Leading Through Chaos: Jayson Morris on Grief, Healing, and Emergent Leadership

Summary

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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)

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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.

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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]

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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.

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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]

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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]

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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.

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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.

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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.

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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]

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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]

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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]

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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)

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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

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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.

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

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Transcript

[A]

Welcome to High Impact Growth, a podcast from Dimaghi. For people committed to creating a world where everyone has access to the services they need to thrive, we bring you candid conversations with leaders across global health and development about raising the bar on what's possible with technology and human creativity. I'm Amy Vaccaro, senior director of marketing at Dimagi and your co host, along with Jonathan Jackson, Dimangi's CEO and co founder. What if the leadership skills that brought you success yesterday are exactly what's holding your organization back today? In a world that's experiencing constant change and uncertainty, from market shifts to the rise of AI, the old playbook for leadership simply isn't enough. Today, we're thrilled to welcome back leadership coach Jason Morris for a candid and timely conversation about navigating this new reality. We'll explore the profound challenges leaders are facing, from managing personal grief and anger to inspiring teams amidst overwhelming uncertainty. We debate when to go down swinging for a cause you believe in versus when it's time to pivot. And we unpack the idea of the leader as healer. If you're leading a team through turbulent times, this episode offers a framework for leading with authenticity and building the resilience needed to move forward. Enjoy.

[B]

All right, welcome back to the podcast and, um, so excited. Today we are rejoined by Jason Morris. Jason, great to see you again.

[C]

Yeah, I'm excited to be back. I've been wanting to come back since the. Since the last recording, so, yeah, we're.

[D]

Excited to have you, man.

[B]

Yeah, I have to say. Yeah, the last episode we did together, pre kind of market melting down, that was one of our most popular episodes of the year. But I also just remember after the conversation, feeling like, oh, my gosh, there was so much more we could get to. So because of all that, we were just excited to bring you back onto the podcast. Feels like a really ripe time to revisit some of the conversations that we started then before we dig in. Well, maybe the first question to start to dig in is, I'm curious, Jason, how you've been doing in the last six months navigating just a lot of changes and turmoil that, you know, Dimagi has been facing, and I'm sure you're seeing it as well. Yeah. Curious just to check in with you.

[C]

Yeah, it's. It's interesting times for. For sure. And I think. I think we connected over the last summer, so last June or July, um, and since then, it's been a whirlwind. My father passed away in the fall, which was, I'M so sorry to hear that. Thank you. It was both sudden and we could see it coming, but was really. 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. So it really connected me with what matters most in terms of family and friends and doing meaningful work and having meaningful connections. But that was kind of in October, and then, you know, with the. The beginning of the year and the elections and everything that's happened since this. It feels like nested Russian dolls of change and chaos and uncertainty. And I think many people are going through that. So excited to. That we get to unpack some of that today. And, yeah, other than that, things have been. Things have been pretty good. Bringing a lot of fun and play back into my life after it kind of going dormant after Covid, and also just really having meaningful conversations and connections with teams and. And with leaders and coaching and trying to navigate this. This chaos.

[B]

You were mentioning a little bit about bringing play and adventure back into your life. I'm curious to hear a bit about that.

[C]

Yeah. Since the beginning of COVID I think there was a lot changing in my life.

[D]

My.

[C]

My dad had some health issues back then, but there was almost this. I think a lot of us turned inward, and, you know, we were in lockdown, and I think people kind of came out of it and went back to normal or new normal at different phases. And one of the things that I noticed was I just gotten more kind of conservative in how I was living my life. And my father's passing was a reminder of this preciousness. And there is a spark that was lit in me to go out and have adventure. I can't remember if I mentioned it in the first podcast, But I spent three years backpacking around the world in my 20s, and so travel and adventure has always been something that's been near and dear to my heart, but has been on pause for a number of years. And so I just kind of defibbed it. I went out and did some epic scuba diving in the Pacific and just decided that I needed to bring some of that in and also bring play in. I think play is really important for all of us. So I started playing pickleball in January, which gets my competitive juices flowing. But it's a wiffle ball, so you can't take it that seriously.

[D]

I call it the bad version of tennis.

[C]

People do, and then they try it and then they get hooked. It's a democratized tennis, really, because everybody can play.

