The State of Online Business and Trends with Charlie Gilkey

Start Finishing with Charlie Gilkey

Tara Newman: Hey, hey bold leaders. Welcome to the Bold Leadership Revolution podcast.

Today we have a guest for you and his name is Charlie Gilkey. Now, typically, we don’t have a lot of guests on this podcast. It is a solo podcast, I keep it that way intentionally. When we have guests, primarily from my community, and my clients because I like to use my platform to support and further my clients and community’s work. However, once in a while, we get somebody who is really sharing something that I think is monumentally important for my audience, something that they would really love to hear about. And so today we’re talking to Charlie, who I’m so excited because he is a productivity nerd, just like me. We’re talking about his book called Start Finishing: How to Go from Idea to Done. There is nothing more important in this world than implementation, execution, and finishing the projects that matter the most to us. Not necessarily finishing every project, I’m not here for finishing all the things. I’m here for finishing the most important things.

Charlie Gilkey helps people start finishing the stuff that matters. He’s the founder of Productive Flourishing, author of the forthcoming Start Finishing, and The Small Business Lifecycle, and the host of the Productive Flourishing podcast. Prior to starting Productive Flourishing, Charlie was a Joint Force Military Logistics Coordinator … which he talks about on the podcast. While simultaneously pursuing his PhD in philosophy. He lives with his wife, Angela in Portland, Oregon. Let’s dive right into this conversation with Charlie. Hey, Charlie, welcome to the Bold Leadership Revolution podcast. I’m glad to have you here with us today.

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

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Tara Newman: Yeah. Like I was mentioning in our greenroom that lots of people have told us that we needed to connect. And I am absolutely a huge fan of productivity. A student of it, and I can’t be more excited to nerd out on this with you. We’re here talking because you have a new book coming out in September … end of September?

Charlie Gilkey: End of September, 9/24.

Tara Newman: Yeah. Okay. And it’s called Start Finishing. This makes me laugh in a way because it’s so divergent. Everybody wants to talk about starting, how to get started, how to start. Right? And so we get all these people started, but then we don’t have anybody finishing. So you’re how to start finishing, which I love.

Charlie Gilkey: Yeah, I appreciate that. Now, what I want to say is some people do have a hard time choosing the things to finish. So they start a lot of things and hoping that some way somewhere in middle of the process, they’ll figure out what they’re supposed to do. Which when I say it that way, it sounds absurd, right? It’s like you try 17 things, and hopefully one of them will stick. But that’s what we often do. But yeah, it’s like, none of us … Well, what’s funny about this Tara is as people talk to me about my audience, and I do interviews, it used to be, “So your people have a hard time with being creative.” I’m like, “No, no, no, no. My people have no absence of ideas. That’s not the problem.” What we’re challenged by is finishing the things that matter most. And we get so distracted, and we chase too many bright shiny objects, and so on so forth.

Charlie Gilkey: And at the end of the week, or the end of the quarter, or at the year we look back and say, “You know what? I was a rocking chair that … I was in motion all year, but I don’t really think I got anywhere.” And that’s frustrating. That’s really, really frustrating.

Tara Newman: It is. It is. Before we even jump into like the meat of your work, I wanted to ask you a little bit about your background and how you got started with this work because you have a really interesting background.

Charlie Gilkey: Yeah. Thanks for asking that. So way back in, say 2007, I was doing two things at the same time. I was completing my PhD in philosophy, and I was an army Joint Force Military Logistics Coordinator. Which is a mouthful, but I basically made sure the different forces were talking to each other and making sure that if one force dropped stuff, that the other force was there to pick it up, so on and so forth. And you’d think these forces at Air Force Army and Navy would be on the same page, but we’re often not. So my job was to do all of that coordination to make sure that happened. And I got to this point I had deployed from … or I had redeployed from Operation Iraqi Freedom, and I was like, “Wow, this is really frustrating and fascinating at the same time.” And what the “it” was here is that though I was able to move battalions and do all this coordination and do really well as a military officer, a 5,000 word essay was kicking my butt on the philosophy side.

