Charlie Gilkey: Start Finishing Your Best Work

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You’re listening to Insights at the Edge. Today, my guest is productivity expert Charlie Gilkey. Charlie writes that if a mad scientist were to do a Freaky Friday experiment and cross an entrepreneur with an Army officer and a philosopher, what would pop out is Charlie. And then, Charlie would want to help the mad scientist do it even more effectively. Charlie is the founder of the community of doers that he calls Productive Flourishing. With Sounds True, Charlie is the author of a new book and audiobook called Start Finishing: How to Go from Idea to Done.

Charlie is an expert who helps us focus on completing what matters—what matters most to our hearts. He calls it our “best work.,” the work that only each one of us can do in the world, and it’s what satisfies us at the deepest level. We can think and dream about our best work; Charlie Gilkey helps us get it done. Here’s my conversation with Charlie Gilkey:

Charlie, you teach people how to not just give life to, but finish what you call their “best work.” And so I want to start off talking about this notion of someone’s best work. How does a listener know, this is my best work, this is what I’m really here to do?

Charlie Gilkey: That’s such a great question. First off, thanks for having me on the podcast, really appreciate being here. So I want to start by taking a step back, and really addressing that one of the reasons we want to highlight best work as opposed to just work is because in our culture, we have a very twisted relationship with work. In many ways, it’s like one of those four-letter words. An oddity of the English language is that many of our crass or profane words actually are four letters long. Don’t know how that happened, it just did. And work can be in there, in that we don’t want to talk about it, we want to get away from it, we want to do as little as possible.

But it turns out that there’s a section of activity of our lives—there’s projects, there are things we want to invest in that legitimately count as work, but they’re different than that other sort of work. And we can go through some of the characteristics about it, but to answer firmly your question, I think your best work, people know it’s their best work when it’s one of those things that they can’t seem to get away from. In the sense that they put it in their virtual or physical drawer somewhere, but it keeps coming back up, like they should get to it.

The other thing is, their soul in some way yearns to do it. Even if it they’re afraid to do it, they know that there’s some piece of this universe that’s theirs to work on and to coax, and mend into something that only they can do. And then I guess a third sort of compass towards this is, it’s the type of work that when you do it, especially if you get paid for it, you kind of feel like you stole from somebody, or you’re cheating the system. It’s kind of like, if they find out that I really, really love doing this, and that I’m on fire and I feel like I’m living from the inside out, then maybe I won’t get to do it anymore. Maybe something will change. They’re always sort of afraid of being found out with this particular type of work.

And the last thing that I’ll say about it is, our best work is the type of activity that simultaneously benefits us in the process and in the outcome, and it also benefits others in the process and the outcome. And that’s important to note, because a lot of times when we’re thinking about maybe our passion work, or we think about some of those things, it’s a very either self-centered or solipsistic activity, and then once we go to start doing that work, we feel the tension between service to the world, and service to ourselves. But your best work actually conjoins both of those, and that can be really helpful for some folks, because if you don’t do your best work, the world is worse off than it would be had you done it.

So we have in some sense a responsibility. And I have to be careful with that word, because that puts a lot of pressure on some folks, but we have this responsibility to do that thing that only we can do, and again, if we don’t do it, the world is worse off.

TS: Now, I want to ask you a question that might be kind of surprising for you. I’m sure you get lots of questions from people about this notion of what really is my best work, but the possibly surprising question, someone who’s listening right now, and even as they just hear you talk about it, they have a wave of some type of grief, some type of sense of, “Oh my god, I’ve gone this long without doing the thing that only I can do.” And at this moment, even just listening to you, they feel that wave of grief. What would you say to that person?

CG: Good, actually. Because if you’re feeling grief … like, we only grieve things that matter to us. We only get envious about things that matter to us. So some of these “dark” emotions that we have—grief, envy, frustration—can actually be really great compasses to what matters to us. So first off, good. You’re where you need to be, and you’re acknowledging what’s important to you. Second off, we all have to start somewhere, and we might as well start finishing today. And there’s a Cherokee proverb, “don’t let yesterday eat up too much of today.” And so though I am all about having a bias to action, I don’t want to override the fact that we can have that grief, we can have that frustration, we can have that sometimes resentment, at the same time that we can reorient ourselves in making the best of the time that we have today.

TS: Beautiful answer. Now, let’s say someone says, “OK, my challenge when I think about what is my best work, is that I’m actually quite talented at several things. I have several kinds of best work. Is that OK, or is there one thing, one project that’s really mine to do?”

CG: It’s absolutely OK. And so I talk about projects a bit differently than maybe common parlance. One thing is, I like to talk about project worlds, and that’s the idea that our professional lives and our personal lives seem to be divided into three- to five-year chunks, or phases, of life. Or our career, so I’ll talk about the life side first. If we’re in a romantic relationship, there’s a certain period of time, tends to be about three to five years, that you really fall into the groove of whatever type of partnership that you’re into. And then after that, it takes a second stage, and you might go through different stages, I don’t want to presume that everyone has kids or things like that, but if that’s their path, kids, there’s that three- to five-year age where they’re doing what they’re doing, and then they go to kindergarten, which is another shift, and then they go to middle school.

And so when we look at from our birth to our death, it seems that our lives are divided into three- to five-year chunks. On the career side it’s very similar, in that we get a job, we’re in that job for a while, we either don’t keep that job because we move on to something else, or we get promoted, or the business changes. But there’s always this sense of dynamism. So we know we should expect that in our personal life and in our professional life, every three to five years something significant is going to be shifting. We’re going to shift from one phase to the next.

And there’s a lot of freedom in that, because yes, if you are a multi-talented renaissance soul, what I have people start thinking about is, of all those things, which is the thing right now that you want to put the most effort towards for the next three to five years? And also, I’m not saying things that renaissance souls don’t already know; each one of those talents or areas of your life requires some upkeep in the form of projects.

