in: Advice, Character, Podcast

• Last updated: September 30, 2021

Podcast #573: Why You Don’t Finish What You Start (And What to Do About It)

How well did you do in completing projects last year? Not just work projects, but also personal projects surrounding family, fitness, or hobbies. If you didn’t accomplish as much as you’d like, then maybe you need to change up your mindset and tactics in the new year.  

My guest today has written a guide to making those changes. His name is Charlie Gilkey and he’s a former Army officer with a PhD in philosophy who’s spent over a decade studying productivity, writing about it on his website Productive Flourishing, and coaching clients in what he’s learned. He now has a book out as well: Start Finishing: How to Go From Idea to Done. Charlie and I begin our conversation going through the most common roadblocks that prevent people from completing their projects, including following other people’s priorities and dealing with what he calls “head trash.” We then discuss how we waste a lot of time doing what Charlie calls “thrashing’ and what we can do to overcome it. We then dig into why you sometimes have to quit things to move forward, how to create effective goals, and why it’s crucial to know which of three levels of success you’re aiming for. We also talk about how to do what Charlie calls “momentum planning” and the importance of creating focus blocks in your schedule. 

Show Highlights

  • Why productivity isn’t really about how much you do
  • The importance of finding the work of your life 
  • Dealing with competing priorities 
  • What is “head trash”?
  • Why planning your day is more of an emotional task than a cerebral task 
  • What defines a project? Why are our lives made up of projects?
  • What are “thrashing” behaviors that people engage in?
  • How to eliminate projects from your life in order to improve it
  • The danger of “should” 
  • Establishing effective goals and recognizing the degrees of success
  • Personal effectiveness vs. community effectiveness 
  • Why “mediocre” goals are okay to strive for
  • What is “momentum planning”?
  • The power of block planning 

Resources/People/Articles Mentioned in Podcast

Start Finishing by Charlie Glikey book cover.

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Charlie on Twitter

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Read the Transcript

Brett McKay: Brett McKay here and welcome to another edition of the Art of Manliness podcast. How well did you do in completing projects last year? I’m not just talking about work projects, but also personal projects surrounding family, fitness or hobbies. If you didn’t accomplish much as you’d like last year, then maybe you need to change your mindset and tactics in the new year.

My guest today has written a guide to making those changes. His name is Charlie Gilkey. He’s a former army officer with a PhD in philosophy who spent over a decade studying productivity, writing about it on his website, Productive Flourishing, and coaching clients on what he’s learned. He’s got a new book out now as well called Start Finishing: How to Go from Idea to Done.

Charlie and I began our conversation going through the most common roadblocks that prevent people from completing their projects, including following other people’s priorities and dealing with what he calls “head trash.” We then discuss how we waste a lot of time doing what Charlie calls “thrashing” and what we can do to overcome it. We then dig into why you sometimes have to quit things to move forward, how to create effective goals and why it’s crucial to know which of the three levels of success you’re aiming for. We also talk about how to do what Charlie calls “momentum planning” and the importance of creating focus blocks in your schedule. After the show’s over, check out our show notes at

Charlie Gilkey, welcome to the show.

Charlie Gilkey: Brett, thanks so much for having me. I’ve been looking forward to this interview for a long time.

Brett McKay: Well, we were talking before we started the show to record, that I’ve been following your website, Productive Flourishing, way back when. It’s like 2008, I think you started it. And I remember I started seeing these free planners percolate, where you could fill in bubbles and I was like, “This looks cool.” And now, this blog you started has turned into this company where basically, you help creative types, entrepreneurs, leaders be more productive and get more stuff done.

And you got a new book out sort of distilling all this stuff you’ve been talking about and writing about for the past 11 years. Book’s called Start Finishing: How to Go From Idea to Done. So, in your work with entrepreneurs, business leaders, creative types, what have you found are the biggest roadblocks that you see over and over again, that prevent people from taking an idea that they have from start to finish?

Charlie Gilkey: I’m glad we’re starting here, but I wanted to start actually by rolling it back a little bit because I do teach a lot about productivity. And the first thing we think about with productivity, since the way that the conversation has gone, it’s about doing more and getting more stuff done. But the reality is, Brett, I actually help my clients do fewer things, but just the more important things. I think part of the frustration that so many of us have is that it seems like we’re doing a lot but when we look back over the month or the quarter or the year, it doesn’t feel like we did the things that mattered most. And so, a few things are more exasperating than knowing like, “Man, I’ve been out on the field, I’ve been checking the list, I’ve been watching, all the stuff’s going on, I’ve been doing the meetings. And yet, thing thing I put on the board that I wanted to do, I’m no further along than I was two months ago.”

So really, what I end up focusing on is like, “You know what? We don’t need to really work on doing more. That’s not getting us where we’re trying to go. We need to work on doing more… or fewer of the things that matter most.” And I know that sounds better when I say it that way, but it’s really about being more thoughtful and intentional on having better priorities around those things that you want to see done and that you want to be celebrating at the end of the year, at the end of a decade.

