520: How to Start Finishing Projects with Charlie Gilkey

Pete Mockaitis
Charlie, thanks for joining us here on the How to be Awesome at Your Job podcast.

Charlie Gilkey
Pete, thanks so much for having me. I’m pumped to be here.

Pete Mockaitis
Oh, well, I’m excited to talk about starting and finishing and getting to done. Let’s start with starting, actually. I understand you don’t choose to start your year in January. How does that work and what’s the backstory here?

Charlie Gilkey
Well, there are several things going on. And thanks for that question. That’s a deep cut. Two things going on. One is the business cycle for the business that I’m in or the year cycle starts actually in August for the back-to-school, you know, back-to-work sort of thing. That’s when everyone comes back online, it’s like, “Hey, we got to get after it.” And so, that’s a really important point for my business.

And I’ve also learned that actually doing your yearly planning, if you’re going to do it on the personal side in February, is a way better time to do it because it kind of lets you shake off the high of New Year’s resolutions and all the things that go along there, and I think we’re way too optimistic during that period of the year. And then if you pay too close attention to the goals you set in, it can be a really good way to feel bad about yourself. But if you kind of wait until February, kind of around Groundhog’s Day and give yourself a redo, what I’ve learned is that we end up making way better sort of annual goals and resolutions during that period.

So, I have kind of two periods in which I do annual planning, but that’s kind of par for the course for me, and then I’m always recalibrating plans and working in it

Pete Mockaitis
That’s clever. Groundhog Day, redo, and I’m thinking Bill Murray right now. Part of that was shot near me in Woodstock, Illinois. Fun fact. So, yeah, that’s a good way to think about it in terms of like the day and where you’re going to choose to start and why. So, thank you for that. Let’s talk about the book Start Finishing. What’s the big idea here?

Charlie Gilkey
The big idea is that finished projects bridge the gap between your current reality and that life you want to live and that work you want to do. And so, a lot of us have, you know, we have really big dreams and visions for ourselves. We have that idea of our best work or our best life, and a lot of times we could feel stuck and we don’t quite know what to do. And it turns out that, again, it’s those finished projects that bridge the gap.

And I think it provides a bit of a different take on productivity, and getting things done, and sort of personal development, which either can be far too granular and focused on tasks, or it can be far too lofty and focused on sort of vision and sort of the big view of your life. And the mess of life and the beauty of life is in this middle world of projects.

Pete Mockaitis
Yes, okay. Indeed, the finished projects bridge the gap. And one thing I think I’m coming to learn is that almost finished projects don’t. And I’m thinking about all these instances in which it’s like the vast majority of the hard work is done but it’s not all the way finished and, thus, it doesn’t turn into something.

So, I remember once, we’ve got a multifamily home here and we were trying to rent out one of the units and things were almost completely renovated, cleaned, whatever but there’s like a bunch of cardboard boxes in the corner. And I think that prospective tenants can know that those won’t be there when they move in but, nonetheless, I couldn’t help but notice that every showing we did where the boxes were there did not result in an application, and those that we did with the boxes absent, totally cleaned up, did.

And so, it’s sort of like almost done doesn’t pull it off for you. But it’s kind of encouraging in that it means that there’s very little left to get to finished project status. So, those are my own musings on the finished project piece. Give me your take on that.

Charlie Gilkey
Well, I love that. You know, I talk a lot in the book about displacement which is the idea that anything you do displaces a practical infinity of things you could do, or you can’t do one thing, or you can’t do multiple things at the same time, right? Barring simple things like doing the laundry while listening to a podcast. But when it comes to this significant work that we need to do, what I call best work and what I call those things that really light us up and are part of the matrix of meaning-making that we’re in, we tend to only be able to do one thing at a time.

And the frustrating thing about those half-finished projects is that they suck up all of the time that could’ve been going to something else, but they’re not bridging that gap. They’re not doing the work that they’re supposed to do to power your life. And it would be like investing a hundred bucks a month, for however long you want to do it. Let’s just say it’s 12 months, and you don’t get the return on it until the 13th month, and then you decide on the 12th month to just stop, and then everything disappeared, right? It’s like you’ve already sunk in all of that money, you’ve already sunk in all of that time but you don’t get the reward for it just because you decided to jump to something else. So, absolutely.

And one of the things that I really stress in the book is that we should really be focusing on throughput and not load. And by that, I mean I think we commit too quickly to ideas and end up carrying too many projects around with us and too many things that we’re not going to be able to finish. And so, if you make that commitment to where this week you’re going to, like, “I’m going to do these 17 projects,” and you only do three, well, you’ve carried the additional 14. And I think, unfortunately, what we do is we’ll say, “Well, this week, I overestimated this week so I’m going to do 12,” and then we do three projects.

Well, it turns out that if we just focus on the three that matter most and we get through them faster, not only is it just about efficiency but it’s about that momentum that you can build with these finished projects. And so, depending on where you want to take this, Pete, a lot of times when I tell people I like to focus on three to five projects, the first thing that they’ll do is, like, “I can’t. I got all the things.” But let’s do a reality check here, are you actually finishing those things or is it just a continual state of juggling and a continual state of sort of commenting about the status of a project but not actually moving that project forward? Or is that continual story that you’re going to get to but you don’t?