And projects in my language, when we’re talking little “p” projects, are anything that take time, energy, and attention. So if you’re a musician, an engineer, and an activist, right, you’ve got some time that you’re spending playing music, probably getting better, probably doing things around that. You’ve got some time that you’re spending being an engineer, the learning and work and everything that you’ll do around that. And you have some time that you’ll spend in being that civic activist—you know, the weekends, evenings, throughout the day, whatever. So every major aspect of our lives requires some upkeep, and if we don’t attend to that upkeep, we leave a trail of dropped balls and unmet expectations, and frustrations, behind us.

So I’m not going to be the person that says, “Look, you’ve got all of these horses in the stable, but you can only ride one.” But I will remind folks, if you’ve got that many horses in the stable, they all need to fed, they all need to be watered, they all need to be cared for. And that may prevent you from really getting the mastery with one horse that you might otherwise do. And some of us, our best life—which is really what this is about, we do the best work that leads to our thriving. And some of us are going to thrive by the variety and the professional amateurism that comes with riding a lot of horses. And I’m not going to judge that and say they shouldn’t do that. I just want them to be conscious and aware that the cost of that is that they may not be truly masterful in any one of those things. And so choose your horse, as it were.

TS: Professional amateurism that comes with … that’s a powerful phrase for the person who is a multi-great worker.

CG: Yes, and I know that amateur can have such a negative connotation to it, and there’s just that difference between someone who has devoted their amount of time to do, as say, Steven Pressfield might say, and turn pro, and really cultivate one craft over the long-term, versus someone who’s good at a lot of things. I’ve got to be clear, I’m a professional amateur when it comes to a lot of things, and I’ve just learned to be OK that when it comes to those things that I’m not prioritizing in a way that’s significant, I am going to not be as good.

Like, I’m not going to walk into, say, looking at where I am with my philosophical background, right now I’m not as read up on the literature as I would be had I remained in academia. So if I’m in a conversation with a deeply read, deeply researched, well-practiced philosopher, I am not going to be able to really be in the conversation at the same level that they might be. However, when it comes to the things that I do, they’re not going to be at the same level as I am, even if they are a dabbler. So again, I think it’s OK to be an amateur, it’s OK to choose where we’re going to be mediocre. It’s just understanding that that’s a bed that we need to fully lay in, and not assume that we can have a mastery level of performance, or competence, or renown, when we’re putting in a minor amount of effort in that particular activity.

TS: Now Charlie, your book, your new book, Start Finishing: How to Go from Idea to Done, and we started off emphasizing this notion that you’re not just helping people realize and actualize any idea, but it’s their great work in life that you’re helping people start, and finish. Start finishing. And early on in the book, you make this really important distinction, that there’s a difference between ideas and projects. And we’re talking about projects like these—you mentioned horses in the barn, and just this teaching that our ideas need to become projects, I think, is a very powerful point.

So if you can explain that to our listeners, what it means to take an idea—this idea we may have even about what our great work is—and actually turn it into a project.

CG: Yes, that’s a great place to start. And I agree, it’s one of those things that when I teach it, I’m like, this is so simple and everyone understands it. But sometimes the most profound things are simple, and as creative souls, and by being human, we are creative. We take in a lot of different ideas, and unfortunately, we sometimes make the translation in our head that if I’ve taken on an idea, I’ve taken on a project, and that’s not true. We can take on a near infinite amount of ideas, but we have a limited lifetime, limited amount of time, energy, and attention to actually do the projects.

So when we look at going from idea to a project, we have to start thinking about what’s the goal. How do I convert that sort of fuzzy idea, which normally starts as a hunch, or an “it would be cool,” or just sort of a tug—how do you convert that tug into something that’s more directional, and more specific, in a way that harnesses your creative, emotional, mental, and spiritual energies?

So I want to pause here, because a lot of times people, I think, will thrash in the goal-setting stage of things, because they want to leave the possibilities open to serendipity, or synchronicity, or so on and so forth. But when you leave it open, it’s hard for you to channel your limited energy towards a certain thing. And we often get more perspective by trying one specific thing, and winning or not, than we do with canvassing a lot, and sort of half-touching a lot of things. So just want to head that off at the pass.

So one of the first things is, we start thinking about what that goal would be, and then we start thinking about what level of success we’re going after. And I’ll pause here, because I think this is one of those significant things that will generate a lot of peace in our lives. We tend to think in terms of success or failure, but that’s a really myopic way of thinking about things. And because I want to talk about success more than failure, we can look at three different levels of success: with small success, meaning, you got it done, you’re proud to have it done, but it’s nothing major; moderate success, which is more than that, but it’s in-between that epic success—or if you’re not a Millennial, extreme success—where that’s the type of thing that is a significant inflection point in your life, or at least it feels that way to you. It’s the type of thing where you’ll call your folks up, and say “Hey, this happened,” or it might be your Oprah moment, even though Oprah moments are different now than they were when I was growing up.

And the benefit of choosing your level of success is that you can, at the same time, choose the level of investment of effort that you’re going to put in to getting there. If you want an epic level of success, you’re going to have to put in a lot more effort than a small level of success. And once you, I think, get to the point where you’re like, “I can choose for this project that it’s a small success, and I’m OK with that, because I want to do it, but it’s not the big, big effort in my life,” then when you do the work and you get that small success, you don’t have to beat yourself up about, well, you can do more. And there’s so much more potential, and you know that. You knew that going into it, but you chose to invest your energy in a different way, towards something else. And it’s a really powerful way to ease, I think, that low-level anxiety that a lot of change-makers have, about the things they want to do in the world, and how big of a change they want to make.