Brett McKay: I was going to say that makes sense. The first thing that’s probably a roadblock is just people have other, wrong priorities that prevent them from getting started on the stuff that really matters.

Charlie Gilkey: Yeah. Well, I’m tricky about saying “wrong priorities.” I call them “competing priorities” because there are some priorities we have that are clearly ours, and then there are some priorities we have that are essentially other people’s priorities. And sometimes, we can’t really clearly distinguish between the two. And even when it’s just our own competing priorities, the classic sort of “I want creative freedom” versus “I want a secure paycheck” comes up a lot when it comes to entrepreneurs and creatives types because there seems to be this tension between the two, but we can think more generally…

And I want to pause here because really, Start Finishing, it’s a productivity book, yes, but more broadly speaking it’s a book about changing your life because to go from your current state of your life to some future, better version or your best version of yourself, there’s a big gap there for a lot of people. And you bridge that gap through completed projects, through finished projects. And if you’re not doing the types of projects that are going to build that better future for yourself, you’re going to stay stuck. And I want to say that because as we unfold this conversation more, I’m going to be talking about weaving the work of our lives into our schedule and prioritizing that just as much as we do the economic work or the life or our work.

And I think that’s one of the challenges to go to it, Brett, is that so many of us have these competing priorities and so many of us can feel that resentment or exasperation or regret because when we sit down to say, “These are the ways I’m going to spend my day,” what happens is our economic work gets prioritized. It gets scheduled, it gets thought about. And unfortunately, the work of our lives gets the afterthoughts or maybe gets squeezed in the cracks that are left over from the economic work. And so, what we ended up being is, if we do that too long, we become these husks of people that go to work, we punch the clock, we do the commute, we do the meetings, we do all the work, but then when we look we’re fundamentally not fulfilled because we’re not doing the work of our lives.

So, competing priorities is one of the first places I will generally go when people are telling me that they’re not doing what matters most to them. And so, just working through those competing priorities and “are these your priorities or are there… ” Sometimes on our own priorities, we have really powerful priorities that we don’t acknowledge. So, I’ll take parenting. I’m not a parent myself, but many parents say and understand and act out the fact that kids take a lot of time and care and a lot of energy and a lot of your life when you are raising children. We know that. And yet, when we set new year’s resolutions, when we set big plans for ourselves, a lot of times we don’t think about the amount of temporal weight, emotional weight, logistical weight that having kids can have. And that’s going to sit on our availability to do other things. And so, that’s just one of those where I know a lot of people can, on the one hand, really say truthfully like their kids and their family are their number one priority. But when it comes time to how they think about what they’re going to do with their month or what they’re going to do with a quarter or what they’re going to do with their year, they forget how much weight that’s going to take up, and they overplan on top of that very weighty, that very important thing.

And I’m just going to pause here and then move on. I just want to remind folks that being a great parent, being a great family member, being a great member of your community is being productive. I hate the conversation of “I could be productive or I could be with my family.” I think we need to readdress our priorities there. So, I know I’ve been hitting on this one quite a bit, Brett, but that’s really one of the first places I’d hit.

The second one would be head trash. And head trash is just the amalgam of self-defeating stories we tell ourselves, some of the cultural BS that we’ll pick up, some of the ways we see the world, and they don’t have to be that way. But the thing about head trash is it doesn’t have to be true of the world for it to work on us.

So, I’m a writer and even though I’ve spent the last couple decades of writing, I can occasionally have that thought, because creatives are insecure folks a lot of times, I’m like, “Man, I’m a terrible writer. What am I doing? I should just go get a normal job, quit this writing stuff,” and so on, so forth. Now, the reality is I’m either a good writer or I’m good enough to keep doing it and keep getting paid to do it. But that head trash, if I were to let it take hold, can actually determine what steps I might take. It might determine what goals I might set. It might determine what projects I might do even though it’s false. And so, if you had that teacher in third grade that told you you were terrible at math and that you’d never be anything and you hung onto that, yes, it sounds overly psychological or like a cliche, but the reality is if you hold onto that belief and you let it guide your actions, you’ll end up playing that script out even though it’s not actually true of you. And so, those two things tend to account for a lot of the reasons why people get stuck and they’re not filling that gap and finishing those projects.

And the last thing I’ll say is if we start talking about the work that we need to do with other people, the other major challenge is poor team alignment. And by that, not just your work team but your life team as well. A lot of times our teams are not aligned because we haven’t told the team where we want to go and why we want to go there. And there’s this frustrating thing that, despite evidence to the contrary, we keep expecting people to be mindreaders and understand where we want to go and what help we need and how our priorities line up. And that doesn’t happen. And in lieu of us being clear about the direction we want our life to go, it’s more likely that we’re going to be in a tug of war with other people who may otherwise, if brought into alignment, be very powerful forces of change for us.

Brett McKay: One thing that’s interesting that the problems you laid out that you see over and over again, they’re not so much like tactical problems. People aren’t planning incorrectly. They might be doing things that can help them along, but it’s like it’s a mindset problem. And you have to deal with that stuff first before you get to the more tactical “here’s how I plan my day out” sort of thing.