[D]

Yeah, but if you Grow up playing tennis like I did. You want, you don't want to democratize. You want to feel superior to everybody else playing. Yeah, I know, it's, it's, it's fun. And, and the point of the COVID switch is interesting because if you think about a lot of people's arcs, right, you know, we had this crazy two year period of, you know, just everything changing and then obviously physically being much more conservative for almost all of us, either by legal requirement or just, you know, culturally. And then obviously many people, dimaggi specifically, had a much bigger work from home. So you're interacting with people a lot less physically and in person. And then if you're in the development industry, things radically changed again. So we've had one, one massive change after another for the last five years now. And it's been something that I think takes extremely dedicated thought to how you want to show up, how you want to prioritize different components of your life right now. And with work being as challenging as had been, one choice my, my wife and I made was, you know, we really wanted to, to go on some big adventures with the kids, our, our two sons. And that's been awesome. But it's a lot of hard work to plan. It takes a lot of resources and so it's, it's definitely a choice for the family. You got to try to prioritize doing some of those big adventures and finding the time to take away from work and things. So it's taken very deliberate effort, you know, in a way that I, I don't remember were feeling like it needed to be so deliberate at past points in my life. I don't know if that's just remembering fondly, you know, the past in a different way, but it definitely feels like it takes a lot of proactive effort these days to find that time for adventure and find that time for joy.

[C]

Yeah, and giving ourselves permission, I think it's easy with. I mean, there's so much going on in the world that's horrible. We don't need to go into that. But I think sometimes we won't give 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.

[B]

Yeah, it's really fascinating to think about. Like the COVID happened, it was this massive shift, but it's so far in the, in the, in hindsight that I think I forget and there's, it's interesting to like, I just unpack some of the changes that happened that are still present today. And yeah, even just like within my own little nuclear family. I feel like the last few weeks my wife and I have been like, talking about entrepreneurial ideas that like we had pre Covid and then during COVID we were just like, nah, we just want full time jobs. Right. We just want to be secure, stable, you know, insurance, all that. And then we kind of just forgot about, you know, and so just starting to like open up some of those ideas with my, My wife is. Has been taking care of our daughter right now and she's not going back to the. My daughter's going to go into daycare soon, so she's got some time opening up. So just brainstorming there. But it's. Yeah, it's fascinating to like unpeel some of those layers of like risk aversion that maybe came through Covid. Right. And other factors. Yeah.

[D]

And I would say risk aversion that might have come through Covid, but also, you know, the news is, as Jason said, is very challenging day in and day out right now and is, you know, catastrophic for the development sector. And it's incredibly hard to have an entrepreneurial mindset right now or a mindset of curiosity. Jason and I will be having a session coming up with myself and one of our executives trying to figure out, like, how do we get back to a place of mutual curiosity? Because it's so hard to kind of feel open to things right now, I think, you know, on the one hand, if you're an engineer by training like I was, or running a tech company like I am, you're just like, do we all have jobs in five years when AI keeps getting better, and then coupling that with just everything that's changing in terms of what is the future going to look like for my kids? It's really hard to come at it from the right angle of open mindset, an adventurous mindset, a curious mindset, versus just kind of closing up and wanting to be kind of heads down and be like, well, let's just get through this next week. And you keep doing that and all of a sudden you're halfway through the year and you're like, what just happened?

[C]

Yeah. And there's all these compounding circumstances. So we've got of the whole individual and collective trauma that was Covid and some of the fallout there. We're increasingly getting more isolated. You know, I mean, zoom is wonderful. I use it all the time, but I know I don't get out of my house some days, quite literally. And then AI again, a Powerful tool that we might talk about later and has its ramifications. And all of this impacts us. And yet those social fabrics, that sense of belonging that we need, that is going to help us, it's increasingly harder to access. We feel like we have less time, we're under more stress, and then we pile shame on top of that. And we think it's just us, you know, we're the only ones struggling. So it's a recipe for challenges right now.

[B]

Yeah. I do wonder about the ways that AI is shaping collaboration. Right. Because whereas it used to be, you'd go to your coworker and ask a question, like you now can take that question to AI and ChatGPT and get probably a better response immediately. So, like, how does collaboration. What is, you know, what is, how does collaboration evolve? Right. In this new world? It's. Yeah. Fascinating to see. And speaking of kind of evolution, Jason, I'm curious. You know, I think in our last conversation we were talking about this idea that the leadership skills that got us where we are today are not what's needed for the future. And that feels so much like, so true even, you know, perhaps especially more so today. What are you seeing and what are you feeling around, like, what new or different leadership qualities are you seeing as required of leaders today in this, in this moment in time?

[C]

Yeah, I can't wait for John's thoughts on this too. I mean, I think over communication was what really jumped to the top of my list. This, that. I mean, things are changing so fast and that, that need, I think leadership. It used to be this notion that the leader had everything figured out and needing to be in these places of not knowing and supporting emergence and sensing, but, but normalizing that. And so being that role model. And the other one that's been coming up a lot with clients is this concept of leader as healer. And there's that title comes from a book written by Nicholas Yanni, Leader is Healer. But this idea that in these challenges, it's. It can be more than, than business. And that being grounded, being empathetic, being a source of stability amidst all of this chaos, as a leader, you can have profound impact on everybody in the organization and on your team. And so it's not just what you say, but what you do and how you show up energetically that people are looking to, for guidance in these, in these really trying times.