And I get to say, you know, over the decade I’ve been doing this work with people. There’s momentum, there’s more pride, there’s more joy, and there’s more results just from coming from focusing on fewer things, getting them done, and moving to the next thing.

Pete Mockaitis
Yeah, boy, that’s well-said with regard to load because you could feel that, and the word itself, it’s like, “I am shouldering a burden, a load, like a camel or an ox. Like, there’s a lot of things on my plate, on my back here.” And so, you identify these are the things that we’re actually going to sail right through here, we’re good to go.

And it’s intriguing that when you mentioned three to five, you’re getting pushback because, I guess I’m thinking about Jay Papasan who we had on the show with the One Thing, it’s like, “Oh, man, you’re being lenient. You’re giving them three to five instead of just one.” So, let’s talk about that for a moment. Why do you think that’s perhaps the magic number there, three to five projects?

Charlie Gilkey
It’s partially because enough studies both with my own clients and work, and external study showed that that’s about the limit of which we can do. Now, I want to pause here. I love Jay’s work and I find that most people can’t just commit to one thing because when you commit to one thing, I think you often forget. Well, there’s different ways of understanding his book and the message, so that’s one thing to talk about.

I want to make room for projects that are not just economic projects. So, for me, anything that takes time, energy, and attention is a project. And so, finding a place for those cardboard boxes you’ve mentioned, that very well could be a project, right?

Pete Mockaitis
Yeah, that’s why it wasn’t done.

Charlie Gilkey
That’s why it wasn’t done.

Pete Mockaitis
It took multiple steps. There’s too many to just shove in the alley so I had to take another…do something else there.

Charlie Gilkey
Yeah, you got to find out where they are, and you got to sort, and you got to figure out which other closet you’re going to put them in, and then you open that closet and realized, “Oh, crap, there’s something in there. This got to go somewhere else.” It’s kind of like a shell game and stuff sometimes, right? But, also, getting married, getting divorced, having kids, moving across the United States, getting a new job, like all of those things are projects.

And, unfortunately, we tend to prioritize economic projects, or creative projects, or work projects, or however you want to say that, and we try to squeeze the work over our lives and the leftover, the time leftover from the economic projects, and we’re just not getting to it. And so, again, not to go overly critical of the One Thing, but it’s like we are not just work-related people. Like, our thing in life, our thing at work is one of the many things that we might want to attend to. We might also need to attend to our aging parents that we need to help transition into elder care, right?

Pete Mockaitis
Oh, yeah, absolutely. And I think that in the conversation, Jay mentioned, “Hey, what’s the one thing within like a context or a domain?” “The one thing in my marriage, the one thing in my business, etc.”

Charlie Gilkey
Etcetera. And so, I think people misunderstand his message in that way, and so I just wanted to say, like, we’re actually super aligned in that way, but that’s where we start saying the five projects, or three to five projects. Yeah, you have to look across the domains of your life and not just pick the one thing, and not just pick like one domain, and say, “I’m going to go all in on that.”

And so, for instance, right now, I’m in the middle of launching this book and doing the PR too for this book, and it’s a major project. I’m also in the middle of reintegrating back into my business after working on the book for so long, so that’s another project. And I’m also getting back into the gym and working with a personal trainer. That’s a project, so that gets me through it.

But, anyway, you asked why three to five. I think that many lets you invest in the buckets of your life that matter without spreading yourself too thin. Two, I think it’s when we look at sort of the cognitive load that we humans can bear, we sort of heard the five plus or minus two, I think, is now four plus or minus two, like, the things we can remember. Well, when you have a fewer number of projects and you can always rattle off what you’re working on, it turns out you don’t need a super complicated productivity system or an app to help you with that. You can always just sort of have those things front of mind.

And the last thing is every one of the projects, another way of thinking through this, every one of the projects that you carry, they need fuel. And I talk in the book about focused blocks which are 90 to 120 blocks of time where you can sit down and make substantial progress on things. So, if it’s a creative project, it might be that time where, let’s say it’s writing, where you actually are able to sit down and get some good words in, lean into the project, get out of the project rut. But it doesn’t have to be creative work, it can be, again, going back to that garage.

A lot of times we don’t end up cleaning the garage because we look at it, it’s like, “Oh, I think I can just move it around,” but you know that it’s going to take you three to four focused blocks because you got to figure out where everything goes and do the organizing. And because we don’t schedule that time, we know we won’t be able to make any meaningful progress, so we don’t actually start.

And so, when we look at the sort of the three to five projects, it’s like, how many of these focused blocks do you have in your life, and in a week, that you can allocate towards these things?” And no focused blocks equals no momentum.

Pete Mockaitis
Okay. Well, yeah, I’m seeing how the pieces are coming together. So, I’ve got my three to five projects, I’ve got focused blocks for 90 to 120-ish minutes, and then I’m allocating particular focused blocks towards particular projects in order to get momentum. So, I understand you’ve got a full-blown nine-step method, so I think we’re already getting into a couple of them. How about we sort of get the full view here?

