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Blog, Career Nation Show, Career strategy

Episode 14: Career Nation show with Charlie Gilkey

“We didn’t commit as much as we could have because we were afraid of what might happen if we win. What are our notions of success that keeps us from doing meaningful work and making the change? We’ve talked enough about the fear of failure. Let’s talk about the fear of success.”, says Charlie Gilkey in episode 14 of Career Nation Show.

Charlie Gilkey is a US army veteran, business growth strategist, author, speaker, and entrepreneur.

Here are some highlights from this episode:

+ Why smart people struggle and give up halfway?

+ Why shouldn’t you consider thrashing as bad?

+ The downside and fear of success

+ How to create space for our special projects?

+ How to find the balance between your professional and personal relationships?

+ How to tell your career story?

You can get the copy of Charlie Gilkey’s best selling book, Start Finishing, from here: https://amzn.to/2RiNEUx

Career Nation:
Hey Career Nation, welcome back to the Career Nation show. Today, we have a treat. Today we have a special guest who is a great creator. He’s an army veteran. He’s an entrepreneur. And now the bestselling author of a brand new book, ‘Start Finishing’. Please welcome to the show, Charlie Gilkey. Charlie, welcome to the show.

Charlie Gilkey:
Abhijeet, I’m so pumped to be here. Thanks for having me.

Career Nation:
Oh, the pleasure’s all mine. Charlie, for those in the audience who don’t know much about you, tell us a little bit about yourself.

Charlie Gilkey:
So, as you mentioned, I am a pretty prolific creator. I’m a blogger, I’m an author, I’ve got a podcast, I’m a, you know, speaker. So basically if there’s a way to get ideas out there in the world, I’ve experimented with it and I’ve tried it and I’ve probably got some, content trail that represents that. You know, I started productive flourishing, which is whereof all my work kind of goes to. I don’t do well having multiple brands. I started this in 2007, and at the time I was an army logistics officer. So I was army joint force military logistics coordinator, which means I was making sure the Army, Air Force, and Navy or dropping equipment where they needed to and getting it picked up and you know, taking it where it needed to go. And you would think that would be a well old machine. And it is because people like me are doing that oiling all the time. It’s not nearly as automated as you might think. And I was also completing my Ph.D. in philosophy. So I’m an Ethicist and social philosopher. And I had recently returned from

Charlie Gilkey:
operation Iraqi Freedom. And you know, it sounds so sophomore to say like, this too when I say it now, but at the time I was like, ‘Man, I just got to get my stuff together. I’m not getting it done. You know, I’m not being able to finish these papers and I’m not quite the person I want to be’. And so I started doing some research, like a good scholar and a good officer does. And says, you know what, I’m not the only person with this problem. What are people doing? And I started doing a lot of researching and synthesizing and that’s actually what became productive, flourishing. And so for the last 10-12 years, it’s really been focused on how we in the creative class can focus on finishing the work that matters most to us. And oh, by the way, the work of our lives is just as important is the work of our careers. So that’s really a background on what I do. So throughout this interview, I might go different directions. There might be some military voice, it might be some philosophy voice. But it really is that like that focus on how do we become the best people we can, that we can be in. Largely that’s through finishing projects that really, really matter.

Career Nation:
Well, there are so many nuggets there that I would love to unpack, Charlie. The, you know, the one thing that sort of, caught my eye was sort of your, background about the sort of, helping with logistics and operations and sort of getting to sort of execution and getting it done. And so that’s been sort of that recurrent team. And, is that what sort of inspired you to write a book about productivity or are there other factors or different factors that led you to write a book on productivity? Tell us some background on that.

Charlie Gilkey:
Well it is, you know, the blog started, the, my work started with productivity. And actually start finishing as my second book, right. My first book is The Small Business Life Cycle, which is really what to expect when you’re expecting for entrepreneurs. And I was involved in so many great conversations with entrepreneurs and executives and leaders and really the change makers of the world. But they all came back to not being able to get it done,, right.

Charlie Gilkey:
And so sometime around 2014, I put a stake in the ground and I was like, ‘Look, I know we want to talk about these big ideas. I know we want to talk about these great products in the ways we’re going to change the world. But at the end of the day, if you can’t get it done, it’s just all social Sodoku. Which is all playing this big game. It feels good when we’re playing, but nothing changes in the world’. And so I wrote Start Finishing to be that foundational piece so that we can get that, the base of ability and competence and mindset around getting this stuff done. And then we can layer on top of that. Yes, we’re building businesses. Yes, we’re building careers. Yes, we’re building products. Yes, we’re changing the world. But we know how to do that. And so for me, the conversations at a certain point felt really hollow and really purposeless because I’m like, at the end of the day, tomorrow you’re going to be stuck with the same problems that you had before we started talking. So let’s address those problems and move forward.

Career Nation:
And Charlie, when you, when you talk about sort of, you know, going over the finish lines, finishing things, execution is, is this sort of productivity thing, et cetera to you, is this a muscle that all of us should develop and hone and, you know, build over a period of time? Or do you think it is just sort of a, just sort of another skill, that you may need to know and you may have some competencies but you may not need to exercise it every time? What’s your philosophy around, is this a muscle? Should I build it every day and you know, that sort of thing?

Charlie Gilkey:
Yeah, I would probably push it as more is a lot. Not that it’s a muscle, it’s like the skeleton. It’s one of those core skills that I don’t think any of us get out of learning. Right? And, you know, we, no matter, you know, we might be a great product designer. We may not need to know, you know, management finance. Like that can be a periphery sort of skill. But this skill is a universal one that we all need to learn. Because especially for the creative class, our livelihood depends on taking ideas and converting them into market value. Right? if you’re not able to do that or you’re not able to do that, well you don’t have a roof over your head. You won’t have the career advancement that you want. You won’t be able to take care of your family. So it is very much a core skill. I won’t say it’s ‘the’ core skill because there are a lot of, you know, there might be three to five clusters of core skills, but it’s one of those.