So once you’ve chosen the goal, and your level of success, you can build a team around, I call it a success pack. And then finally, or not finally, you build a roadmap, get that on your schedule. So there’s a process that we can go through, and we’re making this conversion from an idea to a project, and then getting it on our schedule, and then pushing it to done. And that’s so helpful for a lot of people, because it lets you, at the beginning, decide whether an idea is truly worth going through that process for you, and if not, you can leave it as an idea. There’s no commitment to it. You can give that idea to somebody else, it can be their project. But you’re not walking around feeling like you’re in some sense of idea or a project debt that you’re never going to get out of.

TS: You know, Charlie, the way you approach this is so sober and realistic about the number of projects that we can care, cultivate, feed, and take care of at any given time, what level of success. Make it concrete for the people who are listening. What are some of these great work projects? Maybe one at a small level, one at a moderate, one at an epic—I’m going to use the word even though I’m not a Millennial—an epic level of success. That really people you work with, and you’d say, “Oh, these are the kinds of things that people commit to, to start finishing, because they reflect their best work.”

CG: Absolutely, and that’s a great way to think about it. Since I’ve worked with so many entrepreneurs, and people who are responsible for making stuff, their livelihood depends upon creation, I’m just going to talk about writing. I understand that’s not a native capacity for everyone, but I think most of us understand. So a week sized project for someone might be writing an article, or a blog post. And I need to back up and say I do talk about thinking about projects in terms of week-sized, or month-sized, or quarter-sized, because it helps us understand the commitments that we’ve made with ourselves at any given level.

So in the book I’m talking about the five-projects rule, which is the nerdy way that only Charlie’s going to say it, but I have to say it every time, is no more than five active projects at any time perspective. So, no more than five month-sized projects at any given time. Because through experience, and research, and reading, and all sorts of other things put into it, what I’ve found is that most of us are not going to complete more than that amount of projects at that time perspective anyways. We’re not going to complete more than five meaningful projects per quarter, per month, per week.

And so finding something like a week-sized project, which may be writing an article, if they’re a practice writer, that gives them an example of what that might look like. And they might be writing—a different level of success might be, “Well, I am going to write and just post it on my blog. I don’t have to have any permission, I don’t have to do anything,” so on and so forth. Versus, “Hey, I’m going to write this article so that it’s published at Sounds True, or Fast Company,” which is a different level of investment, a different level of effort that it would take to get that published, so on and so forth, versus, “Hey, I’m going to write this article so that it’s featured in The New Yorker.” And you might disagree with my levels of how difficult it is, but you can kind of see that there’s a different level of investment and work, and things that it would require doing that one and the same project.

For a month-sized project, it could be something as straightforward as thinking about the roles of the job that they need to hire for, and spending a month, and thinking through what that role would be. And if there are any entrepreneurs or small business owners listening to me, their first impulse, especially if they’re newer, is like, there’s no way that it takes a month to do that. But you realize after you’ve done it a while, yes it does, it’s a month-sized project by the time you get all of the fact-finding, so on and so forth.

And to sort of piggyback on that, hiring that person may be a quarter-sized project. Because by the time you create the job description, get the applications in, start the initial vetting, that takes at least three months to do. And again, we can apply the levels of success in the same way, because you may be looking for a very specific type of talent that’s in high demand, that’s really competitive in the marketplace, and you’re going to have to show up differently for that candidate than you may need to for a different role that doesn’t require such a high degree of competencies, and experience, and pay, and perspective, and so on and so forth.

So that sort of gives, I think, a few projects and how you might think in the different levels of success. Is that helpful, Tami?

TS: It is, and we’ve got to quarterly. But I’m thinking of, let’s say someone who’s listening to this has a bigger idea. Like my best work would be creating a nonprofit that would influence this group of people, help this group of people. And it’s going to take me three years to get that done. Where does the three years fit into the quarterly map that you just described? And for the record, I want it to have an epic level of success.

CG: Yes. So again—let’s say it’s a food bank so that I can make it specific. And there’s a big difference between—and so I’ll start with the goal, because I’ll almost always have to, Tami. And there might be a difference between a food bank that’s set up to feed a thousand kids a year, let’s say, versus one that’s set up to feed twenty-five thousand kids a year. So if the thousand a year may be a small success, maybe it’s moderate depending upon one’s capabilities, but you can kind of see how you would build an engine that would feed a thousand that is nowhere near sufficient to feed twenty-five thousand.

And so I would say twenty-five thousand, even the work that I do with nonprofit, is quite an ambitious goal, quite an epic goal. And how that translates to breaking it down for the quarterly, yes we do have yearly perspectives, and what I have found is that many people, once we start getting into sort of that two-, three-year timeframe, were actually doing a lot of visioning, but not so much planning, and that’s perfectly fine. I think people often will try to plan out to a too-level of detail, too far out, and then get frustrated when reality has changed in significant ways in six months, and they have to do that work all over again.

So part of the process of momentum planning, which is what this dynamic process that I call goal-setting, creating the plan, looking at what happens, adjusting the plan, and so on and so forth, is understanding where for you, uniquely, you need to convert from fuzzy vision to a more specific goal, and a more specific plan that guides action. And that’s very general, I understand, but I think that’s part of the challenge is that we so often conflate clarity and certainty, and I have to show how I’m getting there. A lot of times people will spend a lot of time making plans, because they’re trying to get to a place of certainty that if they invoke that plan, that they’re pretty confident that a certain outcome is going to happen.

When it comes to our best-work projects, we have to in some ways hang on to clarity but let go of certainty. Because if we’re really creating a new abundant possibility that doesn’t exist now, we have to be open to the fact that it’s going to look different when we create it than when we started it. So we have to remain open enough that we can remain clear on our purpose, and clear on broadly who we’re trying to help and why, but be adaptive to the changing reality of what’s on the ground. Because you may find out, to give our example, that twenty-five thousand is, there are not that many kids in your local area, so maybe you downscale it to a certain thing. Or maybe you figure out that, wait a second, that was not nearly as difficult as I thought once I’ve gone on, and I need to change what I’m doing to account for that.