[D]

That how, how leaders are showing up right now, whether it's at, you know, the CEO level or executive level, I think has such a profound impact on people because again, with, with the Zoom culture that we're now in, you get tiny moments of, you know, EQ and reading, body language and energy and these things that you might have 1/2 hour call with a ton of people that. But that's the only time that team of people was seeing the CEO of the company and how they're showing up that week. Right. And so it is, it is very difficult for me personally to grapple with that when, you know, the things going through my head might be pretty pessimistic at various points in the day, you know, or at various points in the week, I'm just given what I'm seeing in the news or other things. But being, you know, being that ballast for other people to not just see that energy, see that curiosity, see that forward momentum, but be able to latch onto that and use that as hopefully positive feedback loop. And we just had our management team together a couple weeks ago and like, man, it's getting more true every time I see people in person where I'm like, it's just not like working to be remote nearly as well as it used to two years ago or even during COVID like the in person time, maybe you mentioned that how's AI changing collaboration? But there's the, you know, there's the literal, are we collaborating to come up with a better plan or better idea in this one meeting or for this one idea? But then there's all of the other aspects to what collaboration causes between humans who are in that moment of collaboration, who are building that interpersonal relationship that then pays off down the road, you know, so it might not be that that one idea got any better. In fact, it might be worse than if you just iterated with an AI. But now you're not building up that trust and that human capital or social relationship capital with your colleagues. And so the next time you have a really hard debate that you do can't go to an AI for, because you're trying to convince somebody that their idea is wrong or could be better, they're trying to convince you you don't have that capacity, you know, to do that. And so for, for me, like, particularly just given how challenging everything is right now, like, I really am trying to figure out ways to see people in person to make sure I maximize that time when we are together and maximize the way that we're showing up, you know, to be positive and despite very challenging times. And I think that the, the positive energy that you try to project through Zoom can be extremely tiring to do. And I just had to think and she's like, how you doing? I'm like, eh, you know, so I didn't, I wasn't even doing it an hour ago with Amy. But it's, it's something that I think is really important for leaders, you know, whether it's the CEO or others right now or just a manager for their team because it's really hard out there right now for a lot of folks in our, in our industry.

[C]

I love what you were just saying John. And, and as I was thinking about that whole thing about well that all of the intangibles of that collaboration outside of the idea and it really what comes to mind for me I have a, a mentor, friend, guide who says trust is sewn one stitch at a time. And it, and it, and it's that notion of social fabric and all of our social fabric that relating happens. So much of it happens underneath the verbal. And I think that we are such a society that values the head and the ideas and only that output that we're forgetting and in your case remembering which is wonderful that there's so much more that we need for our own belonging, for our own safety, for our own social well being.

[D]

And I think also in like this, this moment of just severe uncertainty with you know, from just a pure business lines of what markets are going to be profitable, who's going to accrue the profit in the development sector, what funding is going to be left and what's it going to look like. One of the sessions I recently did with some other CEOs was talking about how to lead with huge uncertainty. And you know, Covid was actually one of those periods where we had this massive uncertainty and just had to move. And in general people like to have more evidence of the direction they want to head in than they're going to be able to. And for me personally it feels pretty uncomfortable at various times to, to be asking the company, you know, move in this huge big direction with less certainty than I would like. But we just have to, you know, in, in today's moment there's no option to stand still. There's no point to trying to, you know, stay in businesses or markets where you think it's gone. So you do have to find that next place to land. But it's way less certain than any of us would like right now. So you also have to be able to bring all this energy, bring all this curiosity and someh, you know, also lead with authenticity where you're acknowledging, yeah, there's massive uncertainty. I wish I was a Lot more confident in what the future looked like. But that's just not the time is really right now. You know, that's not the position that the global development market is in.

[C]

And one of the things I appreciate about your leadership style, John, is that you do the self reflection and the then you share quite candidly what what is known and what isn't known. And, and that's one of the things that I think is so that humility to say, hey, I don't know or I am scared or worried. You know, courage is not the absence of fear. It's feeling the fear first and then acting. And I think you bring that, I've seen you bring it in in group settings. So I think leaders need to, to embrace that.

[D]

I appreciate that. And I think one of the things that really helped when we were talking offline, you know, I was on behalf of dimagi, but I was really struggling with this decision of as we both continue to do what we know is high impact, what we know is working in the field, what we know is creating huge amounts of value for our users, for our communities. But we know the market is changing rapidly from underneath us. How do we go to where we hope the market ends up where we think we can create unique value. And we had this phrase that you and I were talking about which is like we want to go down swinging. And you really made it, had some good insight of like, why is that the thing that's noble to go down swinging if you think you're going to miss? Right? Why? How's that noble versus trying to move as quickly as you can to where you think you might actually hit the ball. And that's a huge mental struggle I think right now for a ton of us who've spent decades demagi, but many other firms just doing amazing work in the field and just watching it evaporate and wanting to fight for every single last drug, every single last patient, every single last household you can help while also saying we have this amazing team, we have these amazing skills, amazing learnings and experience. Where do we need to apply that next as well? And what is noble thing to do, if we want to use that word, that maximizes the potential to create as much impact as we can. And it's a huge struggle for us as a firm right now, for me as a leader, to figure out that right balance with what we had been doing and what we had been so good at, what we want to be shifting into. And for me at least there was another way to kind of lead without being Transparent. Like, this is really hard. It's not as if I'm claiming we should just completely jump to some other new market because there's as much uncertainty there as there is in the current markets.