Charlie Gilkey: Absolutely. Because planning your day out, I think people mistake it and think that it’s a cerebral problem, but it’s really an emotional problem because it’s not hard conceptually to plan out your day. It’s really hard, when that day comes, to maintain your boundaries, to say the right yeses to say the noes where you need to. And if you don’t have this foundational layer of priority-setting and value-setting, it’s easy for those plans just to crumble by what seems to be urgent and what… well, what is urgent and what seems to be important that’s right in front of us, when the reality is we unfortunately have bought into the tyranny of the urgent a lot of times through our devices, through our smartphones, through email and things like that. And we end up thinking that everything that is an… or acting, I’ll say. We don’t think it; we end up acting as if a lot of the urgent stuff is the important stuff. And we end up in this whirlwind of incoming text and social media, email and whatever. And like that rocking chair, got a lot of motion but no progress, we end up in that swirl so long.

And it becomes easier to get out of that whirlwind, it becomes easier to get out of that tyranny of the urgent when you can just look at something and say, “You know what? That’s really not important to me,” or, “That’s going to suck to not be able to do that and I might have to face some consequences for it, but this thing over here is more important to us.”

And think about it this way, Brett. I think the challenge that we have with doing the projects that matter… Quick sidebar: A project to me is anything that takes time, energy and attention to complete, which means not just your economic projects, it also counts the projects of your life, so closets of doom, getting married, moving across the sea, moving across the nation, finally getting your kids off the couch and on to college or to their first career or at least out of your house. All of those things count as projects.

So, there are times in our life when an true urgency and importance comes up. I’ll go back to the parenting thing. When the school calls and your kid is sick, you don’t think about everything that’s on your list of stuff to do today. We don’t have to do some big conceptual matrix of what we’re doing. We go pick our kids up and we take care of them. When your partner is sick or in a car accident or if your parents or elders are aging and you’re taking care of them, there are very clear priorities like that, where we don’t seem to have nearly as much of the head trash around it. And our priorities become super clear.

The thing about these life-changing projects that I keep referring to, these projects that take our time, energy and attention, is that a lot of times they’re not of the type that we have permission to do them or we have some clear manifesto to do them. So, we have to claim that space to be able to do them. And I think that’s when a lot of the head trash will start to pop up. And that’s where we get competing priorities because the head trash will pop up because let’s say it’s writing a book, starting a business, starting a nonprofit, creating a hobby farm, getting married, whatever. That’s when we have those mini existential crises like, “Am I the right person? Is this the right time? Do I have what it takes? What if I fail?” And that’s where that stuff comes up. And unfortunately, we have somehow encoded the belief, or at least the working principle, that if it’s hard that we shouldn’t do it, and if we’re not certain about it then we shouldn’t do it.

When the fact of the matter is a lot of times that emotional flailing, I call it “thrashing,” that when we thrash it’s because something matters to us. We don’t thrash about taking out the trash or doing laundry, changing the dishes, doing errands. There’s just a lot of things we don’t get that involved in. We either do them or we don’t do it. We might be frustrated by them, but it’s not that sort of existential “who am I? Am I the right person? Am I good enough? Someone else is doing it.” We only do those when it comes to projects that really, really matter to us.

And that’s one of the insights that I want to get across to people because I want us to be running towards those things that are difficult. I want us to be running towards those things that make us uncomfortable, rather than staying over here on the shallow shores of the comfort and the low-hanging fruit and the just checking the box and getting something else done because we know what that gets us. And we don’t like where it takes us.

Brett McKay: So, you mentioned thrashing behaviors. What are some examples of thrashing behaviors you see in people you work with?

Charlie Gilkey: “Research.” When you ask them about something and they’re like, “Oh well, I’ve been researching that for like two or three months.” Now, there’s a certain amount of research that we all need to do, but in any of these sort of “best-work projects,” which is what I call these life-changing projects, there’s always going to be this gap between the amount of information available and the amount of information that would really help you make the decision. And there’s always that leap. And so, what people try to do is try to make that gap so small that they’re taking that certainty there.

Procrastination, for a lot of people, is thrashing and just avoiding it. Now, the funny thing about that is, or I find it really interesting, is we don’t really procrastinate and we don’t really need an accountability system and we don’t really need accountability buddies to eat ice cream or whatever your dessert is. If it’s in front of us, we’ll eat it. And there’s an insight there because we typically, typically, don’t procrastinate from things that we either really enjoy to do or that we manifestly know are tied to something that truly matter to us.

Now, I say “typically” because we will procrastinate when it comes to ideas and when it comes to some of these really impactful ideas because that’s mostly head trash, and that’s mostly us trying to get ready to be ready to get ready, if that makes any sense. So, it’s like, “Oh, I got to work up to it. And then once I’ve work up to it, then I can do it.” And we spend so much time working up to it that if we just started doing it and figured it out on the fly, we’d be better off. So, procrastination can be one.

