EP 52: Charlie Gilkey: Leading With What Matters Most

Uncategorized May 06, 2022

When you are not clear on what truly matters most to you, how you decide to use your precious time can leave you feeling overwhelmed and lost. 

And even your sense of time and what you can get done gets skewed by the tyranny of the urgent. Or comparison to how others are doing life and work. 

Striving and grinding is still the norm in so many spaces. The message is still suck it up, chin up, get it done. And falling or failing is on you and you alone.

This mindset is deeply problematic as many are pushing back on these approaches to how we use our time and the expectations around how we do work recognizing how culture and many of the systems we work in contribute to burdening our sense of time.

Boundaries around your time mean disappointing people. So if you are focused on over-delivering and making everyone happy, things can get messy, fast.  

If what matters most means meeting metrics that are set by others, burnout and disillusionment are inevitable.

These dangerous messages have us chasing something we think will give us relief when in fact, we only feel worse when we put this kind of pressure on ourselves.

My guest today has an approach and a philosophy to time and getting things done that has transformed my relationship with work, time, and my calendar.

Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing (2019) and The Small Business Lifecycle (2012), and host of the Productive Flourishing podcast. Before starting Productive Flourishing, Charlie worked as a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon.



Listen to the full episode to hear:

  • Why our problems are with expectations, not time management
  • How we need to shift our relationship to productivity to prioritize values, self-awareness, and compassion
  • How we end up with so much of what Charlie calls project debt, and how to dig ourselves out of it
  • Why we need to stop reinforcing the narrative of the busy party
  • Why leaders need to stop playing the hero or the martyr to their teams

Learn more about Charlie Gilkey:

Learn more about Rebecca:


Scroll Down For The Full Episode Transcript:

Charlie Gilkey: I need to accept that I'm not gonna get all the other stuff done, but it's better for us, time and time again, to do the things that matter most that are gonna move the needle for your work, for your life, for your community and accept the things that we can't get to versus being overwhelmed and not doing the things that will push the needle the furthest, and instead, running around feeling productive but not being productive. 

[Inspirational Intro Music]

Rebecca Ching: How do you make time for what matters most to you? How do you even figure out what truly matters most to you as you work through your growing to-do list. Now, like you, I have breathed in the messages around the imperative to optimize my time, my body, my business. 

Now, Merriam Webster defines the verb "optimize" as, to quote, "make perfect, effective, or as functional as possible." So when I step back from this narrative, I see how it wreaks of perfectionism. Be perfect. Do perfect. Be seen as perfect. Optimize. [Laughs] Anything less than what I perceive as optimized leaves me feeling like a failure, and the pressure to maximize and optimize often conflates with what matters most to us, and when productivity becomes centered on optimizing over just doing the things that matter most, we end up sacrificing what matters most to us. 

I'm Rebecca Ching, and you're listening to The Unburdened Leader, the show that goes deep with leaders whose burdens have inspired their life's work.  Our goal is to learn how they’ve addressed these burdens, how they rise from them and become better and more impactful leaders of themselves and others.

When you're not clear on what truly matters most to you, how you decide to use your precious time can leave you feeling overwhelmed and lost. 


Even your sense of time and what you can get done gets skewed by the tyranny of the urgent or comparison to how others are doing life and work and what we should be doing. I think my fixation on time stems from my season as a scheduler for a United States Senator. Getting things in my calendars and planners and checking and rechecking things, it calms my nervous system, and, for many years, I actually thought I could be the boss of time (which is so embarrassing to say this here), meaning, my former boss's schedule was like a puzzle where I thought I could bend time to my will like Doctor Strange. It gave me this sense of control (in many ways, it was totally a false sense of control), and it also gave me an unrealistic sense about time and how to use it for my own life because there were so many things that went into making my former boss's schedule come true -- a whole team of people -- a huge team, right? 

So when I was younger, I would spend more time going over my calendar and organizing versus really taking action, and if you're like me, you've invested in various planners and read many books on time management, but the focus of these books is about doing more with less. You know that saying, "My eyes are bigger than my stomach?" Well, my eyes have always been bigger than the time available on my calendar, and no one taught me about time boundaries. In fact, I saw people around me pushing themselves to do more with less time, less resources, less support as if it was a badge of honor, and the movies and TV shows I watched growing up glorified this. 


No one I was exposed to was talking about health or well-being or equitable workspaces around the use of time. It was all about striving and grinding as the norm, and the message was loud and clear: suck it up, chin up, get it done, and falling or failing is on you and you alone. This mindset is, obviously, deeply problematic as many are pushing back on these approaches today to how we use our time and the expectations around how we do work.

Now, boundaries around time means disappointing people. So if you're focused on over-delivering and making everyone happy, things can get messy fast. If what matters most means meeting metrics that are set by others, burnout and disillusionment are inevitable. These dangerous messages have us chasing something we think will give us relief when, in turn, we only feel worse when we put this kind of pressure on ourselves.

Now, today's Unburdened Leader guest has an approach (even like a philosophy) around time and getting things done that has transformed my relationship with work, time, and my calendar, though, I'm still a work in progress. [Laughs] Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing, and The Small Business Life Cycle, and he's the host of the Productive Flourishing Podcast. Before starting Productive Flourishing, Charlie worked as a joint-force Military logistics coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon. 

Now, pay attention to what Charlie identifies as "The Busy Party" and how often we all show up to it, and notice Charlie's take on how we get servant-leadership wrong, and how this flawed lens on servant-leadership is wearing us out. 


Listen, also, to how Charlie breaks down the importance of clarity on what matters most so we can best manage our time.

Now, please welcome Charlie Gilkey to The Unburdened Leader Podcast. Charlie, welcome to The Unburdened Leader Podcast. 

Charlie Gilkey: Rebecca, thanks so much for having me, and I'm enjoying that we're continuing conversations that we've had over multiple years, and so, that's really fun. 

Rebecca Ching: I'm really looking forward to this. I've been in the rabbit hole in your blog since I booked this interview, and I keep going back. It's like a little PhD on your website. 

So, for those of you listening, go there. Enter at your own risk of time, but you will be better for it. Speaking of time, I want to kick off our conversation -- 'cause this is something I know you think about, write about, and work with leaders and teams a lot about, and it's one of our most valuable resources and also one of the most challenging things to manage, especially after a disorienting two years. I've read that you believe we don’t have a time-management problem (which I thought was so provocative) but really a priority-management problem, more specifically, a self-management problem. 

So I'd love for you to talk about what you mean by priority-management problems and self-management problems, and how this lens on time is different from conventional wisdom around time.

Charlie Gilkey: My thinking has changed a little bit on this since writing this post.

Rebecca Ching: Mm.

Charlie Gilkey: I think it's just a different word that I want to put in there, and I think it's actually we have an expectation problem.

Rebecca Ching: Oof.

Charlie Gilkey: And that has become even more prevalent as we've been working through this pandemic cycle, and I'll start there, right? 


