Managing in the Age of Uncertainty
Summing up “Career as a Story”
Ok, I tried Claude.
I write about the impact of AI and the era of efficiency on career planning for millennials and gen-z — and how managers need to adapt. It’s why I named this newsletter, “Managing in the Age of Uncertainty.”
My research into the future of managing showed we need new management concept to support development and career planning for millennials and gen-z. I call this new development concept “Career as a Story” — distinguished from the corporate ladder that boomers experienced.
I built a framework to help managers navigate this new reality called the “Five Dots of a Career Story.” As readers know, I dedicated five issues of this newsletter over the past two of months to each of the dots.
In today’s newsletter, it is my goal to “sum it all up” and bring all of the concepts together in one place.
So I felt at this point, I needed to eat my own dog food and see how AI could help me summarize the ideas in an infographic. My goal was to see if I could produce the graphic without hiring someone to help me with the graphic — or calling my daughter Annie to do it. I’ve personally never created one. (Although I realized now that my PowerPoint skills are similar.)
My friend Fauzia Burke shares ideas here on Substack about how writers can better leverage AI. She’s gently nudged me to try AI. Another friend Patti Sanchez suggested I try Claude.
So Claude and I started working together.
The infographic below sums up the “Career as a Story” management concept. Email me at ron@ronricci.com if you want a PDF of the infographic. Let me know if my partnership with Claude produced a solid end result!
Summing Up the “What”: Career Ladder vs. Career Story
To remind everyone, this generation isn’t counting on the corporate ladder to get ahead. Instead, millennials and gen-z are looking for job roles where there is an opportunity to write a chapter in a career story that leads to growth and advancement.
I told Claude I wanted to use something I learned from Cisco: a “From - To” comparison to help me distinguish between the career ladder and a career story.
There are five essential differences:
Summing up the “How”: The “Five Dots” of a Career Story
The “five dots” framework is the way managers “connect the dots” for millennials and gen-z employees. Again, Claude proposed this graphic, but the words are mine to describe what’s expected of managers in this era.
As a reminder to managers, the key concept in the “Five Dots” model is alignment. As I’ve said, I reject “employee engagement” as management idea. Aligning a job role on the team to what’s on a manager’s dashboard of priorities, goals and metrics is the single most important act a manager can do to help millennials and gen-z write a chapter of career story.
Manager Thought of the Week
"Rapid iteration, play to each other’s strengths."
I asked Claude to summarize what it was like working with me. Rapid iteration. Pretty much sums up the value I think I got from Claude.
Claude is very positive in its outlook, and added this about working together:
"Working with Ron on these infographics was a perfect example of how AI and human expertise can collaborate effectively. Ron brought deep knowledge of generational management differences, while I contributed design and technical execution. The iterative process - refining colors, adjusting layouts, splitting into two focused pages - showed how the best results come from combining human strategic thinking with AI's ability to rapidly iterate and implement changes."
In Summary: Principles of Managing in the Age of Uncertainty
I left Cisco to answer this question with research and evidence: What does the manager of the future look like? What are millennials and gen-z seeking in a manager? Which behaviors, tactics, skills or processes matter? What’s it going to take to attract and keep the best people over the next decade? In short, how to be a great manager.
Based on this research, the core philosophy of this newsletter is rooted in one idea: successful managers in this moment in time, for this generation of talent, need to be “career dot-connectors.” The next-gen doesn’t expect to spend their entire career on your team — that’s an idea boomers grew up with. A job on your team is like a chapter in a career story to the current generation. If you want the best people on your team, you have to connect the dots between roles on the team and the career opportunities of the people working on the team.
What is the“Age of Uncertainty”? If the industrial age was about taking predictable steps up the ladder, the age of uncertainty is about finding or discovering the path of a career without any predictable steps, without an obvious ladder — it’s why being a career dot-connector will differentiate you as a manager.
How to be a Great Manager in the Age of Uncertainty: Be a Career Dot Connector is available on Amazon.
What kind of manager are you? Take my free self-assessment and learn about yourself.




Thanks for the shout-out, Ron. Before I met Claude, I was skeptical that AI could meet the high standards of professional writers. But Claude proved me wrong, and now she's practically my bestie. Welcome to the club :-)
Woo hoo. Thanks for the plug, and I agree with Claude. Our best work comes from collaboration!