Author and Speaker, Charlie Gilkey on How to Accomplish More by Surrounding Yourself with These 4 Types of People

In this week’s episode of the Garlic Marketing Show, modern-day renaissance man, Charlie Gilkey is helping listeners re-work their mindset to accomplish more and to surround themselves with the right people. 

Are you someone that has a lot of projects that you just can’t seem to move the needle on?

Charlie’s recent book, ‘Start Finishing: How to Go from Idea to Done,’ gives you a 9-step method for success. Beyond the 9 steps, Charlie does a deep dive into the challenges that get in our way. Pay close attention because he gives incredibly valuable information and tools to help you rework your mindset to see your ideas through and ultimately, feel fulfilled.

What You’ll Learn:

  • How to FINISH those lingering projects
  • How to use focus blocks to fuel your best work
  • The 4 kinds of people that you need in your success pack
  • The 2 types of people that hinder your success
  • How to prioritize your tasks and projects


Links & Resources:

Full Episode Transcript:


Ian Garlic: Welcome to the Garlic Marketing Show. Ian Garlic here, and today’s guest- We are going to geek out on a lot of topics. I feel that this interview is going to get super nerdy, so you should be ready for it. But before we get started and I introduce my awesome guest, Charlie. 

This podcast is brought to you by STORYCREWS. If you are looking to become an authority and leader, video is the way to do it. And the best way to do it is to hire people trained in storytelling and marketing. Go to STORYCREWS.COM to find videographers trained in storytelling in your area. 

All right. Charlie Gilkey, friend, author, Eagle scout, former cheerleader, philosopher, military veteran, old soul, what else can you- you’ve done it all and we’re going to talk to you about your book ‘Start Finishing Today’ because I think it’s one of the most important things and getting some detail about how to finish projects, which is, I think most of the people listening, it’s their biggest problem.


Ian Garlic: But Charlie, let’s do an interesting bio that you haven’t done before. You’ve got a lot of stuff on here, but how did you get to this point where, you know, we just talked about inflection points, but real quick, how did you get to the point of being a writer and a coach and entrepreneur?


Charlie Gilkey: So real quick, first, thanks for having me. I really appreciate that, Ian. So I guess there’s sort of two things to look at here. One is growing up where I grew up in the South, being multiracial black like there was a lot of just having to figure stuff out because no one was giving me anything.

Right? And so it was like, you don’t know how to do X. No one around you knows how to do it. So you get in there and you figure it out and you’re like, “Oh, that’s how you do it.” So I learned very quickly, that for most things I wanted to learn to do, someone had written a book on it. 

I learned this as a child (eight, nine years old). I’m like, “I want to do X. I’m like, so what are the books that you guys?” People write. They write books about things they do. So I started that pathway, but a really important inflection point for me was when I started teaching at a boy scout camp when I was 13, and so I started out being an aquatics instructor for two years, and then I became a trail guide, then became sort of program director.

So I’m doing this when I’m 13, 14, 15, 16. Just going in there and being in this group of kids from all sorts of different backgrounds doing stuff, figuring it out, teaching, writing about it, teaching about it. It just really became that DNA. And in part of that experience, as I had some friends and we were like- I’m looking back and I was like, I was reading that way too early. 

So I remember reading “Zen and the Art of Motorcycle Maintenance” when I was 14. 


Ian Garlic: Me too!


Charlie Gilkey: Right? No one, like I had never taken philosophy. I had no idea really what was going on, but I was like, I love this. And so then I sort of branched off into other sorts of philosophy.

I came home. I was at the laundromat one time and my mom was sitting there and she looked over and it was, I was reading the Republic by Plato, right. I was 14 or 15 and so she was originally like, 

“You know, most kids are pissed about having to go to the laundry mat, but you’re fine with it. Cause you put clothes in there and you go back and you read a few. But what’s The Republic about?” 

She had never read it. Right? And never heard of it. And so I’m trying to explain, I’m 15 not really trained, trying to explain this to my mom. Anyways, so these forces kind of came together and created this amalgam.

And so I’ve just been this way. Like one, I love Marie Forleo’s title of her new book, ‘Everything is Figureoutable’ right? When you sort of learn that everything is “figureoutable” and two, you learned that a good way of figuring things out is to read books to shorthand the experience that you then need to go out into the world and actually get, and then three, there’s this power in lighting the path for other people and being there. 

So that’s still what I do. I’ve been doing this in some version of this since I was 12 or 13, and so I  just turned 40. So yeah, this is a different way of doing the same thing I’ve always been doing. 


Ian Garlic: Your website and blog, this Productive Flourishing, because I think that, you know, you talk about reading and learning and stuff, I think a lot of us read and learn it, but executing it is the next level of it to really bring it in. I feel like Productive Flourishing is around that, but explain that to people. What does “Productive Flourishing” mean?


Charlie Gilkey: All right. So it’s really important that “productive” modifies “flourishing.” Okay? Especially in sort of the productivity and “git ‘er done” literature, it’s all about doing, doing, doing. Righ?.

And there’s very little conversation about to what end are you better off from all the doing? So Productive Flourishing is really about how to thrive through action, right? How do you become this best version of yourself? You can’t just do it in your head. So then you gotta do it in the world.

What I’ve learned, for the longest time, and I’m just super anchored on, is that you’ve got to do it with people. You’ve got to do it with the right people. So if you want to thrive- I’m Aristotelian in the sense that I think we become by doing. People are like, “You know, I’m not a very courageous person.”