During the pandemic cycle, what most of us did not realize is that the pandemic created a new macro project for us. So, in Charlie's world, a project is anything that takes time, energy, and attention. So it took all of the ways we work, all of the ways that we negotiated ourselves in this society and dumped them all out on the table and said, "You know what? Figure it out again." That, in and of itself, is a project. If you got sick because of COVID, that's a project 'cause time, energy, and attention. If you had to start home-schooling or co-teaching, that's a project. And so, all of a sudden, the life that we knew, the expectations that we have for how we use time, how we orient to priorities changed, except it took a lot of us a long time to figure out we need to change our expectation about what's possible for us to do during this period. 

I remember so vividly -- 'cause it's March two years ago, right -- people being like I'm gonna read all the books, and I'm gonna start a thing, and it's like well, yeah, you may not be going to work, but you have these other projects that are replacements for it. And so, why I've framed it more as expectation problems these days is because when we think about 24 hours (the amount of time we have in a day), we don't actually have those 24 hours. Some of that's spent sleeping. Some of that's spent eating. Some of that's just spent with the routines of life, but most people, when they wake up in the morning, are like okay, I've got eight hours at work, if you're on the standard sort of thing. Actually, you don’t, right? Of those eight hours, you might have two to four solid focus hours, and then you might have a few meetings and you have some admin time, but our expectation is that when we start planning and we start doing those things that we base it off of eight hours, when it comes to certain types of work, and we're just not seeing that clearly.

So once you start seeing that, it's like oh, if I only have, say, two to four hours of really focused work a day to do that, you know, what Cal Newport calls "deep work" (I call it "focus work"), maybe instead of expecting myself to do six to eight hours, maybe I reprioritize and say you know what, these are the projects and the priorities that matter most, and those get those two to four hours, and I need to accept that I'm not gonna get all the other stuff done. 


But it's better for us, time and time again, to do the things that matter most that are gonna move the needle for your work, for your life, for your community and accept the things that we can't get to versus being overwhelmed and not doing the things that will push the needle the furthest, and instead, running around feeling productive, but not being productive.

Rebecca Ching: Okay, to follow up to this because I think you're spot on with the expectations piece, and I remember, I think, it was after first being exposed to your work I realized -- you know that saying, "Your eyes are bigger than your stomach?" Well, my eyes were bigger than my calendar, and so, I started to put everything on my calendar 'cause my expectations of what I could do were ridiculous, but here's the thing, Charlie, I'm not exclusive to this. This is everybody I know, and there's a few people that maybe master what you teach, but that's the outlier. There's this kind of massive expectation, you know, disorientation around what we think we can do with our time, and then the other piece, when you say we have to accept what we can't do, I mean, I can feel parts of me puff up, and I've seen this in others, "Oh, no, I'll get it done. Oh, no, no." 

Charlie Gilkey: At what cost?

Rebecca Ching: At what cost? My well-being, my relationships, my joy, but there's still this dissonance with myself and with others, that, "But maybe I'll do it differently." There's like this, "Yeah, but. Sure, sure. I hear you." 


I know this is not news to you, so what's continually contributing to this massive expectation disorientation around our sense of what we can do each day?

Charlie Gilkey: I have some theories here. I say theories 'cause I haven’t validated them with hard research yet, right?

Rebecca Ching: Mm-hmm.

Charlie Gilkey: Part of it is the omni-present social media world that we live in. 

Rebecca Ching: Yeah.

Charlie Gilkey: I don't think we understand how much we're primed. Every time you flip and you see someone else's accomplishments, that creates a pace, unfortunately, for what we think we should do. So if I wake up and I see all of my community has done a bunch of things and I haven’t, then I feel like I'm behind. I feel like I'm not doing enough, right? We forget that the scope of things that we're watching is just hard for our brains to process. Like, wait a second, it's not that people are 30 times faster than I am, I just saw 30 people doing things at their own rate and I accelerated that. 

Rebecca Ching: Mm.

Charlie Gilkey: I think another part that's going on is some of the worst parts of productivity culture that tries to get you to maximize and squeeze every minute out of every damn thing. 

Rebecca Ching: Yeah.

Charlie Gilkey: This is why about every three or four years, Rebecca, I'm like I'm done with productivity. I'm out. I do not want to be a part of this conversation. Then, I get all in my feelings about it, but I'm like you know what, actually, they are taking the conversation in that direction, and we can steer it back this direction.

Rebecca Ching: Well, I want to dig into that more because I agree with you, and I see the word "productive" weaponized around time and how people end up not feeling good enough because they connect their worthiness to not doing enough or being productive enough. So yeah, I want to hear more of where you want to steer the conversation because we're trying to hack time. We're trying to hack health. We're trying to hack everything. We're hacking physics. I don't know, and it's not enough. 


It fuels the scarcity, and then there's this sense if you try to not hack it that you're doubting yourself and you're settling. It's just this weird mind-F I see happening, and it's hard for people to unhook from it, and it feels really insidious, and, in many ways, I think it's dangerous.

Charlie Gilkey: Well, it is. If we want to go deep, deep, part of it is the Protestant work ethic that's at play.

Rebecca Ching: Mm-hmm. 

Charlie Gilkey: For those of us in The United States or in The West that like -- you know, good returns come after hard work, all those sort of things, so we've got that going for us, against us. We've gotten -- yeah, I'm gonna go there. Part of our white supremacy culture is a “more is better.” That's one of the elements, one of the characteristics. If you want to read more about this, read Tema Okun's work on the characteristics of white supremacy.

Rebecca Ching: It's fantastic.

Charlie Gilkey: But more is better, more is better, more is better. As long as more is better across all the dimensions, if you're sitting there on the couch and it's not more, it's worse. When most of us sink into our deep selves, we realize more is not better, necessarily; better is better, obviously, right? Sometimes would you rather have more friends that you feel exhausted with trying to keep up with all their expectations and feel like you're letting them down, or would you rather have a smaller group of friends that you can be in tight community with? Most of us, when we think about question is like, actually, I would rather have a smaller set of community and have some peace and some ease than have a larger community. 

Money is one of those things where it turns out more can be better, but I think there are some deep cultural elements that affect us, that's not our own head trash, not our own baggage, but the thing about head trash and this type of baggage is it doesn’t have to be true for it to have an emotional effect on us. Emotion drives action. 


So if we're feeling that sense of shame that we're sitting on the couch on a Tuesday afternoon, that shame has mode of force on us, and that's where a lot of this agita comes from, right, is all of these sort of things going on, and, unfortunately, most of us have become functionally ADHD. We may not be ADHD, but around devices and with our work it's such that, and we lose track of that time. I'm one of these offenders where I'm like it's 2:15, I can't just chill. But, like, oh, yeah, Charlie, you got up at five o'clock this morning, naturally, and you've been working since five, right? That's a full day, right? But in that moment, I might be like, "Oh, well, it's 2:15. I should be doing something. I should be --," even though that's counter to my own work and counter to what I know to be true and sound. 