I have a buddy, really successful buddy, and I had to call him on it. We’re in a mastermind group. And I know that he’s thrashing when he starts setting up a bunch of interviews with people and conversations and meetings with people about a project that he already knows how to do. Because we’ve talked about it and he knows how to do it, but he’s still in this sort of “I’m going to talk to a bunch of people, I’m going to see the lay of the field,” so on, so forth. But I know him well enough to know that he’s going to do it his own way, and not much of that information is actually going to be useful for him whatsoever. And so, he can spend six to nine months just in conversations with folks and kind of fishing and dabbling, where if he just spent that nine months making the first steps on his own, he would be that much further along.

Sometimes, shopping could be a way that people do it. So, I guess one way to see thrashing is some of us have our own ways of productive procrastination. Other of us know… and most people, Brett, when I talk to them as their coach and I say like, “So, when you’re scared of a project and you’re thrashing, what do you do?” They could tell me what they do. They know they’re doing it. I’m like, “Hey, I noticed that you’re doing that thing there.” And they’re like, “Oh crap.” And so, those are some of the ways. And most of the time, people know what thrashing looks like for them.

Brett McKay: Yeah. That makes sense. I know my thrashing. I’ve done the research. I do the research thing like, “I’ll just keep researching, researching. I’ll wait.” I got to stop this and just start… I got to do one… I got to start taking action on this. And once I start taking action, things start solving themselves.

Charlie Gilkey: Yeah. The army calls it “gathering intelligence through action,” which… What we would say in the entrepreneurial or creative space is “do stuff and see what happens.”

Brett McKay: Simple as that. Well, so, let’s go back to this idea of competing priorities. As you said, this is one of the first places you start with clients. You look at their competing priorities and try to help them figure out the stuff they can eliminate, the projects they can eliminate from their life so they can focus on the things that really matter to them. So, how do you go about that? What questions do you ask to help them figure out those, the answer to that question? What should you eliminate from your life? Because that’s hard to do because I think a lot of people when they say, “I’m going to stop this project,” they think, “Well, I’m quitting. Quitting is for losers. I don’t want to do that.” So, they just keep doing it. So, how do you walk a client through that?

Charlie Gilkey: Yeah. So, a little bit of setup there. So, these best-work projects, again, I’m going to go back to bridging that gap. So, we talked a little bit about that, but there’s this other thing that we have to remember, is that this is the concept of displacement, that anything you do displaces or prevents you from doing a near infinity of other things that you might’ve done with that same time, energy and attention.

So, it turns out that a lot of people are doing projects that would have built the type of life they wanted to have two years ago, but they’ve moved on and something is different now. And the project is not taking them fundamentally into this best… or into this better future that they want to live in. And so, if that’s one of those scenarios, the very best thing that you could do is drop that project midstream. And yes, I know quitting is for losers and things like that, but think about it. If it’s going to take you the next three months to complete that project, but that project does not take you where you want to go, one, you spent three months on that project; but two, more importantly, that project has displaced another project that could have taken you there.

And so, one of the reasons we end up getting so overloaded, and I don’t use “overwhelmed” much when I’m working with clients and people in my community. We get to say “overwhelmed” two or three times, but then after that point I switch it. I say, “Look, here’s why we’re not talking about overwhelmed. We’re only overwhelmed when we’re overloaded.” Overwhelm is an emotion. I love understanding our emotions and being there, but the only way we get out of that emotion is if we change the load. And so, if we just replace that “overwhelmed” with “overloaded,” then we can start to say, “Okay, how do I pull my load down?”

And one of the ways you pull your load down is, again, looking at those projects. One of the things you could do is look at those projects that yes, you committed to; yes, you may have spent a certain amount of time doing it; yes, you may have spent a bunch of money; and you may have said you were going to do it and so on, so forth. But fundamentally, if that project is not taking you where you want to go, you need to let it go because it’s displacing something else.

But usually what this looks like, Brett, is just asking folks. Let’s imagine it’s the end of the year. Let’s say it’s 12 months from now and we’re celebrating. We’re meeting up for drinks. And I’m like, “What are three to five things that you want to be celebrating?” And then most people know. They know sort of the things that they would like to celebrate. And then of that three to five, I ask, “What’s the one that would make the most difference, that would be the most compelling, that would change your life the most?” There are different ways of asking that question. And a lot of people… that one gets trickier.

Another way that I’ll say that is “let’s imagine all these plans that you have for yourself, especially at the life level as opposed to the project level. Let’s imagine that there were that small handful of things that you want to do. Which one hurts the most if I were to say, ‘I’m going to take that project from you’? And you’ll never be able to do it for the rest of your life. It’s just done. Never ever.'” That one tends to wake people up in a lot of ways. Because once they can kind of see me grabbing for it, they’re like, “No, not that one.” And you can sort of start triaging and sort of feeling which ones have the most weight. And that pain is super important because at the end of the day, emotion drives action. That’s what we forget. We think our brains drive action, but not so much. It’s actually emotion. And so, tying to those things that you most want to do can be super important by just noticing that pain, that wince, that ugh.