And I’m like, “Well, do the things that exhibit courage and you’ll become courageous.” Like, I don’t know that anyone just sits there and like, “I’m just that person that’s courageous.” We always become, by doing. So Productive Flourishing is I guess a super nerdy way of saying we become by doing and the point of doing is to thrive.


Ian Garlic: Yes, and that is a very valid point because a lot of people are just like, “Boom, boom, boom” and then, “Oh, I gotta do this. Oh, so-and-so’s doing this.” I see this all the time. Like, “Oh, I saw so-and-so doing this, so I’ve got to do this,” and “I saw so-and-so doing this, so I’ve got to do this.” People think that and they connect that doing with success.

But you’re talking about having intention on it. So what ways do you make sure that you have that intention?


Charlie Gilkey: I’m glad you mentioned success because success is not the rock bottom thing we’re after. Success gets us something else, right? One thing that I do is help people think about what that something else is in their life that they’re really going after.

Sometimes these are root sort of things we don’t need to explain anymore. Like happiness, strong relationships with people we love, fun, play, freedom. Like those types of things are the root things that we actually care about. And if quote-unquote, success is pushing you further away from those things, guess what?

You’re not succeeding, right? You’re playing the game that you’re seeing on Instagram, that you’re seeing on TV. You’re sort of trapped in this prison that you created for yourself. People inside that prison are not happy. They’re not in great relationships. And so that’s, that’s where I want to keep people anchored on.

And whether we’re talking about our work (economic work) or whether we’re talking about our life, I’m always going to be like, 

“Okay, how is that getting you closer to that thing?” 

There are so many people, for instance, that focus on financial freedom and that’s a great goal except for they get there, and they don’t know what to do, right? They’ve been spending their last few decades trying to get out of debt, trying to get to a minimal lifestyle, maybe their Mustachian and then they get there and they’re like, “But like what for? I don’t know what to do with myself. Who am I? I don’t have to work now, but who am I going to be?”

And that’s what we’re trying to avoid is getting to that point in our life where we’ve stacked all the bricks, we’ve done all the projects, we’ve been on the ladder of success, and we get there and we say, “But you know what? It’s not it. It’s not what I have been working for these last decades.”


Ian Garlic: And when you say “it’s not it,” do you mean it’s not the right ladder or they got to the on the right ladder but didn’t want to be at the top of it?


Charlie Gilkey: It can mean multiple things. Again, I’m not going to be super normative here and say, “Here’s how you should live your life” or anything like that. But you see people climbing the ladder the wrong ladder on the wrong wall, and they’re getting higher up and people like that they’re climbing. 

But at a point, they look down and they’re like, “Shit, I’m on the wrong ladder and on the wrong wall. I’ve been doing a lot of climbing for nothing.” 

Sometimes it’s because we think there are things that will make us happy and they ended up not. So if you read, um, Oh, it’s stumbling on happiness, it’ll come back to me…

Marty Seligman’s book ‘Stumbling On Happiness.’ One of the thesis from that book is that we’re terrible about predicting what’s going to make us happy. We’re super terrible at it. He gives some strategies for how to do that, but part of it is we’re terrible at predicting what’s gonna make us happy.

The second is, we, unfortunately, live our life by shitting on ourselves. Meaning, we see someone else’s values, we see something else that someone else cares about and we say, “Oh, we should want that” or “That’s what we should do.” and we end up in some life version of the Fyre Festival where we’re caught up. And if you’re not familiar with the Fyre Festival, it is basically a bunch of smoke and mirrors and people over-promising a certain lifestyle.

But when they got there, it was a complete crap show. Right?


Ian Garlic: I love that movie.


Charlie Gilkey: We sort of life in that, in that world, and it’s too easy because I think… I’m a, like an early millennial, right? Or late millennial, depending upon where you draw that line.

But I look at people that are a little bit younger than me that have grown up on really digital, social validation as a metric for what happiness is. Yeah. So they see people that they’re doing all the things on Instagram and they get the thousands of likes and things like that, and they’re like, “Oh, that’s what happiness,” or “That’s what success is,” or “That’s what I want.”

But ultimately, a lot of times it’s not.


Ian Garlic: It’s true. It is true and it’s easy to default to like, “Oh, that’s what happiness is. That’s what success is.” Cause it’s, it’s scary to define it yourself. So, I want to talk about finishing, cause I feel like this also, you know, obviously your book here.

‘Start finishing.’ Awesome stuff. It’s important because I think, you know, a lot of people listening to this, they’re good at getting stuff started, especially when they see it. They’re like, “Oh, let me get this course. Let me get started cause I want 80,000 Instagram followers,” or “I want, I need 500 likes per post.” “I want to be a YouTube influencer.” 

And like you said, “To what end?” and I want to talk about deciding that in a second, but I want to go a little, geeky on the philosophy since you’re a philosopher and I noticed you were talking about ‘Zen and Automotive Motorcycle Maintenance,’ and you have some Taoism in there. So how does this line up with a whole Taoist idea of non-action, of moving without action?


Charlie Gilkey: Yeah. I think “Wei wu wei” which is what you’re talking about is often misunderstood. Right? I think a better way of understanding that for Americans is acting without striving. Right? So it’s not about non-action. It’s about that striving, that push, that two tight hands on the wheel, right?

Sort of, I got to drive everything that focuses your attention just on that train. As opposed to finding those ways in your life where there’s this natural flow between your principles, your priorities, and the way that you’re spending your days. So when you get into true non-action or wei wu wei, it’s actually, you’re getting a lot done.