Charlie Gilkey:
And what I furthermore say is we all know, aside from sociological and cultural factors, we all know that the people that are getting the pay that is getting the advancement that is getting team leadership are the people who are able to get stuff done. And the other thing I’ll say here is while Start Finishing is really about personal foundations and personal self-mastery and getting things done, you know, it also incorporates a huge element of collective productivity. And so the book that I’m working on now, it actually goes more that way. But if you can’t get your own stuff done, you can’t lead a team, right? if you can’t focus that team and figure out why they’re not getting stuff done and that team is not going to be successful. So no matter whether you’re like, I’m that visionary, creative and I’m not, I’m not in charge of getting stuff done.

Charlie Gilkey:
Well, there’s still somethings you need to do. You need to be able to articulate a clear vision for people, right? You need to be able to follow up with people and you know, chunk things down. And so Start Finishing really does help people do that and we don’t get away from it.

Career Nation:
Wow, that’s so great because I totally agree with you. There is a foundation within the individual that we need to get our stuff done. That’s a core skill. And then of course as a team, we have to work together to produce those outcomes and results that we want and the value that we want to create. I love it. And it looks like there is probably a Part 2 there somewhere for the book. So I can’t wait. So that’s awesome. And so, you know, one question is always sort of puzzled me. In fact, I’ve struggled with it as well is, there are many smart, ambitious people out there. They have great ideas and they start out on that idea and then somewhere in the middle they either give up or they let the idea languish or they are just not able to get it done and get to the stage where the idea actually goes out to the world. Everybody, you know, takes advantage of whatever they are creating a product or service or what have you. Have you observed that? I’m like what would you recommend? What’s sort of the silver bullet here?

Charlie Gilkey:
Yeah, so here’s the thing. Like some of us thrash… Thrashing is sort of the meta-work that flailing the quote-unquote research, you know, all the work you do on something that doesn’t seem to actually take it anywhere forward. Like, we all thrash at different stages of the product. And you’ve mentioned the middle stage of a project, or excuse me, you mentioned the middle stage of a project. Some of us thrash at the beginning of a project. Like before we actually accept that we’re going to do it, like, are we the right person? Is this the right time? Am I ready? Some people thrash there, some people thrash in the middle when like all of the novelty of the idea and all of the promising idea has crashed into the realities of getting it done and the competing priorities that we all face. Some of us thrash at the end, like at that last 90% where just before we’re about to show someone that’s when all the demons and head trash and all stuff comes up. And then some of us thrash throughout the entire project. Right?

Charlie Gilkey:
And so that’s, we’re just, that’s who we are. Right? But yeah –

Career Nation:
– They’re perpetual thrashers.

Charlie Gilkey:
– We’re perpetual Thrashers. And you know what, one thing that I’ll say about that is, in our society, we’ve made something, we’ve somehow, integrated that thrashing is bad. We’ve all somehow integrated that if you’re struggling with something, if it’s hard, then maybe you shouldn’t be doing it. It’s sort of the perverse talent myth, right? They’d like people who are good at things, it comes easy to them. So, therefore, if you’re struggling with something, it’s not a talent that you have. Maybe you should go find what you’re talented at and stop doing that thing. It’s total BS. But we somehow deeply have integrated that. So when we start thrashing, it’s a clue for a lot of, or many people read it as a sign that something’s wrong, right? Like maybe I’m, you know, maybe this isn’t the right project. Maybe I’m going about this the wrong way. Maybe you know, maybe there’s some other way out there that I need to go research for the next six months to figure out how to do that. As opposed to just saying like, no, thrashing is a part of any project that matters. And think about it this way. We don’t thrash about taking the trash out or doing the dishes or doing the laundry or going to get groceries. We either do it or don’t do it. We might procrastinate, but we don’t have that many existential crises of am I in the right place? And we only do that with things that really matter to us. Right? You start thinking about getting a new job or doing a major new career initiative or starting a business or getting married or you know, moving across the nation or you know, becoming the next bat. All of those things will get you to thrash. And so my point here is that I want people to recognize thrashing as a sign that you’re doing something that matters to you. And two, it’s not a sign that you’re not capable of doing it, it’s just that you’re having to rise to a different type of challenge. And maybe it’s the exact type of challenge that you need to rise to.

Career Nation:
And Charlie, you mentioned this in the book, which is when the goal or the objective is very important to us, we develop more of this thrashing and we develop sort of the symptoms and why is it, why does that happen? Why is it like if there’s something that’s so special to us, so important and we feel like we have all of these thoughts and doubts in our minds and other things going on. That sort of moves us away. What, why does that happen?

Charlie Gilkey:
Two simple reasons. There are a lot of reasons but two sorts of generic reasons. One is we’re afraid of failure. And if we fail on these things that really matter to us, as we make it about our identity. It’s not just some random thing that we are doing that we didn’t do good at, right? It’s who we are as a person. So I’m going to give an analogy here. And this is, this might resonate with some, but you know, we’re in the age group where most of us have played video games at some point over our time, whether it’s solitaire or whether it’s something else. Like when we play games like that and we fail, we don’t make it a character mistake. We don’t make it, you know, something that says about who we are. We try again, right?

