What was the best job you ever had? And why does it matter now?

It’s fall. It’s getting colder, darker and wetter—there’s a feeling of hunkering down for the upcoming winter. In this season, along with hunkering down, people I know are also reflecting, reminiscing on their past “younger self” experiences. 

If you’re finding yourself in a reminiscent mood, and are in—or considering—a career transition and you’re not sure of the path ahead, here’s an exercise for you:

Think about the best job you’ve ever had. Hone in on what made it so great, and then seek those qualities in your future work. 

When I ask this question to each of my clients, I get a wide variety of responses. Here’s a recent response from Client A: 

“The best job I ever had was serving lunch and washing dishes in grade school. Every other week, a few pals and I did this work in exchange for free hot lunches. The cooks were super nice, their food was really good, and I loved the smell of treats baking. I really liked the satisfaction that came with accomplishing simple tasks—huge piles of trays and silverware stacked, sprayed down, and then sanitized in the commercial dishwasher. I loved seeing my friends pass by in the lunch line (and serving them the extra-large pieces of cake). It was peaceful, productive and fun.”

Here’s another, from Client B:

“My best job ever was working on a tall ship schooner as a first mate. I was proud of being in the minority as a woman on board the ship, doing work that isn’t necessarily within the realm of the typical. I liked being in charge. I liked sharing what I learned.  I liked being out of my comfort zone.  I liked developing mastery of the skills of sailing—the combination of the art and science and physics of sailing.”  

Are these folks headed toward jobs as school cooks or ship captains? Probably not. The reason I ask this question to clients as they consider future endeavors—and why I encourage you to do the same—is so they can hone in on its key elements in order to help identify (and then land) work with similar attributes. 

The assumption we’re proceeding from is that what made one feel happy or fulfilled, important or in “flow” in the past will make one feel similarly in the future. It works the other way too—think of the worst job you’ve had, identify why you hated it, and strive to avoid those aspects. 
Client A may focus on seeking a great team and work that allows achievement of tangible results while Client B might pursue leadership/teaching roles in a challenging and active learning environment. 

While this exercise clearly can’t provide an exact prescription for the work ahead, it’s a helpful grounding in what might matter most in identifying meaningful work going forward. 
Try it out and let me know how it goes!