I was is like, “What is it about this particular type of project? What is it about this creative work that makes it so much more difficult to do?” And also, “What can I apply from my military life?” Now, and at the same time, I was maintaining those two careers, I was trying to be a decent husband. We had just bought a house, and so the demands of life were weighing on me. I was like, “I got a lot going on and I’m not getting it done. But I’m not abnormal in that, other people have figured this out. So let’s go do that.” So I did a bunch of research. I did a bunch of exploration. And I started to distill what I was learning from the great books like Getting Things Done, Seven Habits of Highly Effective People, books like that. And I was like, “It doesn’t quite nail it for me.” Because my problem was that it wasn’t the big life values, where I wanted to be, sort of that principles and personal development camp.

Nor was it the getting stuff done in the five minute rule … or excuse me, the five minute action. And the next action focus of getting things done. My problem was in the middle with all of these projects, and none of them really showed how to get projects done. It turned out that that’s actually what the military was really great at, was helping you get projects done, and helping you figure that out. And so I started recombining, and synthesizing, and sharing this. And much to my surprise, people dug it. And I was like, “Okay, this is a thing.” And so I’ve just been following that thread of how do we actually get this work, these ideas, these hunches, these intuitions, onto our schedule, onto the page … whatever your page might be, and done? So that’s been my work.

Tara Newman: That’s so fascinating. When I was just still finishing grad school and I was working for a boutique consulting firm and then my client wound up hiring me. So this is my first really big role in an organization, and I had all the ideas from being in graduate school. You know how that goes. All the theories. But I remember that the Executive Vice President … I was the productivity girl. And he used to run around and he used to tell me, “Tara, your only job is to get them to focus and finish, focus and finish.” And he would just yell after me every chance he got. He was like, “Are they focusing and finishing? Have they finished yet?” It was like he realized the importance of making sure that what got started, got finished. And it had such an impression upon me, and it has really informed my work over the last few decades as well. So I really love that you’re taking this perspective. I also love that you read these books. I think that there’re a pretty homogenous group of authors who write in the productivity space.

And nowhere in the books do they really talk in real world language about some of the things that you mentioned, like trying to be a good husband, and working on your dissertation, as well as working in the military. And having like multiple irons in the fire, so to speak, and having a life.

Charlie Gilkey: Absolutely. And I think that’s why so many people check out the productivity conversation, because it tends to be just about work. And I have to be careful here because my view of work is much more expansive. But in this context, I’m saying it’s more career focused or business focused. I understand where these authors are coming from because of who they’re trying to sell to, and all that sort of whatnot. But when we look at what’s actually going on in our lives, work is a major part of it, but it’s not the totality of it. And when we look at what matters most to us, is often not work. And that’s what the definition. It’s our family. It’s our relationships. It’s our wellbeing. It’s our spirituality. It’s our sense of creativity in play. It’s all of these other things besides what we’re doing 9:00-5:00, and how much money is in our account. Unfortunately, that tends to be where that’s coming from and it’s really exclusive on the one hand because it leaves out so many people who have different values.

And the other thing is that it tends to really define the conversation to actually make us more overwhelmed. Because here’s what happens Tara, we have conversations around work life balance, right? I hate that conversation start with, even though I understand what’s going on with it. Really what it means is there’s this work stuff that we do that has this economic and societal value, and then there’s just life stuff that we do. But unfortunately, what we do is we apply different ways of thinking and different ways of prioritizing to one camp versus the other. And in my experience working with hundreds of people on this, what happens is the life stuff ends up being someday maybe, once you get the work stuff figured it out. Once you get work stuff and economics figured out. But in the middle of our daily lives, is all this life stuff that happens, the parenting, the pet playing with, the video games, the hobbies. Whatever it is, that is the stuff we most want to do and most want to enjoy.

But we shame ourselves from enjoying that, and we forget that work and money are just intrinsic things that get us what we actually want. Which is that quality time with family and friends, feeling that sense of love and belonging, that sense of progress on things that matter to us. And we get it all messed up. I think that’s one of the reasons why people check out of the productivity conversation. I get so infuriated by it, because there’s another reason they check out. It’s because it’s like the 72 ways to hack a shoe box sort of conversation that I have no time for. I’m like, “Really? That’s where we’re going? And that’s the conversation?” Because while you’re hacking that shoe box, maybe there are other things that are more important than that. That just becomes a tool for procrastination and distraction.