[B]

In some ways, I want to dig in on that go down swinging concept. I don't like that. I don't like the go down part. The swinging, yeah, I can get behind.

[D]

I don't think Demogi will go down, but I think, you know, unfortunately there's a lot of parts of our business that, you know, particularly health system strengthening funding that might just be gone, like the entire market, you know, work that we found incredibly impactful. That I think was great ROI in a lot of areas. But that finding, you know, I don't think an RFP has been released in the last six months to do that kind of work, or at least the style that the monkey would have been on. So when I talk about go down swinging, I don't want to give up on that work. I never wanted to give up on that work. You know, I thought, I thought we were great at supporting that kind of work. And so the, the challenge for us, though, is if nobody's funding that work, what does that mean for us and how do we apply our skill set in a new way? And there's, you know, one school of thought that could be like, well, governments don't need this. We should still be doing it even if nobody can fund it. Let's just hope somebody will come to the table. Or they're saying, like, look, nobody's going to come to the table. We still need the things we're doing now more than ever, but it's got to show up in a different way in the market. So, yeah, I don't mean that the moggy is going to go down swinging, but I just mean for some of our business verticals, like, I'm not ready to give up on them. We, we were doing great. I think our staff is absolutely phenomenal at doing a lot of the areas that I unfortunately think, though, that the revenue's not there anymore, you know, or the funders aren't there anymore. And we, we, we could, quote, unquote, go down swinging and like, hope that some funding comes in or figure out how to, how to transform ourselves into where we, we think there might be more potential.

[C]

And one of the interesting parts of the conversation, and then the, the conversations with the rest of the leadership team was defining what is going down swinging. You know, in a finite resource environment is going down swinging, spending every last dollar on Something that you've always been doing that we know has impact until that runs out or is going down swinging, grabbing the resources you have, stepping back and saying, how can we parlay this into something else that's going to give us a chance to, to try something different. And, you know, we played with a number of different analogies and then I got to leverage and harness the power of AI to really discover some of the case studies of companies that have done that. You know, Kodak went down swinging on print film. Fuji went down swinging by saying, this is not going to work. Let's, let's figure out what we know, what are our core competencies, and let's go out and try all of these different things, from pharmaceuticals to chemicals to all kinds of things. And Fuji survived. So, you know, there's a we. I. One of the other examples was the notion of the QR code. And I, I think it was Takeda, but they knew that this QR technology was incredible, but there was no market there yet. And so what they did is they went down swinging by saying, we're going to build this code and then put it on a shelf. And then it came back several times and went dormant several times. So that notion of where do we put our resources is, I think for a lot of leaders right now is really hard to figure out because the landscape is shifting and we don't know how things are going to turn out.

[B]

Jason, something that you said earlier was supporting emergence for teams, and I haven't, I'm not familiar with that term and I'm curious to kind of explore that a little bit and thinking maybe it kind of dovetails into what we're talking about here.

[C]

Yeah, it. I've heard it in a few different, or learned it in a few different coaching schools. Emergence is kind of this idea that, that the path unfolds in front of us and that we, you know, we used to have this idea and I think this is really challenging in business right now where we could create these three to five year strategic plans and we could see the path as it was laid out and see the obstacles and know exactly what we need to navigate. The idea of emergence is more sense making of, of taking the next step and seeing what comes from that, how the vantage point shifts, how our own sense of what needs to happen shifts. And there's a beautiful book that I have a few clients reading right now called the Lion Tracker's Guide of Guide to Life. And it talks about this, this concept of emergence as it relates to what do we want to do with our lives. But 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? What can we learn from this track? Because every track has all kinds of meaning to it and then slowly taking steps and sometimes having to back up because we've lost the track. And that, that is a beautiful metaphor for being fully present in the moment and seeing what is unfolding, what is emerging from there.