So I’ll say that. But what we would do with that three-year goal would be like, OK, let’s divide this into, let’s say, year-long phases. Because that’s where many people’s vision, and their ability to convert vision into action really centers. And so we would break down into three-year phases, and then we’d say, “OK, let’s not worry about phase two and three at the detail level, or year two and three at the detail level at this point. Let’s just focus on year one; now let’s focus on what quarterly projects we would need to get there, which we could go through all of the list of steps that might need to start happening,” I’m not sure if you want me to do that in this one. But then we would look at, OK, we’ve got the first year at the quarterly level figured out, now let’s look at this first quarter, and go down to the monthly level, and think about where we need to be for the next three months as far as the size of projects. And then at the weekly—

TS: Yes, that makes sense. I mean, you’re chunking it down. You’re chunking it down, chunking it down, taking it out of what you said, the fuzzy land, and getting it really concrete, step by step.

CG: Yes.

TS: OK, now Charlie, I have to ask this right now, because I mentioned right at the beginning when you talk about people’s best work, they could have this response of sadness, or grief, or as you said, envy even. “I haven’t been doing it. Look what Charlie’s doing, he got his book out, I’ve been thinking about my book for decades now, I haven’t done it, I haven’t followed his method.” Whatever it may be in people, and you’re saying, “OK, good, let’s go, let’s get started.”

But then somebody is listening to our conversation, and they say, “Wait, you know, I have some really important objections here. What is actually happening in my life? What’s actually happening in my life is that I have financial constraints, I can’t do this, because I’m under financial pressure, I have a family to support. No, it’s not my best work, what I’m doing, but let’s get real.” So let’s talk to that person for a moment.

CG: Let’s talk to that person. So we all have an air sandwich of sorts, and we can look at the air sandwich as like, top slice of this bread of life is our big vision, our goals, our aspirations, who we want to be. So, that vision that we have of our best self. And then the bottom level is the day-to-day reality, and the choices, and the challenges, and the fire, and the nitty gritty stuff that comes up. And it’s frustrating for a lot of us. I’ve yet to meet a person, actually, who is not frustrated by the air between the two, that big gap between what they see they can do in the world, and what they’re actually doing.

But it turns out that in between those two slices of bread, as it were, there are five universal challenges that come up. Well, you mentioned one of them, so I’ll just go through them briefly, but then I’ll talk about the one that you specifically mentioned. They’re competing priorities; head trash, which is just the stories and the limiting beliefs we have about ourselves that keep us from taking action that we otherwise could; there’s no realistic plan, which we just touched on; there are too few resources, which again is the point you just brought up; and poor team alignment, with team understood as people in your personal life: your partners, your family, your neighbors, your friends, as well as your coworkers and your professional people.

And the reality is, we all have some of those challenges working on us at some given points and times, and what we have to do is as best as we can, don’t let what we can’t do keep us doing from what we can do. And so to that person that’s like, “I’ve got too few—I’ve got kids, I’ve got a job, I don’t have all the money,” so on and so forth, what I would say is, inevitably, there are 30 minutes or two hours a week that you can carve out to work on that thing. Inevitably, there’s always some time that you can steal from something else that may not matter as much to you. The exceptions I might give is if you’re in a caretaking position, where you’ve got family members who need 24/7 constant care that you can’t actually get any time away from, and you have no help and things like that, then that’s a real constraint. But what I would say is actually the caretaking you’re doing is a best-work project.

And I want to be more inclusive about our projects, so that they include these projects in our personal life which could include the relational projects that often get left out of these conversations. The raising of kids, the taking care of partners who are sick, the caretaking of parents and other beings around us, the community building. Tami, you can’t believe how frustrating it is for me that those get left out of the conversation. Not only because they’re important human activities, but it’s also either directly or indirectly sexist, in the sense that when we look at the way our society is socialized, those are the jobs that we end up sliding towards women in our society. And at the same time, we’re saying that’s not work that matters, that’s not work that counts. It’s only this making of things—and I know I’m on a rant here, and I need to get off of it, but …

TS: No, it’s a really important rant, and I was going to ask you about it, so I’m glad you’re taking it. It’s important. I was going to ask, is being a mom considered being somebody’s great work? I think a lot of—or a dad, or a grandchild taking care of a grandparent, grandparent taking care of a grandchild, however it may go. Are those great works?

CG: Absolutely.

TS: And you’re saying yes.

CG: Absolutely. Absolutely. And it feels foreign for a lot of people to apply some of the skills, like goal-setting and things like that, but one could see how you could do that if you were to take it seriously, and say, you know what, that’s what I am here to do. I think is a powerful thing, because it enables us to set up the boundaries and the discipline that we need to do that, and it also helps with that grief that we mentioned, because again, our reach will always exceed our grasp. Our reach will always exceed our grasp. And so the question becomes, are you grasping onto the things that will matter the most to you?

You know, I hate to do the morbid at-the-end-of-your-life thing, but it’s a good tool when you say, at the end of your life, when you look at the choices that you’ve made, would you make those choices again? Or are you at least content with them? You may not be over the moon joyful about it, of all the different constraints that come up, but would you have made a different choice? And I’ll make this personal, because I had a similar thing that happened with me with my dissertation a few years ago, Tami. And I had checked in, I was like, man, I left academia before I finished my PhD. By the way, be very careful if you’re thinking about doing that, because it makes it very tricky to finish it.

But anyways, I was like, “I have a certain amount of time, I think I know how much time I have, but I’m just going to check in.” And when I checked in, I got the email response back on, of all days, election day 2016, that I had to finish it in 2017 or it needed to be done by 2017. But in traditional sort of, or in normal academic thinking, it wasn’t clear whether it was the beginning of 2017, or whether it was the end of 2017. So I didn’t know what degree, or on what scale of screwed I was. Because if it was two months later, there’s no way I could do that. And if it was a year later, there’s major choices like not writing this book that we’re talking about now, that I would have to make.