Tara Newman: Can you define briefly what productivity maybe means to you and what it is? Because I think that the term “productivity” gets such a bad rap. I think that people wind up giving this word meaning and emotion that it doesn’t necessarily have, and that everybody is so used to thinking about it in terms of doing more. And that’s not what it means to me at all. And I’m pretty sure that based on what you just said, that’s not what it means to you. So can you share with me your definition or your thoughts on productivity?

Charlie Gilkey: Productivity is about doing what matters most. It’s not about more. It’s not about quantity, per se. It’s about instantiated your values and priorities in the world. That’s it. Now that means for me, going back to what I was saying about work and projects, the other thing that I have to say is if it takes time, energy, and attention, in my book, it’s a project. So cleaning out the closet of doom, that’s a project. Backyard project, that’s a project. Getting your son out of the house finally, is a project. Getting married, all the trips we want to take. If you really want to get technical, taking out the trash can be a project, right? But all of this stuff that requires time, energy, and attention, are projects. And that can be really overwhelming because just when you sit and think about, it’s like, “Wow, I have a lot of projects.”

But also the grace in that is that you realize it’s not just that you’re not getting stuff done, it’s not that you need to do more, it’s that you need to have a better view of what all you’re actually doing and start making better choices to figure out are the things that you’re doing, getting you towards your thriving? Is it instantiated your priorities? Is it instantiated your values or not? And if it’s not, try to find a way to stop doing or to start doing less of that. Or get way more efficient, so you can do the same amount in the same amount of time. But I really … Work is not a four letter word for me. So let me explain.

Tara Newman: yeah. Let’s go here.

Charlie Gilkey: Yeah. There’s an oddity of the English language, that so many of our crafts and curse words are actually four letters long. I don’t need to go into them all because you they’re all four letters on. Very, very strange. But work sometimes ends there there. It’s the stuff we don’t want to do. It’s the stuff we want to get away from. It’s the stuff we don’t talk about. It’s just that sort of stuff that we just don’t want to deal with. But I think when we really look at people who are thriving, their work is sacred. Their work, it’s things that they want to do more than other things. So it’s a type of work that when you go on vacation, you’re ready to be off vacation, not because vacation can be its own stress, but because you miss that thing that you do. It’s a part of yourself in a way. I call that your best work. And it turns out that many of us want to do a lot more of our best work. But we have to start doing less of all the busy work, of all the other work.

There’s this oddity about your best work is that though you most want to do it, it’s often the thing that scares you the most. Because it is tied into your identity. So I talked about a lot about thrashing in the book, and thrashing is this meta work, the flailing, the working around the work. That’s not actually pushing the ball forward, that’s all that sort of emotional stories and all that stuff. I’m not saying that emotional is bad, it’s just not doing the work. And it turns out that you thrash more when something matters to you. Or the more something matters to you, the more you’ll thrash. None of us go into a mini existential crisis about taking the trash out. We don’t.

Tara Newman: True.

Charlie Gilkey: Right?

Tara Newman: Yeah.

Charlie Gilkey: Going shopping, we don’t care. It’s a thing, we might not want to do it but it’s not that it growling, and “What am I going to do? Am I the right person? What do I want to do when I grow up?” It’s not that type of stuff. But you start talking about starting your own business, getting a new job, marrying someone, moving across the nation, being a digital nomad. Whatever your thing is, that’s when all the thrashing will come up. And we can spend years in this thrashing process, not actually getting anywhere. And unfortunately, what happens to us is: one, we have a view of work going to what we were talking about earlier where that’s more important to us. We got to do that, we got to pay the bills, we got to look and live a certain way. And then we have this fear that, “What if I tried to do my best work and it doesn’t work? And I’m not cut out for it? Oh, that’s super scary. Because I’ve done all of the things I need to do to set that up, and what if I can’t?