So much about productivity needs to be centered around self-awareness, needs to be centered around compassion, and needs to be centered around values, and, unfortunately, it's centered around optimizing time.

Rebecca Ching: What does that mean to you, then, if you're looking at productivity through the lens of self-awareness, compassion, and values? How does that shift, then, from the supremacy culture sense of urgency (everything now and bigger, better, faster, more)?

Charlie Gilkey: Yeah, well, I'll retract and say without getting over-definitional -- you've got to worry about my philosophy background 'cause I'll do it, but I'm not gonna -- being productive means doing the things that help you thrive, doing the things that help you thrive. Thrive is what does a lot of the lifting here, 'cause what does it mean to thrive? What does it mean to be a full-spectrum human? What does it mean to be more than an economic unit in a larger society, right?

And so, when you start unpacking that and you start addressing that thriving is very individual -- though, if you're Aristotle there are four dimensions. If you're Charlie there're ten, right, where humans, where relationships -- we need play, we need work, we need family, we need friends, and we need to be able to balance and thrive on each of those or make intentional choices that some of those elements are not that important to us, right? 


Some of us may decide you know what, I'm gonna have a small friend set or I'm gonna spend a little bit of time in hobby and play, and that's what works for me, and I'm going to address that or maybe I don’t spend as much time working and doing the economic work because I want to focus more on family, I want to focus more on spirituality. We get to make those choices, right? That is where the self-awareness comes in. The reality is, not choosing is a choice. I know I sound like an existentialist philosopher, but, hey, that's my lineage. We don’t realize that every time we choose to over-work, we're choosing to under-live.

Rebecca Ching: I totally track that, and I'm also recognizing, for me, that choice is a bit of a privilege, too. 

Charlie Gilkey: This is why it's very, very individual, and it's not a cop-out, it's just understanding that just like we have bio individuality when it comes to diets and foods and medicine and things like that, we have bio individuality when it comes to how we need to spread out values around.

So I'll say two things. One, for you -- this is not for your friends -- you, over-working and living a life that's off-kilter for you helps no one. It doesn't help them.

Rebecca Ching: No. 

Charlie Gilkey: It doesn’t help you. It doesn’t help your community, so whatever shame that you have around that privilege, being out of integrity doesn’t fix anything.

Rebecca Ching: Mm-hmm.

Charlie Gilkey: So that's for you, Rebecca, and I'm the same way. I grew up hella poor. I get families who are working multiple jobs with kids, kids with special needs, multi-generational families, I understand all of that, and that's where (just to shout out those folks) they are doing the best they can to feed all the different buckets that they have to. 


And so, their range of choices around, say, self-care and recovery and discretionary time and discretionary funds are just different, and that's sad, and we need to fix that, but we don’t necessarily fix that by the rest of us being out of integrity, by the rest of us not doing the things that actually address the systemic parts of our society that lead to those outcomes.

Rebecca Ching: I think this is what I've been rumbling with, that part of the self-awareness you're talking about, that's not the endgame, it's pregame, right? So if I have that self-awareness and can do that inner work, then I can be a part of something bigger than just me. 

Charlie Gilkey: Exactly.

Rebecca Ching: I think sometimes the end game is just well, this is what works for me, period, and this is something that I'm working on expanding myself. So how can we have a healthier relationship with time and productivity?

Charlie Gilkey: I think if you don’t have aligned goals that fit your priorities and your values, your time is gonna be wobbly and you're gonna be scattered.

Rebecca Ching: Yeah. 

Charlie Gilkey: So that's when you start coming back to what matters for me, what matters now. To your point, what matters for me and what matters now is not necessarily this self-centered side of things. It might really, really matter right now that I'm involved in a community project that's fixing some of these things. That's what matters, not me watching another two videos on YouTube, right? Or maybe for me to do that work out in the community,  I need some decompression time cause, guess what, we're all carrying a lot.


Part of what we learn from social work, social change, is if your well is empty, it's very, very hard to fill up other people's, right? Some of us are not counting the, quote unquote, "waste time" because, really, what it is is decompression time. It's open time where we can settle, where we can do that. In a lot of my teaching that's why I have recovery blocks. People are like, "What do I do in recovery blocks?" I'm like, "I don’t know," but what the activity is is not as important as what it does for you.

Rebecca Ching: [Laughs] 

Charlie Gilkey: And so, if you watch two hours of people reacting to Chris Stapleton on YouTube, and it gives you joy and it’s fun and helps you decompress, guess what? That can be a recovery block. Just claim that, 'cause that's clearly what you need because we don’t need the extra shame and resentment and all that stuff on top of it because that's what creates the very pressure that you need to depressurize from, right?

Now, maybe not you, but someone was like, "Well, wouldn’t I just be lazy?" No. So here's the thing. 

Rebecca Ching: Yeah, yeah. Let's go there with lazy. I want to hear what you have to say about this.

Charlie Gilkey: Oh. I've said this in my book, Start Finishing, where it's like my starting point with conversations around productivity is that one, you're not fundamentally broken. 

Rebecca Ching: Mm, I love that. 

Charlie Gilkey: You're not uniquely defective, and I say that because a lot of times we see what's working for other people and we're like yeah, no, but that won't work for me because I've got a thing, whatever that thing is. There's something unique about me that's defective that these principles won't apply, right? Second, this is not about character. This is not about "if you were just more disciplined and you had more --," all of that sort of stuff, not helpful, right? Thirdly, you're not fated to continually be unable to get your shit together, right? 


There are people who have those stories of no matter what I do I'm going to be behind. Those are not helpful places to start. When I look at most people who talk to me, they are doing the best they can, they are carrying too much, they are naturally driven, and they want to do good in the world.

Rebecca Ching: Yep.

Charlie Gilkey: That's our starting point. So when people come at me like, “How do I do more,” that's like, “Well, how do I be more productive?” But I'm like, “Well, let's change this conversation because I'm not gonna tell you how to do more.” It's not useful, right? I'm going to try to help you do what matters most and make peace with the things that you have to let go of along the way. My job, at the end of the day, is to help people find more peace, to find more purpose, and to find more hope in their work. To do that, we have to let go of this idea that we are, tomorrow, gonna figure out how to put 14 units of stuff in a 10-unit bag.

Rebecca Ching: Right. Peace and purpose and hope. I think we need to drink a lot more of that right now. We need it on the regular. You know, and you talk about creating recovery blocks, and, again, I remember when I first started trying to do that, and I remember sitting down in the middle of the week having a break, and it was so hard to train myself just to be. I grew up in Minnesota, so I have that in my DNA, in my bones.

Charlie Gilkey: Mm-hmm. Yep.