It just doesn’t feel like that push, that drive that, you know, you don’t need 18 cups of coffee a day for that drive to work. I think that’s where, again, when we think of non-action, I think that often is misunderstood. It’s actually wei wu wei means “doing, not doing,” which doesn’t translate very well to the United States or to Americans. But I think that’s what that is more of what’s implied. Or like when you look at the totality of the data chain, that’s really what’s being said.


Ian Garlic: And that’s amazing. I mean, then we’re talking about a flow state in your work. Getting into that flow state…

I mean, you’re coaching people, you’re obviously thinking a lot about this. What are the keys then to finding that right ladder? Finding that way and making sure you’re doing? When you set out to make that plan, that it’s the plan that will most likely get you into that flow state?


Charlie Gilkey: Yeah. I think one of the things to think about is planning, and people think planning is a cerebral exercise and it’s partially a cerebral exercise, but it’s also a really emotional exercise. If you don’t create a plan that is compelling and drives you to do it, and makes you super clear and regretful about the things you’re not going to be able to do because you’re doing that,

You haven’t really dived in deep enough. You haven’t really gone deep enough yet. Right? You’re still in that place of, “All things are possible.” As much as an abundant thinker as I am, that the fundamental frustration that we have is that as humans, we are unlimited sentience in a limited body.

Right? We can dream of all the different things that we might do. We can see how that could happen. Unfortunately, there’s only so much time and energy in a day. So that would be the first thing, again, if you’re making a plan and you don’t feel those things like that positive tug that I got, “Oh yeah, this is gonna be awesome.” You know, some version of whatever that feels like for you. 

And two is like, “Dammit, but I can’t do these other things.” Probably not digging deep enough. Two would be- it’s really about the people that you wrap around yourself and you put into it. So I call it your success pack, which has four different types of people, guides, peers, supporters, and beneficiaries.

And we can go through those if you want to. 


Ian Garlic: I definitely would love to,



Charlie Gilkey: But importantly, too many marketers, and I’m going to focus on marketers, forget about the people, right? We get into the numbers and we get into the likes and we get into the proxy side of that. I use numbers as a proxy, but beneficiaries are those people who benefit from the completion of your project, right? Both process and the completion of your project. 

They benefit one of two ways, cause you’ve got to remember, no matter what we create, we’re doing one of two things. We are solving a problem or we are delivering a delight. Sometimes we do both, right? And so not really being connected to the people whose problems you’re solving or or who you’re delivering delights to can create the scenario to where all things are possible, you do something, and this is, I guess – I don’t want to be over projecting here- but at a certain point in the early stage of starting, say your content marketing or social media and marketing things are fun, you’re getting all the likes. 

Actually getting all the things. It’s a new thing, like people like you, they really like you, that sort of thing. But at a certain point it becomes work, right? And you just got to get in and you put the work in and so on and so forth. And when you think of the hedonic treadmill or the hedonic adaptation, which means that you get used to a new level of success and happiness, and that becomes normal, so you don’t feel it as much. 

It’s easy to get emotionally distanced from the people you’re speaking with and talking to and trying to persuade. So I’m going to the root, sort of- you know, Seth Godin from ‘This is Marketing,’ like marketing is just about persuading people to act right?

That’s really what it is. You forget that. That’s I think, where we get stale marketing that doesn’t work, right? It’s formulaic, we found out that the headline hacks that work, we find out the templates that work, and it’s just a content mill that’s not connecting.



Ian Garlic: Yep. 


Charlie Gilkey: The third thing that I would say is understanding that the more something matters to you, the more you’re going to thrash with it. And thrashing is the term I have for that meta work, that flailing, that quote-unquote research that’s around the work but doesn’t actually push the work forward.

Right? And think about it like no one really thrashes about doing the dishes or taking out the laundry, doing errands. We might not want to do it, but it doesn’t evoke an existential crisis. Like, “Am I the right person? Is this right? But somebody else is doing this, this, this right now. Like, what if I get it wrong?”

But when we really do things, and this is important for marketers because sometimes, you know, I just mentioned not caring in a way about the beneficiaries, but sometimes you care so much that it gets in your own damn way because what if you do the thing and it fails. What if you put your heart and soul into this asset and it’s crickets, right?

“What if,” and so that’s a top-line story that we tell ourselves. The more deep one, which is what we often don’t talk about, is what if it succeeds? Like we have so many know ins scenarios, we tell ourselves about success, that it’s like if I do this thing and it goes viral- which is always don’t get me talking about people wanting things to go viral-

But anyway, if it goes viral, then “What if it changes my business? What if I become known for that? What if I ruffled some feathers? What if that’s when all the trolls that have just been waiting on that perfect moment that pounce on me? That’s when they’re going to get me right?” We have all sorts of stories around that, so we’re scared to fail and we’re scared to succeed at the same time.

So what do we do? We jump on Facebook and click somebody else’s link, right? We do something that’s safe and predictable and likely to get the results and follow the templates and the best practices and we end up either not being seen or looking exactly like somebody else.


Ian Garlic: Yup. What you’re saying, I think people need to stop and listen to it and listen to it again, because it’s really what’s preventing a lot of people from doing the right thing.

It really is. I see it all the time, in our clients and in people I consult with and like, here’s what you need to do. And they’re like, “I know I needed to do that. “ Oh, but then they come up with some, you know, “I’m too busy. That’s always the one, “I don’t have enough time. I’ll get to that.”