Or what if it doesn’t work? Or what if I don’t like it? And I’ve been telling myself for the last 20 years that there’s this thing that I’m going to get to and I finally make room for it, and I don’t like it. What do I do with that?” And so we end up continuing to do the work that pays the bills, the work that’s okay, sometimes it’s good, and putting off our best work because we’re thrashing, and because we’re scared of what might happen if we do our best work and it doesn’t work out for us.

Tara Newman: Yes. And what I see a lot too is work just being … it is. It’s like a four letter word. It’s like a bad word. People don’t want to do the work, I think pretty much because of what you said. But also because in the online space, we’ve conveniently looped people in to this belief system that you can have it all without working. Passive income. Just show up and do some stuff on social media and you can make money. And it becomes a lot of distraction from doing their deepest, most meaningful work. That business becomes like fake work.

Charlie Gilkey: I agree. And I’m going to start by saying this. I appreciate Tim Ferriss. I actually love Tim Ferriss, and I love his work. But part of it is the title of his book, The 4-Hour Work Week. Actually-

Tara Newman: Yeah. Can we talk about that?

Charlie Gilkey: It kicked off a lot of this idea that you can get your work done in four hours a week, and then you can just spend the rest of your life doing all these cool things. If you actually read the book, that’s not what it’s about.

Tara Newman: Yes. I know.

Charlie Gilkey: But he’s a brilliant marketer, and that’s what he knew at the time. It’s a great book, it still sells because people walk down the shelf, or walk down their library or they’re on Amazon and like, “I’m tired of all the work. I’m burnout, I’m done. I just want to do all this life stuff.” And then they see a title like The 4-Hour Work Week, and they’re like, “Boom, I’m on it. That’s what I’m trying to do.” But when you really look at what he’s saying in the book, that’s not it at all. But unfortunately, nuance and deep thinking does not survive well on the internet. And so we have encoded this idea of the four hour work week of just doing as little as possible. And the whole thing … I’m a business coach and strategist as well, and the first thing when people want to talk to me, it’s like, “Well, I want to build passive revenue.”

And I was like, “That’s great.” And the first thing I’ll tell you is there’s nothing about passive revenue that’s passive. It’s where you want to put the work. So to build a passive revenue engine, you do a lot of work on the first two or three years. And it might work out such that you reap that harvest in the three to five years that follow with a lot of maintenance and a lot of things that go on. But it’s not like you spend four hours working on something and you’re done. And then you get paid six figures rest of your life.

Tara Newman: Yeah, I think that’s atypical.

Charlie Gilkey: it’s atypical. Sometimes it happens. I’m not going to say … There are some folks out there that make it happen for them. But I think in the online space, we would do much better to talk about the mean than to talk about the outliers. Because when you talk about the mean, and what happens for most people, I think we get a truer sense of what’s going on. And more importantly than a true sense of what’s going on, there are a lot of people out there that are the mean or above the mean, but they think that they’re somehow uniquely defective because they’re doing all the things and they’re not getting the results that they’re supposed to be getting. They’re not sipping mojitos in Tahiti, and things like that. Like the dream has been sold to you, right?

But I want to change the conversation around work, though, because I don’t want it to be, “How can you live your life so that you only spend four hours working?” To, “How can you spend your life so that you’re working on the things that matter most to you, in the degree that you want to?”

Tara Newman: Yeah, that has meaning in the purpose.

Charlie Gilkey: It has meaning in the purpose. And you know what? I’ve been reading a lot about farming, I’m considering getting a small scale farm, and things like that. And which is a really unusual choice. But when you really look at the lives of a lot of farmers and people working with their hands or things like that, turns out they’re a lot happier than those of us that are looking at computer screens all day and doing the typical knowledge work thing. There’s a lot of reasons why, I won’t necessarily get into it. But my point there is, they may work a lot more, but their fulfillment in that work is a lot higher. And so sometimes we have to ask the question, “Would you rather work four hours a week and have an unfulfilled life? Or would you rather work 40 hours a week and have a really fulfilled life?” Now, that’s a really strong man and a false alternative because there’s a range in between. But it’s really that fulfillment, it’s really that thriving, it’s really that meaning that I’m after. And going back to productivity, you become by doing.