Rebecca Ching: So it's like you're lazy, who do you think you are? I had to sit there and work through a lot of that, and also as someone who gets up early, it's hard to realize what's a typical day, but there's this weird message of -- maybe some of this is the agrarian culture, too, which I've been influenced by, and I have such deep respect for, too. There really is -- we have to learn how to recover, and I think I just see it breaking us in so many ways.

I want to touch on something briefly that you write about, “project debt,” and I think that's a nice phrase. How does that relate to the intersection of boundaries, burnout, and time?


Charlie Gilkey: Yeah, so a lot of us creative souls have this habit of having an idea, and then immediately applying some commitment juice into it, and then thinking we should do that idea. We're taking in ideas and we're committing to things faster than we're shipping them.

Rebecca Ching: Mm.

Charlie Gilkey: And so, what ends up happening for us is we end up with this huge pile of quarter-finished, half-finished projects that some of our soul is attached to. We spent our life energy doing stuff with that. We've got to finish it. We've gotta do something. We've gotta -- I can't just let it go. That's a waste. So we end up getting exhausted. We end up burned out, and we end up, even on those great weeks where the universe aligns and we have our great focus blocks and nothing goes wrong, we get to the end of the week and we're like, "Yeah, we did the thing!" But then we creep and look in that black hole where all the projects live, and we're like, "But I didn’t do the other things," right? We end up getting project debt that's just like financial debt. 

We’ve gotten to the point to where we're carrying so much that the emotional weight and the conceptual management of those projects exceed the value of the projects themselves.

Rebecca Ching: Wow.

Charlie Gilkey: And so, we just end up paying that debt over and over again. Like, "Oh, well, I'm gonna go mess with Asana. I'm gonna re-plan this all. I'm gonna re-prioritize it all 'cause I'm going to get to it." 

Look, here's the thing. A lot of people are gonna want to punch me in the eye today, Rebecca, and I'm here for it. I learned this from Mihaly Csikszentmihalyi, and I don't remember when I read this, maybe 2014-2015. 


I'm paraphrasing, but he’s like, "Look at your schedule two weeks ago. Unless you make significant changes in the way you make decisions and set boundaries, your schedule two weeks from now will look the same way." 

That's the thing. Our problem with projects and time -- and if you're listening to this, think about four months from now -- four months from now feels like it's open space, like I've got all the time. No, you don’t actually 'cause four months from now, you're going to sleep, you're going to eat, you're going to go to the bathroom, you're going to do your daily routines. There's gonna be the stuff of work and life that shows up that's already pre-accounted for. You are not starting, four months from now, with a clean slate, I'm sorry. So if you want four months from now to look different than today or four months ago, you have to start making different decisions. 

It's really about choice. If you're okay with where you were four months ago or today, then you coast, and that's great, right? You don't always have to be changing and optimizing and leveling-up and taking stuff to eleven. You don’t have to, but understand that productivity -- I keep saying this about different things, but one of the aspects we keep coming back to time and time again is choice.

Rebecca Ching: Mm-hmm.

Charlie Gilkey: Look, no productivity system is gonna override your choices. Asana's not gonna do that for you. Trello's not gonna do that for you. Our new app, Momentum, is not gonna do that for you 'cause you can program all the stuff you want to, and then do what humans do, look at it and say nope, and then go do something completely different. Why? Because your choice and how you're choosing on a day-to-day is really what's driving this bus here. So unless you choose to do something differently, the project debt you have today is going to be the same or worse four months from now.


Rebecca Ching: That totally lands because even becoming aware of project debt, it took me months to get out of it. Once I realized it, to really get my calendar to a place where I had some more space -- this was before COVID, and now I'm still trying to recover from COVID and just all that happened with that, but it does take time. Even just identifying project debt isn’t just a switch to flip. I was like oh, my gosh, what am I finishing? What am I just ending? What do I need support with? It just took time where I could get to a place where I felt like I could breathe so I just wanted to name that too. It's not just a decision to make. I guess it could be. [Laughs] 

Charlie Gilkey: The simplest thing that people could do to help themselves is also the hardest thing.

Rebecca Ching: Always.

Charlie Gilkey: Which is just to go and delete and archive a lot of those projects. That will clear up a lot of the cruft of yesteryear, but you have to make peace with that.

Rebecca Ching: How do you do that? How do you make peace with that?

Charlie Gilkey: Well, multiple ways here. Part of it is that self-awareness piece of it, and understanding that the only way that you're going to pay those projects off and get them done is if you choose to say no to incoming projects for the next amount of time that it takes to get those off, right, 'cause you're already at capacity. One unit comes in, one unit's gotta go out, otherwise there’s just gonna be this continual piece of debt. So it's a choice that we have to make here, right? I’m either going to look at my current projects and current opportunities and prioritize them and trust that they are the best of the available options ahead of me because what's coming to me now -- this is a mindset sort of piece -- we forget about. So I'm a year stronger and better than I was a year ago, right?

Rebecca Ching: Mm-hmm.


Charlie Gilkey: I've lived more. I've become more capable. I have better opportunities. So why should the opportunity set of last year weigh so much on me today when the opportunities that I'm creating today are better than the ones I had last year? 

Rebecca Ching: Hmm, okay. That takes a lot of self-trust, and that's that self-awareness. I think that's what I see a lot of people are like, "How do I know I'm making the right decision? What if I'm letting go of the wrong thing and not committing to it?"

Charlie Gilkey: Yeah.

Rebecca Ching: So I think that I see people spin, and I've been there too.

Charlie Gilkey: Well, that's the perfectionism element of white supremacy culture. 

Rebecca Ching: You got it.

Charlie Gilkey: I guess we're just hanging out in this one, right? So a lot of times when I'm coaching people or when they're in our academy and they're getting stuck around this, I'm like, "Okay, so what would you do if there were no one right answer here?"

Rebecca Ching: What do people do when you ask that question? [Laughs]

Charlie Gilkey: Sigh, normally, and smile. Typically, they instantly know what they would do.

Rebecca Ching: Yeah.

Charlie Gilkey: Right? 

Rebecca Ching: It's not a binary.

Charlie Gilkey: So it's like what made us think that there was only one right answer here, right? Let's unpack that a little bit.

Rebecca Ching: Mm-hmm. 

Charlie Gilkey: And so, what if this choice was a small stake and reversible one. There wasn’t a van-down-by-the-river moment. We do these weird things to ourselves, Rebecca. It's like we think that if we make one bad decision we're gonna be in the "van down by the river," right? We're like one step away from failure, but yet, we seem to think that we're five years away from success. How does that work? Why is it that a bunch of choices stacked together leads to success, but one wrong decision means you're in a van down by the river?

So that's how you start thinking about that, and so, when you start talking about what matters now, it's a complex question because it's not just what matters, it's what matters now, and that project -- and we've had to do it as a team, and trust me, I do not like doing this because when you let go of projects that really matter to you, if you're really doing it, you're gonna have to make space to grieve.


Rebecca Ching: Absolutely, and we don’t do that. We grieve so horribly in our culture.  