Charlie Gilkey
Yes. So, the full nine-step method would be, well, there are different ways we can say this. But where people often will fall down is that they go immediately from idea to working on it, and that’s really not a great way to do it because we don’t do ideas, we do projects, and so we have to do some work to convert that idea. But before we can get there, in chapter two, well, one of the steps is really getting clear about the obstacles that are in the way from you doing this life-changing work that we’re talking about. And if you don’t start with looking at that, the first thing that you’ll do is choose an idea, start working with it, and then see, all of a sudden, that you’re upside down with it and you can’t go forward with it and sort working backwards. So, it’s a root-cause approach.

So, the first step is getting in touch with some of those root causes that keep that gap between our current reality and the life we want to live. So, second sort of step is to pick an idea that really matters to you. And that seems like obvious except for what matters to us is oftentimes not the first things that we’ll pick because of fear, because of the seeming difficulty, and we end up choosing low-hanging fruits, or we end up choosing other people’s priorities.

And then when we get into the messy middle, or towards the end of the project, we don’t get anywhere. And that’s largely because, at the end of the day, that idea did not matter enough to us, it didn’t supply the amount of meaning and sort of commitment juice that we needed it to, and so there’s just a certain point in sort of imagine this lever of, like, at past a certain point of difficulty and grit, if you don’t have the amount of internal emotional buy-in and sort of spirit in that project, the difficulty of it is going to win, right?

Pete Mockaitis
Understood.

Charlie Gilkey
And so, you have to pick an idea that matters enough for you to invest a life force that is going to take to push through it.

Pete Mockaitis
Okay, certainly. And I think that’s well-said with regard to just because you’re doing it doesn’t mean that it matters to you. You very well could’ve chosen it because you passed up the bigger things out of fear, or, “Ooh, that just sounds hard.”

Charlie Gilkey
Yeah, it just sounds hard. And I want to pause here because, over the last few decades, I think we’ve lost a lot of grit and we just sort of baked into some sort of talent myth, like if it’s hard it’s not for you because if we look at all the prodigies and the people that seemed to do things super easily, it’s like, “Oh, they got that talent. And the people that have the talent, they should go do those things. And if you don’t have that talent, maybe you go find something else that’s easier for you to do.” Right?

And what that ends up doing for a lot of us is that when we start something and it gets difficult, we sort of encode that maybe that’s a sign that we’re doing the wrong thing, maybe it’s a sign that there’s something else that I should be doing because it shouldn’t be this hard. And my whole point is, first off, if it’s worth doing well, it’s worth doing badly in the beginning. Bottom line, if it’s worth doing well, it’s worth doing badly in the beginning.

And, second off, in almost all these cases, these effortless talent displays that we see, it’s a lot of hard work and cultivation of those people behind the scenes, so they have a certain amount of budding seed time that we don’t have. And so, I want people to orient themselves so that when they see something that’s difficult, or when they see…well, let me say it this way.

I talk in the book about thrashing. And thrashing is sort of the meta work and emotional flailing and “research” that you’ll do to push an idea forward but it doesn’t actually push an idea forward, right? It’s just thrashing and flailing. And the thing about it is we don’t thrash about things that don’t matter to us. Like, no one has a mini-existential crisis about doing the laundry or taking the trash out. There’s no “Why am I the right person to do it? Is now the right time? What if I’m not good enough?” It’s like you do it or you don’t do it, right?

But when it comes to time to some of these best-work projects, which is what I call these life-changing projects that really only you can do and that change the world in really phenomenal ways, those are the ones where we’ll have all those sort of mini crises, and those are the ones where we’ll start wondering if we got what it takes, and so on and so forth.

And so, it turns out that the more it matters to you, the more you’ll thrash. And so, it’s a really good sign when you’re feeling that feeling of, like, “Wow, this is…” not just that it’s daunting, because you can take on a project that doesn’t matter and could be daunting, but you’re thinking like, “Wow, I don’t know if I’ve got what it takes. I don’t know if I’m ready for this,” those are actually really good signs that the project matters to you, because if it didn’t, you wouldn’t be feeling that way.

Pete Mockaitis
Oh, yeah, that is one worth sitting with it and remembering because you want it to come to mind when that feeling occurs again. Indeed, wow, yeah, so many implications when you’re experiencing, “Oh, my gosh, I don’t know if I have what it takes.” It’s indicative of that’s something you care about a lot or that thought would not have occurred to you at all, the, “I don’t know if I’ve got what it takes to…” And it’s not just about how challenging it is, because you might say, “But I don’t know if I have what it takes to take out the trash every day.” The take-out-the-trash challenge, you know. It’s, like, that’s probably not go do it. It just sort of says, “That’s dumb. I don’t feel like bothering.” So, yeah.

And I’ve often had this thought. I’ve said to my wife numerous times, like, when I’m feeling frustrated by something, I think, “Well, you know what, it’d be a lot easier if I didn’t care so much.” It’s like, “If I didn’t care, if my clients were getting great results in ROI from our trainings, then I’d just be like whatever.” But I do and, thusly, I get a little bit worked up associated with if folks are doing the exercises and understanding and connecting with the stuff.