“What are they going to say about that?” And getting it inside your own head is super important. So how do you overcome that? I’m assuming that that’s all part of the finishing because I also want to get back into that success pack, but how do you overcome that?


Charlie Gilkey: The thrashing piece?


Ian Garlic: The thrashing piece.


Charlie Gilkey: One, is to understand that thrashing is not a sign that something’s wrong. Right? A lot of times you get that discomfort and it’s like, “Oh, something must be wrong.” Because unfortunately we’ve grown up and through cultural osmosis, we picked up on the really terrible talent myth. And the talent myth states that there are those people who are really good at things from an early age, that they just do it and it’s effortless, and they should do those things.

And if you are doing something and it’s hard, you don’t have a talent in that. So maybe you should go find your talent or maybe you’re talentless. Right? And so what happens is when we start struggling, there’s a piece of you that’s like, “Well, maybe like you’re just not good at this. Maybe this is not the thing you should be doing.”

“Like maybe you should go hire, you know, Ian, cause he knows what he’s doing. You don’t.” Right? And so that’s the first thing we tell ourselves. So it’s like, “Nope, that’s hard. I’m going to go do something that’s easier.” And that’s the problem, right? I say, beware of the siren call of the easier project, right?

Because you’re struggling and you’re like, “Oh, there’s this, this easier project” and you jumped to it. One of two things happens. One is a project that’s not nearly going to be as impactful. Two, it might be equally impactful, but whatever was challenging you with the first project, guess what? It’s going to come over with that second project.

It’s not like you jumping projects automatically made you better at managing time and automatically made you courageous. It automatically changed something like whatever you’re struggling with here, you’re going to struggle with there. So the question a lot of times it comes, is this the time that you say, “You know what, enough. I’m going through, I’m running towards the dragon. I’m running towards this discomfort versus running away from it” and really, what’s running away from it gotten you? Right?


Ian Garlic: Yep. 


Charlie Gilkey: So run towards the creative fire, run towards the creative dragon.

That’s the other thing too, be open to talk to people. Right? Once you understand that everybody thrashes about things that matter to them, you don’t have to feel so damn defective when you’re struggling, right? Every writer knows what writer’s block is.

So when writers get together, you’re like, you’re blocked. And it’s not like this big principle of shame. It’s not like, “Oh God, what’s wrong with you? You’ve written five books like you should know better.” It’s like, “No, that crap happens, man.” Like this morning. As an example, dude, I’ve written so many words, it’s crazy.

But this morning I was like, “Man, I’m having to fight my internal editor so hard.” Cause my drafter was like in his happy place. He’s usually cranking a bunch of words. I was writing an email sequence, right? And I was just in the flow writing and then I looked up and I had written something like 1,200 words.

“Dude, this is an email,” that’s what my editor said. Like writing. Right? “You got to go back and simplify this,” and when I was like, “Actually, no. I don’t. I can finish this draft. I can get it out and then evaluate and say, you know what? It’s just this is going to be a long email cause it’s serving my customers,” or am I going to do something different with it, but to stop it and end up with nothing? No thank you, editor.

That’s not what I came down here to do. So again, just knowing that it’s a part of the process of being able to say, ”Man, I’m stuck. I’m thrashing.” And what can be super powerful here is with your success pack, and again, we might come back to that, if you let them know what thrashing looks like for you, they can call you on your stuff, right?

They can just be like, “Nope.” Right? “You’re thrashing.” That’s really what’s going on. So like, I have a friend, a brilliant guy, and I’ve worked with him for a decade or so now. And I know when he’s thrashing because he’ll, line up a bunch of interviews with a bunch of people around his project and just talk a whole bunch, and six months later end up in the same space that he started with because he already knew what he wanted to do. And he was all along with those conversations, he was the smartest guy in every one of those conversations, and so he just spent six months confirming that his idea was the right one. I was like, “How about we just take action on the idea now and avoid the six months things?”

But it’s a work in progress. Right? I’m gonna throw in a quick ADHD aside here, cause you mentioned your clients say that “Something else came up.” With my clients after about the third meeting, “I didn’t have time” is not something that we can say anymore.

It’s, “I prioritize differently.” 


Ian Garlic: Yup. 


Charlie Gilkey: Right. Okay. Now we’re having a different conversation. Would you want to prioritize? Looking back now would you prioritize the same way or was there something else going on? Right. And so again, taking that choice back because if you let it, you’ll never have time, right?

So this is just a side, but understand that we are, understand that we are making these choices, and we can choose differently and then we’ll have different outcomes. But if you’re under the tyranny of the “urgent now” and you don’t do something to prioritize differently. Two weeks from now, you’re still going to be under the tyranny of the urgent, two months, two years.

It will not change until you change it.


Ian Garlic: Very true. Very, very, very true, and it is prioritization with an exception of if you’re an emergency room doctor. Most of us, say, “We don’t have any time.” I’m like,” it is prioritization. Very few things actually have to get done- have to get done right now. 


Charlie Gilkey: Yeah, and even if it’s like “I had to do it or I’d lose my job.” Okay, well your job is the priority. Now we know that going forward for everything else that you say, and so I’m going to be asking, “How does it work from your job impact, what we’re talking about here?”

Because if it turns out that if “you don’t do it and you’re going to lose your job” is always going to be the operative principle. Then we can assume that there’s no point in which you have this free space that you pretended that you had two weeks ago.


