The Paradox
Leaders contemplating retirement can get stymied by a paradoxical belief that goes something like this: I need to retire so I can figure out what I will do when I retire. Believing this Catch-22 can block you from making any progress on a plan, and leave you plugging away a bit aimlessly at your current role, putting your future on hold.
When I look back on my experience with transitioning from my "big job" to my current portfolio career, I can see how I missed opportunities to experiment and learn before I made that very big step. There was a sense I just didn't have the mental capacity to hear myself out about what it is that would engage me for the next 20 years or so.
Take Small Steps
Rather than putting off planning for your next act until the curtain has come down on the current one, there are a number of small steps you can take to make progress. Some additional good news is that there are many resources available to you as you explore your future; helping successful leaders become even more valuable as they transition to a productive "2nd act" is becoming more and more of a recognized need.
Here are some ideas on breaking free from that Catch-22 mindset:
Experiment. Rather than view this project as primarily an internally-driven search for some ultimate truth you will in future discover about yourself, run some real life experiments now. Take a class. Join a group that has activities that interest you. If there's an area you'd like to research, treat that like a real project, bringing the same professional skills to it that you'd apply if you were getting paid to do this.
Talk to people. Consider if it might work for you to even explore options at your current company; if so, who might you speak with about a dramatic switch in your role? Or perhaps you know others who are alums of your current business who have made a transition to "retirement." The more people you talk to, the more ideas you'll likely generate.
Learn from resources. As mentioned above, there's a growing supply of resources about retiring into a "2nd act". Even if a particular resource doesn't provide a eureka moment for you, educating yourself on the topic is likely to expand how you are thinking about your next steps, and help you break out of this paradoxical belief that's keeping you from moving forward.
There are many available resources, here are just a few to help you get started:
Books
Working Identity: Unconventional Strategies for Reinventing Your Career - Herminia Ibarra.
Herminia Ibarra provides a fresh perspective that she calls the "Test and Learn" model, which explicitly targets the problem of getting lost in an unending internally-focused search.
The Adult Years: Mastering the Art of Self-Renewal - Frederic M. Hudson. Frederic Hudson puts personal and professional transition in the context of a comprehensive model that's both inspiring and motivating.
Podcast
Retirement Wisdom. Joe Casey's podcast features a wealth of ideas through his conversations with researchers and experts that primarily focus on gaining clarity on how you'll use your future time most rewardingly.
ChatGPT / AI
Unlike a standard online search that would just supply some links and leave it to you to sift through the results, an AI assisted search can be both more on target and surprising. Even "wrong" responses here can trigger an idea that will help you get moving.