Charlie Gilkey:
It’s like, Oh, that didn’t work. And we can spend entire days in games failing and not make it about our character and not make it about our competency. We just assume we haven’t figured out how to do it yet. But when it comes to our life and our work and when we fail, we don’t have that same, we don’t apply that same freedom. Right? Granted there are social pressures, there are other things that are going on, but more than that, our internal narrative, it can be, I’m not good enough. Right? I don’t know what I’m doing. Maybe this is too much for me. So we tell all those stories about meaningful work that can kind of cripple us. So that’s the obvious thing. Many people know that they’re afraid of fear, that like, the other thing that people don’t recognize that they’re often afraid of is a success.

Charlie Gilkey:
Because if we do this really meaningful work, it might change the status quo of our life. It might change some of the relationships that are around us. It might change relationships with our family, with our partner. It might change the relationship with our coworkers. It might change the relationship with our boss and you know, as much as we like change, we’re really schizophrenia people sometimes and that we want to change, but we also like, like things to stay as they are. And so, sometimes that fear of success and how it might change and some of the no wins scenarios we’ll tell ourselves about success such as, you know if I’m successful then I’ll wreck the relationships around me. If I’m successful, then I’ve somehow sold or sold out or become a less, moral or ethical person, or less, you know, valuable person.

Charlie Gilkey:
Or if I succeed, then, I’ll set a bar so high for myself that I, I won’t be able to live up to it again. And then I’ll always be like, I’ll be crestfallen. And then the fourth one is, if I succeed, it’s gonna come at the cost of my health and sanity and spiritual wellbeing, right? So as long as we have those no-win scenarios around success when it comes to our meaningful work, it’s obvious why we can get stuck in the middle and right as soon as we’re about to start approaching success, we’ll start self-sabotaging, we’ll throw in the way or we’ll switch to an easier project that allows us to stay in this emotionally safe space of gray mediocrity where we’re neither really winning nor losing. Because, you know, we don’t want to lose and fail. That’s just a normal human. But we also don’t want what we perceive as the cost or the downsides of success.

Charlie Gilkey:
So we just shoot for that middle and on a weekly basis, on a monthly basis, that seems to be the right call. But when we look back over the course of a year or five years or a decade, what we regret is that we didn’t play as big as we could have. And we didn’t commit as much as we could have because we were afraid of what might happen if we win. So that’s the story that I want us to have this more about is what, what are our notions of success that keeps us from doing the meaningful work and doing the change, making work. Because we talked enough about the fear of failure. Let’s talk about the fear of success.

Career Nation:
Yeah, totally. And, what you just said is so fascinating. Which is fear of failure, which is sort of the more commonly known fear and then the fear of success? That is fascinating. And you’re so right about living in that gray zone in the middle for too long. It feels comfortable, but it actually is not productive and doesn’t get you to where you should be playing. And let me ask a followup on that and that’s sort of around prioritization and a lot of folks in our audience who are in tech and sort of other sorts of fields, they are always full of ideas. And, what in your mind would be sort of a way to prioritize. Because, I used to be a product manager and as the product manager I would think, the highest economic value gets is basically the number one priority for me in terms of my ideas that I would like to implement as a personal project. Or maybe there are some other criteria there, but what would you recommend as a sort of, an approach to prioritizing a lot of great ideas?

Charlie Gilkey:
Yeah. So you mentioned one of them obviously is what’s going to give you the biggest economic Pat. But I want to pause here because I’ve been talking and I sort of set it up in the beginning, but I want to slide this in cause it’s important. We over-focus on the economic work of our life and deprioritize the work, or excuse me, the career and economic work and we deprioritize the work of our lives. Okay. And try to find space and time in the leftovers of our economic work except for we overcommit on the economic and career side of things so that we’re overfull there and there’s just no space for our life to be fit into. And so throughout this conversation, when I say work when I say the project, there’s no necessary difference between economic work and the work of our lives.

Charlie Gilkey:
So you know, a project is anything that takes time, energy and attention. And when you really understand that, what we see is that there are a lot of things that we’re doing in our day to day lives that actually project that we’re not making space for, we’re not getting. So any of those hobbies that you have, trips, relationship, community, all of those things actually end up being projects that don’t get prioritized. They don’t get plans, they don’t get scheduled and they don’t get done. Okay. So I’m just going to put that out there ’cause that’s one of the things that I would have people be thinking about in this, in this broader macro prioritization is what are both the projects of your career? And what are the projects of your life that you need to be sorting between and making sure that their space, their space for both in accordance with what your values are?

Charlie Gilkey:
So if you’re a career person and that’s just how you set up the meaning of your life, I’m not judging that. You’re going to place more weight on career projects and less weight on personal projects. And that’s okay. You just got to know that, that regret, that frustration, that exasperations you may have about not getting projects, personal projects, done are consequences of the ways that you’ve set up your life, right? You may decide that, you know, maybe career is not as important and you’re going to prioritize the personal aspects of your life and you have to be okay with the consequence that you may not have quite the career advancement. You may not make the money, you may not have quite the stellar career as someone who’s focused on that. Now, there’s a lot of freedom in that because you get to choose, right?

Charlie Gilkey:
But you don’t get to choose to do one thing and expect to get the outcome of a different choice. Right? So don’t be mad about results you didn’t get from work you didn’t do. So I’m going to kind of set that up. So to your actual question though. What’s going to provide the biggest economic payout is a great one. The second one is what’s in this. this is from the book The One Thing. I think it’s by Keller. I’m looking at it here. So, yeah, Keller and Papasan. What project, if done, would set your life or your career up, in the most important way, right? And so it may not be that it’s an economic project, so it might be that you could create this project, you could create this product that has a huge economic payout. But it could also be that you focus on building a team that is able to create products like that in, you know, in a workflow or in a chain that’s far better than what you would be able to do if you just focused on the economic project.