Ian Garlic: Very good. So, “Success Pack.” Let’s talk about who those people are and how do you develop those people? Cause I think this is critical, what you’re talking about here.


Charlie Gilkey: Great, thanks for that. I’m going to start with the four kinds in a second, but I want to start with who is not on your team, because this is super important and we do this wrong. So Naysayers and Derailers are not on your team.

And that seems obvious like, “Duh, Charlie. Who would put a Naysayer on their own project team?” We do it all the time, right? It’s like that one person out there that we’re trying to make happy. Right? And they’re like, if we make them happy, then the projects go? Not. So here’s the thing, the poet, musician, and philosopher, Taylor Swift said it correctly, “Haters gonna hate.”

It’s actually Kat Williams, but we’ll not go into who said what. And Naysayers are going to do what they do, right? And the very worst thing, and this is what people don’t understand, the very worst thing that you can do is win over a Naysayer because then you’re sort of beholden to their standards, and at some point, they’re going to revert back to the normal selves like so don’t put them on your success pack.

Don’t put anyone on your success pack where you feel that pit in your stomach, about how they’re going to punch you or beat you up or you know, kneecap you when you talk to them and that includes the derailers. The difference between Naysayers and Derailers is Naysayers, they have a principal.

They’re either out to get you, they don’t like what you’re doing, or they have appointed themselves the arbiter of good standards. So they’re out just to tell people what’s right and what’s wrong and what should be done. So on so forth. Derailers are often people you love that can be friends who really do mean the best for you, but every time you talk to them, it just rubs you the wrong way, right?

It’s just you tell them about your project and they’re like, “Well, that doesn’t seem very important.” You’re like, “Well, shit. There went two weeks of motivation I’d built up” or you know they tell you, that whole, “It won’t work.” All those types of things. It’s those people, and I don’t know why- You know, I’m originally from the South, I said that, but like, I’m going to say it in this way, 

The devil’s advocate guy? Right. (And it’s always a guy actually, or usually a guy) that’s like, well, you say something and they go, “Well I’m going to play the devil’s advocate here.” And it’s like, the devil don’t need no advocate. He’s doing pretty good on his own. All right. You don’t need that. Right? 

At this point, if someone asks you to be the devil’s advocate, then be the devil’s advocate, but don’t volunteer, right? Cause that’s really just a way of you cloaking to be able to like ask questions in a way that shield you from the impact of those questions because otherwise you wouldn’t say, I’m going to play devil’s advocate. You just ask a heartfelt but constructive question. 

Anyways, so derailers they also don’t go on your project, and that might mean your brother, your mom, your PO, your life partner may not need to be on that project. That can be super hard because we want those folks sometimes we want to be able to, you know, go to the library or coffee shop and get some great work done and come home and share it with the people.

And unfortunately, those people may not be the people that support, that areon your system, on your success pack. There are different strategies and tactics for how to deal with it, but the fundamental thing is, is that if you’re always having to fight with the people that you want to talk about your project with and celebrate with, it’s a losing battle. Every time you’re going to lose it every time.

So what we want to do is stack the deck with Yay-sayers and Yay-sayers are the opposite of those people. These are the people who already believe in you. These are the people who like whenever you say you’re going to do something, they’d be like, of course you’re going to do that. That’s who you are, right?

Or when you say something and you get worried about failure and they’re like, “look at all the other things that you’ve done. You can do this too.” Like they are those types of cheerleaders and people on your side that positively fuel your project. Okay, so don’t worry about all of this energy that we can sometimes have about proving your Naysayers wrong.

Like, I’m going to show them I can do this. How about you prove your Yay-sayers, right, right? And say, “You saw that I went and did it. You were right. Thank you.” Right? 


Ian Garlic:  That’s great. 


Charlie Gilkey: Completely different energy. Yeah. Four kinds of people. Four kinds of naysayers. And before I set this up, you want three to five of each of the kind that I’m talking about per significant project.


Ian Garlic: Oh, wow. Okay.


Charlie Gilkey: Okay. He’s like, “Oh wow, just got real.” 

Guides. Guides are your Gandalf’s, your Yodas, your Morpheus’, your sort of wise sage on the road that you pull onto the project because you’re pulling your guides on, not for their hands, we’ll talk about that in a minute, but really for their eyes.

They see the world in a way that you don’t, and they see possibilities that you can’t see. And sometimes they’ll see the things that you’re doing that keep you from doing it. So you’re pulling them on for the vision. So your guides, they’re not going to people who opened doors for you. Right? They’re not going to people that like give you that secret key to success that once you have that thing, all the world would be better. 

They’re probably going to remind you that you already have something that you need and you just got to use it or that you’ve got to get out of your own damn way, right? So those are guides, you pulled them on for your vision. 

The second group, are your Peers.

These are your phoner friends. These are the people that are sort of side by side with you. You’re pulling them on the team for their brains, your soundboard and you’re picking them up like they can support. By some of that, they can do a little bit of work, like more work than your guides, but again, you’re not getting them because they’re going to do work that pushes the project forward besides advising you being good, good strategic partners and sound boarders. 

Three are your supporters, and these are the people who supply hands for the projects. They do one of two things. They either do some work as part of the project or they do work that lets you do the work. So, and this is what I want to really stress to folks, is so often we just think of a team as our work team, but it could be that neighbor kid who watches your pets or kids or elders while you go to the coffee shop and get some, some useful work done.

