Podcast Summary

Podcast: High-Impact Growth
Episode: Leading Through Chaos: Jayson Morris on Grief, Healing, and Emergent Leadership
Air Date: September 22, 2025
Host(s): Jonathan Jackson (CEO and Co-founder, Dimagi), Amie Vaccaro (Senior Director of Marketing, Dimagi)
Guest: Jayson Morris (Leadership Coach)

Overview

This episode dives into the evolving demands on leaders navigating chaotic and uncertain times, particularly within global development and social impact sectors. Returning guest and leadership coach Jayson Morris joins hosts Jonathan Jackson and Amie Vaccaro to candidly unpack personal and collective grief, the necessity of authentic and adaptive leadership, and strategies for building resilience amidst ongoing change. The discussion moves from the impacts of COVID and market turbulence, through the need for healing and emergence in leadership, to practical advice on processing difficult emotions and embracing uncertainty with courage.

Key Discussion Points & Insights

1. Personal Journeys Through Uncertainty and Grief

[02:20]

• Jayson Morris shares about the unexpected passing of his father, the impact on his perspective, and the renewed focus on meaningful connections and adventures.

  • "It brought me in acute awareness of this paradox of life, that it's both short and fragile and can feel very long and unpredictable...It really connected me with what matters most in terms of family and friends and doing meaningful work." – Jayson Morris [02:37]

• Post-COVID reflection on risk aversion and how personal and collective experiences have influenced openness to adventure, both professionally and personally.

  • Jonathan Jackson and Jayson discuss the deliberate efforts required now to carve out time for adventure, play, and joy, as an antidote for ongoing societal heaviness.
  • "Giving ourselves permission...to have fun, to experience joy. And we need it. We need that fuel. It’s what builds the resilience to do the tough work." – Jayson Morris [07:38]

2. The Lasting Impact of COVID and Accelerating Change

[09:10]

• Hosts and guest explore how COVID increased risk aversion, shifted perspectives on work, and continues to shape leaders’ comfort with uncertainty.

  • "It's incredibly hard to have an entrepreneurial mindset right now or a mindset of curiosity." – Jonathan Jackson [09:10]

• Isolation—Zoom culture has facilitated work but stripped relational fabric, trust-building, and moments of co-regulation among teams.

3. Leadership in a New Era: Overcommunication, Healing, and Emergence

[12:17]

• Jayson spotlights the increasing necessity for leaders to “over-communicate” and support “emergence” rather than rely on static plans.

  • "Leadership, it used to be this notion that the leader had everything figured out... [now it’s] needing to be in these places of not knowing and supporting emergence and sensing, but normalizing that." – Jayson Morris [12:28]

• The “Leader as Healer” concept:

  • Leaders are called upon to act as stabilizing, empathetic anchors for their teams amid volatility.
  • "Being grounded, being empathetic, being a source of stability amidst all this chaos—as a leader, you can have a profound impact." – Jayson Morris [12:54]

• Jonathan adds on the challenge of authenticity and emotional regulation in remote work, where brief digital interactions become the main visibility for senior leaders.

  • "The positive energy that you try to project through Zoom can be extremely tiring to do." – Jonathan Jackson [15:52]

4. Collaboration, AI, and Remote Work

[11:18, 16:41]

• Amie Vaccaro raises the shift in collaboration styles as AI becomes a go-to solution source, diminishing human-to-human learning and deeper trust-building.
• Jonathan highlights how remote work can stagnate interpersonal trust, making hard conversations and collaboration more difficult and more easily personalized or misinterpreted.
  • "You’re just completely missing that [social] offset...It can feel like an attack because...that’s the only interaction you have with people." – Jonathan Jackson [36:17]

5. Embracing Uncertainty: "Go Down Swinging" or Move Forward?

[17:38, 19:46, 23:32]

• The hosts and Jayson explore the difficult choice between persisting with once-proven strategies/markets ("go down swinging") vs. rapidly pivoting to new opportunities.

  • "How is that noble—going down swinging if you think you’re going to miss—versus trying to move quickly as you can to where you think you might hit?" – Jonathan Jackson [19:46]

• Jayson introduces analogies from business (Kodak vs. Fuji, QR code development) to illustrate organizations that either clung too long to the old or boldly repurposed capabilities.

6. Emergent Leadership and the Power of Sense-Making

[25:37, 27:15]

• Emergence is presented as “sense-making”—taking the next step, assessing what unfolds, and adjusting rather than sticking rigidly to strategic plans.

  • "The idea of emergence is more sense making...Lion tracking is not about knowing where the lion is. It’s about finding the first track and then sense making where’s the second one?" – Jayson Morris [26:24]

• Jonathan shares how Dimagi had to abandon a five-year plan, challenging his own longtime leadership frameworks in favor of presence, adaptation, and experimentation.