Charlie Gilkey:
Right? But I talk a lot about the project world. And the project world is basically the idea that our life is divided into coherent three to five-year chunks. And I’m going to focus on right these both. On the life side and our personal relationships people change every three to five years, our life changes, you know, kids grow up, siblings’ age, parents age, we age, we get in and out of relationships. In every three to five years, there’s some sort of,

Career Nation:
– By the way, you don’t seem to age at all, Charlie, but keep going.

Charlie Gilkey:
– I appreciate that. There seems to be something that changes in their life that there’s a new sort of macro project. And in our careers we take new jobs, we get new positions, you know, we change, we pivot our business, like all sorts of things happen. So every three to five years, a chance to be a significant Metro project.

Charlie Gilkey:
And I’ve been thinking about this for a long time, but when I was, you know, doing the research for the book, I figured out the Stewart Brand who’s like the Renaissance, he’s like the Renaissance soul par excellence of our age, right? And so he sort of said something similar, which is significant projects take at least five years to see through. So, what you can do is take you, you know, take your age, subtract it from 85 and divide by five. That’s the number of significant projects you have remaining in your life. And so another way to prioritize projects is, is this the main thing that you’re working on? Is it worthy of one of those remaining five or one of those remaining projects? So for me, I’m cresting 40. So that means I have about nine major projects remaining in my life that I could do.

Charlie Gilkey:
Okay. And so when I’m working on, you know, if I decide to work on the next book I’m in essence deciding that that’s taking one of those projects lots at the rate that I write books, right? if I start a new business, if I joined a new board, if I do any of those types of things, I’m always assessing, is this one of, is this worthy of one of those nine slots? And it doesn’t have to be about money, right? It can be about the legacy that I’m leaving. It can be about the impact that I’m wanting to make in the world. It can be about the way that I want to be in the world as opposed to the things that I want to do in the world. So there are different ways of sauteing that, but I find that people, you know and on one hand, it can feel like the earth is sitting on your chest when you realize you have a limited number of significant projects.

Charlie Gilkey:
It’s like, Oh, what do I do with that? But once you accept that constraint, it really does help prioritize the major projects that you’re working on and how that feeds into this broader story of your life. The last thing that I’ll say here is, work on the project that would pain you the most to let go of. And so sometimes when I’m working with clients, you know, like I’ve got all these ideas and it’s like, okay, what are they? And now I list them. They’ll list of bunches like, so imagine I’m reaching for one of those and if I grab onto it, you’ll never be able to do it again for the rest of your life. Which one causes the most pain? When I start reaching towards the most creative folks, they know, like when I get closer to them and they get super mad, right?

Charlie Gilkey:
Like not that one. Right? And it’s like, okay, that’s an important sign because here’s the thing, if you don’t choose to do that, time is going to take it away from you, right? If you don’t choose to do that project, it won’t be Charlie and his thought experiment, it will be time that comes and says, you know what, five years have passed. You lost that one, right? You lost some of your projects every five years, every seven years. You know, we can quibble about whether it’s three years or five years or seven years, but there’s a certain amount of time that we have for these significant projects. And so that last exercise can really grip people because once you know that, like you feel that tug and that pain want to start grabbing forward, that’s a sign start going towards it because if you don’t, time is going to take it from you.

Career Nation:
You’re so right. I mean, for a lot of people the pain of loss is higher than the pain of gain and that’s such a beautiful thought experiment. I would actually love to do that for some of my clients who are currently struggling with multiple priorities and projects. And let’s say, you know, we go through that thought process and we arrive at the project that this is our project that we want to do. And let’s say I am actually going through the motion and sort of planning for it, et cetera. And you mentioned this in the book, which is sort of creative space for your project. Like how in this world full of distractions devices, how can one go about making space for that special project? Because of the demands of other people’s time on us are always there. The devices are always going off and notifications. So how do we create space for that special project?

Charlie Gilkey:
You know, I love that because there are lots of different ways to take this conversation, but there’s a really simple way to address it. it all comes down to what I call focus blocks, which are 90 to 120-minute blocks of time where you can focus on a project, right? And you know, for creative projects, you know what, what that means. Like you have to be in that sort of work zone of coding or designing or writing or whatever that is. But it can also be, you know, if you need to clean out your garage like there’s a certain amount of time it takes to really get into that and figure out what’s going on. So it’s just focusing on that project. Now I can talk later on about how to firewall a focus project, but the fact of the matter is if you don’t have any available focus blocks for a project, you’re not going to move that project forward.

Charlie Gilkey:
Right? And a general rule that I would tell people is three focus blocks per week per project. If you can’t carve out 90 to 120 minutes of dedicated time to work on that project, you’re simply not going to move it forward. It’s not about your procrastination, it’s not about your capabilities, it’s not about your, you know, any of that sort of stuff. It’s simply you don’t have the type of time you need to move it forward. So step one, when we start talking about making space is look at your schedule and be realistic about where you can create those focused, you know, those focus blocks and where you can’t. And if you see that work and you see that the other commitments of your life are eating all of the time that you have for focus blocks, what we have to have the conversation about is like one of two things is happening.

Charlie Gilkey:
One is your life and your work is basically in alignment with your priorities. So we don’t need to change anything. Or your work in your life or out of alignment with your priorities, which means we need to change something, right? And you know, there’s what I’m trying to do here and, and you probably see it, Abhijeet is that I’m trying to take that pain and that frustration and that sort of, creative constipation that we can often have. And I’m trying to put that at the beginning of our decision-making process rather than spreading it out and diffusing it over weeks and quarters and months and years. Right? I would rather say Abhijeet, look, I know you want to do these projects, but this is your life right now either accept that your life is in accordance with how you want to live your values and your priorities.

