Mid-level leaders have something to learn from Odysseus when it comes to coping with ambiguity. Seems like a stretch? Try listening to this week’s conversation between the Mode/Switch team and Dr. Jamie K.A. Smith about being a manager accustomed to ambiguity.

His book Make Your Home in This Luminous Dark might not strike you as a business-forward must-read. But our intergenerational conversation—David Wilstermann, Xer; Emily Bosscher, Xennial, and Jake Aupperlee, Gen Z—explored the managerial usefulness of ancient mystic thought.

The best things about talking with Jamie is his capacity for questions. We brought him on the show as an expert, but he quickly mode-switched from expert to novice. By answering our questions with questions of his own, he did more than urge the importance of humble curiosity. He embodied it.

Two questions emerged that matter for mid-level leaders:

1. Emily asked when uncertainty, ambiguity, and mystery become smokescreens. How do people in the middle of organizations discern the difference between ambiguity exploited and ambiguity earned? (Jamie’s response helps leaders discern when mystery becomes mystery-mongering.)

2. 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 podcast.)

I think you'll experience this podcast as surprisingly epic. The energy and humor and spirit probably came from the fact that Jamie was in-studio with us. Together, we found ways through the fog of working community.

You’re on your own odyssey. You’re trying to get home, seeking a place of where work feels safe and meaningful, yearning for flourishing for yourself 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.

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
A stat that should needle you (87% of workers see manager capability as a company risk) — and 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 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.