At 45, I found myself face-to-face with an impossible situation: I couldn’t quit the academic affairs administrative post that was becoming intolerable in its tedium and repetition and yet I couldn’t bear the thought of risking something as significant as the income, title, and to-do list that gave me some form of purpose to mark the passing hours of the workday. As I circumambulated my way through these past ten years or so, an ebbing and flowing but all-pervasive uncertainty replaced any initial sense of direction and purpose I had cobbled together earlier in life. Yet I again found myself trying to assemble the rig once more out of the spare parts remaining from the disintegrating persona I had built assiduously throughout my life before embarking out into the world many years ago.
Enough of this fading semblance of a personality remained at the outset at 37 years old to power me through several attempts to reach an escape velocity that might have pulled me out of that untenable situation but I just couldn’t quite make it no matter how hard I convinced myself. Before too long, regardless of how sound (or unsound!?) any of my plans were, uncertainty would well up from beneath my feet, as if there were psychic hydrostatic pressure capable of overwhelming any plan I hatched with flood waters that left me with no further interest in it once the bloom was off the rose. I would find myself withdrawing investment and libidinal energy from whatever scheme I was cooking up until I walked away from the idea altogether, shaking my head and wondering what that was all about. Only to do it again when the next great idea would come.
“…uncertainty would well up from beneath my feet, as if there were psychic hydrostatic pressure capable of overwhelming any plan I hatched…”
As the years went by, I finally started noticing the design/refine/resign pattern I had evolved, leading me to a further insight: what fascinated me wasn’t the shiny new plan but the very process of attempting meaning through iterative plans and planning. I had seen this movie before but I couldn’t quite recall when or where. No, what caught my attention was the persistent lifeforce that kept arising only to dissipate in order to give rise to the next idea. Life was repeating and I finally caught myself in the act. Is this familiar to anyone reading this?
My emphasis in life up until that point had been on building certainty, which I had initially found in my own life’s journey when I left a humanities doctoral program for a professional program where I did indeed end up earning a PhD. This led immediately to directing academic libraries, which led to the beginning of the end of the persona I mentioned earlier. That’s a whole other story best suited for another post that I’m itching to write but what I want to focus on in this particular post is the uncertainty itself. My attention in my hoped-for, post-academic machinations had demanded not only a respectable level of complexity but also a similar amount of certainty that my ideas would sustain me through to a stable and secure place on the other shore I was aiming for. I was understandably frustrated throughout the first seven years of this yoyoing back and forth and felt like I had lost some part of myself.
Perhaps I really did lose something, not least the ability to power my way through a conventional career path with reasonable plans. But with this loss came gain as well. I learned to appreciate the uncertainty that had a way of toppling my apple cart of schemes. While it was initially paralyzing in that it kept me stuck in a professional situation I simply couldn’t ideate and execute my way out of, the uncertainty was ultimately what I was seeking. Systems do what they are designed to do and where I was initially concerned that something was profoundly wrong with the system of self, I’ve come to embrace that the self’s production of uncertainty at this stage in life is exactly what the mid-career and midlife moments (years!!!) should manifest. The system of self is perhaps doing what it is designed to do, as unsettling and disruptive as that feels. While I had mastered the ability to plan my way to success, a part of me wisely was never willing to step out onto ambition’s path for a second time; a part of me wasn’t up for yet one more round of the new endings and beginnings, beginnings and endings, not to mention the upheaval that the substantial life changes I was plotting would bring.
In retrospect, it’s perfectly clear what was going wrong: I was mistakenly trying to craft solutions to the greater uncertainty that was making itself known to me with its own goal of making itself known through me (to wit, this inaugural post subject matter). David Leviathan puts it better when he writes:
“The mistake is thinking that there can be an antidote to the uncertainty.“
You see, when I noticed the self system in action, I couldn’t blindly follow its siren song of doing the same old things, only better this time (humorous aside, this is also a not uncommon refrain of academic administrators on job interviews trying not to spook the faculty). All that had carried the certainty within me was up for grabs, every part of me was ready for a new bargain with life that would make room for uncertainty. As psychologists sometimes say, we become one-sided by a certain point in life. I had developed a strong sense of certainty that took leave of me when I least expected it. It happened right when I needed it most as I was making a career progression that could launch me much higher into larger academic libraries and fulfill the initial career plan I hatched at some late point in graduate school.
And with that, part 1 of my book of life closed and part 2 opened. This meant many things. It meant that I had to leave behind many of the achiever’s implements that got me thus far, including:
- A non-skeptical belief in my striving self;
- A half-baked perfection I held myself to;
- Deliberate and intentional plan making;
- A serious demeanor devoid of play;
- A deep-seated impatience that no longer served me;
- A kindergartner’s ability to know when the juice is worth the squeeze.
And while I haven’t lost them yet, I have sensed that fear and scarcity’s death grip on me has loosened, even if I’ve yet to find the courage and abundance I would prefer to replace them with. Another way of slicing this dichotomy is that certainty is fear-driven by a certain point in life while the latter is ultimately a growth mindset for the second half of life. And it is risk that runs right between them. What is risk, then and how does it relate to certainty? Rodney Smith in his book Lessons from the Dying states that it is:
“[…] action taken without certainty to free ourselves from dullness. We do not know what will happen, but we also know that the alternative—staying the same—proves intolerable.”
…”the alternative—staying the same—proves intolerable.“
I’d never really thought about my midlife transition as marked by dullness but the repetition that was building in my search for certainty was turning into something like a stuckness, or even a sickness…unto death. And to take the Kierkegaard reference a little further, underneath the stuckness was an anxiety that was trying its best to keep the uncertainty in check. Smith continues:
“The truly remarkable thing is not that we become dull but that we stay in dullness until we die. It is remarkable because we know what we are doing yet are still afraid to risk.”
And this is the insight I’ve gained over the past year or two – that I could stay in this pattern until I die, I could wake up at my retirement or death and wonder how I got here. And that, aside from some dullness and repetition, it could be easy to do! After all, all I had to do was not risk and not develop new capacities within, such as:
- Risking certainty for uncertainty;
- Surrendering achievement for intention;
- Dropping impatience for presence.
And my heart was aware of something that my mind hadn’t assimilated yet – certainty will abandon you at its whim and leave you rigid and ill-prepared for an uncertainty that can and will swallow you whole. The last part of the Smith quote blends uncertainty with faith in a way only the heart can understand:
“With experience, our faith in this uncharted path of the heart will mature, and our mind will give up its battle for control. There is no other way to open the door to our heart except by risking our fears. What do we have to lose?”
Last fall I heard Peter Block say something similar in his pithy way:
“The line to the counter for security is very long. But the line to the counter for adventure, there’s no one in it!”
Not counting the day I told my boss I was returning to faculty, the launch of this website and blog marks my queueing up in the line for adventure. As far as I can see, my only job is to push my rickety old wheelbarrow of uncertainty as steadfastly and faithfully as I can.

It wants to go where it wants to go and you can’t push or pull a wheelbarrow from the front. Something else, whether that be serendipity, synchronicity, spirit, or some transcendent function can and will have to do their part, but I’m finally ready to do mine!
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