Charlie Gilkey:
Or we have to start making some changes in that change may be uncomfortable. It may invoke some thrashing and may be difficult, but you can’t continue to do what you’re doing because you’re going to get to the same result. So that’s the first thing that I’ll say. And it’s like if you can’t carve out those focus blocks, you’re not going to be able to do the project. Now I say three focus blocks per week because that gives you some momentum on that project, right? You may be in your life where you’re like, I can only do one. I can only do one focus block a week. And I’m like, great, do that one focus block, make some progress. But again, don’t fall into comparisonitis and despair when you’re looking at your buddy that has allocated five focus blocks for their project and you’ve allocated one like you’re not, they’re going to be cumulatively outrunning you, right?

Charlie Gilkey:
And it’s not just that they’re going to be running five times faster, it’s five times plus some compounding interest of their momentum. They’re just going to be outrunning you. And that has nothing to do about them being better than you, is smarter than you, having their stuff figured out. It’s just the amount of time that they’re putting into the gym that we call life, right? If you don’t have that much time, you’re not going to get the results. And again, that can be really frustrating. But I’d rather us be frustrated about the reality of things and be able to assess it the way things are than to create stories about ourselves, about we’re not good planners, we’re not good executors we’re procrastinators. We don’t know what we’re doing. Cause that’s our default is like not looking at the situation and seeing that it is, but telling stories about ourselves and ultimately handicappers.

Career Nation:
Yeah, you’re so right. Sorry to jump in there. But I think that sort of creates sort of a negative spiral for a lot of people, which is I’m not good enough. I can’t do this. And then basically it reinforces negative behavior, negative thoughts, et cetera. You touched upon not touch upon actually you go through this concept of Gates in the book, which I found so fascinating. Tell us a little bit about that.

Charlie Gilkey:
Yeah. So Gates are your genius Affinity’s talents, expertise, and strengths. And I know that each means something different, but I really want it to be like that special sauce that you, that you uniquely have that enables you to do things. And they’re not always what would go on like your resume or go on your professional skills. So you might have a gate of curating music, right? Or you know, being able to organize spreadsheets or you know, being able to a party that’s a totally, you know, one of your Gates, but you may not list that on there.

Charlie Gilkey:
But what we do Abhijeet, is we pick a goal, we see common ways that people go about those goals. And we pick one of those common ways and then we jump into the project about the middle of the project. We figured out it’s super hard, right to do. What I want people to do is when they’re thinking about their goal, just start thinking about their Gates and say, Hey, how can I leverage what I’m great at? What’s native for me to get this goal done? This might mean you have a completely different pathway than the common way of getting there, but you know what, that pathway will work for you. So I’ll give an example here. To someone, I’ve given a book. I had a reader reach out to me. His name was, he’s Ernie. That’s not his real name, but we’ll call him Ernie.

Charlie Gilkey:
So Ernie reached out to me and he’s like, Charlie, I want to grow my blog. I’m terrible at writing. I don’t like writing. I’m good at you to know, conversations and video, but I want to grow my written blog. So what should I do to grow my written blog? And I was like, am I being punked here? Like, am I being trolled? Because in his, in his email, he had basically, he had already said, well, what the problem was like. And so I responded back, I was like, Ernie, don’t grow a written blog. Like, that’s not your goal. Your goal is to actually develop a platform and you know, build a business or do something like that. A blog is a pathway for doing that. You don’t like writing, you’re not good at it. You don’t want to do it. Right? Pick the things that you’re great at.

Charlie Gilkey:
Start a podcast, start a video-blogs. Like, use those skills to get to that goal. And when I say it, it sounds simple like duh. But I think most of the time when I say people can go back over the last two weeks and think about something they’ve done, the hard slash conventional away. And thinking about how they could have done it if they really would have used one of their geniuses Affinity’s talents, expertise or strengths to get that thing done. So, and the other thing that I’ll say is a lot of our Gates are actually collaborative and social. but we don’t use them because we have, head trash and negative stories around asking for help. And so because we glorify that sort of self-made person and we glorify that person that’s like doing it all by themselves, that becomes our model.

Charlie Gilkey:
And so we’ll go and we’ll struggle and we’ll thrash and we’ll push as hard as we can before we have to ask for help. Because we don’t want to owe anyone, we don’t want to show that we’re less than. And we want to credit them for doing it by ourselves. Right. And so what I would also remind people is that pulling people into your project earlier on and really working them in is the joyful, rich, and faster way usually to get things done. But you have to sort of front-load that. You don’t have to crawl through the desert of that project or you’re like, I’m gonna make it. And then right as you’re about to run out of the water, you’re like, help please, right. You don’t have to do that. You can ask for help from the beginning. And that helps sets up very natural and organic, accountability with a group of people that you are in that actually gives a lot of momentum and fuel for the project.

Career Nation:
Yeah. That is so true. In fact, one of my mentors tells me that, about this med of self-made person and basically he said, there is no one here that is self-made period, end of story. And, you’re so right about finding out what those Gates are, what are those areas of your genius, affinity, et cetera. And then, figuring that out and then moving back into your project and making sure that you are taking others along. And, you know, there are so many tools in the book that I would love to double click into, but before that, we do want to know you a little bit better. So if you’re a game, we would love to play the favorites game with you.