[D]

I love that analogy. And the video I recently watched that we were discussing in a peer group with, it was Simon Sinek talking about confidence. And exactly that concept of, you know, in certain moments you can't wait for the evidence, you can't wait for the confidence. It's all about following a path. And your confidence and your evidence actually comes from following the path. You gain more confidence, you're on the right trail. As you see those steps unfold and you gain more confidence. You need to back up and take a different approach. And that is so hard when you thought you had it. I think for a lot of people coming out of COVID the development industry was pretty good. In 2023, 2024, you had these five year plans coming out, you had funding coming in, you had trust based philanthropy and big bets and like, so it's just such whiplash to go from, oh, I had this great five year plan that I released and we had to do this. We literally tore up our five year plan because we're just like, this doesn't make any sense anymore. Even that strategic planning construct doesn't really make sense. Right. But it is, it is hard to get back into that mode. You know, when you, when you were like excited by your plan, thought you had a good plan, thought you had a good strategy, you know, within two months, everything changed on you and you got to go into a totally different mode of leadership, you know, into a totally different way of, of trying to chart a course. That's tough. And I think, um, it's, it's really still a struggle for me to, to try to figure out how, how do I change how I'm showing up? How do we change how we're guiding the company in moments like this when there's so much uncertainty? And historically you kind of think, oh, your job as a leader, your job as the CEOs, like you come up with the direction, you know, that you're confident is the thing. Everybody should be aligned to set up the organizational structure and, and go. And it's like, it's one Step at a time right now, you know, it's not point the hill and go take it. Let's just go on this track and see what happens tomorrow. And that's just a very different mode of trying to operate and trying to also come up with the staff to be like, look, we'll all need to show up differently in this moment. It's not going to be this five year plan that we can take slow, rational steps towards.

[C]

And you and I have talked about it. There's a step in there of grieving. You know, the loss of the strategic plan, the vision, all that's been invested has been the rug has been pulled out from underneath you on, underneath so many people. And there's, there's emotion that comes with that and, and that need to process it. There's sadness, there's grief, there's frustration, there's anger. Um, it's, it's a key piece in that being able to then, like you said, take a breath and rededicate yourself to, to something entirely different.

[B]

I appreciate the acknowledgment of grieving. Right. Like, it's really hard to move forward without kind of moving through all of the feelings. One of the, like, visuals that I'm is coming to me with all this kind of talk of going down swinging and sort of sense making is actually like a monkey, like going through a jungle swinging from like branch to branch or something. And like just being like having to be so present to figure out where is that next branch gonna be? Right. And John, I'm, I'm curious. This is such a hard time for, for a leader and yeah, I'm curious to kind of hear your, your reflections on like, how you've noticed yourself evolving and changing through this period and like both what you're seeing and also like what you're wanting from yourself in this, in this moment. And that probably leads into what you want from your teams as well.

[D]

That's a big question, Amy. I mean, I would say mostly not being very successful showing up as the idealized leader I'd want to be right now. I mean, there's too much stress, there's too much anxiety and there's too much anger, frankly, you know, at just how what's happened to our industry, what's happened to our colleagues, you know, it's, it's hard to overcome that anger and that grief for everything we've seen. And so that's been a big challenge to overcome. I think I've been incredibly fortunate to, you know, have good health in my family and Extended, so I don't have additional stressors, you know, coming in right now, which has been great because the amount of stress I feel at work is pretty. I could take a lot more, you know, beyond that. But at the same time, we, I think, put the company on a trajectory years ago coming out of COVID that is in. In a lot of ways even more relevant today in this massive disruption in our market than it was when I set ourselves on this course back in 2022, 2023. So there's also been a fair amount of quiet confidence and comfort that I take in the direction that we all have been excited about for the last couple years, that now we have to accelerate way faster than I thought we would. And, you know, rather than it being a both and it might be an either or with some of the markets we wanted to serve and some of where we wanted to get to with our pay for outcomes and pay for success ideas. But it all comes down to trying to figure out what is our unifying factor going forward. And I think I'm really excited that we have aligned on creating more value per dollar for frontline workers, for communities, for governments, and really trying to change how we offer products and services in the market to do so. But it's hard. And so much of what we've been great at for the last 20 years has changed so dramatically under the last six months right out from under us, and I'm kind of mad about it. So it's hard to, on the one hand, lead with confidence and give people the space they need to try and fail. It's not like, on the one hand, AI is changing everything. The market's changing everything. On the other hand, hand, like, we're the same people we were yesterday. We still need to have the chances to try and fail. We still need to learn by dealing. We still need to do all these things. And so I also have this, like, big impatience too, you know, because I feel like, oh, Demagi is so fortunate, the position that we're in right now relative to a lot of the challenges our peers are facing. And we still have significant resources and great ideas and great support. And so I also want to get there faster, you know, some angry at the market, the way things are playing out in certain ways. And I'm like, impatient, you know, at the same time, to. To get to where we're going. So at a high level, it's. It's very, very challenging. I'd say this is the hardest period I've had of, like, trying to do emotional Regulation and, And just, you know, nerves and how one shows up that I've had, you know, in a really long time, possibly forever. I mean, the only other period I can remember this challenging was Covid, you know, in terms of a little stress and things.