I was giving a presentation for this book and one of my friends who is also a client, he had said, “Charlie, I thought I was done with writing books.” He’s written two, three books now. He’s like, “But then when we did that exercise and you started talking about taking some potential projects away from me, I felt a visceral pain when you grabbed for this next book concept that I kind of been toying with. And so, I’m writing that book now.” And that’s one way that we can really sort through and figure that out.

Another way of doing that would be just having people think more clearly about which of the projects and goals tie to who they most want to be versus who they think they should be. It doesn’t take very long as a coach before you realize how disastrous of a word “should” can be because people should all over themselves all day. And so, just about any time that I see someone saying there’s something that they should be doing, I mean it’s like 90% sure that it’s coming from some external source because that’s not the language that we use when it’s our own stuff. We use, “I want to do,” “I get to do,” “I’m looking forward to it.” We use a much more positive language. But when it’s an external priority and when it’s something that they believe is important to them because of other people’s belief systems and things like that, we’ll almost always use “should” there. And so, that’s a tell that that’s a potential project that might be able to go if we can’t find the internal alignment between that project and their own priorities. So, those are a few ways I would work through that.

Brett McKay: No, that’s great. So, this is all very high-level stuff. You’re trying to get aware of your competing priorities and eliminating the ones that don’t really call to you, or even using that loss aversion like, “Which one would hurt if you took it away?” And you’re also getting aware of the head trash you’ve been telling yourself, the stories you’ve been telling yourself. This is really important stuff because a lot of times people overlook this and they go right to, like I said, the tactical. But once you’ve taken care of this stuff, and I’m sure this is something that’s not one-and-done, you’re constantly working through the stuff the entire time, but once you’ve got a good idea of what are your best-work projects you want to do, that’s when you start getting more brass tacks.

And you start off, the first thing you got to do, you got to start planning. And the first part of a plan is establishing a goal. Now, I think everyone’s heard about goals and they’ve set goals for themselves, but most people set goals that aren’t very effective. How do most people construct goals? And what’s the better way to do that so it’s more concrete?

Charlie Gilkey: Yeah. I think people can get super confused about… well, part of it is just unclear goals. And so, we talk about the SMART framework, which there’s the more corporate version. There’s the one that I use in the book, which is specific, meaningful, actionable, relevant and trackable. And first off is just knowing where you’re trying to go and what that looks like. And one of the things that I think people don’t do a good enough job of is when it comes to that realistic one, and that realistic component of trying to think about where they currently are and where they’re trying to go, and the amount of effort that they’re going to put behind that change.

And so, in the book, I kind of shift the conversation towards thinking about three levels of success. So, there’s small, moderate, and epic. And if you’re not a millennial, you can say “extreme.” It’s cool. And those three different levels of success as a gauge for thinking through where you want this project to go and what you want this final outcome to look like. And the reason I started doing that is I actually fell into that one backwards from my coaching work because I noticed that people were starting with a very black/white version. So, it’s like you either succeed or you fail. And that was it. And I was like, “Well, there are layers here. There are degrees of success and degrees of failure.”

And once we started talking about more degrees of success and really being realistic about what we could do, then it’s really helped people change things because, for instance, I think what we often do is a lot of people want, say, an epic success but they’re not willing to put in the epic effort it takes to get there. And when we think more clearly and cogently about this and say, “You know what? I want to do this thing. I’m okay with it being a small success because it’s more important that I do it, and that that’s the amount of effort that I could put behind it, than I don’t do it.” And so, I think that sort of go-big-go-home mentality has crept into the way we plan and the way we set goals so that we don’t see that “you know what? I don’t have to… ”

So, let’s say you have a fitness goal. You don’t have to go from sitting on the couch to running a marathon. Small successes might be “you know what? I’m going to go from sitting on a couch to going to the gym twice a week. And I’m okay with that because that fits in with my broader goals. I’m going to be healthier that way. I don’t need to be a marathon runner. I don’t need to be a gym rat. I don’t need to go that far.”

On sort of the business side of things, especially for creative entrepreneurs and small business and micro business owners, I think too many people are not comfortable with saying, “You know what? The goal of this business is to provide a healthy living income for me. That’s all I want it to do. That’s all it’s set up to do. It doesn’t need to be a $10-million business. It doesn’t need to be much bigger than that.”

And where this comes up, Brett, is when we go back to those competing priorities, if you set the difficulty level up to moderate and epic across all places of your life, you’re going to be stretched super thin. And so, dialing it down and say, “You know what? With this project, I’m looking for a small success. I’m looking for a moderate success. Looking for an epic success. And I’m going to modulate or I’m going to apply the amount of effort relevant to that level of goal-setting as opposed to putting in a small amount of effort and expecting extreme or epic results.”