Right? It could be the barista. Like I considered the Barisa- In fact, I was there this morning. I know all their names. They know what I do, they’re actual people, right? We have conversations and they know what I’m going to order. So when I walk in, I don’t have to say what I’m going to order. Which is really important when you’re a writer and you got sort of writer’s stumbly brain first thing in the morning.

Ordering cappuccino can be the hardest thing in the world, right? And I don’t have to do that. So they’re part of my support, my success pack as well. 

So. Recruit people in it- And so this is one of those sidebar things, but an important thing. I want us to shift the conversation from like individual/ personal productivity to collective productivity.

How do we get important things done in groups and how do we create those groups around ourselves? 

The fourth group and I mentioned this earlier, are your beneficiaries. These are the people who benefit from both the process and the outcome of your finished project. You’re pulling them on because they are the heart of your project, right?

They help you in two different ways. One, is when you’re mentally stuck and you don’t know what to do, rather than spend six, nine months Googling and random wandering and sketching out 18 different variations of the thing. You can, send an email or text or phone call to someone, you’re actually making the thing for and say, “Hey, I’m trying to do this. How does this land for you?” And shut up and listen hear what they have to say. Right? You can shortcut that six to nine-month to like two days, right? So that’s one thing. 

The second thing that they could do is when you’re feeling emotionally stuck and you’re ready to phone it in, you’re ready to just give up.

You remember that if you don’t complete the thing that you’re doing that person is worse off or they are at least the same as you found them? Right? That the light that you are trying to deliver is not delivered. That problem you’re trying to solve is not solved. And so we try, when I talk about this the first thing people say is like, “Oh, I got to go get more guides. I need guides.” No. You need closer and tighter relationships with your beneficiaries. That’s the secret sauce, right? 

Cause your guides are just going to tell you like it’s always going to sound like a fortune cookie after the fact, right? You won’t get it. And they’ll tell you what you’ve already got what you need and you’re like, “That’s not helpful because I don’t feel like I have what I need later on.”

You realize that, “Right? But you couldn’t see it at the time.” But your beneficiaries are actually the people that are going to get you through this project. Yes. Oh, a quick note on here. I said three to five per. That means you end up with 12 to 20 people around this project. 

One, there are several reasons for this.

One is it’s really hard to hide from 12 to 20 people. Like if you just got one person on the project, you can play all sorts of shadow games with that person and convince them of why. Like what you’re doing. Whatever labyrinth of a story you’re telling them is completely reasonable, right? You can’t do that with 12 to 20 people. 

Two, these are the people- I like to sometimes call them like “your reality distortion field.”

But people read that the wrong way. They think like they are altering the reality, but no, they’re actually reminding you of the reality of what you can do and what’s possible, right? And they provide just enough buffer against the rest of society telling you, you can’t do it. Why you nine out of 10 businesses fail in the first year.

That’s super hard when you’re starting a business to hear, right? So they are the people that distort that reality. These are the people that will remind you when you’re done. And so here’s what- I’ll say this, as we think about projects and we forget about what happens after we complete a project, and that’s actually the most, one of the most important things.

One of the really powerful things about your success pack is they will remind you to celebrate, to amplify, to publicize, and to integrate the success that you’ve done. Otherwise, you’ll sort of slide into home and start getting ready to swing the next one. And they’re like, “No, no, no, no. Wait a second. Like this is significant. You’ve been doing this for two years.”


Ian Garlic: Yeah. I mean, it’s such a great mindset shift that you’re talking about here because you don’t want to think of people that you talk to and you get people that are super positive and it’s easy to listen to.

Like it’s easy to brush off someone that’s super positive and go, “Oh, they’re just being positive.” But when you surround yourself with the right people, there you go. And also ignoring the naysayers and identifying them, I think that’s a crucial thing. That we really haven’t done as been able to identify those people and go, this is where this person fits and this is their role for me.

On a side note, beneficiaries, you know, I talk about them all the time with my clients, get to know the people you work with as much as possible.

Cause it’s going to make you feel better about yourself, but you’re going to come at a thousand times better marketer. Yeah.


Charlie Gilkey: Yeah. And so I’m going to say it this way, and I’m a call out the guys on this one, right?

Cause I know sometimes how we work. In a non-creepy way ask people about their families, right? Just on meetings when you’re talking about marketing or something like, “How are the  kids doing?” and “How’s your wife?” Get involved in it. The reason I say that is because that’s where we start to see the totality of people as humans.

And it’s not just transactional, “Like we’re in a meeting and we’re going to do this 32-minute meeting format that I’ve set up that increases efficiency so and so forth.” And like whenever efficiency tramples over empathy. You’ve lost. Right? So just simple enough, “Hey, how are the kids? Like, I know last time we talked, you know, one of your kids came home from school.” Like, learn their names.

So this is the thing, what I did when I deployed overseas is I was a follow-on Lieutenant, meaning my unit had left before I did and so I was meeting them in a theater. And so super hard to do as a second Lieutenant. But I was like, “Okay, I don’t know these people, they don’t know me. We’re going to be doing tactical combat convoys. All right,  are we going to be doing tactical envoys at the time that these guys have figured out how to blow us up? This is not a good thing, right?” And so it was like, how am I going to do this? So what I did is I went through their personnel records, which I had access to.

I wrote down their names, where they live, the name of their spouse, the name of their kids, and how old they were and memorized every one of my 45 troops where they live, not like their addresses, but like, “Oh, they live here. They live there.” Really figured out these relationships and it made a difference when I would talk to them and you know, we’d be talking about something and it’d be sort of after you’ve done most of the business, you’d just be kind of hanging out.