[B]

Yeah, I hear that. And I also think, like, we've lost the critical kind of in person co regulation moments. Right. Like, which, you know, I know for you, John, as a. As a extrovert, like, as super valuable. Right? So you're maybe feeling more isolated even though you're on Zoom all day long.

[D]

Yeah, definitely more isolated. But also, it's not just isolation. It's definitely that, but it's also like, it's just too annoying to argue with people over Zoom. You know, I think, like, it's just like, it's just too. Nobody has, like, I don't. And the other person on the other end of the zoom doesn't, you know, like, it's. It's. I think we drained the battery, you know, and it's really hard to fill it back up. I think when we entered Covid, everybody's battery was full, you know, because most of us were in person a lot. So, like, when we went through that period, you had a lot of battery reservoir to have those arguments over Zoom, to be constructive, to show up in the right way. And now I find it's just really challenging to have constructive conflict, you know, remotely.

[C]

Well, and, And I think probably remote versus in person, but also just the. All of these events that have happened, you know, since COVID Not that there weren't problems before, but it feels like one after another. And I think people are exhausted from that. There was no kind of, hey, yay, we made it through Covid. Let's all take a break. And so I think that there's just a individual and collective fatigue and.

[D]

And I think, you know, I don't know what. I'm sure there's better ways to articulate the. The balance, but, you know, people talk about how in D.C. democrats and Republicans would duke it out during the day, and then, you know, go drinks together in the evening. And that dynamic of, like, we can kind of be pretty fierce, you know, during a meeting, and then that's not personal. It's not, you know, an attack on you is trying to get to a better place overall. And then we can go have dinner, go have drinks, but, like, you're just completely missing that second part of the thing. So it does. It can feel like an attack because you're like, I'm talking to you. For, you know, 30 minutes this week, and you're telling me my work's bad or, you know, you don't like my idea. It can feel a lot more personal, I think, because there's no. There's nothing to offset it. Right. That's the only interaction you have with people. So it's like there's no offsetting. Oh, right. You weren't, like, attacking me. You were just trying to get, you know, the project to a better place for the product.

[C]

Right. And you're not going to see them in the hallway later that day and they're like, hey, just checking in to make sure we're okay. It's like you're off to five other zoom calls or whatever.

[B]

Yeah. And those comments are just kind of bouncing around in somebody's head for the next week. And you have no idea where that. Where that lands. Jason, I'm curious for your. Like, how do you guide leaders who are coping with that? Like, just the anger, right. Or the grief or the frustration?

[C]

I think the first step is, is normalizing it, acknowledging that it's okay. And it's expected that people are going to be feeling this. And I think that's really important because I think leaders can normalize that within their teams as well. And John said something earlier that had me think it's like giving people outlets to process what their emotions are, whether it's grief, whether it's anger, giving them ways to channel some of that. And I think that's one of the unique things that entrepreneurs do. It's like alchemy of being able to take anger and frustration and despair and turn it into something creative. So normalizing is one thing. Feeling it really, you know, and John will probably laugh, but it's like slowing down and feeling the feelings and the body sensations is really important because otherwise we tend to bypass it, either push it down or try and distract ourselves from it. And then it can really, you know, left unconscious, it. It controls the system. And then lastly is exercises. And this is where we get into some of the somatics of how do we move it. And we can move it gently through walking or through talking to people. We can also really, as it relates to anger, bring it up and then find healthy ways to express it. And I think if we look around and you look at, particularly on the road these days, people do not have healthy ways to express anger. So it leaks out in very unhealthy, very toxic ways.

[D]

Yeah. Definitely feel that the anger can leak out in unhealthy and toxic ways. When you don't find more positive outlets for it. One thing, Amy, that you and I have talked about, too, is how do you balance that grief, anger, vision, setting? What's the right balance of these things? The team. Right. And what does the team want to hear and need to hear, you know, at various points and in a company's journey? And that's also just, you know, crazy hard to think about right now. And what do I need, right, like, as the leader, like, how do I need to think about that? One of the emotions I didn't name, aside from the anger and the grief, also is like, fear. You know, if you're a. In a position like myself, where I've been, you know, on one trajectory for a decade plus. And then, you know, I, I think we made amazing bets and, and strategies along the way, but, like, we didn't plan on, you know, the development sector going to zero, and had we bet on that, we would have maybe acted differently. And so you also have this fear of, like, oh, did I just screw it up for the last decade plus, and am I leading us into something that. That is another worthwhile bet? And at an intellectual level, the answer, I take a step back. I'm like, absolutely, it is. We've made great bets. I'm proud of every single thing we've done along the way, and I'm excited and proud of where we're heading. But emotionally, you're like, oh, feels like you just lost. And it feels like you lost big. And so also grappling with that and what that does to your psyche, which is probably much more subconscious than conscious in terms of the way it's affecting how I think and how other leaders might be thinking. Because I would have said historically, one of my strengths was leading with, you know, significant levels of uncertainty in the business and the outcome. But something definitely feels. I mean, the magnitude of this is different, but something feels different internally to me too, you know, in a way that I haven't felt that as much in the past, that I'm also trying to grapple with.