Charlie Gilkey
Absolutely. It’s kind of like envy as a compass. And by that, I mean we’re not envious of other people when they don’t have something that we want. We’re only envious when someone has something that we actually care about. And, unfortunately, we try to wash out the envy, we try to wash it out, but, for me, I’m like, “Oh, maybe let’s pause a little bit and say, ‘What is it in this moment, in that sort of feeling that you have that’s telling you that something matters? And what are you going to do about it?’” as opposed to just pretending like you shouldn’t feel it.

Like, you like what you like, and you value what you value, and that’s one of those learning to center those fundamental truths and that it’s perfectly fine to like what you like and to value what you value, and you have permission to do that, then let you say, “You know what, that man with the shoes on over there, those shoes are really kicking, man. I love those shoes. I wish I had them.” So, what is it about that and what do you want to do to address that?

Maybe you decide later on, “No, maybe I was just being materialistic,” or maybe, just maybe, you like the shoes, and that’s enough for you to say, “You know what, I’m going to do something about that, meaning I’m either going to buy it, or if I can’t afford it, it’s worth it to me to do the work that I need to do to exchange my labor for money I need to get those things.” And that is a choice that I don’t think we allow ourselves to really sink into a lot of times unless they are socially-approved values and likes, in which case it’s kind of a given that we get those.

Like, many people, I know this is kind of straying in the personal finance land, but many people don’t question the value of owning a home because it’s one of those given, it’s like that’s just what you do. You go to school, you get a job, you get a partner, you buy a house, right? And so, deciding not to buy a house and deciding to be a renter for the rest of your life because you realize that 3% to 5% of you the cost of your home is going to be spent in maintenance, and those type of things in general. Like, that becomes important but a lot of people don’t give themselves permission to say, “You know what, this whole home-buying thing, not something I care so much about. I care more about freedom. I care more about that.”

And, again, I’m not trying to make a strong case for that particular economic choice. I’m just trying to say there’s a lot of decisions like that, that we default to the socially-approved cues and, unfortunately, end up living our lives doing work that we would rather not do to get stuff that we really don’t want, and then miss out on this one precious life that we have in front of us and that way we could have lived it.

Pete Mockaitis
Yeah, that’s adding up and resonating there in each of those components in terms of this is just what you do versus you’ve given some real thought to it. And when it comes to envy, I think it’s also intriguing to look and see if there are some finer distinctions because you got my wheels turning in terms of I saw this Netflix documentary about Bill Gates and I had some envy, but I don’t at all have envy for Elon Musk, right? And so, here are these two super rich people who are innovating but there’s a distinction and that is sort of rich fodder for potential insight. So, it’s like, where do you have envy and where is there a similar situation where you don’t? And then we’re really homing in on something.

Charlie Gilkey
Yeah. So, what does that envy tell you about your values? That would be the question, right? And where is the lack of envy in other places, not do the same things? So, again, these are really good tools. And the thing about it is, especially productivity but I’ll say the broader sort of personal development, we approach it from a headspace in like a thinking space. But when it comes down to actually doing the work that changes lives, changes our lives, changes other people’s lives, and having the courage and being able to set up the boundaries, it’s always going to come back to your heart space. It’s always going to come back to stuff that really matters.

And so, I encourage people to actually steer with that as opposed to getting caught into all the things sort of in that headspace of what you should do. And, just while I’m on that, just about any time you’re telling yourself you should do something, pause. Because, usually, what you’re telling yourself is that there’s some external standard that is a guideline for what you ought to be doing. And where I want you to pause is say, “But is that really true for me? Is it really true that that’s the right thing for me to do?”

And sometimes when you should, in the case of given who I am and what I care about, this is the thing that I need to do, but I’ve learned so oftentimes, so many times we only use the word should when it’s an external rule, an external guide. And when it’s our own sort of compass, we say, “I get to…” or, “This matters to me,” or, “I want to…” or, “This is meaningful.” Like, we use all sorts of words that are different than the should word. Does it make sense, Pete?

Pete Mockaitis
Oh, absolutely. Yeah, I have been thinking about should a lot lately in terms of, I guess, when I see or hear should, I get very curious as well in terms of “What do you really mean by that?” And I find, often, that should, all that really means is, “If one were to invest additional time, energy, money, resource in this domain, there would be some kind of a benefit.” But, like you said with regard to opportunity cost, well, is that really worthwhile?

And I’m really intrigued when I hear it with regard to people talking about TV or Netflix, like, “Oh, have you seen the latest season of this?” And I say, “Oh, no, I should really watch that.” And I’m thinking, “Man, really, should you? I think you got the right idea and I’m the one who should watch less Netflix.”

Charlie Gilkey
Yeah, stop shooting on yourself is a long way of saying it.

Pete Mockaitis
Certainly.

Charlie Gilkey
Like, if you wanted to do it, you would have watched the show already. If it really mattered to you, it just turns out that, I talk a lot about cage matches, whether it’s a priority cage match or a project cage match, and that’s just a homage to my upbringing in the ‘80s of professional wrestling, where the basic idea, if you’ve never seen this, it’s like a bunch of competitors get into the ring, and the strongest one, some way or the other, ends up throwing everybody else out or beating them into submission. So, I know, terrible metaphor for this particular context.