Charlie Gilkey: We grieve so horribly. So instead of grieving and making space for that, we'd rather add to project debt.

Rebecca Ching: Oh, that's right. We try to numb that with more work. You nailed it.

Charlie Gilkey: "I'll get to it! I'll put it on there! I'll get to it tomorrow! I'll pay a little bit more tomorrow!" How the hell are you gonna pay more tomorrow? What are you going to do differently, right? When people start saying, "Here's what I'm gonna do differently. I'm gonna eliminate these distractions." Like, okay, that might actually get you some time. You actually have a plan on how to do this, but a lot of times it's like I'm gonna do different tomorrow, and there's no real plan for what difference means besides work harder and grind a little bit more. I'm like no, no, no, no, no, you can't work hard and grind yourself out of burnout. That's not how this works, right? 

Rebecca Ching: [Laughs] You can't grind yourself out of burnout, no. So you're talking about what matters now, and that's a big anchor question that you teach and talk about. 

Charlie Gilkey: Mm-hmm.

Rebecca Ching: Walk me through the process that you use to discern what matters now.

Charlie Gilkey: I'm gonna go mostly for me in this cause because, obviously, if I had someone else like how do you figure that one out. I want to pause here because a lot of times we end up in this sort of existential spiral when people ask us what our values are --

Rebecca Ching: Right.

Charlie Gilkey: -- and what our priorities are, and so, I talk a lot about the gap. What are the felt gaps between where you are now and where you want to be. I say this in Start Finishing. Look, finished projects are the bridge between your current reality and the life and work you want to be living in and doing. Finished projects are that bridge. If you just start a bunch of projects and don't finish them, you haven’t built a bridge, right? You've maybe got some columns, and that's even more frustrating, right? So most of us are aware of that gap, so let's start with that gap. 


What of that gap is true for you versus you playing out society's narratives or your parents' narratives or your "shoulds." When my community starts talking about "shoulds" to me, they know it, I'm like, "Oh, hm, this 'should' language. Let's talk about that. What's your favorite dessert, Rebecca?

Rebecca Ching: Oh, my gosh, a good brownie, for sure, with ice cream. 

Charlie Gilkey: A good brownie. When have you ever said in your life, with full seriousness, "Oh, I should totally eat a brownie right now; I should be eating a brownie right now?"

Rebecca Ching: Hmm, I've said I want to, [Laughs] but I don’t think I should on myself around eating a brownie, no. I've should on myself about other things. [Laughs]

Charlie Gilkey: Yeah, we only should on ourselves about things where there's an external narrative or that we have some sort of -- the proper language that we would say is, "I want a brownie. I want to do this." You can tell immediately when people start just by their linguistic structures and the words they’re using --

Rebecca Ching: For sure.

Charlie Gilkey: -- what of the things they're doing that are OPP which is other people's projects and priorities, right? What are the projects of yesteryears? What are the do-outs that the ghost of yesteryear put on them that they're still holding onto?

Rebecca Ching: Mm.

Charlie Gilkey: Right, and once we start shifting it's like, you know, that's emotionally weight-y stuff --

Rebecca Ching: Yes.

Charlie Gilkey: -- but it doesn’t actually matter.

Rebecca Ching: Okay, and I think a lot of people have a hard time differentiating their worthiness in mattering from the work they do. So when they hear that, they hear "I don’t matter." Does that come up with those that you work with too? I suspect yes.

Charlie Gilkey: Yes, usually not literally in that way. That connection between self-worth and work --

Rebecca Ching: Yes!


Charlie Gilkey: -- and value is, like, four-level subterranean under what people are actually doing, right? And so, they're like so you, when you're sitting there trying to have that Tuesday afternoon recovery block, and you're struggling with it, underneath that struggle (and why I keep using the word shame) is like but if I'm not working, I'm not valuable. I'm not contributing. What's my worth if I'm not valuable and contributing? Ah, tension. We would never, ever tell our kids -- well, I hope not --, "Look, if you're not working hard, you're not valuable," and yet, that's exactly what we tell ourselves, right?

And so, our worth as human beings has nothing to do with how hard we work, the amount of money we make. That's all a separate sort of scenario, and we know that. We matter because we're human and we matter. That's the baseline.

Rebecca Ching: Period.

Charlie Gilkey: Period. Anything above that is just different narratives that we're starting to pile on top of things. Now, you know, the President of The United States, in certain context, matters more than I do, right? That role has certain decisions and things like that, that were that role not being there -- we get that, but that's not normally what we mean, right?

Rebecca Ching: Mm-hmm.

Charlie Gilkey: We normally mean there's something about hard work or us constantly working that means we're being valuable. I want to push back and say you know what, we're not merely economic units. We are economic units, but we're not merely economic units.

Rebecca Ching: That's not our sum. That's not our entirety. 

Charlie Gilkey: It's not a sum; it's a part.

Rebecca Ching: You got it.

Charlie Gilkey: How much of a part it is depends on how much we let it be.


Rebecca Ching: I think there's another part of this, though, too (as I'm thinking in my own journey and things I hear from those I work with) that if I slow down and take that recovery time, it will be too painful, and I'll have to sit with the stuff that I've been dodging and I didn’t even know I was dodging it. It's not even conscious. It's very reflexive like, "No, no, no, no, that's not comfortable. I've gotta just keep going. I've gotta keep going," until they crash, and that's kind of the cycle, right? Go, go, go, crash. Oh, well, at least I've burnt out so then it's justified, but then they're not really sitting with -- they're not feeling, they're just working. [Laughs] You see that cycle too, yeah?

Charlie Gilkey: Yeah, I see it a lot. I mean, we've gotten to the point of, not only do we glorify our hard work, we glorify burnout too. 

Rebecca Ching: Totally.

Charlie Gilkey: Right?

Rebecca Ching: Yeah. 

Charlie Gilkey: It is uncouth to show up to a thing with your friends and everybody's commiserating about how busy they are, and everybody's talking about how overwhelmed and overloaded they are, and then they get to you and you're like, "I don’t know, I left work at one today. I feel pretty good." There's no space for that. [Laughs]

Rebecca Ching: No, you're kind of the jerk if you say that.

Charlie Gilkey: You're the jerk. You're like oh, well, if you had kids, and maybe you don’t understand, and your boss -- you start getting piled on, right?

Rebecca Ching: [Laughs]

Charlie Gilkey: It's like maybe I just made different choices that are supporting me, right?

Rebecca Ching: That's scary. That's scary for people I think.

Charlie Gilkey: It's scary because you have to go so counter-cultural and counter-narrative on this one.

Rebecca Ching: Yeah, I think that's the scariest thing for me is that counter-cultural 'cause it really separates you. It can separate you from community. It can feel like it hurt your reputation. You might be misunderstood. There's a lot on the line. 