[B]

Yeah. And it seems like just such a challenge to, like, how do you show up confidently right when you're also just processing all of this? And how do you, as a leader, carve out the space to go through this and really embrace it, but then also be mindful of how you're showing up? I think one thing I'm noticing, even just for myself, in doing a lot of, like, thinking and sort of introspection around the importance of regulating my own nervous system and how I You know, how I show up for my team, it's a little bit of this, like, balance between, like showing up calm, regulated, like just able to take the balance, the energy right in the room and like, notice, like, take that, like peripheral vision, like wide, wide angle view of things. All of that with the reality of like my own sort of like ambition and impatience and desire to kind of move something forward. And yeah, how do I, like, I don't really know how to hold those, those things feel like at odds sometimes. And how I show up as a leader and it's, you know, it's new territory. So curious, Jason, if that sparks anything for you in terms of your guidance.

[C]

Well, it's so funny, I, When I heard you talking, I was like, wait, acknowledging your humanity. Leaders are allowed to do that. It's so true, though. Like, there's, there is, there's kind of the issue and the emotions and then there's how we hold it. And, and one of the things that I appreciate about what both of you have said and one of the things that I work with leaders on is it's okay to have fear, to, to have different emotions moving around. How do we actually hold that and model that holding of our, of our humanity that. I think leaders can be really inspiring for teams and beyond teams with that. This notion of like the bionic leader, I think is, Is a total fallout. I mean, you see it out there still and it, but it kind of, you can tell that it's a facade in so many ways. So that authentic leadership of, hey, these are the challenges, or this is part of what I'm bringing in and dealing with. But I'm going to, like you said, Amy, like, bring a groundedness or acknowledge the fear and we're still going to act with courage. That type of steadfastness, centeredness, inspiration, I think is what people yearn for. The pedestal leaders, you know, there, there's, there's no connection and people can't relate. And so then it just perpetuates this kind of differentiation and isolation. So I think bring them both and label them both.

[B]

Yeah, I really appreciate that response, Jason. One of the things that we dug into a bunch in our last conversation was burnout. And you really candidly shared your own story of burnout. I've definitely been through burnout phases. That really shaped me. I'm curious, like, are you seeing burnout at a whole new level right now, given, like, your work across sectors? Like, how are you holding that and creating space for it?

[C]

Yeah, that's a great question. I went through another kind of. I wouldn't say it was burnout, but I, you know, I mentioned obviously, the passing of my father, and there was work stuff and estate stuff and supporting my mom and my own emotional processing. And I got through kind of April, man, I was like, man, I'm tired. And I just felt it at a different level. And for the first time, I think, ever, I gave myself permission to rest and to not be on all the time. And I think that that is something. So that's my own personal experience with it. But with leaders, yeah, I think there's new levels of fatigue and there's a frenziedness to everything. There's so much going on in the world. And as a species, we continue to accelerate rather than decelerate. And AI is another version of this incredible resource. But we've got this. We're being sold this dream that somehow it's going to solve the time crunch and the mortality. You know, you're all of a sudden going to be able to have time to relax. We know where that goes. So I think it's. Again, it's this idea that acknowledging it first of all and really allowing. Giving people permission to feel tired, to feel that, to touch into the despair of it all. And then what are the practices? And there's a lot of my coaching right now, I'd say is micro practices. And what. What in some of the coaching language in some of the schools where I've learned is called immediate concerns. Like, things are coming at us right now so fast, and so we're in that defensiveness. So how do we take a breath there? And. And how do we feel? Okay, taking a breath there? Because a lot of times there's guilt that comes with how. Well, you know, um, and. And I sit here today, you know, speaking from a place of privilege in San Francisco and, you know, in a single family home. And so we need to acknowledge that, but. And not have that kind of. Not be ashamed of that, but also, you know, really give people from this place a chance to process, put on their own oxygen mask as leaders and then support people. Because we can't do it if we're burned out. If we have no resource, we can. We can't offer that which we don't have ourselves. So. Go ahead, Joe.

[D]

Oh, well, I, I think one of the points I. I raised with our leadership team when we were together was a different word than you were using, but I was talking about selfishness. You know, I was like, in this moment, we need to be selfish. On what we need as leaders, you know, the types of teams we want to run, the types of projects we want to work on. Because if we don't do that and we're, you know, trying to do it for the greater good or do it for Tamalegi, like, I just don't think people are going to agree without being burned out, you know, in this climate.

[B]

Right.