And the last thing I’ll say here, while you’re thinking about goal-setting, is if you can do it by yourself without the help of other people, it’s, at best, a moderate success. It’s probably a small success. But, at best, it’s a moderate success. You only get epic success when you recruit other people and when you bring in other people and shift the conversation from personal productivity and personal effectiveness to community effectiveness. That’s the only way you get epic results. And so, a lot of people are like, “I’m busting my butt and I’m going after this big goal.” But you see that they haven’t really built a team around them, built an alliance around them. Odds are they’re either not going to meet their goal or they’re going to do so at such a high cost and it’s going to take them so long that it’s really not going to work out for them in a way.

And last thing I’ll say about this whole epic goal and bringing people into it is if it truly matters to you, as one of the super important goal, it turns out it’s much simpler to build a team around that and to build your life around that. But you can only do that something, own something that truly, truly matters to you.

And last thing that I’ll say here is don’t try to do everything epic. Choose one thing at a time to go that hard at. And be comfortable with the other things that might need to be at small and moderate success. And I originally got this from my good friend, Michael Bungay Stanier, who, in his book, Do More Great Work, talked about acceptable mediocrity. And the basic insight that he had then, and he was talking about largely people working in corporate America, is there are plenty of things in your job that you can be acceptably mediocre at and you won’t get fired. And so, if you really want to do more great work, to use his language, and I sort of piggybacked and said, “If you really want to start finishing things that matter most, find those areas of your life where good enough is good enough. And reallocate that emotional energy, that time, that attention, and that money towards the projects that really, really do matter to you, that you’re willing to put that additional heft behind.”

Brett McKay: That was a really great insight about the small, mediocre, and epic successes in the book because yeah, I think a lot of people… I think a lot of times… not a lot of times, but oftentimes people set epic goals because they think they should. They should want a company that grows fast and gets VC funding and whatever, but when they actually try to do it, they don’t like it. But they keep doing it because they think, “Well I should be doing this. It’s what you do when you start a business.” When they could be like, “You know what? I’m going to have a moderately successful business, provide me a good living for my family. And that’s great. I enjoy that.”

Charlie Gilkey: Yeah. “I enjoy that. And that lets me actually enjoy the fruit of the labor with my family. And that lets me be this multifaceted person that can have hobbies and that can do all these other things because I’m not all consumed by this one thing.” So, I absolutely think it’s right. That’s where a lot of the “should” comes in.

Look, I’m not the guy that questions people’s goals… or excuse me, questions their values and priorities. If someone said like, “Charlie, I want to build a $20-million company. That’s what I want to do.” “Okay, well, let’s figure out why so I know where this ties into things.” But if it turns out that that’s really their jam, then that’s what we’re going to go about building. Anything else is not going to be that… they’re going to rebel and self-sabotage on anything that’s not directed towards that. However, a lot of times when you really get down and talk to people about why things matter to them, you realize that there are many other ways for them to reach where they’re trying to go.

Brett McKay: So, you got your project, you got your goal. And you talk about in the book, of course you’re not going to… You’re going to want to break this down into chunks. You can’t just be like, “I’m going to get married.” Well, there’s a lot to do to get married or put on a wedding. And I think people naturally know what those chunks are. And then you can plan on a monthly and a weekly and a quarterly basis. And you go through that in the book. But one thing that I found really powerful, and this is something you’ve been talking about since way back in 2008 when I first discovered Productive Flourishing, this idea of momentum planning and daily and weekly planning. What does that look like for people? And does it have to be really complicated? And how can this help people move forward with their goals they set out for these different projects they have for themselves?

Charlie Gilkey: Yeah. Thanks for that, Brett. Momentum planning is just the continual process of using the different scopes or the different time perspectives to trigger the amount of planning that’s relevant for that amount of time. Now, that’s very abstract so let me break it down this way. When it’s a new month, you do your monthly plan. When it’s a new week, you look at your monthly plan and your monthly plan guides what your week should look like. When you do your day, your week should guide what the day should look like. And so on.

And the hard part of it is the original setup because it’s a different way of thinking about it. It combines another powerful planning framework that I have called the Five Projects Rule, which is… the long way of saying it is no more than five active projects per time perspective. And so, per time perspective is… just that’s meaning that I think most of us intuitively know the difference between a week-sized project and a month-sized project. We intuitively know the difference between a month-sized project and a quarter-sized project. We intuitively know the difference between a quarter-sized project and a year-sized project. And that could be really helpful for us because where we often get super stuck with planning and prioritization is we’re spanning over too many different time perspectives and so we’re… And it can get very tactical here.

I know most of our conversation here today, Brett, has been fairly higher level, but it comes down to I could look at someone’s to-do list and the way they write their action, their action items, and know how clearly they think about time because you’ll see things. You’ll see two, three items that are week-sized projects; and then you’ll see two task on there; and then you’ll see a year-sized project that’s not chunked down all on the same list. And that makes our brains go haywire because it’s trying to think about the size of… It’s the analog of trying to think about the size of an ant, the size of a basketball and the size of America at the same time. Our brains just can’t do it.

And so, what momentum planning does is it helps us stay constrained to the time perspective. We’ll say, “You know what? This week I’ve got five projects that I’m going to work on this week, five of my active projects this week. What are my months? How do those relate to my five month-sized projects? Can I chunk it down?” So on, so forth.