And so I thrashed around with that a few months, felt all that grief and frustration. But then it sort of hit me—eat your own cooking, Charlie, because I go through this a lot. It hit me like, would I have made a different choice anywhere along the way, that would have made that year-long-and-change project hit my schedule for it to be done? And I wouldn’t. I wouldn’t have changed it. And so I had to sort of accept that the reality is, I was doing what mattered most to me, and that was not it. And until it mattered more, I wasn’t going to do it.

And then it kind of comes what I call a project cage match, which is a wrestling metaphor. But it’s like, you know, certain projects are going to get thrown out of the ring pretty quickly, and then there are some that are not. And so it’s always—for the last decade and some change, it’s always been for me, am I going to write the book first, or am I going to finish the dissertation? And I’ve just been called and drawn to finish the book more. And one, it helps me with my mission more than finishing a dissertation that six people, four of whom I’ll pay to read, will actually read, versus writing the book. But that’s an example where all of that grief, and frustration, and envy, and annoyance, and head trash came up, and it just came down to the fact of, was it truly matterful or meaningful to me in a way that I would have changed my choices? And I wouldn’t.

And so I would say for the person that’s in that extreme caretaking position that we mentioned, or who’s focusing on the stage of their life where they’re focusing on kids, or seeing an elder pet off gracefully, or whatever that case may be, that great. That is your priority. Own that, embrace that, lean into that, and understand that guess what, three to five years from now, you’ll probably be in a different phase, and that may be the time that you focus on that thing that matters more to you at that time because you’ve seen that other priority through.


Kriste Peoples: Seane Corn’s new book, Revolution of the Soul, is available now. Brought to you by Sounds True and Lululemon’s social impact program, Here To Be, both dedicated to bringing greater access to yoga and meditation for all. Learn more at

TS: OK, so I started this question talking about the person who feels financially pressured. They don’t feel they have enough security, and you said, you know, look, even in such a situation, something like that, outside of these exceptions that we just talked about, where it’s a real 24/7 caregiving role, you can always find a couple hours. And what if somebody says, “You know, yes, I can find a couple hours here, a couple hours there, but that’s never going to generate the kind of epic success I want as a musician, or some other type of creative art where you’ve really got to put in a lot more hours than a couple hours here, and a couple hours there. But the truth is, I’m generating financial security right now. This is what I’ve got, this is my current situation.”

CG: Yes, I would say then at some point, the financial security and what you’re doing is actually what’s more important to you than the other thing. And it goes back to whether we want to talk about being a professional amateur, or whether we want to talk about honoring the constraints that you have. It can be frustrating that we can’t do all the things that we want to do. The question I would then have, or just what I would come back to is, how are you going to change your current days, your current priorities, such that it creates room for that? And/or, are there ways that you can weave in this activity with the resources that you have available?

It turns out that in the United States, for most of us in most places, especially with the Internet, there are ways where you can trade your time to get resources, or to get money that you can then buy the things that you want. So we can convert time into dollars pretty easily, and it turns out that at a certain level of wealth, it’s hard to turn dollars into time. And so again, I think yes, that is a real constraint. I’m not trying to say it’s not, and I’m not also of the position where I think we should have as an expectation of ourselves that we can do all things right now. I think it’s about choosing what to do with the time, energy, and attention that we have, sorted by what matters most to us. And what that’s going to be for an individual person is really unique to them.

TS: OK Charlie, you know, I have a long list of the objections that people have of how they, and why they can’t finish the various best-work projects they really want to do. But instead of going there, I’m going to go someplace else, because you talk to a lot of people, and magnetize a lot of people to you who are standing tall and claiming—you have this phrase, “creative giants,” people who are claiming their own identity as creative giants. I want to know what are the qualities, and then also let’s talk about the habits—both the qualities and habits of these people who are creative giants. What do they do? What are they like?

CG: What are they like? I think in some ways, we all have the potential within us to be a creative giant, and I want to pause here saying many people have objections to identifying as a creative giant at first, because it seems braggerty. It seems like you’re puffing up your chest, it seems like you’re trying to claim something that you’re not. And also we have in our language creative giants, and we think of people like Leonardo Da Vinci, we think about Emily Dickinson, we think about hyper-prolific, hyper-creative people like those people who did that work that we’re talking about 200 years later. Those are creative giants, I’m just a person, right?

But what I want people to realize is that those people writing those, creating that work, became that by doing the work. That’s the difference. They did the work, and they did it at a level, and they were lucky in a lot of ways—but luck is a part of all of our careers, so right?—where they became these cultural icons. We have that power within each of us, too, because we’re just people too. But creative giants, in my language, they’re not just the people that are renaissance souls that have a bunch of ideas, they’re the ones that we mentioned earlier that have a hand in a lot of cookie jars. Actively doing something.

So it’s not that they’re multi-talented, they’re multi-doers, and actively out there doing things. And they have a real bias for compassion, and serving the world. So they’re not just out to make themselves better, they’re out to make the world better, and this creates all sorts of problems for them. Because one, they end up over-committed, because there’s a sort of truism that we operate by where we give the busiest people more stuff to do. We never give the people who don’t have stuff to do, more stuff to do. Or we don’t—I won’t say never, but there’s a tendency to overburden the people who are able to get stuff done with more stuff to do.

[They] have bigger issues with boundaries than others, because again, they’re trying to make the world better, make other people better, at the same time that they’re trying to get their work done. So take on too many requests. I could go on, but one of the challenges that we already alluded to is that they’ve got the curse of being able to do too many damn things at once, right? And it’s one thing if you’re the one-trick pony, because you’re just going to do that trick over and over again. But when you’re a menagerie of tricks, and feints, and you’re just this walking magic show, then it can create a situation where when you sit down on any given morning, you don’t know what to do, because you could do any of them. You don’t have the constraints that you need to, to go forward.