7. Grieving the Loss of Certainty, and Emotional Processing

[29:39, 31:08, 37:46, 39:25]

• The group acknowledges grief, anger, and frustration as inevitable in times of upheaval and emphasizes the importance of actually feeling, processing, and expressing these emotions.

  • "There’s a step in there of grieving...there’s emotion that comes with that, and that need to process it. There's sadness, there's grief, there's frustration, there's anger." – Jayson Morris [29:39]

• Jayson advises leaders to normalize, feel, and find healthy outlets for emotions (like walking, peer conversations), and warns against bypassing feelings.

8. Finding Balance: Authenticity, Nervous System Regulation, and Humanity

[42:45, 44:53, 47:41]

• Amie and Jayson stress the need for leaders to accept their humanity, acknowledge internal conflicts (ambition vs. regulation, boldness vs. humility), and hold space for both themselves and others.
  • "How do we actually hold that and model that holding of our humanity? I think leaders can be really inspiring for teams...this notion of like the bionic leader...it's a facade." – Jayson Morris [43:12]

9. Burnout, Permission to Rest, and Selfishness vs. Self-Interest

[44:53, 47:41]

• Burnout is at new highs; Jayson shares his experience giving himself permission to rest, and urges leaders to practice "micro-practices"—small, intentional moments of pause and self-care.

  • "For the first time…I gave myself permission to rest and to not be on all the time." – Jayson Morris [45:10]

• Jonathan encourages leaders to embrace “selfishness” in the sense of honoring their personal needs, warning that self-sacrifice without boundaries only accelerates burnout.

  • "Otherwise, I just know we’re not going to survive as individual leaders...given how uncertain everything is." – Jonathan Jackson [48:17]

10. Final Reflections: Grace, Boldness, and Slowing Down

[50:30, 51:32, 52:42]

• Jayson closes with a reminder to embrace paradox, give grace to ourselves and others, and move with intention even if that means reversing course as new opportunities arise.
  • "It’s challenging times...it’s acknowledging it and accepting it. Giving ourselves that little bit of grace...and then boldly go there. But don’t be afraid to reverse course." – Jayson Morris [50:30]
• Jonathan echoes the importance of grace and permission to slow down:
  • "Slowing down might actually be the fastest way to make progress on what you’re ultimately trying to get to." – Jonathan Jackson [51:52]
• Both close with the shared mantra: "Slow is smooth, smooth is fast." [52:42]

Notable Quotes & Memorable Moments

• "Trust is sewn one stitch at a time." – Jayson Morris [16:41]
• "Courage is not the absence of fear. It's feeling the fear first and then acting." – Jayson Morris [19:19]
• "One of the emotions I didn’t name, aside from the anger and the grief, also is like, fear." – Jonathan Jackson [39:25]
• "Acknowledging your humanity. Leaders are allowed to do that." – Jayson Morris [42:45]
• "If we swing to either side of that pole too much…whether we swing to the selflessness side so much that we burn out, or we swing to the selfish side so much that we isolate or harm, either pole is not going to support us. It's finding the middle ground." – Jayson Morris [49:03]
• "Slow is smooth. Smooth is fast." – Jonathan Jackson [52:42], (corroborated by Jayson as an old self-defense motto)

Timestamps for Key Segments

• [02:20] Jayson shares personal grief and reflections on change
• [04:05] On bringing play and adventure back post-COVID
• [07:38] The importance of giving ourselves permission for joy
• [09:10] How COVID and broader negativity impact entrepreneurial mindset
• [12:17] New leadership qualities: overcommunication, emergence, leader as healer
• [16:41] Building trust and the loss of social fabric in remote work
• [19:46] The struggle between “going down swinging” vs. pivoting
• [23:32] Business analogies: Kodak vs. Fuji, QR code innovation
• [25:37] Sense-making and emergence—leadership as “lion tracking”
• [29:39] Grieving loss of strategic certainty
• [31:08] John’s reflection on his leadership evolution
• [36:17] The difficulty of constructive conflict and lack of offset in remote work
• [37:46] Strategies for processing grief and anger; somatic practices
• [44:53] Burnout, rest, micro-practices, and permission to pause
• [47:41] Embracing “selfishness”/self-interest to avoid burnout
• [50:30] Closing reflections: grace, embracing duality
• [52:42] "Slow is smooth, smooth is fast"—final mantra

Takeaways for Listeners

• Embrace emergence and adaptability: Strategic certainty is gone. Leaders must experiment, sense, adjust, and give themselves (and their teams) space to grieve and process lost bets.
• Model authenticity: Showing up with emotional honesty is vital for building trust and resilience.
• Prioritize self-care and boundaries: Leaders can't serve others if they're depleted themselves.
• Restore balance: Boldness and humility can coexist; it's not an either-or but a daily recalibration.
• Remember to slow down: In moments of heavy volatility, deliberate, reflective action is the fastest route to sustainable progress.

This episode is a must-listen for anyone grappling with leadership, uncertainty, and personal or organizational transformation in a time of profound change.