Now, it gets pretty quick because once you’ve done the homework or once you’ve done the work of setting up what you want your, say, quarter to look like or your month to look like, any planning, any time perspective under that is super easy plan, especially if you use the Five Projects Rule. And you also don’t have to, say, be thinking about your month-sized plan and getting into the nitty gritty of what you’re going to do each day. That makes no sense. That would be like planning every bathroom stop on a trip from California to New York. You don’t really need to do that.

So, what it typically comes down to is once people get set up doing it, it takes them about two hours a week when they start using things like the 10/15 split. 10/15 split is you spend 15 minutes at the end of your day reviewing what you’ve done, and reviewing what you need to do, and setting up what you need to do the next day. And then you spend 10 minutes the next morning looking over that plan, making sure nothing’s shifted and doing it again. So, when you do it frequently enough, it’s about like anything else you do that you’ve habituated yourself to do. It’s super simple, doesn’t take as much time.

And it’s way better than trying to figure out via email what you should do for the day, which is unfortunately many people’s default, is wake up, look at email. Email determines what they should do, but think about that. That means that usually someone else’s agenda has anchored your day before you’ve even thought about what your agenda is for the day. And that’s one of those ways we end up upside down in this priority and productivity game, is that we spend so much time chasing other people’s priorities and then figuring out at three o’clock in the day like, “Wait a second. I had these other things that I wanted to do today,” but your time’s all up. So, momentum planning is just really that process of giving us the grace of not being great at planning and not being great at seeing what’s coming down the pipe, and developing a daily process of adjusting for that and getting ever better, and when reality changes to change your plan.

Brett McKay: No, I love that because I think a lot of people have this idea that planning is going to take a lot of time, but it doesn’t have to. I mean, when you first start doing it, it’s a skill you have to develop. It’ll take you a little bit longer. But once you do it on a regular basis, you can get it done really fast.

Charlie Gilkey: Yeah. I mean, you can get it done really fast. And the thing about it is, is when it comes time to any of these new habits, new ways of working, what I always remind people is the first thing we’re going to find is we’re going to find fat that we can trim from your current schedule. We’re just going to find stuff to steal from. And so, sometimes people are like, “Oh, 30 minutes a day. I can’t do it.” And yet, if you were to look at their time logs, you’d see that they spent 75 minutes on social media. And it’s like, “Well, you have the time. You’re just using it differently.” And so, what was that? It’s a paraphrase of Henry Ford’s like, “I get ahead in the time people waste.” And so, we just look for those times. And so, that’s what I would want to ask. When it comes to some of these other projects, like developing a meditation practice or mindfulness practice, people are like, “Oh, how am I going to find 20 minutes a day?” A lot of us could find 20 minutes a day, it turns out.

Now, there are some people, like if you’ve got a special needs family and you’re the primary caregiver and it’s just literally you have to be on vigilance all the time, then yeah, I get that. May be really, really hard. And so, there are outliers through this, but most of us, we can find 30 minutes, an hour a day that we can steal from something else. And so, what happens there and we kind of…

We didn’t talk about it earlier, so I’m going to say this. A lot of folks have what I call “creative constipation,” which is they’ve taken in so many ideas, they’ve taken in so much inspiration, they’ve taken in so many things that they want to do and they’re not moving on them that, at a certain point, it gets toxic on them. It starts backing up. They start getting frustrated. And we’ve all seen people who are creatively constipated. And I think many of us have been creatively constipated in our life. And the reason I want to throw that in at this point in the conversation is when we start talking about some of these changes that you need to make, it’s always what I’m going to ask is “would you rather be moving the projects that are going to change your life and make you feel better, or keep doing what you’re doing that’s got you creatively constipated because that’s your default?” All right.

So, if you want to get out of that, yeah, maybe we find and we steal 15, 30 minutes from somewhere else. But you know what? That 15, 30 minutes that you’re spending on whatever you’re currently spending is making you unhappy. It’s not taking you where you want to go. So, losing that isn’t an actual pain. It may feel like it in the moment because we are creatures of habit and creatures the way we want to keep doing what we keep doing. I get that. But the payoff from finishing some of these best-work projects is so high that it’s worth it. And if you can steal 30 minutes a day from this week… So, it’d kind of be one of those challenges. Every day, find 30 minutes that you could steal some time from, and apply it to a best-work project. And again, doesn’t have to be a work project; it could be getting in shape, playing guitar, playing video games if that’s your jam. Don’t care. I don’t care what it is, it’s just that it fires you up and it makes you come alive.

Do that this week. Maintain it. Try to find another 30 minutes next week so that you’re stealing an hour a day. And you reclaimed an hour every day. Then next week, find another 30 minutes. You’re going to reach a point to where you can’t find an additional… It’s hard to find six hours of fat in our schedules every day. But I’ve been doing this over a decade, Brett. A lot of folks can find two and a half, three hours a day pretty easily.

