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What Story Are You Writing? 6 Lessons to Fuel Your Next Chapter

Second act careers

Credit: iStock

by Joe Casey

What will the next chapter be in the story that you’re writing?

I had the pleasure of attending a CIRKEL intergenerational networking event in New York City this week with our 21-year-old daughter. It was a great experience – and it was interesting to compare notes on the way home on our different perspectives and takeaways.

It’s a terrific idea. Bring generations together for mutually beneficial mentoring. This CIRKEL event featured three New Yorkers from three generations sharing their life stories.  (The fact that all three came to New York from elsewhere – Boston, Texas, and Minnesota – resonated with me as a native of the Boston area).

Their talks provided compelling snapshots of fascinating lives in progress at different stages. The youngest, Pat Dagle, is a former lead singer turned Creative Director; Alzo Slade, is a correspondent for VICE News Tonight, photographer and stand-up comedian; and Ruth Wooden, is a former advertising executive, former President of the Ad Council and Public Agenda, who recently completed a Masters degree in Theology in her 70s.

While the three people are very different, I was struck by the common themes that emerged from their stories.  Whether you’re contemplating a career change or considering an encore career in your early retirement, these lessons can be valuable – at any age or stage.

1. Ditch the Grand Plan – Iterate Your Future. While all three have strong interests and aspirations, they are not achieving them through any type of Master Plan. Bill Burnett and Dave Evans, co-authors of Designing Your Life, encourage people to “think like a designer and build your way forward”. That approach was evident in all three stories, with people moving from one endeavor to another, weaving their way forward. Their moves were not random. All three seemed intentional, but they were flexible in experimenting with new options that surfaced along the way.

2. Be Open to New Experiences. Each person who spoke at this event is immensely talented. However, each life and career pivot that they described emanated from their openness to try something new, their belief in themselves and their willingness to take risks.

3. Cultivate New Relationships. No one succeeds on their own. These life stories all cited seminal moments where key people made all the difference. Keep building your social and professional networks. Get out there and meet new people in new spaces. Create opportunities to collaborate. Reach out and seek advice from people who are doing what you aspire to do.

What can you learn from other generations? Lots. Click To Tweet

4. Be Resilient. At any stage of life, all kinds of obstacles will be encountered, so resilience is a critical skill to build and strengthen. Their stories include overcoming racism, sexism, and ageism. Alzo Slade told how he pursued an interest by independently studying Philosophy for his personal edification. He secured a meeting with the head of the Philosophy Department at a university where he was applying to the Master’s program, only to be mistaken by another employee for the new janitor expected to start work that day. He shared how he managed his emotions to navigate that encounter, keeping his end goal in mind. He went on to get his Masters and became an adjunct professor in Philosophy, among many other things).

5. Be Aware of Your Context, But Don’t Let It Define You. When you’re born does influence many things. The cultural, economic and political environment you’ll work in will shape your narrative and the types of opportunities that will emerge. For example, the two younger speakers at this event are pursuing an independent portfolio of interests in contrast to the singularly focused corporate career path of yesteryear. But sometimes the chatter about generational traits can go too far. There’s a great deal of heterogeneity within each generation. Look around you at your own generation. Don’t buy into the hype. Embrace what you believe in, ride the waves of change, but make your own way.

6. Be Ready for Serendipity – and Make Your Own. Ruth Wooden, who worked on Madison Avenue in the Mad Men era, noted that luck plays a role in any success story. But she pointed out that you need to position yourself to take advantage of it. And sometimes actions you take can create serendipity for yourself. She shared a great story of how when a senior executive role that was perfect for her opened up, she networked her way into others recommending her to the executive recruiter handling the search, positioning herself as a prime candidate. And there’s research that backs this up. There are things you can do to tilt the odds in your favor and create your own serendipity.

Luck is a skill? You can do things to tilt the odds more in your favor (according to science...) Click To Tweet

This CIRKEL event concluded with a fun interactive exercise, where each person attending wrote seven words on a card describing different things of interest to them.  Paired with a partner, each person picked a card from each other’s set and explained why that word was important to them. Then each pair worked together to come up with an idea for a new product based on the combination of your two words.  (My daughter worked with a Creative Director seated nearby. When their product idea was shared with the audience a woman behind me whispered: “Now that’s one that’s worth stealing.” ).

I highly recommend CIRKEL events. If one comes to your city, make the time to attend. It’s time well spent.

The generations before you and the generations after you can be sources of inspiration and motivation that just might fuel your next chapter.


Joe Casey is a former HR executive, who’s transitioned to a second career as an executive coach. As a Certified Designing Your Life Coach, he works with people to help them discover what’s next after their primary career. Learn more at and The Retirement Conversation podcast.


If you’d like to learn more about the story behind CIRKEL, we recently interviewed its founder on our podcast.


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