Let’s do it. You know that I may have to give you three favorites, but I’ll do my best to give you the one favorite. Yes. You’re allowed to cheat, allowed to cheat it just a little bit, Charlie. Okay. Charlie, do you have a favorite app?

Charlie Gilkey:
At this point in time? Ulysses, which is a writing app. And what’s great about Ulysses is that it just focuses on the words, and lets me figure it out. Just distractions and get content where it needs to go. So given that writing is what I do, I love it.

Career Nation:
Well, you did not cheat on that when you gave us your favorite app. That’s awesome.

Charlie Gilkey:
I had two or three other there. Don’t do it, Charlie, don’t do it.

Career Nation:
I love it. Do you have a favorite quote that you either like, you have stocked up on your, you know, closet somewhere, it’s on, on your personal note journal? Like do you have a free coat?

Charlie Gilkey:
Yes. And this is from Lao Tzu in the Tao te Ching. And it’s, I’m going to give you, I’ll give this version of it. “He who can conquer the world, I count as strong. He who can conquer himself, I count as truly powerful.”

Career Nation:
Oh, well that is deep. I love it. And I also love that fact because knowing yourself is such a liberating and powerful thing at the same time and it really allows you to go out and start finishing things. Wonderful. Do you have a favorite book?

Charlie Gilkey:
Ooh, now this gets trickier. By process of what gets quoted the most, it’s probably the Tao te Ching. And so as the book I’d just referenced, but it wouldn’t be the one that, you know, I have a small list of books that I would take to an Island. Like if I got, if I was to cast away and I got to pick five books, I could not have Tao te Ching there. So yeah, I would say that one.

Career Nation:
Wonderful. And I know you’re in wonderful Oregon. Do you have a favorite restaurant?

Charlie Gilkey:
So again, going with Gandhi’s action expresses priority, it would probably be Hopworks Urban Brewery, which my wife and I eat at probably twice a week for different choices that they have there. So yeah.

Career Nation:
Is there a favorite brewery as well over there?

Charlie Gilkey:
I love their, help cider. I’m a hard cider guy. And so their cider is really great too.

Career Nation:
Very cool. We’ll check that out. I don’t know if you get that here in Northern California, but we’ll see.

Charlie Gilkey:
You down. It’s a local company.

Career Nation:
Got it. So Charlie, thank you for that. And why don’t we shift gears back into the topic of the book and, I really wanted to ask you this, which is what would be sort of the top three ideas that you would share from the book that have for you personally stood out as like, Hey, if I want anybody to read this book and take these three things away, these would be it.

Charlie Gilkey:
Okay. So, yeah. Great. So the first one would be the idea of success packs. And I’ve alluded to collective productivity throughout our conversations. But your success packs are the group of ‘Yeah-Sayers’ that you put around your projects that help you do that near. Four different types of people you put in there.

Charlie Gilkey:
I can go, we can double click down into this and if you want to, but success packs and definitely the idea of, what’s important about success packs is one, you recruit them before you have a plan. And that’s counterintuitive for a lot of people, right? But they help you make a better plan and success packs help you convert how problems into who solutions. Right? So whenever you don’t know something, it’s not, I got to go figure it out. It’s like who do I ask? Oh, and are already part of my team. So success packs as a major one. The second one will be the five project rule, which the long way of saying that it is no more than five active projects per time perspective. And so both to explain that the time perspective is the easiest gateway into there. So we all know, I think intuitively the difference between a week sized project, a month sized project, a quarter-sized project and a year sized project.

Charlie Gilkey:
And we also know that the higher up you go in those time perspectives, the more those projects contain smaller projects at the time perspective over them. So how this gets really useful is that when you’re doing your weekly planning, you can say, okay, what are the five projects that I want to make the most progress on and or finish? And you can just focus in that time perspective. The trick here is that our brains don’t do well with different time perspectives at the same time. Right? It’s like the analogy is trying to think about the size of an ant, the size of a basketball and the size of the United States at the same time. Our brains can’t do it. Right. But when we start making plans and when I look at people’s to-do list, I can tell, Abhijeet, cause I’ll look at their to-do list.

Charlie Gilkey:
There might be 10 items on there and two of them are sort of like month size projects and you know, three of them might be week size projects and then there’ll be something that will take them a day and then there’ll be a bunch of tasks. And because I can see it, my brain goes haywire cause I’m like what’s going on here? But their brain is going haywire too. They just don’t know it. So the five projects rule really helps you focus for that time perspective, prioritize, do just in time planning and get those things done and see how they build towards the future that you want. So that would be one. The third key concept, I believe we’ve already talked about, but it would be to use your Gates more. So I struggle with the third one cause it’s either Gates or the no in scenarios that I talked about because again, so many people don’t realize that they’re actually afraid of success.

Charlie Gilkey:
And no matter what your plan is, no matter how much you put to it, if fundamentally you’re afraid of success, you’re not going to be as successful as you would otherwise be, cause you’re always gonna pull back and leave some in the tank. So that’s, I sort of asked like between Gates and no one’s scenario. So I’m going to cheat and say four. There we go.

Career Nation:
I love it. That’s such a great summary. you know, there was another concept that a really personally liked in the book that was around momentum planning. And, you know, momentum is fun. You, it’s hard to tell when you have it, but when you haven’t, you know, you know you have momentum, you’re making progress. How do we achieve momentum? How can we actually make it happen and sort of taking that from sort of this abstract view to him in a manifestation of that in our project, in our lives to make progress?