But there are certain priorities and certain things that they’re always going to win that cage match. If you are a parent and something comes up about your kids, you’re going to displace almost everything else to make sure that their needs are attended to. And so, what I want more of us to do is to look at all the OPP, the other people’s priorities, not the Naughty by Nature O.P.P. song, but that’s also a great song, right? I want to look at everyone else’s priorities and say, “You know what, why and how are those more important than my own?” Because you could be that person that runs around trying to fill everybody else’s priorities and end up exhausted and depleted and frustrated, and still not be able to appease everyone and fill their buckets.

Or, you can say, “You know what, I can’t be everything for everyone. I’m choosing for the smaller set of priorities to be who I am and to live in the way, live and work and allocate my time in a way that really accentuates those values.” And that does mean that there are a lot of people who might be mad at you, there might be a lot of people who decide not to be friends with you, or there might be a lot of other, like there might be some social fallout for that. But, again, look forward into a decade, would you rather have done the things that really are going to power the type of life you want to live or just continue to maintain other people’s projects and priorities?

Pete Mockaitis
That’s great. And while we’re here, as I’m rolling with it, what are your pro tips on saying no?

Charlie Gilkey
Pro tips on saying no. It depends on where it’s coming from, so I got to start with that. Obviously, if your boss walks into the door, walks into the office, and is like, “Hey, I’ve got a new project and priority for you,” be careful about saying no to that because you may not get to say yes to the job tomorrow, right? And so, there’s a context there. And even with bosses, and I’ve had to do this in the military, back when I was in the Army, where it’s like you get handed this project, or you get handed this mission, you’re like, “Okay. Well, I can do this but it may displace some of these other priorities that you have for me and that we’ve already talked about. So, do you want me to do this instead of that? Or like what’s the priority conversation here?”

And that I think always returning to, especially the work environment, to priorities is a good way to talk about it, because you’re not saying, “Screw you. I don’t care.” You’re saying, “I’m here to do a certain job, or I’m here to make sure that I’m providing the best value to this team that I can. We’ve already discussed these other ways in which I could provide that value. Now, there’s this new thing. Is this better than that?” And that’s a good conversation that a lot of teams can have even that a lot of people can have with their boss.

I think when it’s with your friends and family, first off, my observation is that we spend too little time talking to friends and family about what actually matters to us, and so we end up negotiating a bunch of trivial things. We get invited to go to the club, or you get invited to go to watch the football game on Saturday, or you get invited to all these sorts of things, or you get expected to, like, “Hey, can you watch my kid today?” or, “Can you come over?” and there’s never been that talk of, like, “Actually, Saturday is the day that I spend in community service, and that’s why I’m down to soup kitchen every Saturday because that’s super important to me.” We haven’t established our priorities first and so we’re always negotiating what matters on the backside of things.

So, step one is to have more intentional conversations with your friends and family about things that matter to you, the projects you’re working on and how they fit into this life that you want to live, in that way when you do get asked to do something or requested to do something, there’s a preexisting conversation about some things that matter. It changes it, it changes the conversations because the people around you understand that it’s not like you’re sitting at home on that Saturday evening just looking for something to do, right? You have these other plans for yourself and other things that truly matter, so it does help with that conversation.

The second way that I would look in on this one would be to, where it’s a resonant request, meaning it’s from someone who can legitimately make that request, and it’s something that, in general, like you’re open to doing it but perhaps can’t do it right now, is always provide that alternative. It’s like, “You know, I’m sorry that I can’t do that that day because I have some preexisting commitments. Is there a way that I can do that Wednesday or Friday or this other period of time? Because what you’re requesting from me, I actually do care about and I care about the relationship that we’re in here. That particular time is not the best time.”

And the last thing that I would say is, and this goes back to talking about things that matter and being honest with your friends and family, is if there are certain things that you’re being requested to do and they don’t resonate, and they aren’t something you’re ever going to do, don’t BS people and be like, “Oh, yeah, I’ll get to it,” or, “Yeah, it sounds great,” or, “We’ll have coffee in three months.” If you know that you don’t want to have coffee in three months, avoid that. Avoid setting that sort of precedent. And I know that seems perhaps obvious, and maybe it seems hard, but I think too many people are not honest with the people around them for fear of rejection, or for fear of becoming a social pariah, or whatever that is, and we end up negotiating a lot of things that, if we were just being forthright with folks, we wouldn’t have to be negotiating.

Pete Mockaitis
Charlie, I have no interest in drinking coffee with you.

Charlie Gilkey
Hey, I got it. Cool.

Pete Mockaitis
That’s not true, Charlie. I think it’d be a lot of fun.

Charlie Gilkey
Yeah.

Pete Mockaitis
So, how does one say that?

Charlie Gilkey
How does one say, “I’m not interested in having coffee”?

Pete Mockaitis
Yeah. Ever.

Charlie Gilkey
Ever.

Pete Mockaitis
Because I think that’s kind of what you’re saying. They’re saying, “Hey, in a few months when things quiet down,” it’s like that’s kind of what you mean is that’s just fundamentally is not worth doing to you.