And so creative giants are in this perplexing position, to where they are natively capable, they’re natively driven to spend the time on this Earth really, really well, and because they’re service-centered, they end up with tensions that other folks may not have. So I’ve talked to a lot of them, but mainly it’s the reminder, it’s sort of the neo-Aristotelian synthesis of just reminding folks that we become by doing. We become by doing. So if you want to become a certain type of person in the world, whether we’re talking about a character goal, or a career goal, or whatever goal that is, there’s a certain amount of doing that has to be prioritized so that you can become that thing. You don’t become that thing merely by thinking about it.

TS: OK, so this is very interesting to me that the qualities of these creative giants, their courage to be people of service, et cetera, the bodhisattvas out there, the multi-talented bodhisattvas, that they also end up being over-committed and having issues with boundaries. How do you help creative giants be balanced humans? With a level of serenity, groundedness …

CG: Yes, yes. You know, we produced a product at Sounds True that is really tailored for the spiritual seekers who are listening, that I think would also be a good thing to listen to. Because it turns out, especially if we add in that bodhisattva, or that spiritual seeker aspect of things, that we have so many deeply embedded stories from our spiritual and religious traditions that actually create unnecessary tension here. And some of those stories revolve around our primary goal being to be of service of other people. Which means depending upon how we translate, interpret, or stress that, which means that any time we choose to take care of ourselves, we feel that we’re in some sense a disalignment with those spiritual traditions. And whether you want to call that sin, or whether you want to call that, whatever you want to call that particular out of alignment, it creates that tension that so many of us feel.

But what we have to remember is that we are one of the people that are being served, and our needs matter too. I’m going to slide here and go a little bit Kantian, from Immanuel Kant. What people forget about Kant is that your self, you yourself are a person who you can’t be used as a means to an end, and you can’t be used as an object for someone else’s satisfaction, or someone else’s needs. But all too often, we remove our individual needs, our individual wants, our individual desires from the equation, and end up in a place of martyrdom and in a place of burnout, and in a place where we’re not doing our best work because we’re depleted. So we’re not doing it for other people, but we’re not able to do it for ourselves.

So first of it, first thing that will help people really sit with, and work through it—I don’t like saying get past, because it’s something that will come up every day. But to really put themselves in the mix of people who are being served, and prioritizing that in a way that they would prioritize a partner, a child, a parent, or a pet. If that pet, that person, that being had needs, wants, and desires, how do you orient towards that, and why don’t you orient towards yourself that way?

So there’s some deep inner head trash and stories, I think, that keep us from leaning into that, and once we dislodge some of that, we can say “Wait, wait a second, my own happiness, my own pleasure, is inherently valuable. I don’t have to do all of this hard work, I don’t have to prove and do all the things I need to, to deserve happiness. To deserve pleasure. To deserve peace.” Those are inherently valuable, and you can get them in and of themselves.

And then we can also start looking at the ways in which, whether we want to talk about the time that they take for recovery, and recharge, that that enables them to do their service work more powerfully. Enables them to show up in the world more powerfully. To show up in the world with a sense of continued completion. And I want to pause here, because especially for people who are wired to be creative in whatever way that you’re being creative, there’s a qualitatively different feeling when you have made space for the work that you are called to do, and then you engage with the world in a powerful way, versus not having had that completed, not having that sense of ownership of your own inner needs, and then interfacing with the world.

So that sense of resentment and the buildup of what I call creative constipation actually ends up leaking into your relationships. It ends up leaking into—I mean, ends up leaking out of your wallet for a lot of people, in the sense of the consumerism, the excesses of consumerism that we’ll get into, because we’re not fundamentally doing what we’re called to do. So it has these costs that I think it’s two levels below the surface. But once you surface it, people realize that wait a second, they’ve framed the situation one way, but the better way of looking at it is, if you truly want to do your best work in the world, there is a responsibility, a need, and a calling for you to take care of yourself. If not first, in a way above everyone else, but at least equally with everyone else’s needs that you’re trying to serve.

TS: You know that phrase, “creative constipation,” I think it’s very visceral, I think people get it. People know it in their own experience. What are the signs, Charlie? Like someone says, “Yep, that’s me, these are the signs.”

CG: So there are many signs, but I’ll give what people have reported to me, and what I’ve felt. So part of it is just the frustration. You don’t want to take on any new ideas. You’ll go through that binge of watching TED Talks every day for two months, but not taking action on any of those ideas, and then there’s that morning where you just wake up and you can’t stand the idea of it any more. You’re just so done and frustrated, because you know deeply that you’re not doing anything with the ideas. There’s oftentimes resentment of people around them. Of the people around them, and what I call OPP, or other people’s priorities. And people keep asking you to do things, and I keep doing things for other people, and I don’t have time. So you end up building some resentment towards other people.

That can lead, for some people, to depression and/or long bouts of melancholy. Because what’s the point? If you’re never going to get to do that thing that really matters to you, and you’re just this walking husk, going from job to job and going from one bit of work you don’t want to do to another bit of work, what’s the point of that? And so there’s that demotivation that can happen. Burnout can also happen, because you don’t have the inner spark that keeps you engaged with your work. Let’s see, what else can come up? Sometimes it can manifest as weight gain, or severe weight loss, and that’s just a psychosomaticism of finding other ways to fill voids that will come up.

So there are a range of ways, and what I want to say is, fundamentally, our nature as people is that we are either creating something, or we’re destroying something. And the creative energy is tied to destructive energy, and that’s why so many of the spiritual traditions have that Shiva energy that can create and destroy. And that’s why the Abrahamic religions have God who can be really merciful, and really creative, or he can pull down floods that can destroy everything. We understand throughout our traditions, and just looking intuitively at the world, that creativity and destruction are very intimately tied together. And so creative constipation will often lead to destroying the things around you. Destroying relationships, destroying the time that you have. Destroying the resources, the money that you have. And unfortunately, the thing that we reach out to destroy that’s easiest to destroy is ourself, in the ways that we treat our own humanity, the ways that we treat our own bodies, the story and head trash that we tell ourselves.