Charlie Gilkey: Here's my thing, and this is Charlie. I'm not saying this should be everyone. If the cost of me being in a community is my sanity and health, that's not a community I want to be a part of.


Rebecca Ching: Amen. Amen. 

Charlie Gilkey: And so, if I need to choose different friends, if I need to choose different scenarios, if I need to choose different professions, unfortunately, that's the choice I am going to make because I can't serve the world and myself and my family under those conditions. So I'm sorry, but if that's the cost of being in community, I'm not willing to pay it 'cause I know there are other communities I don’t have to pay.

Rebecca Ching: I just want to let that breath because I think that’s it. I think we don’t realize that sometimes what we're striving for is actually not making us better. There are other options, and that's power. That's standing in our power to say no. 

Charlie Gilkey: I know that there are a lot of people, especially women (given the way we socialize women) that are like, "Charlie, you don’t get it. I can't just do that. I've got to do all the things," but I want us to really honor how much we are participating in the very things that are leading to our struggle and burnout just by continuing to do it. The more that you are the person that shows up and joins the busy party, the more you're reinforcing to everyone that this is who we are, these are our values, and it makes it harder for people to say, "You know, what if we didn’t know? What if we made a rule as friends that we show up and instead of talking about all of the things going on and kids and work and things like that, we talk about the thing that lit us up this week, the funniest thing you've seen this week?" If we go to some of those conversations and have that crowd out the busy conversation -- 

Rebecca Ching: Yes. 

Charlie Gilkey: -- maybe we would actually learn more about each other and enjoy those more.


Rebecca Ching: There’s something that feels indulgent, and maybe some of that's that Protestant work ethic and that don't draw attention to yourself. There's a lot of mixed messages especially with social media. You touched on something in your book, too. You have some archetypes around folks who tend to burn out and have a hard time sorting out what matters. At least the people I work with, and I know for me, for a long time, I knew what mattered to everyone else around me, and I kind of morphed that into what mattered to me, but it wasn’t what mattered to me. And so, we're so good at knowing what matters to everyone else but have a hard time (and feel like it's indulgent) to figure out what matters to them. 

How do we figure that out and then prioritize what matters now to ourselves and not conflate with everyone else's what matters?

Charlie Gilkey: Yeah, so I might push back a little bit on this one. There are some of us who truly do forget what matters to us and truly do forget what it means to play and to be happy and to experience joy. That happens. I think most of us know those things and won't give ourselves permission to do those things because other people's needs matter more than mine do, and so, I want to be clear here. As we're talking about this, it's not that you take what you want and need and desire and push out everything else and that's all that matters, I'm just trying to get our needs to get on the damn table amongst other needs. There's Rebecca's needs, there's Angela's needs, there's Amy's needs, there's Corey's needs, and there's Charlie's needs. How do I balance all of those and how do I make room for myself and understand that my need to have an additional 25 minutes of just open-thinking time is just as important as Amy's need to have 25 minutes of socialization time.


Rebecca Ching: I think, for me (and I had this reckoning earlier this year when I was serving on a leadership team) that part of what messed me up was being indoctrinated in "the customer's always right" combined with some other family of origin dynamics. I think there was a little bit of a cluster that happened, and I think with culture right now, too, I'm like no, everyone's entitled to their opinion, and it's disorienting. So there's something about that messaging I grew up with in the '80s and the '90s of "the customer's always right, the constituent's always right. You're not. It's not about you. It's always about them." 

Charlie Gilkey: Yeah.

Rebecca Ching: I'm seeing that around me a lot too.

Charlie Gilkey: Yeah, this is why I will go on a rail against servant leadership sometimes, right, especially when it goes toxic because the simple version of how people taken servant leadership is like well, you find consensus with everyone, and you make sure everyone buys into something, and then you do all that and it's like actually, sometimes, the best way you can serve your team is to give them a strong vision that they can rally behind. Sometimes the best way you can serve your team is to say, "No, we're not doing that. It doesn’t make sense, and here's why," right? Sometimes the best way to be a servant leader is not to be what it can sound like -- and extremes can be which is that sort of epi-phenomenal or that sort of thing that's just hanging out there calling itself a leader. Sometimes you have to take a bold stance and make a hard decision and roll with it. Sometimes, as a servant leader, you need to look at yourself and say, "What do I need to put in place for myself so that I can be the best leader for this team?" I know all of that can be baked into servant leadership, but we compress it to these tropes, right, where the team's needs matter more than my needs.


Rebecca Ching: That's so true.

Charlie Gilkey: But we celebrate that, and then everyone that's a part of the celebration models "that's what it means to be a good leader is to continually be overwhelmed, to be that hero that saves the day all the time, right?" To be that martyr that can come in, and we create these hero versions of things that none of us can live up to, and then we wonder why we struggle, and then we over-work, then we get depleted, then we get snippy with our teams, and all the things we want to do -- a wrong thing in a touch point in a five-second Slack exchange, undermines trust and credibility that you've spent the last four months working for, right? We don't see those cycles 'cause we're not self-aware and we're not stepping back and saying, "Okay, what's really going on here?"

I come from a model leadership or at least my aspiration is much more Daoist, right? There's a line that's, largely speaking, "The best leaders are those that you don’t recognize are there,” right?

Rebecca Ching: Mm-hmm.

Charlie Gilkey: People are like okay, that means servant leadership, right? No, not necessarily because there are certain things that you put in place where your team can just operate, and it feels really seamless for everyone. It feels like things are just working. It feels like, "Hey, the boss is gone, things just work. Great!" That takes a lot of work to get there. You have to stop micromanaging. You have to give people context. You have to empower people to make good decisions. They have to know what the standards are. There has to be enough team cohesion and trust. You’ve got to have good team habits. 


All those things have to be in place for that set of conditions to happen. It doesn’t happen on its own. If it did, we wouldn't have so many damn leadership books. 

Rebecca Ching: Oh, my gosh, yes. [Laughs] So true.

Charlie Gilkey: It's hard work; it's just different work.

Rebecca Ching: We're looking for the easy, quick hack versus -- and also comparing to others, trying to fit our life and values and what matters to us into what someone else says. This is the way, the truth, and the light.

I'm curious for you, especially after the last couple of years, what matters to you now, and how has that changed, if at all, over all that we've been through?

Charlie Gilkey: I think what matters to me more now -- and it’s always mattered, I think just the fail-iency of it has become more important -- is the role community plays in helping us thrive all the way around, right? So that matters a lot to me now, and at Productive Flourishing (PF), a lot of what we do is re-centering our community, re-centering what that looks like. On the personal level, it's been during this weird time of COVID -- I'm an ambivert, but I do so many conversations like this and I have a team that, at the end of the day, I'm like I'm good on people actually, right? I love them, also I love my time away from them, but I've been thinking like okay, in this time of COVID, how do I get the hell off the couch and get out and get involved in the community again 'cause email and social media ain't cutting it for me, right? 

