This week, while vacationing with my family at Flat Iron Lake, I finished Homer’s The Odyssey. Sounds like a bibliographic flex, I know. But I was just getting ready for Christopher Nolan’s epic later this week.
It’s a story of a man trying to find his way home. Even though Odysseus is an ancient Greek hero, he feels utterly recognizable: lost, lonely, at his wit’s end, utterly castaway. (A little disconcertingly in a story of heroic masculinity, the man cries all the time.)
Odysseus survives by dint of his relentless yearning to get home. But even when he gets home, he doesn’t recognize it. The guy is endlessly uncertain and distrustful.
To my surprise, Odysseus is not an entirely admirable person. He’s a trickster, a pirate, and a liar. But he is all these things, in part, because he finds himself in a world of shape-shifting realities. Even when he finally reunites with his wife Penelope, after a twenty-year odyssey, he can’t shake the urge to test her fidelity.
I think mid-level leaders feel a lot like Odysseus, when it comes to living with uncertainty and mistrust. Am I reaching for literary cred? Well, you tell me, after listening to this week’s conversation between the Mode/Switch team and Dr. James K.A. Smith. It’s a podcast about being a manager in intensely ambiguous conditions.
Jamie’s new book Make Your Home in This Luminous Dark might not strike you as a business-forward must-read. But I think our intergenerational conversation—David Wilstermann, Xer; Emily Bosscher, Xennial, and Jake Aupperlee, Gen Z—will show you the managerial usefulness of ancient mystic thought.
The best things about talking with Jamie is his habit of turning the table with questions of his own. We brought him on the show as an expert, but he mode-switched from answer man to curious questioner. He did more than preach the importance of humble curiosity. He embodied it.
Two questions emerged from our conversation that matter for mid-level leaders:
Emily asked when uncertainty, ambiguity, and mystery become smokescreens. How do people in the middle of organizations tell the difference between ambiguity exploited and ambiguity earned? (Jamie’s response helps leaders discern when mystery becomes mystery-mongering.)
David asked when a leader’s embrace of uncertainty covers for incompetence. In other words, appealing to the “ambiguity” of a situation can disguise a leader’s ignorance and sloppiness. (Smith responds with the concept of "learned ignorance,” and it’s worth the whole episode.)
A picture I stole from the website promoting the lake’s gorgeous preserve.
I reviewed the final edits of this Mode/Switch Pod last night at sunset, while kayaking on Flat Iron Lake. (I’d tucked my smartphone in a ziplock bag to protect it from the wine-dark sea.) Maybe because I had just finished reading about Odysseus and his dark ship, I experienced this little podcast as—epic. But maybe the energy and humor and spirit came from the fact that Jamie was in-studio with us co-hosts. Together, at the Mode/Switch Table, we found ways through the fog of working community.
You’re on your own odyssey, I’m sure. You’re trying to get home, at least in the sense of seeking a place where work feels safe and meaningful for you and for your team.
Think of this podcast as a thirty-minute map. It offers the guidance of focused, substantive, multidirectional conversation about leaders in the luminous dark of their organizational life and work.
Podcast Table of Contents
00:00 — Cold Open
Why does information overload always seem to hit hardest when you’re already feeling insecure with your team? That tangle is the whole episode.
02:31 — Welcome, Jamie Smith
Jamie’s origin story on the back of a pickup truck. What actually changes when a leader stops trying to win and starts trying to invite? Jamie walks through his own experience of an existential and communicational mode/switch.
05:58 — Learning to Live with Mystery
Can you build real tolerance for uncertainty without turning into the leader who’s just checked out? Here’s the line Jamie draws.
08:19 — Reassurance vs. Reorientation
“We got this” or “here’s where we actually are” — which one does your team actually need to hear from you?
09:08 — Earned Ignorance
Is “I don’t know” a strength or a dodge? David’s question splits the episode open, and Jamie’s answer — by way of Augustine — hands you a phrase you’ll want to keep.
10:39 — Can’t Think Our Way Out of the Culture Wars
More information keeps failing to make anyone less polarized. Jamie’s fix starts in an unlikely place: the mystics.
13:00 — Should Leaders Weigh In?
You probably don’t want your CEO tweeting about Iran or Ukraine — but you might want something else from them instead.
15:57 — Wonder, Curiosity, and Barry Lopez
Four questions a nature writer asks of a place might be the best onboarding tool you’ve never used.
19:44 — The Practical Pivot
One thing to actually try this afternoon. No retreat required.
21:39 — Post-Show Roundtable
What happens when you ask a candidate what they’re curious about? When you answer a nasty email with humility instead of a rebuttal? The hosts try the episode’s ideas on themselves.