It’d be like, “Hey John, how’s Amy doing? Like I know, how’s she doing with you being deployed right now? Cause I know it’s really hard for all of us. I’m just wondering about your family.” And he was like, “Wait a second. How. Who, what, like, how do you know this and why?” Like, and not in a creepy way, but just in a, like, I care enough that you’re not just Sergeant Smith to me. Like you’re a person, you have a family, you’ve been pulled out of this. How are things going? It just makes a huge difference. And it took me two or three days to do it. Paid off the whole time,


Ian Garlic: Man. When are you saying that? I’m just imagining if everyone listened to this, picked out 40 of their favorite clients, followers, whatever, and just dug in and really got to know them really, really well and had those conversations, their business would transform, they would transform their marketing, and their life would transform. I mean, a complete transformation.


Charlie Gilkey: Yeah.


Ian Garlic: And it’s a, it’s a simple thing to do, but man. You know, I think that’s where a lot of people in marketing, entrepreneurship, they talk about scale, scale, scale, scale, and if you jump past this. I’ve talked so many people are like, well, I want a scalable business. I’m like, well, how much have you sold?

Nothing? Well, how many people have you helped? Nothing. Well, let’s help 10 people really, really well before-


Charlie Gilkey: Yeah, if you haven’t nailed serving, don’t worry about scale. Right. Cause you haven’t served people yet. Once you figured out how to consistently serve people, deliver that delight, solve those problems, then maybe start worrying about how you’re going to scale that.

But if you can’t do it with four people, you can’t do it with 40 or 400 or 4,000 and 40,000.


Ian Garlic: Yeah. No, this is great. It’s this fantastic stuff. So I want to shift a little to a little more tactical- I mean, not that that’s not tactical, but it’s, it’s beautiful, but if you go to Charlie’s website at and you click on free planners, you’re going to be blown away by these tools here.

Talk to me about these tools especially, I love the idea of the digital momentum planner, cause nothing, I think nothing in business can overcome momentum. And keeping it up. It’s hard to get, but once you get it, you can rock.


Charlie Gilkey: Yeah. I really appreciate you calling this out because I mean, I’ve created a lot of things, but it’s still one of my favorite pages because one, it’s free stuff that like we don’t ask for an email address to download you can just get it. 

Obviously there are places you can download, but you don’t have to, or you can put that in, Really what those tools do is give people containers for their creativity and energy and that’s where people are either going to love them or hate them. So they’re not calendars in the sense of like, no one needs to replicate what Google calendar has already done.

You’ve got a meeting, you put a meeting in, it does that for you. Right? But what these do is like help you figure out like, okay, I’ve got these five-month sized projects.

Which I might need to talk about the five projects rule here in just a second. Sorry., 

So I’ve got these five-month sized projects. How do I break them down into week size chunks and on what weeks am I going to put those week sized chunks and how am I going to put them together so that you don’t go from something like, you know, “write a white paper” that mysteriously hangs out on your project deck for like six months to like outline white paper, which might take you two hours to do right.

Or research, you know, you can break that down into smaller, smaller chunks. And so that’s really what it does, is it helps you- We have a momentum planner for every time perspective. So we’ve got one for the daily, weekly, monthly, quarterly, and annual. And the reason we do it that way is because where so many of us created people really spin ourselves out is when we try to think of like a year-sized chunk of time.

And then we immediately at the same time, started to try to start figuring out what we’re going to do tomorrow. But that’s like thinking about an ant and the size of the United States at the same time, you just can’t mentally do it. Right. So when you’re thinking of all of our momentum planners, what they help you do is like- for instance, I’ll take the monthly, which a lot of people can get their arms around a month, the monthly planner is going to say, “Okay, what are your five major projects for the quarter?”

So the time horizon above it. Okay. What are you doing this month? Okay, what are your priorities, your month size priorities for this month? And then, okay, now that you know those two things, where do you schedule those chunks in the weeks? So they’re always going to do that for you, it helps you have that one higher view, the view you’re at, and then the one that helps you actually plan.

So it’s really helpful for a lot of people. It’s a mind shift though. I will say that, right? Because, you want to talk about brains going haywire. when I see so many people’s task lists and action lists, I’ll see like three-month sized projects and then I’ll see like four 15-minute tasks and then, you know, two or three weeks size projects all on the same piece of paper.

And I look at it and my brain just can’t do it. Right. But that’s because I can see it and I know the complexities, but like we’re doing that to ourselves every day. 


Ian Garlic: Yeah. 


Charlie Gilkey: And so one of the things to think about is like if you’re making your daily plan, at most, you want to have some idea of what you’re trying to do this week, and then everything else should be like at that daily time horizon.

Right? So you’re talking 15 minutes. So this isn’t one of those takeaways when you’re looking at the daily/weekly level. Break your work down into two slices or two. I’m going to say Quantis cause I’m a nerd and I can get away with it too. Sort of quantities of time, 15-minute tasks or two-hour chunks, two-hour blocks.

All of your work can probably be fit in those two types of things. Here’s why I want people to do that. People are overwhelmed by email, right? Constant sort of thing. What they don’t understand is by the time you archive all the easy stuff and delete all the easy stuff, you end up with, most of us end up with, six to eight emails that take at least 15 minutes on average, a piece to do. That’s two hours of work. Where does that two hours live on your schedule? So if you start saying, “I’m going to respond to these 10 people today, when I look at my clients’ list,” I want to look at people’s lists. I’m like, “Okay, you’re responding to 10 people.