So community matters a lot for me right now. It always has. We have certain events like in religious cultures; we have these defaults that happen and we don’t have to make a whole a lot of decisions. 


You go to church on Sunday. You see people on Sunday. You do all of that human stuff. You have the social time, you have the emotional time, you have the spiritual time. Then you go home. Then next Sunday, you do it again, right? Maybe you go to Wednesday or maybe, like when I was in Boy Scouts, Tuesday night was Boy Scout night. So you just have these default social gatherings that keep you connected, that keep you in community, that keep you in relation, right? COVID stripped away a lot of those. You don’t just show up -- well, in Portland, Oregon right now, you don’t just show up to a random place and have an after-hours social. That's not a thing anymore. It used to be, right? You don't just meet up with your buddies. You have to do a lot of coordination and negotiation and those types of things. And so, community has always been important. I just realized how many default social gatherings I had that made that work, right? Conferences, which is where we met on two of them. We were talking about that in the green room, right? 

Rebecca Ching: Mm-hmm. 

Charlie Gilkey: They were default social gatherings. I was like oh, well, I'll see Rebecca sometime in the next six months somewhere because we sort of flock around these same events. It's great. I don't have to make a special plan to do that. After two years of not having those and not realizing wow, there are 200 people who I would normally see every six months or every year that I've fallen out of touch with. It's been forever. It feels like five years 'cause COVID times, but also, we don’t have these things.

So, for me, it's been how do we re-create some of those? Also, Angela, my wife, and I have been having a lot of conversations about how do we get out of the no to people and events and things like that, that we've had for COVID, to be like hmm, maybe it's a yes or it's more yesses. 

Rebecca Ching: Yeah.


Charlie Gilkey: How do we go through that? So that's what matters a lot to me now, aside from business stuff like the book I'm working on and the app we're launching and things like that, but outside of that, that's really what I'm thinking a lot about.

Rebecca Ching: I think community is meaning something new to a lot of people, too. I don’t think people really saw it three-dimensionally before COVID. So thank you for sharing that.

I'd love to talk about success as we wind down. I know that's a big topic and you write about it in your book, Start Finishing, also. I'd love to hear how you define success and how that's different from what you were taught. 

Charlie Gilkey: I'm gonna state, I guess, what seems obvious to me. Success is contingent on goals, priorities, and values in that sort of sense. So I can't think about success without thinking about well, what are we trying to do, though, right? I know that sounds obvious, but a word like that, I'm like well, are we talking about my life, are we talking about this book, are we talking about this project because otherwise it's meaningless, it has no grip for me, right? I'm not trying to say it's a bad question; I'm just trying to say this type of question is, like, if I were to be asked what does success with your next book look like, I could tell you that, right -- or the app or things like that. So I always make that question, like, what's the domain of consideration.

Rebecca Ching: Interesting. So what does success look like to you? Do you have a broad metric, or do you only look at success kind of in a domain? Is that how you define success is in these domains based on those goals and values and metrics?


Charlie Gilkey: This is the problem when you've done goal-setting stuff and you've integrated so long it becomes intuitive. Success and thriving are intimately related. When it comes to my life at whole, again, I would start to break that down. Well, really, where does it mean I can't consider myself successful without thinking how's my health, how are my relationships, where am I on play and joy, where am I on some of those, and that sort of macro lens is what helps me get there, to saying okay, success means living in ways such that I'm thriving, such that my family is thriving, such that my community and business are thriving and work in that way. And so, that's why I will always have a gap, and I've come to recognize that, right? That just because there's a gap doesn’t mean I have to be frustrated about it and wake up with that existential anxiety that I'm never going to be there. It's like there's no future version of Charlie that's gonna wake up and say, "Okay, I'm done." It's not gonna happen.

Rebecca Ching: It's not arriving and then coasting. 

Charlie Gilkey: No.

Rebecca Ching: The gap doesn’t mean you're not a success, it's just part of the gig.

Charlie Gilkey: It's just part of the gig. One of the questions I will ask myself a lot when I am stuck with a decision is what's the most abundant possibility I can create in this moment? 

Rebecca Ching: Ooh.

Charlie Gilkey: Then, like, okay, so can I do that? Then, why not? That question, I'm gonna wake up -- if I get to live that long. I'll be 90 and I'll be like what's the most abundant possibility that I can create today in this moment with this interaction? 

Rebecca Ching: Yeah, I usually bristle out the word abundance and abundant because I think it just feels like scarcity, but I like his question 'cause it feels so generous, it feels expansive. It's not about hustling. Wow, that's powerful.  

Charlie Gilkey: Yeah.


Rebecca Ching: I really appreciate that. I'm gonna be bringing that to my next family meeting. My poor kids are like, "What?"

Charlie Gilkey: "Who'd you talk to today, mom? Come on!"

Rebecca Ching: [Laughs] Pretty. Much. Pretty much. 

Charlie Gilkey: "You and this podcast, though, mom!" [Laughs]

Rebecca Ching: [Laughs] They love it though. They love it. 

Charlie Gilkey: Yeah, so I don't focus a lot on success in that way. I'm not trying to escape the question. 

Rebecca Ching: No, this is good. No, this is good.

Charlie Gilkey: I'm just like, hmm. I have people around me -- my best friend who also works in the company with me, he's like, "You don’t get it, Charlie, how much we actually end up creating and accomplishing things." That's not actually what I'm focused on in a lot of ways, right? That happens as a byproduct of a lot of other things that we do, right?

Rebecca Ching: Success is a byproduct of the goals and the values and the alignment and the self-awareness and the compassion. Yes, I'm here for that. I'm here for that. 

So I'm curious, too, is leading Productive Flourishing, your company, what you thought you'd be doing today?

Charlie Gilkey: No. No, not at all. Leading it and where it is today is -- I didn’t think I'd be doing it in this way five years ago, right? And so, I'm imagining because about every five-year cycle I'm like, "Ah, yeah, I know what's going on!" Then five years later I'm like, "I didn’t see this one coming," right? That's fun in a lot of ways 'cause I'm like I don't have to know, right? With the greater possibilities that exist in the world, why the hell do I think I would know all of those right now, of what the most abundant possibilities are. It's like no, I can't know that. It's impossible, right? I can just do my best day in day out with the team and with the community, and we'll see what we co-create together, right? 


And so, it's not at all what I thought I was gonna be doing 20 years ago, 15 years ago, 10 years ago. I knew I would be having Productive Flourishing in 2008 because that's when it became and that's when it started happening, but yeah. What I would say is the way that I'm doing and what we're working on and how we're doing it is not something I would have seen five years ago. 

Rebecca Ching: Well, I'm excited to see where you continue to grow. I'm really struck, too, as I'm taking in everything you shared today, even just what you just said is, "Hey, what are we gonna co-create today?" You have such radical presence. That's something I'm really working on this year. I have to have a presence and a curiosity, and that requires a lot of trust and capacity to sit with discomfort, to say "let's find out" versus "I'm gonna drive it. I wanna manage it. I'm gonna try and control it." So I'm really struck by that, and I really, really appreciate that. 