Charlie Gilkey:
Yeah. So one way to understand how to recognize momentum is the degree to which you need to scaffold and structure the work itself versus just being able to do the work, right? So when we’re really in a group, when we’re really in momentum, there’s not a lot of thinking about the work. There’s much more doing the work. but those projects that you pick up once every two weeks and you work on a little bit and you put it back down and you pick it up and you put it back down, you don’t get much momentum on there and you know it because every time you pick it up you’re like, where was I? What do I need to do? Like, well, that’s just going to look like the finish. And so, really a lot of the work. So there are different ways to think about this, but one of the reasons the five projects, rule is so important is because it actually does help you focus on momentum.

Charlie Gilkey:
Because what we have to remember is it’s not how many projects we start that really matters. It’s how many we finish, right? And so I want us to change our conversations from I’m doing all of these projects, to I’m finishing these four projects, right? And they’re leading to other projects. And you know, so what I will say is if you don’t have momentum right now and you’re really trying to get it, focus on the time perspective where you do feel like you have good control over. So like if you’re the weekly master and you can get weekly momentum done, that’s great. Use that to start focusing on month sized momentum and being able to tie months together if you’re good at months, work on growing into the quarter size because the quarter sized projects tend to be. That will have changed for so many of us, right?

Charlie Gilkey:
Because most of the significant projects we’ll do, one span over, you know, three to five years. But we have to sustain focused on chunks of those projects over quarters and tie those quarters together. So when you get to mastering that quarter, which is why there’s so many books like the 12 week year and the 90-day plans and everything revolves around the corner. Cause we recognize that is probably the biggest chunk of time that most of us can coherently plan and have that plan to be realistic. And it’s the one that someone gave us to falter on. So, that’s what I would say to like really focus on limit them starts with where you already sort of feel that it might be daily momentum. I’m not judging right. If you can master the day, great. Start, you know, working on the week, but don’t try to go from the day to the year cause that’s going to be super frustrating and you’re probably not going to be able to do it. To expand that, that circle of mastery, up to different perspectives of time. Was I clear on that one?

Career Nation:
Oh, it was. And it was sort of like this Jedi trick to get into momentum mode. I love it. you know, I do have a tactical question real quick on that one, which is sort of how do we say no and you know, yeah, I could have five projects. I could have a weekly week project or a month project, et cetera. You know, one of the things that always comes up and because you know, I’m usually well-networked and there’s always, requests coming my way and I think I’m a nice person. I don’t want to say no. And so how do you defend your sort of this momentum from external factors and how do you at the same time maintain a great network, maintain those professional and personal relationships that you value so much?

Charlie Gilkey:
So a few things. One, start from the perspective that you don’t have to defend it, right? In the sense that like you are charting your own sort of project destiny, right? And if people take you off that project, destiny, it’s because you allow them, right? And so I think and the reason I start this, cause I think so many of us start with our default is yes. Unless we can say no, right? So I’m trying to change it so that our default is no unless it makes sense to say yes. Right? And that seems to be a subtle shift, but it’s a really powerful one. Because it enables you to use some habitual triggers. Like the first thing that I would say to you Abhijeet on that one is going on a no diet in the sense of when someone asks you to do something, your response is first no.

Charlie Gilkey:
Because I think that’s going to be a bridge too far for you. But it’s, let me check my schedule and my project deck to see when I can do this. That will give you just enough time to interrupt that, tendency to say yes and that tendency to over-commit. And if you actually look at your schedule when you actually look at your project deck and decide that this request, like, is one of those things you want to do, then absolutely say yes. And the other thing that I’ll say is, and it’s going to sound pretty simple and obvious, but make sure that your schedule accounts for the open time that you may need to say yes to people. And so if you are an especially gregarious person and you say yes to a lot of things, you know, in that five projects rule, you might only let yourself choose four of those projects because you know there’s always going to be space taken by the other ways you’re going to say yes.

Charlie Gilkey:
But what that means is again, Jedi mind trick here, that project slot that you opened up is community projects, right? You’re just making space to support your community. And I think that’s a great thing to do if that’s in accordance with your priorities and values. And, and, and, and don’t assume you get to be heavily involved in a bunch of other people’s projects and priorities and you know, the stuff that they’re doing and get to do your full load of projects at the same time because that’s where you’re going to end up being in that self-defeating perspective or self-defeating position where you say yes too much and then you’re the person that can’t honor his or her commitments. And or not get your stuff done. And it starts to be where you will resent the very people that you’re saying yes to. Because they’re, you know, they’re keeping you from doing the things that you want to do.

Charlie Gilkey:
And so it completely corrupts that energy. And so, far, far better to say fewer yeses. But be able to really lean into those and follow through those yeses. Then to say way too many yeses that you can’t live up to. And that keeps you from doing the work that you’re most, here or most I’m here to do are most called to do. Does that help?

Career Nation:
Oh yeah, absolutely. I love those hacks. I love that shift from a default yes and maybe no to a default bell and then maybe yes. And also love sort of, Hey, let me check my schedule because that allows you a little bit of a buffer to make sure you’re providing the right response. I love it. Are there, so this is sort of a general question as zooming up a little bit. Are there hacks like that, that Charlie has in his toolbox that has not made way into the book? And, are there things that you, you do, maybe it’s your morning routine, maybe it’s your, the way you prepare for, I don’t know, a big meeting. I don’t know. Like, are there hacks like that that you have or that you’d like to share?

Charlie Gilkey:
Hacks! Let’s say very tactical ones in that way. Some of them are going to sound like a sort of general productivity advice, like every day I spend at least 15 minutes cleaning up my office. I’m preparing for the next day. Right? I don’t do well when I have a bunch of papers and stacks on my actual desk. They can be somewhere else, but not on my desk. Friday I have a five-things-Friday where I get rid of five things every Friday. Right? And so whether it’s just boxes that or crew or books or whatever it is. Just intentionally getting rid of stuff too, keeps things simpler and more organized. Let’s see. Another thing is that, one of the major hacks that I have, and I wrote about it in the book, you see me look, and it’s not in here. I wrote the book on an alpha smart Neo. Which is, if you give me just a second, I’ll go get it right.