It needs a legitimate response. It’s going to take at least 15 minutes apiece. Where does two and a half hours of email live on today’s schedule? And if it doesn’t live on today’s schedule, guess what? Something is not going to happen.” Likely you’re not going to finish the work like you’re your quadrant two “important but not urgent work” because you’ve got to get these emails done or something that’s going to shift. 

So it’s just super useful to say, “You know what, I’m just going to count. I’ve got these admin tasks. I’m going to assume they’re 15 minutes apiece. That’s how much you have.” Two-hour blocks are, I call them focus blocks, these are the amount of time that it takes to really get into, especially a creative project, but all sorts of projects to make some meaningful progress on them. 

To get into that ramp up time to get your coffee, to like sort of chew on it a little bit and to wrap it up in a way so that when you pick it up next time, you’re not trying to figure out what you did last time.

Right? That for most people, takes 90 minutes to two hours. I just say two hours. And if you just sort of say like, look. I’m going to go back to writing the white paper. I know, because I’ve done it enough that for most people, that’s going to take 10 to 20 focus blocks to do, right? So I don’t need to go like, how many hours is it going to take?

I mean, we can do that, but, um, I can look at their schedule and say, “Okay, over the next month, where do those focus blocks live? Right? Where do those two hour blocks live?” And that means if you’re getting up this morning, you’re like, “Damn, I gotta write this white paper.” Well, look at your schedule. Where do you have those focus blocks?

And guess what? If you don’t have them, then reality is you’re going to punt that project, and punt it, and punt it and get to the end of the week and be in the same spot. So many people I think, misdiagnosed themselves as either procrastinators or lazy or just can’t get rights. When the reality is they just don’t have enough focus blocks on their schedule to do the deep work that they need to do.


Ian Garlic: Yup. I love that. And you have that focus block planner on there, and I think this is critical and understanding your energy levels too. When you get that, you know where, where is that? Because if you’re going to do something super creative and you know, at two o’clock you’re down, don’t be scheduling that super creative thing at two o’clock.


Charlie Gilkey: Yeah and I go even further than that. There are different ways we can think about time too. For instance, I had a client stuck on a novel for like 12 years. It wasn’t going anywhere. Right. and so she kept making her novel-writing days Friday. And so when I started working with her, I was like, “So can we make a shift? Can we move your novel writing day to Monday and move some of the rest of the stack? Because what I want is your novel to get your best energy of the week, and that’s on Monday. It’s not Friday, Friday, your dad, and you want to phone it in. That’s why your novel’s not going anywhere.” 

And so we switched it and I’d think it was six, nine months and she finished the novel. Right? It’s not like we created more time. We just changed the arrangement of time and the same thing happens in the day. If you know you’re done at two, like don’t- here’s what super hard one, don’t program some focus blocks or some of that deep work to be after two. But two, This is the hard sort of pro-tip here, the hard practice is if your day went, if your morning went sideways and your day went sideways and you see that it’s two o’clock better to say, “You know what? I’m not getting that done today. I’m going to have to reschedule that and figure it out.” Then to beat yourself up and be stuck on a clickhole for four hours.

Because you can’t really do the work, but you can’t let yourself get up. Right? Yeah. Call it. Make better use of your time. Maybe you decide if you, especially if you work for yourself, you have some autonomy over your schedule. Maybe you decide to cut the day two hours short and tomorrow you come back with more energy.

But we’ve all, as creative folks, we’ve all tried to do that push at the end of the day or in that wrong time, and like we ended up in a clickhole somewhere or we struggle and fight. We get like seven words on the page and then we wake up the next morning and realize those seven words were crap and that we shouldn’t have done it anyway.

Right? We wore us out, got seven crap words, and now we’re doubling beating ourselves up. So just don’t do that. Again, that second one is the hard one, guys, I get it and I have to check myself. This is why I have things like Cold Turkey Blocker that shuts me out of social media at 4:30 PM every day.

Right? And so because I know that that’s the time that my willpower dips, and I also know that that’s the time in which if I didn’t get something done, that’s where my engine is like, “do it, do it, do it.” And just like, “I’m going to end up on Facebook and or wherever,” and it just blocks me out of that. So I’m sitting there looking at a screen like, okay, I’m done.

I’m not just going to be looking at the screen.


Ian Garlic: That’s great stuff. We got in so much today. Charlie, thank you so much. I definitely want to have you back. Definitely need to check out, and the free planners, and obviously this book ‘Start Finishing: How to Go from Idea to Done.”

A lot of us can start ideas. It’s finishing because that book 80% done is not helping you. It’s actually pulling on you.


Ian Garlic: Charlie, you got, go ahead.


Charlie Gilkey: Well, I’m going to dive in real quick. Just one thing to remember, finished projects are the bridge from your current reality to the reality you want to be in.

If you don’t finish those projects, you’re going to stay stuck where you are. So if you want a better life, if you want better work, if you want better results, you’ve got to finish those projects.


Ian Garlic: Love it. I was gonna ask you if you have one last tip and that I think that’s perfect. Charlie, thank you so much for being on the show.


Charlie Gilkey: Thanks so much for having me.


Ian Garlic: All right, and thank you all for listening. Make sure to check out Charlie’s book and also check out the free planner is on there. Just skim through it. If you like tools like me like that, you’re going to love it. Thank you all for listening and taking Charlie and I on your journey.

This has been Ian Garlic and the Garlic Marketing Show.