Your relationship with freedom is key to planning your next frontier.

Last Wednesday we celebrated America’s independence, that most fireworks-worthy of attributes. Right? Well yes, in the sense that we’re not beholden to a sovereign power. And yes, in that the opportunity to make something of ourselves is more possible in our country than in most places on earth. Yet there is an amorphous shadow side to personal freedom.

I don’t remember many of my dreams, but the ones I do recall are about just this. I dream that my Do List is empty, my calendar blank, and I’m floating in dark space, unanchored by responsibilities and tasks, absolutely free. Do I even exist if I am consuming without contributing? Do I matter if no one is relying on me to bring home some bacon and fry it up in a pan? I awake with a shudder from these dreams,  steam up a latte, and tear into the work of the day. I keep my plate spilling over…And then complain frequently that there’s too much on it….And then bristle whenever someone asks when I plan to retire and let it all go. The fear that fuels this perverse pattern cuts deep—and is a major reason why I became an expert in helping successful leaders navigate the emptiness of “not knowing” as they move toward their next chapter of marvelous independence (cue the William Tell Overture now).

The message of my dreams is that freedom and living death are pretty much the same thing. This is ridiculous, of course, yet I still struggle with it, which helps me better understand the challenges that major life transitions pose. And what I know for sure is that there is another path, a middle ground of structured and meaningful independence unfettered by the circumstantial constraints that have created guardrails—or prison bars?—around life so far.

Caroline Hall addressing alumni at the Stanford University Graduate School of Business

Caroline Hall addressing alumni at the Stanford University Graduate School of Business

Human beings crave structure. But there’s a big difference between the structure that holds us captive in the busy-ness of life and structure that frames our next expression of purpose and pleasure. Most of us find it challenging to get over the former and get behind the latter. My commitment, then, is to help others go for it and to put my own nightmares to rest once and for all.

I’m not the only Baby Boomer kicking and screaming my way toward retirement. I know that because I ask my peers the question that makes me bristle and they frequently bristle, too. I want all of us to get better at addressing the fear behind the bristling and how we can learn together to embrace independence in life-affirming ways and discover what wants to emerge when busy-ness loses its hold over us.

Join us in charting a next chapter affirmed and lived beyond busy-ness. Check out our programs at Life Reinspired.


Caroline MacNeill Hall is Co-Founder of Life Reinspired, a reset lab for successful Baby Boomers contemplating a meaningful next chapter of life. She is President of MAC Advisors, an executive coaching and leadership development company. She’s also senior faculty for the Coaches Training Institute.