and training have you engaged in beyond high school, college and graduate degrees? Perhaps it was specialized training provided by an employer. Perhaps it was a class on a new type of software or .

Or a communications or leadership development course. Or a hobby you pursued like scuba diving, golf, or gardening. Don’t leave anything out. If you took a class or training on it, write it down. One of these things may be instrumental to your second career choice.


What career and life experiences do you have? This includes projects and teams you may have been part of. It also includes roles like being a mother or father or even a pet owner. What about volunteer work? Church activities? Civic organizations? Write down every experience that has taught you life lessons. Each one of these things gives you stories you can share and insight into your unique skills and qualities.


What are your areas of specialty? Things people ask you for advice on? Things you feel comfortable talking about? Things you’ve researched, whether for work or fun? Communication skills you have? Don’t sell yourself short. For example, if people often say you are a great listener, then include that on your list. Write down all areas where you have even a small bit of knowledge or a skill that the average person would not have. Second careers can be built off an unused area of expertise or talent you have hidden in the wings.


When have you been most excited about what you were doing? What made it exciting? What are other peak experiences in your life where you felt fully engaged and fulfilled with what you were doing, whether personal or professional activities?

Write down three to four times in your life when you felt excited and enthralled with what you were doing at the time. Now see if there is a common element they share. Were they times where you took a risk? Where you worked alone or with people? Where you were researching or presenting? Take time with this exercise. It will give you the most insight into a second career choice that you will find rewarding.


Now, look at your notes. How can you explore opportunities where your education, experience, expertise and excitement overlap? For each of the following questions write down a few action items.

  • Who can you call to learn more about career opportunities in ___________ ?
  • Who can help you leverage your unique set of skills and passions? A career coach? A former colleague or mentor?
  • What assessment tools can you use to help you find a job most suited for you; I have found  (the Kolbe A Index in particular) to be very helpful.
  • What industry associations can you join to network and learn more?
  • What publications can you read to give you ideas on what to do next?

Here are two examples of people who leveraged their own set of talents and passions to find fabulous second careers:

  • loved hummingbirds. He became Executive Director of The Hummingbird Society. He decided to join the National Speaker’s Association and within seven months had launched his professional speaking career with twenty paid speaking engagements on the topic of hummingbirds. Ross found a way (in retirement) to leverage his unique experiences and passions to create a source of income.
  • Lisa Stefan loved training and leadership development work but was ready to move out of the corporate world. She hired a branding coach to help her work through her unique talents and perspectives and launched . Now she pursues her passion for helping other people “ReDiscover Their Mojo”. (If you’re looking for professional help finding your Mojo, from personal experience, I’ll tell you Lisa is fabulous. Call her.)