So do you have a few minutes for some quick-fire, fun questions?

Charlie Gilkey: I do! Let's get it.

Rebecca Ching: Okay, great! So what are you reading right now?

Charlie Gilkey: Okay, this one is a hard one 'cause I tend to read three-to-five books at a time.

Rebecca Ching: All right.  

Charlie Gilkey: So I'm just gonna give you the three that popped up. Zone To Win by Geoff Moore, Distributive Justice by Michael Walzer, and Ten Equations That Rule The World

Rebecca Ching: Ten Equations, ooh, gosh, that one sounds good. What song are you playing on repeat? 

Charlie Gilkey: This is one I would rather not 'cause it sticks with me, but it's Skin In The Game by Nahko and Medicine for the People. 

Rebecca Ching: [Laughs] What is the best TV show or movie you've seen recently?

Charlie Gilkey: I love Star Trek: Discovery. I do. I think it's one of the best Star Trek series and it's been one of the most fun Sci-Fi series, and there's so much I love about it. It's supposed to be quick-fire; I'll be quiet. Star Trek: Discovery.

Rebecca Ching: We're diggin’ [Star Trek:] Picard, so we're on that track. What is your favorite '80s movie, show, or anything '80s pop culture?


Charlie Gilkey: Indiana Jones And The Temple Of Doom.

Rebecca Ching: Hello, oh, my gosh. Is The Temple Of Doom the one where you put the hand in and there were the snakes in there? Yeah, mm-hmm. Yeah, that's burned in my brain.

Charlie Gilkey: Also, "No time for love, Dr. Jones. We've got to go now!" 

Rebecca Ching: [Laughs] Yes! [Laughs] Oh, my gosh. So many memories are flooding back right now. 

Charlie Gilkey: Yeah, now, to be clear, there was so much stuff in the '80s that we can no longer get away from.

Rebecca Ching: Nope.

Charlie Gilkey: So I'm sure I'm gonna have to fill out some HR paperwork for that one, but that line sticks with me with my team where they'll be talking about something, and I'll be like, "No time for love, Dr. Jones. We've gotta go!" Anyways, it's a whole thing.

Rebecca Ching: It’s a thing. What is your mantra right now?

Charlie Gilkey: Right, right now is how's the universe working for me right now? 

Rebecca Ching: How is it working for you right now?

Charlie Gilkey: Really well most of the time, actually. So, to unpack that one, especially when difficult times come up, I'm like, "Mm, I'm so mad about this. This is frustrating." I'm like, "But, how might the universe be working for me or how is it and I just can't see it yet 'cause I'm so attached to certain things.

Rebecca Ching: Yeah.

Charlie Gilkey: So that's one of mine that always helps me come back to presence and look at things more broadly.

Rebecca Ching: Thanks for unpacking that. What is an unpopular opinion that you hold?

Charlie Gilkey: Chocolate is overrated.

Rebecca Ching: Did you just say chocolate's overrated?

Charlie Gilkey: It is.

Rebecca Ching: Man, okay, I'm having a moment here.

Charlie Gilkey: [Laughs] You're like I can't air this episode now. We were aligned, and then now -- 

Rebecca Ching: [Laughs] I know! I lived in Switzerland right near a chocolate factory, so I've got feelings about chocolate. 

Charlie Gilkey: Look, my dad was the same way, right? And so, I don’t know if it's genetic, but I'm just like eh, it's all right.

Rebecca Ching: Oh, my gosh. Who or what inspires you to be a better leader and human?

Charlie Gilkey: The who is super challenging for me, but there's some what, and I think that's just hope, faith, and compassion. Hanging onto those helps me be a better leader and human.


Rebecca Ching: Always. I'm with you on that. Charlie, I know that you are working on a book that's coming out next year in 2023. I'd be honored for you to come back 'cause I didn’t even get to ask a chunk of questions I wanted to today, and I'd love to hear more about that book. Is that something you'd be willing to do?

Charlie Gilkey: I would love to come back and talk to you about that book. I think Four Leaders is gonna give a useful place for them to work on building teams that have better belonging and higher performance.

Rebecca Ching: I can't wait for it. I really can't.  

Charlie, this has been a joy. I'm gonna be digesting this for a while. It was really an honor to have this length of time to hear a little bit more of your body of work. I know so many people are gonna get a lot out of this, so thank you again for joining me today.

Charlie Gilkey: Yeah, thanks for having me, Rebecca.  

Rebecca Ching: When you are crystal clear on your values and what matters most, you feel more engaged and energized by how you use your time. Now, it's a fight to maintain the practices Charlie shared with us today. There sure is a lot of noise and distraction pulling us away from focusing and finishing what matters, but he helped us understand when we develop reasonable expectations around the amount of deep work we can actually get done in a day, shame and overwhelm also have less of a chance of hijacking our time, and if we can release what Charlie called "project debt," you know, those projects that never get finished and keep weighing down our time for deep work, we release the weight of perfectionism and find more space all around.

So, are you clear on what matters most to you? How has perfectionism kept you from releasing or finishing projects on your to-do list? What changes do you need to make today that will give you more space for deep work around what matters most to you? 


Now, I know we can't bend time like Doctor Strange, no matter how much we try, but we sure can get better at how we use the precious hours we have by rethinking how we see time and use it. This is the work of an unburdened leader.

[Inspirational Music Interlude]

Leading is hard, and leading is also, often, controversial as you navigate staying aligned to your values, your mission, your boundaries. Navigating the inevitable controversy can challenge your confidence, clarity, and calm. Now, I know you don’t mind making the hard decisions, but sometimes the stakes seem higher and can bring up echoes of old doubts and insecurities during times when you need to feel rock solid on your plan and action. Finding a coach who gets the nuances of your business and leading in our complex and polarized world can help you identify the blocks that keep you playing at safe and small.

 Leading today is not a fancy title or fluffy bragging rights, it is brave and bold work to stay the course when the future is unknown and the doubts and pains from the past keep showing up to shake things up. Internal emotional practices and systemic strategies are needed to keep the protector of cynicism at bay and foster a hope that is actionable and aligned.

So when the stakes are high and you don't want to lose focus, when you want to navigate inevitable conflict between your ears and with those you lead, when time is of the essence and you want to make hard decisions with confidence and clarity, then Unburdened Leader Coaching is for you, where you deepen the capacity to tolerate the vulnerability of change, innovation, and doing things differently than the status quo.

To start your Unburdened Leader Coaching process with me go to www.rebeccaching.com and book a free connection call. 


I can’t wait to hear from you!

Thank you so much for joining this episode of The Unburdened Leader. You can find this episode, show notes, sign up for the free Unburdened Leader weekly email, along with receiving Unburdened Leader resources, and find ways to work with me www.rebeccaching.com.


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