Brett McKay: No, I agree. And I think some of the other beauty of the daily momentum planning is that it keeps you honest. It keeps you doing things instead of just… I think another way people thrash is planning. They’re just like, “Well, I just got to keep planning. I’m going to plan. Do my weekly plan. Do my monthly plan.” But the daily planning, you see right there if you’ve moved forward with the project at all, if you’ve taken action. And I think that keeps you from that planning thrashing that sometimes people do.

Charlie Gilkey: Yeah, absolutely. And the thing about it is it doesn’t take long because it also ties in block planning. So, block planning is just the idea is rather than using normal calendar planning of 8:00 to 9:00, is rethinking your schedule and thinking, “Okay, there are certain types of blocks or certain types of energy blocks we have today. And I have four different kinds.” But it turns out that focus blocks, which are 90 to 120 minute blocks of time where you can focus on a particular project, it becomes super easy when you’re doing your momentum planner because if there are no focus blocks on a day, you’re not going to move one of those projects forward. You’re just not. There’s no time.

If you look over your week and you’re doing your weekly momentum planning and you see like, “Wait a second. I’ve got these three projects, but because I’m going to be on vacation, I’m going to be traveling, I’m going to be doing these other things, I’ve only got two focus blocks.” Okay. Well, you know from the get-go that one of those projects is going to lose Which one is going to lose? And you can be more intentional about that from the beginning.

I want us to pull some of this pain and some of this frustration to the beginning of our days, weeks or projects, as it were, rather than getting to Friday or getting to Sunday or getting to some terminal point and looking back and feeling like there’s something wrong with you or you’re uniquely defective or you can’t get your crap together. And it’s like, “No, you just didn’t have time. You had three focus blocks that week. That was the limiting factor for what you were going to do. Did you use them well? Did you not? Did you use them on the things that matter most?” And if you can say at the end of the week “look man, I had those three focus blocks. I put them on the project that really meant the most to me. It was the most meaningful. It was going to be the one that set me up as the one that I was willing to go to bat for,” no matter what else happens in the week, you did great. You used what you had to the best of your ability.

I would rather I start that way then kid ourselves and make the normal BS daily schedule that has the 17 things we want to do and then the 32 tasks we have to do and the four meetings, and then get to the end of today and wonder why you didn’t get anything done. Well, you got stuff done, but your day looked like Swiss cheese. You are never going to make that much progress on those projects because, again, focus blocks are the fuel for your best-work projects. You were never going to make progress on that unless you recalibrated how that day looked and made the space for it and made the boundaries for it.

So, I know I’m on a bit of a rant here, but, Brett, I feel you because I… I’m on a rant here because it’s actually… so much of this book comes from wanting people to be more compassionate with themselves and wanting people to find more peace because the way that we’re working is not working for so many of us. And I have conversations with people every day where they’re upset, they’re overwhelmed, they’re regretful and just exasperated. And just finally being able to say, “You know what? You get five projects this week. I know it’s really hard to accept right now, but it’s better than putting 17 on for this week and being so in the whirlwind that you get two done and then you feel bad about it. I’d rather us get three, four done, knock it out, call it a great week, and do that week over week over week,” because, Brett, that’s where that life-changing stuff happens.

It’s not the sprints that we want to go on. It’s not those weekends where you really crank down. It’s “can you show up and keep the work going week after week after week? Because weeks become months, months becomes quarters. And most people, once they start mastering being able to shape and weave quarters together, that’s where they really get some momentum going. Because when you look at a lot of the projects you want to do, whether it’s getting married, the one you used earlier, or writing books or starting businesses, starting nonprofits, doing substantial community work, they’re at least quarter-sized projects but they’re usually much longer than that. So, you got to learn to weave those together and it starts with seeing how your days and weeks are rolling and flowing together.

Brett McKay: We’ll Charlie, this has been a great conversation. Where can people go to learn more about the book and your work?

Charlie Gilkey: If you want to learn more about the book, you go to Again, that’s All one word. And if you want to see the greater body of work, you go to I mean, that’s where everything lives.

Brett McKay: And you got those PDF planners there.

Charlie Gilkey: Yeah. You could go to But if you go to productive flourishing, it’s in the nav bar. Yeah, they’re all free. You don’t have to sign up. I mean, I would love your email address. I’d love you to become part of the community. But you can just get them and use them, learn from the, I don’t know, we’re up to 2,500 blog posts and articles on PF at this point. So, there’s a lot there to learn. And there’s also every month, we have our Monthly Momentum Call, which is a no-cost Q&A community jam session where other people jump on and talk about the projects they’re doing and get some free coaching. So yeah, if you’re interested in all this and you want to start bridging that gap between where you are and that life you most want to live, check out

Brett McKay: All right. Charlie Gilkey, thanks for your time. It’s been a pleasure.

Charlie Gilkey: Thanks so much, Brett.

Brett McKay: My guest today was Charlie Gilkey. He’s the author of the book, Start Finishing. It’s available on and bookstores everywhere. You can also find out more information about his work at his website, You can download some free momentum planners there. Pretty cool. I used them back in law school over 10 years ago.

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