And so there’s a very real cost of not really doing the work that calls to you, and I think we all know that at a certain point, and I think if we were—going back to what we said earlier, if we were looking at a friend that was suffering with creative constipation, or a loved one, we would do a lot to help them unleash whatever was inside that that wants to come out. But when it comes to ourselves, we won’t do nearly the work of creating room, and allowing ourselves to let whatever’s in, come out.

TS: You know, I think your book, Start Finishing: How to Go from Idea to Done, is a fabulous resource, and a step-by-step guide for that person who wants to recover from their creative constipation, and become on the path. And with a project plan, broken down into weekly, monthly, quarterly, yearly goals for their idea-become-project. And you also mentioned this other part of what it takes to go from idea to done, which is creating what you called in our conversation, Charlie, a “success pack.” Some kind of human support of some kind. What’s a success pack, and how does someone create one?

CG: Yes. You know I’ve been asked a lot of questions about the book, and what’s the one thing you want people to take away, and that’s always a tricky question with your own work. But I think the idea of success pack is one of those that is one of the most important, if not the most important in the book, because it helps you bring all the resources that will let you accomplish nearly anything that you’re trying to do, as long as you show up with courage and vulnerability. So, your success pack is the group of people around you that you assemble to help you with your project—or you can think more meta level, you can think your life.

And importantly, these are the yea-sayers that are out there, and I’m going to pause here, because unfortunately, many of us are wired to try to please or try to accommodate the naysayers in our lives. The people who are going to be objecting, they’re going to be Uncle Ron, I think most of us have an Uncle Ron. Every time we try to talk to them about anything, there’s always a downer, and always saying how it’s not going to work. Whatever that might be, right? Or the critics, or the trolls. We all have that image of naysayers out there in our lives, and we try to spend too much of our time accommodating them or being safe around them, when the fact of the matter is, a naysayer is practically never going to come to your side. You’re never going to make them happy. As the philosopher, poet, and musician Taylor Swift would say, “Haters are gonna hate,” and unfortunately, we try to accommodate them too much.

But I want us to focus on our yea-sayers, which are the opposite. These are the people that see your best self, that when you talk about what you want to do in the world, they don’t question whether you’re going to be successful, they question how you’re going to be successful, and how they can help. There’s a very important distinction there. These are the people who, when you do something or say something, or you accomplish, they’re the people saying, “Of course you did that, that’s who you’ve been the whole time. We’ve seen that.”

And your success pack is a group of yea-sayers that have—there are four different types of people that you want to put on your success pack. So first are your guides. These are the Yodas, Dumbledores, Gandalfs, these are the sort of wise mentors that are out there in the world that are just more experienced people, and that have generated their success, have generated their thriving, in ways that are consistent or resonate with your character. So there are all sorts of ways to win in the world; some ways of winning are not going to resonate with you. And so don’t choose people, don’t choose guides, that are dissonant with your values, because you’re not going to pay attention to them in the same way. So your guides’ main job is to really shift your worldview—and oh, by the way, those guys don’t have to be living. So if you have a spiritual teacher that you can sort of have mental conversations with, they can work just the same.

So your guides are paradigm shifters, worldview enlargers, and they tend to have statements of like, “Use the force,” or, “Remember who you are.” They always say these things, and they never make sense in the moment to you, but somewhere along the road it makes sense, and you need it when it comes up. So I know how that sounds, but I think we’ve all had people that have been guides in that way. Where you’re just like, “What are you talking about?” And then six months later it’ll hit you in the head, like, “Oh. Oh. Oh!” You see it once it happens. So those are guides.

The second category are your peers, and these are people who are side by side walking on the road with you. These might be your co-coaches, these might be your mastermind people, these might be your people that you have coffee with once a month and once a quarter, where you actually talk about how life is going, and what’s going on, and how you’re going to do things. So they’re accessible in a way that guides are not, but they’re still not necessarily in the project with you like your supporters are, which are the third category. And these are the people that are—they could be teammates. they could be neighbor kids who watch your kids and pets while you’re doing your work. They could be your partners, they could be family, they could be a lot of different people. And also by the way, family, partners, are not necessarily automatically enrolled onto your success pack, because unfortunately we have family members, and we could have partners, who could be either naysayers or derailers.

Derailers are well-meaning people who by the way they ask questions, or the way they show up, or the way you engage with them, actually derail you, and kind of kneecap the momentum and motivation that you have. And it’s really sad, but it’s true of the world, that sometimes they’re in your family. Sometimes they’re your friends, sometimes they’re your partner. So just because they’re friends, family, or partners don’t mean that they get put on your success pack. However, if you can put friends, family, and partners on success pack, it helps to avoid some of the tension that will come up as you focus on your project. People are really, really sensitive to a loss of status in relationships, and given that so much of our tensions in our modern life is about where our attention goes to, when they lose your attention, it can feel like they’re losing status.

If you are working on your project with them, and they’re involved in your best work—and remember, your best-work projects can be life projects. I want the work of life to be more important than the economic work that we do. We need to prioritize that more. So when you can put those folks on your success pack, you don’t have to make nearly the boundaries and nearly the compromises that you might otherwise have to, between balancing time spent with others—with other people that really matter to you—versus time spent on this project that matters to you.

And lastly are your beneficiaries. And these are the people, including yourself, who benefit from the completion of your project. And as I’ve been teaching this, a lot of people will gravitate towards guides, like how can I get more guides, how can I get more resource people to help me? But I think the real magic is, how can you get more in touch with your beneficiaries so that you really know what they need, and that they are involved in the creation of whatever you’re doing? So that when you get stuck, you can reach out to them and say, “Hey Tami, I’m making this thing for you, we’ve talked about this, is this working for you?” And Tami can say yes, or no. You don’t have to wonder, you can get that live feedback.