Career Nation:
Yes. Go for it. Oh, this is going to be so fascinating. This is for the first time in the show that the guest has left the screen to go get something. And it’s my, it’s my duty to entertain you while Charlie’s coming back.

Charlie Gilkey:
Alrighty. Here we go. so Alpha Smart Neo, which is the 1990s processor. You turn this guy on, I think this is on here and it fires up and you have six lines of writing. And that becomes a sort of a distraction-free area. Or I can just write and focus and I don’t have to worry about email to worry about Google. It’s just me. And this is, it’s like, you know, Abhijeet we’re at that age where we can remember when we went to a computer to do a specific thing and then once we did that thing, we went and lived their lives. Right? So you had drafted and then you go type on a computer, you print it out and then you’d go live the rest of your life. You weren’t, you didn’t do everything on the computer instead of retraining. But what I’ve done is taken that like whatever recognize is that I create better work on smaller screens. So…

Career Nation:
Interesting. Very cool.

Charlie Gilkey:
Yeah. It’s more focused work. So it’s anti the trend of 27-inch monitors and things like that. But all of my creative workflows usually focus on constraining the space to just what I need to be focusing on at that time. Because if I can click on something, if it’s availability I can feel it at this point, draining a little bit of my bandwidth. And so this is kind of this meta hack here is assume that you have ADHD, and build your workflows around that assumption. And even if you don’t have ADHD, it will make your work so much easier to do and it helps help you focus and help you be present with things. Right. So if you, I may or may not have it, I’m not judging whether I do, but assuming that I have it, create better, simpler, more focused, more present workflows for me that allow me to be where I am and not be in 17 different places at once.

Charlie Gilkey:
So that one didn’t make the book. Another one that didn’t make the book is, and it’s not so much a hack as much as it is I working mindset is balancing creating, treating, connecting and consuming. We normally think about creation and consumption, like in the sense of you take in a bunch of stuff and then you create stuff. But connecting with people is a super important thing. And I can tell when I’m off-balance in my work shows up in my life shows up when one of those is not at the right level. And so it’s always sort of tweaking, tweaking or noticing like, Oh, I haven’t read as many books and articles as I normally do and I’m dry on the creative side, or my conversations aren’t as rich my conversations and connect with other people. So I need to do that.

Charlie Gilkey:
Or Oh, I’ve been in a cave for two weeks and I’m really uninspired and disconnected. It’s time to connect with other people. Right? And so just managing that energy is more like a weekly, or I could do it at the moment like, Oh, I really need to reach out to a friend, or I really need to, instead of watching TV or playing a video game, it’s probably time for me to do some high-quality reading or high-quality consumption. So managing that has been something that I’ve been doing for the last 10 years. It didn’t make the book because that was one of the 20%, that was some of the 20% of content that had to get cut. But it makes a huge difference when you start looking at how do you remain in a state of a thriving human being and understanding that it’s those three forces that are working.

Career Nation:
Oh, I love that. And that connecting piece can be so important because that makes you human. It is also sort of, it’s almost like the connective tissue between the absorption and the consumption of information to creation. In some ways, and you may have seen this is sort of also triggers sort of the subconscious mind in some ways because we’re having a conversation. It’s perfectly normal, but just catching up and you will kind of come up with an insight and idea which is like, ah, the problem I was trying to solve weeks ago, days ago, et cetera. Here’s the solution and then you will be rushing back to your notebook or to your Apple device. And I’m trying to try to note it down. I love that. Love that concept. Charlie, this has been phenomenal. I mean, this has been just a ton of value in this podcast episode. As we wrap up here, what would be your advice for Career Nation and as you know, our audiences across the board, we have some folks that are early in a career in the middle of their career, towards the end of their career. And quite frankly, they are interested to figure out how can they advance in their career? How can they create more value? Why parting advice? words of wisdom for them?

Charlie Gilkey:
Yeah. On this one, I would say that it’s your responsibility to tell the story of your career. That’s not your boss. It’s not your employer. It’s not anyone else’s responsibility, but your own to tell that story of how your work is creating value, how your work is coherent. You know, I’m echoing our good friend Pam Slim here where you’re like, you know, it’s your body of work and it’s really about the stories you tell about it. And I think as much as we focus this conversation on the doing of stuff, right? Remember that one of the doing things that you needed to do is to be, telling the coherent story about the work that you’re doing. And I’m not necessarily saying over-promotion and marketing and things like that. But if you’re not really thinking about how the work you’ve done this quarter could end up on your resume, one year is going to go by, years are going to go by and you won’t necessarily be thinking about the work that you’ve done. But two you may not be thinking, huh, this work that I’m doing wouldn’t show up on my resume. It’s not what I would want to tell the world that I’m doing. I need to create different work. So again, it’s your responsibility to tell that story and it’s your responsibility to chart, you know, the map of your work. And so, tell a good story, chart a good map.

Career Nation:
What a great way to end this episode. Tell a great story. Chart a great map! Charlie, thank you so much. It was phenomenal. We appreciate your time and good luck with the book. For those of you who want to get a copy, you can get it at your favorite bookstore. And we’ll drop a few links in the show notes – Start Finishing. Charlie Gilkey, thank you so much.

Charlie Gilkey:
Thanks for having me, Abhijeet. It’s been a blast.

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