Charlie Gilkey
Yeah, that’s a tricky one, right? Well, here’s what I’ll say. Very rarely do I have someone out of the blue who doesn’t know just ask me to go for coffee, right? So, typically, it’s in the context where they know I got a lot of stuff going on, and so I can say, “Ooh, I’m going to have a hard time.” Or, what I will normally say is, “Hey,” especially if I don’t know them and I really don’t want to have coffee, like, “What’s your thought there? What are you thinking?” And this may just be peculiar to my line of work because I am a coach and things like that.

If it comes up with doing all these things, like, “I’d love to have coffee because I want to pick your brain about something,” then I can say, “Hey, Pete, I’d love to have that conversation. I am a professional coach, and the best way for us to have that conversation would be under this sort of structure. Are you open for that conversation?” And, basically, what that’s saying in some way, without being a butthole about it, is, one…

Pete Mockaitis
It ain’t free.

Charlie Gilkey
It ain’t free. And, two, if it matters to you, like if it matters for you enough to do it, then let’s have that conversation. But, for me to show up and do that for free, like, again, that’s displaced other people who pay me to do this, right?

Pete Mockaitis
Certainly, yeah.

Charlie Gilkey
And, on that note, I have a certain amount of time that I just think of as service to the world and community service and things like that. And so, there are some people who are like, “You know what, that’d totally be something that I would pay…” like someone would pay me to do. But, in this circumstance, I just feel called that this is a conversation that I want to be in and so I’ll do it.

Pete Mockaitis
Right.

Charlie Gilkey
But, again, I don’t get a lot of that. I know women actually get a lot more requests for coffee, and it’s kind of one of those things. Are they requesting you to coffee to pick your brain? Which is basically that conversation we were just having, Pete. Or are they wanting to establish a friendship? And so, I think, largely speaking, the best way to say no sometimes is to say, “Let’s determine what we’re actually trying to do.”

If you want to avoid that tendency to say yes too quickly, and this does seem to contradict what I was saying a little bit earlier, your go-to is always, “Let me check my schedule and see what projects I have, and see how I can make that work.” And then say, “Let me get back to you in a day or so.” And then that at least gives you enough time to not overcommit yourself, but also think about how you’re going to disengage from that.

Pete Mockaitis
Understood. Thank you. Well, Charlie, we got a lot of good stuff here. I had a big list going in. You’ve distinguished three different ways projects get stuck, and I think that’s worth mentioning. So, can you give us, what are these three categories and how do we deal with those?

Charlie Gilkey
Yeah, can I get a three and a half here?

Pete Mockaitis
Oh, 3.5, yeah.

Charlie Gilkey
Three-point-five because I kind of want to talk about the red zone on this one.

Pete Mockaitis
Okay.

Charlie Gilkey
Because the red zone is a metaphor, I’m appealing to American football, where as you get in that last 20 yards of the drive, a lot of teams will fumble it, or a lot of teams will screw up in that last 20 yards, and then end up in a field goal situation, or a turnover situation. And the reason you end up in a red zone is because they’re such tight space that everything working against you doesn’t have to spread itself so thin.

And so, projects can get stuck in that red zone where you’re in that last sort of 3% that seems to take as long as the full 97% before, and a lot of that is just about, again, that’s when your perfectionism is going to come up, that’s when your procrastination is going to come up, that’s when all of the implications of the scope and goal will creep, start coming up. And so, just understand that that’s a normal part of the process.

And in the book, I do give some ways to work through the red zone, but part of it is doubling down at the end and not thinking that you’re just going to be able to slide it home. I’m being super quick there because I’m conscious of time.

The other three sort of ways projects get stuck, so there are cascades, there are logjams, and there are tar pits. Cascades are when you have a series of projects that you got to do step A before you do step B before you do step C, and step A gets behind, so step B gets behind, so step C gets behind, and you might have a whole cascade of those. And at a certain point, I think we’ve all been in that where you start spending more time trying to keep your projects up to date and communicating with people about those projects than just getting those projects done in the first place, and it just keeps slipping on you.

And so, the trick of solving the cascade is you actually have to clip both ends of the cascade. You have to stop new projects coming in and, in a lot of times, you have to look at those projects that are backed up and start deferring them, start dropping them, and start focusing on getting the ones that you can through so that you get it going again. So, you can’t just focus on the new projects.

So, there are times, Pete, where people will come to me and they’ll tell me what they’re doing, it’s like, “All right. So, first thing is we’re on a new project diet, right? You don’t get to take on any new projects until we get these ones done because we don’t have any space to add anything anyways. It’s just going to be a frustrating conversation for both of us three weeks later because you’re going to tell me, ‘I didn’t make any progress on anything.’ And I’ll ask you why, because you didn’t have time, so on and so forth, so let’s not do that.” New project diet.

So, you got to sort of clip both ends. Once you get enough of those projects going, then maybe start accepting new projects back into the pipeline. And how that might work in a work context is, again, talking to your boss and being like, “Look, here’s what’s happening. I’m not able to get any of these projects done because of the rate this is coming. I need two weeks or I need a week where I can just focus on getting these things caught up. Here’s my plan for that. Is that all right with you?”