And the second thing that I’ll say about beneficiaries is that they help you when you’re cognitively stuck, but they can help you when you’re emotionally stuck, because again, if your project is just about you, you might check out of it. We unfortunately are much more likely to check out on ourselves than to check out on other people, in the same way that when you make a commitment to go to dinner, or have coffee with a friend, it’s a bigger ordeal to just decide not to go, than if you were just trying to do that by yourself. So beneficiaries will allow you, in those moments of darkness, to remember why you’re doing it, and even if the head trash has got you, and you’re thrashing like crazy on the project, you can say, “You know what? All that’s true, and I’m not giving up on this because it’s going to be better for Tami, or it’s going to be better for Jeff, or it’s going to be better for Angela, and I will push through for them, if not for myself.”

So I think we should focus more on our beneficiaries than on guides, even though that’s the first thing that people have told me, that’s their first thing, is “How do you get more guides?” Especially when I’m working with individual clients, or in workshops.

TS: You know, this idea of beneficiaries is so powerful. It makes me think not just of the people, the handful of beneficiaries who might be part of my success pack—and I’ve heard you teach about this, Charlie, but imagining and keeping in our heart all the people who might benefit from us finishing our best work. It could be thousands and thousands of people, tens of thousands, who will read the book, or listen to our music, or be touched by the nonprofit that we create, or whatever it is. But keeping them in our heart, that’s such a motivation, I think, to actually get it done.

CG: I think so too. And I think it’s an “and,” like we need to see that every best-work project that we finish, it leaves our fingerprints on the universe. We were here, we did something, and the universe is different because of the work that we’ve done. So yes, I think it makes a lot of difference. I know for me, and I know for a lot of the people that I work with, it’s just one of those things where it’s just like, “What about Tami, what about Tom, what about Ben?” And then it’s like, “Oh, I’m not done yet.” There’s a little in the tank left for the world. And sometimes, oftentimes when you’re doing your best work, you have to draw into that little bit that’s left in the tank.

TS: Charlie, to conclude our conversation there’s just one last thing I want to bring up, which is in my experience, it takes a certain kind of courage for people to actually complete their best work. There’s so many different things that come up on the way—we have to turn it into an actual project with timelines, and face all of our inner obstacles, outer obstacles, et cetera, et cetera. Talk to me a bit about courage and what you think really goes in, character-wise, to creating that courage inside of us.

CG: Yes. I love that we’re ending here, because I think we need more courageous people, and we need people practicing courage in the world right now. We don’t need a bunch of smarter people, we don’t need a bunch of more well-read people, we need people who are being courageous. And I want to be clear here, a lot of times when we’ve talked about courage, it’s kind of like big-C Courage: The people jumping into fires to save babies, or people who do brave things on airplanes, or firefighters and police officers, maybe military service members. And all of those are true, but I think there are little moments every day where we can practice courage. There are little moments to where we can be a little bit more vulnerable. There are little moments to where when we have that doubt that we’re the person who can create something that matters, or that can change the world in a positive way, that rather than backing out and letting our head trash win, we say, “You know what? Nope. I’m going to give it a shot.”

There are moments of speaking up, and speaking out, and standing up that are just the part and parcel of every day. And so I want to embrace that little-c courage, because that, I think, that we can cultivate. And I think we can do it proactively, and we can do it reactively. I’ll start with reactively. Look in your inbox, look in your text messages. Look at the interactions that are coming up with your professional team, look at the interactions that are coming up with your life. There are moments where we can decide to call out people’s best selves. There are moments where we can decide to channel our best self, and really be there.

And there are moments we can check out, right, and so I think reactively we can check in—I know it’s hard to say check in and then check out. But we can really say, in this moment, am I going to take the slightly harder road? Am I going to be a little bit more vulnerable? Am I going to risk something? Am I going to do something that might not work? Am I going to leap before I have it all figured out? And reactively, I think we can do that, and then proactively, we can look at the different parts of our life, the different dimensions of our life, and for lack of a better word, build a courage plan or maybe if you’re a person who likes gamification, and checklists, maybe you start looking at the different ways that you can proactively be more courageous. Maybe that’s more proactively setting boundaries that you then will need to honor through a bit of courage and discipline. Maybe it’s setting goals for yourself that make you accountable to people in public, that will also require you to show that inner part of yourself, or show that piece of you that wants to come outside to other people.

So I think when we look at little-c courage, and we look at how important it can be, and the difference that it can make between us creating the road as we walk along it, it’s much more accessible, and I guess I’m going to reference Aristotle again here. What lies in our power to do, lies in our power not to do. We can flip that, in the sense of, if we can be courageous and choose not to, we’re choosing the vice of that, which is being cowardly. And no one wants wear the mantle of coward, that’s not how we want to show up in the world. And we have these choices, these little, magical, mundane moments that happen throughout our days, and that’s the wedge in our life where I think we can inch ever closer to becoming our best selves, and doing our best work.

TS: Well Charlie, as one of the beneficiaries of a project that I think clearly is a best-work project for Charlie Gilkey, your book Start Finishing: How to Go from Idea to Done, as a beneficiary of that book, and the project plan, and step-by-step method that you outlined, I just want to thank you. Thank you for being a courageous, heartful person in the world, and instead of writing that dissertation, you wrote the book. Thank you! It’s a new book and audiobook from Sounds True, it’s called Start Finishing: How to Go from Idea to Done, and if you want some help and some structure to really be able to complete something that is in your heart, your best work, I heartily recommend it. Thank you, Charlie, God bless you.

CG: Thanks so much for having me.

TS: Thank you for listening to Insights at the Edge. You can read a full transcript of today’s interview at And if you’re interested, hit the subscribe button in your podcast app. And also, if you feel inspired, head to iTunes, and leave Insights at the Edge a review. I love getting your feedback, being in connection with you, and learning how we can continue to evolve and improve our program. Working together, I believe we can create a kinder and wiser world. waking up the world.

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