[D]

And so that was a big theme, what we talked about, and similar to what you were saying of giving yourself permission to feel tired, acknowledge you just needed space or break or whatever that was. I've never told people to be selfish before, myself included. That's not why we started this company. That's not a word that has positive connotation, but I just think it's necessary. Otherwise, I just know we're not going to survive as individual leaders. If you're not working with teams you want to be working with, working on projects you want to be working on. Given how uncertain everything is, that resonates a lot with having to accept different things, acknowledge different things, label things differently today than we would have in the past.

[C]

Yeah. And I would say having self interest is not being selfish. And if we swing to either side of that pull too much, you know, whether we're swing to the selflessness side so much that we burn out, or we swing to the selfish, selfish side so much that we isolate or, or. Or harm, like, either pole is not gonna support us. It's finding the middle ground on that.

[D]

Amy. On the middle ground, a lot of the team was like, one of our values is be a little bit humble. And they're like, how about we be more bold and less humble for a little bit? So, you know, figuring out like, you know, where do you recenter things? I think it's funny, but it's also very serious. I mean, you know, we. We evolved our, Our company, our values, and how we show up as leaders under one set of circumstances, which are now extremely different than the circumstances we find ourselves in. And we have to figure out what that means for us as, as leaders and as an organization in terms of where and how we want to be contributing.

[B]

Yeah, absolutely. And luckily that. That is one of our values. Right. We. We evolve and learn and share openly. Something like that. I'm getting the wording wrong, but yeah. Well, this has been a, A wonderful conversation. I feel like there's so much more we even didn't get to dig in on. Is there any closing words that you'd want to leave with folks? Starting with you, Jason?

[C]

I'd Say we're in it, we're in this really challenging times and just giving ourselves grace. And I, you know, kind of like John was saying, kind of that sensing into where to be bold, where to be humble, where to be strong, where to be soft. Like it's embracing the duality and the paradox of it. So I think it's just, it's challenging times. So wherever leaders are right now and wherever their organizations are or other individuals, it's acknowledging it and accepting it. Giving ourselves that little bit of grace because it is part of the human experience and then figuring out what's right, what's the right next step if we take it back to the lion trackers, like, what's the track? Where should we go? And then boldly go there. But don't be afraid to reverse course and find another track if needed.

[B]

Yeah, I love that. I think one of my mantras lately has been slowing down, right? Like it's okay to slow down. And that actually might be the best way to move faster in the long term or move further. So that really ties to that. John, any final closing words from you?

[D]

I will build on the grace comment, Jason, that you mentioned. Because when I talked about selfishness, people were like, can we call it giving ourselves grace? Instead I was like, no, I mean selfish, but it's a better way to articulate it. But Matt Theis, who recently rejoined us, he brought up at our management summit a saying that I've also heard on my running app that is slow, study. Study is smooth, smooth is fast. And so I think in a lot of ways, in this moment in particular, slowing down might actually be the fastest way to make progress on what you're ultimately trying to get to. And it's impossible to really internalize that, at least in my head, but I'm trying at various points.

[C]

I was going to use that quote too. I used to be a self defense instructor and we used to say that slow is smooth, smooth is fast.

[D]

Yeah.

[C]

So awesome.

[B]

Great place to end. Thank you both, really appreciate it.

[C]

Yeah, this was fun. Hopefully there's a part three, as you said, there's so much more to talk about.

[B]

I think there's a part three in store.

[C]

Yeah, anytime, anytime.

[A]

A huge thank you to Jason Morris for rejoining us and sharing his incredible timely wisdom and experiences. And thank you to each of our listeners for tuning in. For me, this conversation was a powerful reminder that in times of great change, how we show up as leaders is more critical than ever. A few key takeaways that are staying with me are first, the shift from expert to healer. In a chaotic environment, a leader's most vital role can be to provide stability, empathy and a grounded presence for their team, acting as a source of calm amidst the storm. Second, embrace emergence over rigid plans when the future is unclear. The goal isn't to have a perfect five year plan, it's to be like a lion tracker, finding the next track, taking a step and seeing how the path unfolds from there, adapting as you go. Third, we must process difficult emotions to lead effectively. Jason reminded us that feelings like anger, grief and fear are normal. The key is to normalize them, allow ourselves to actually feel them, and then find healthy ways to move that energy.

[B]

So it doesn't control us.

[A]

Finally, remember that slowing down can be the fastest way forward in a world that demands constant acceleration. Giving ourselves and our teams the grace to be deliberate can lead to smoother, more sustainable progress. And as the saying goes, slow is smooth and smooth is fast.

[B]

That's our show. Please Like Rate Review subscribe and share.

[A]

This episode if you found it useful. It really helps us grow our impact and write to [e-mail] with any ideas, comments or feedback. This show is executive produced by myself. Parthana Balachandar and Michael Kelleher are producers and cover art is by Sidan Shikanth.