And a lot of times, when faced between you not getting something done, and you getting something done, bosses and teammates would much rather you get something done. And so, it’s not as hard of a conversation as people make it. You just have to admit that the amount of inputs that are coming in exceed your ability to put them in the output mode. And that’s a hard conversation for a lot of us to have, but having that conversation after four months of struggling, doesn’t do you any favors. If you see that, you might as well get ahead of it.

You know, a lot of what we’ve been talking about today is about taking the hard parts or maybe the pain parts of getting stuff done and putting them on the frontside of things, because the idea is that at some point, if you’re going to be falling behind and overcommitting and your projects are going to be stacking up on you, there’s a certain amount of pain that that’s going to cause. We know that. And so, it’s not necessarily avoiding the pain. It’s, can you put some of the pain at the beginning of it so that you don’t have to face so much of it later on? So, cascade, that’s how you handle cascades.

Logjams are when you have too many projects competing for the same amount of time. This is the classic case where you have five deadlines on Friday, and you start looking at all the work it would take to do those deadlines. There’s just no way you can do them all at the same time. So, it’s different than the cascade, because cascade, you can kind of think of like projects stacked back to back. A logjam is like projects stacked on top of each other, and there’s just a certain amount that’s kind of like trying to push the golf ball through the garden hose. It doesn’t work, right?

So, with the logjam, some of it is similar in the sense of like a no-new-project diet will help but you really have to get real about, like, “Which of those projects that are trying to compete for the same amount of time have to be done?” Like, if you don’t do them, you’ll get fired, or it will cause a lot of pain, and which ones are nice to do? And those nice to do ones, or would be good to get done, or the ones that get deprioritized so you can focus on getting those ones that will get you in hot water done, and then you can sort of reestablish the flow of your projects again.

And the last one is a tarpit. And I’ve learned this for a lot of creative projects, but a tarpit is when that project is like you sort of touch it a little bit, and then the second you let it go, it starts sinking in a tarpit, in like one of those Jurassic tarpits, it gets stickier and deeper and deeper. And not only do you have to work to pick it up, you have to work to pull it out of it all over again. So, if you’re ever stuck with one of those projects and the mental or spiritual or literal closet, you know what I’m talking about. It’s so hard to resurrect those things. And then once you do, the second you let it go, it starts sinking back in there.

And so, the thing about tarpits is a lot of times it’s some layer of fear that keeps that thing hiding in the background, or there are some deep sort of emotion around it, and you’ve got to get clear about what that is before you get back into that project, because if you don’t address it, the same pattern of it sinking deeper and deeper is going to keep happening.

And then the other thing about tarpits, projects in a tarpit, is you want to make sure to give it enough time, enough of those focused blocks that I’ve talked about, that you can go ahead and clear all of the muck and get some significant progress on it, because, I’ll tell you what, there are a few things better than seeing one of those tarpit projects and figuring out, it actually does still matter to you, you’ve just been daunted or overwhelmed or steered by it, and then it’s knuckling down for two weeks, three weeks, four weeks, getting it done. It’d be like, “You know what, it’s done. It’s out of my soul. It’s out my emotions, out of my brain, and I can move onto the next thing, feeling so much more buoyant, and not just weighed down by that project that’s just sort of haunting me from the closet.”

Pete Mockaitis
And can you give us some examples of projects that often fall into the tarpit category?

Charlie Gilkey
Yeah. So, creative projects and creative, broadly speaking, so if you want to write a book, yeah, that can be a tarpit project. If you’re a musician, you’ve been meaning to write an album, those fall into the tarpit pretty quickly because it can be challenging to bare your soul in the ways that it takes to do that type of creative work.

A common tarpit project that I’ve seen from people, I haven’t had this problem yet because of the age of my parents, but it’s when you end up with heirlooms and sentimental items that you inherit from your parents when they pass. They end up in garages and closets where you just can’t get in there, and you can’t figure out what to do with your mom’s baby shoes that she gifted to you for some reason.

And so, those types of projects, and anything around clearing out the material belongings or material items that exists from relationships, so it could be that you have that box. I know of a few of my female friends that have boxes of letters and cards from boyfriends they had in high school, right? And I’m like, “Well, okay. So, what’s that about?” But just getting in there and figuring out what to do with it and things like that can be a total tarpit.

For a lot folks, financial stuff, getting your taxes in order, figuring out where all your money has gone, is going, might go, anything around money can be one of those tarpit projects which is like, “You know, I want to get in it, I get in there, I poke around a little bit, but I don’t actually make the investment. I don’t actually buy the insurance. I don’t actually do the thing that I need to do.” Those tend to be classic sources of tarpits.

And what else? I think those are three pretty good cases of that.

Pete Mockaitis
Okay. That’s lovely. Thank you. Well, tell me, Charlie, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Charlie Gilkey
I know we’re wrapping things up, but I wanted to talk briefly about success packs because it’s a game-changer for people. And success packs are just a group of people that you put around yourself and your project that really help you figure out how to go. I would normally talk a little bit more about this, but the thing about success packs is they help you convert “how” problems into “who” solutions.

And when you use them, it takes a lot of that overload that we can feel, that overwhelm that we can feel about having to have it all figure out ourselves, and all the work that we might do, and feeling alone, and just realizing that we have a team of people that we can reach out to for different reasons. And so, whenever you’re wanting to do work that matters for you, before you start making heavy plans, before you start jumping headlong in there, think about the group of people that you would want to put around you that will be your advisors, that will be your helpers, that will be the people who benefit from the projects, and that will be your guides so that, again, you’re not stuck doing this type of work alone.

Pete Mockaitis
Understood. Thank you. So, now, tell me about a favorite quote, something you find inspiring.

Charlie Gilkey
This one is from Lao Tzu from the Tao Te Ching and it goes, I’ll give this version of it, “Because the master is aware of her faults, she is faultless.” And the idea there goes that because she’s honest about her limitations and constraints and who she is, those limitations, constraints and character quirks don’t end up tripping her up and making her life harder than it needs to be.

Pete Mockaitis
Understood.

Charlie Gilkey
And so, I love that because I think a lot of times we don’t want to talk about those constraints and limitations and challenges. It’s kind of like when people are like, “Well, we don’t want to talk about the hard things because it makes them real.” But if you arm is broken, like you talking about your arm being broken doesn’t break it. It’s already broken. So, what are you going to do about it? And so, I love that one because whenever I’m, one, it allows a lot of room for humility but it also allows a lot of room for hope at the same time.

Pete Mockaitis
Yes, thank you. And how about a favorite study, or experiment, or bit of research?

Charlie Gilkey
I’ve been really geeking out on the marshmallow test, and especially that they got it wrong.

It turns out that that was largely, when they did the research on the data and they tried to run it again, what they found out was actually a determination of someone’s social status was actually what was determining their ability to hold out or not. And the reason I’m super pumped about that finding is, one, having grown up as a poor kid, and just seeing how different realities manifest because of just where you grew up on the opportunity divide, gave me a lot of hope there. But it also reminds me that we need to be super careful about the judgments we make on people, and that we need to dig deeper when we’re starting to see some of these types of trends.

And so, again, it’s one of those big things that’s largely grit determined what you would be able to do in life, and it turns out that where you start in life determined how much grit you may have. And that means, in some ways, grit is a muscle that we can all work on, and our future is not necessarily predicated by where we grew up, even though that has a super strong influence on it.

Pete Mockaitis
Thank you. And how about a favorite book?

Charlie Gilkey
Well, since I got the quote from that, I probably should say the Tao Te Ching by Lao Tzu.

Pete Mockaitis
Okay. And a favorite tool, something you use to be awesome at your job?

Charlie Gilkey
The tool that’s popping up to me is the AlphaSmart Neo2 which is a late ‘90s word processor. It’s, basically, a keyboard with an LCD screen on it. And it’s really helpful for writing when you’ve been super distracted, or when you got a lot going on. It’s actually what I wrote about 95% of Start Finishing on. And when it comes to quality words and volume of words, I have yet to find a better solution than the AlphaSmart Neo.

Pete Mockaitis
Fascinating. Thank you. And how about a favorite habit?

Charlie Gilkey
That would have to be my morning routine. And so, I drink tea and meditate for at least 25 minutes in the morning, and that 25 minutes setup the rest of the day. And there’s a marked difference when I don’t have that 25 minutes than when I do, or when I don’t prioritize it. So, that is the habit that keeps all the other habits going.

Pete Mockaitis
Okay. And is there a particular nugget you share that really seems to connect and resonate with folks; they quote it back to you often?

Charlie Gilkey
I don’t have a really good one but what resonates is a quote but something that a lot of readers have said about this book, is really commenting that the part about them not being uniquely defective really stands out. So, I can say it in a quote form. So, in the book, I talk about, in chapter one, I just remind people that we’re not uniquely defective. We’re not fated to being able to get our stuff together. And we’re not fated to always be in struggles with that. And I think that’s such an important point because a lot of times we approach really important stuff from a frame of like there’s something uniquely defective about us that’s going to keep us from being successful.

And when you let go of that belief, when you let go of that way of orienting yourself to the world, and you see that, to quote Marie Forleo of like everything is figure-outable, and you are fundamentally able to change if you will yourself to do it, it opens up the world of possibilities. And so, yeah, that’s the one I would put down as you’re not uniquely defective.

Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?

Charlie Gilkey
So, if you’re interested in the book, go to StartFinishingBook.com, that’s all one word. If you’re interested in the broader body of work that I’ve got, you can find it at ProductiveFlourishing.com.

Pete Mockaitis
And do you have a final challenge or call to action for folks seeking to be awesome at their jobs?

Charlie Gilkey
Yeah. In the next full week that you have, reach into that closet of your soul where you put one of those projects that really matter, one of those ideas that really matter, that will make your work better, that will make your colleagues work better, that will make your workplace better, and start thinking about, “How can I spend at least two hours this week bringing that idea to life and turning it into a project?” Start with that two hours and if that’s all you’ve got is two hours a week, better to work on that and make work awesome than to leave it in there waiting for a better time.

Pete Mockaitis
All right. Charlie, this has been so much. Thank you and good luck in all of your finishing projects.

Charlie Gilkey
Thanks so much for having me, Pete.