You have to create those conditions in the world that lead to your thriving, that lead to that fulfillment. And if you’re not doing that work, you’re not going to create that sort of thing. And so it’s not like you get out of the work. And it’s not like once you get it, that your work is over. It’s just … You know what? We all have 24 hours a day. And some folks are spending that time in ways that really lights them up and makes the world better. And some folks are spending that time waiting for their day to do that thing where they are lit up, they’re making the world better, they’re happy. My hope is that more people start spending their days and start making those wedges in their days so that they find that meaning, purpose, and fulfillment now and stop waiting for that someday that’s never going to come.

Tara Newman: Yeah. I think it’s becoming increasingly more difficult too, with the level of distraction that is happening in our society and this whole concept of the attention economy. And so it becomes harder and harder to place a container around your productivity and your work. But I, like you talk about the air sandwich in the book. And there’s these factors that go in that’s in between. Do you want to talk about that?

Charlie Gilkey: Yeah.

Tara Newman: Because I think that speaks a bit to why people struggle to really drill down on what some of that meaningful work is.

Charlie Gilkey: Absolutely. So it’s the air sandwich because you can look at the top slice of bread as that big vision, that big view that you have of yourself and how you want to live in the world. This is normally where we start talking about values, and priorities, and vision. It’s up it up there at the top. At the bottom layer of the sandwich is the day to day grind, the stuff that just happens day in day out. And what a lot of people notice is this way they want to live their life, this goal they have for themselves, who they aspire to be, is so radically different from their day to day reality. And there’s a lot of air between those two, so it’s the air sandwich. But when you really look at it more deeply, it turns out that there are five things that are stuck between that top layer bread and that day to day reality. And those five things are competing priorities, head trash, no realistic plan, not enough resources, and poor team alignment.

I can go through each one of those, but I want to say I hope most people understand head trash pretty easy. I hope that folks understand that. But the last one called team alignment, I’m going to stick here a little bit because a lot of times when we talk about team and we talked about the people around this, again, we’re so focused on work … excuse me. On economic work. That’s how I’m going to call it for this podcast, economic work. We’re so focused on economic work, that we don’t look at the people in our lives as part of our team. We don’t look at that neighbor kid who’s a babysitter as part of our team. We don’t look at our parents and friends and the people around us as part of our team. We don’t look at our partners as part of our team. And what we end up doing is not asking for the help, and not setting the vision or not talking about our vision for ourselves with those people, so that no one knows what’s going on. No one knows how to help us.

We’re not getting the help that we need, but we are getting the help that we need in the economic work. So those things go forward, but we don’t have the team alignment on the personal domain, on the life domain. And so really when you look at all the reasons we’re not doing our best work, it comes down to some combination of those five challenges. And obviously, if one story we tell ourselves all the time is like, “Well, if I just had more money.” Or, “If I just had more contacts.” Or, “If I just had more time.” Or,” If I just had more of that thing, then I would be set. Then I could do whatever I wanted to do.” It ain’t true because you’d have that, and you’d be worried about squandering it, or you wouldn’t apply it. We’re always not going to have something that we want. That’s the nature of being human. Right. So we keep telling ourselves that these are valid reasons not to start finishing the stuff that matters most, when really they’re not. They’re the same challenges that everybody faces, and it’s just coming to grips with them.

Tara Newman: Yeah. I love when you talk about team alignment. Back in … I don’t know, like 2012 or 2013, I wrote a blog post that was titled Life is a Team Sport. And that really resonated what you were talking about around creating your success path. You want to talk a little bit about that? Like creating this group of people around you, and you are going into who you need in your success pack.

Charlie Gilkey: Yeah, your success pack. Now, when I wrote Start Finishing, one of the ways that I wrote the book is I wanted people to focus on one project. And the reason I did that is because one of the let downs with productivity is that some conversations around productivity, you need to be more fair there. Is that they don’t give us grip into specific things in our life that we can start working on. So we get a bunch of tools, but we don’t have anything that we particularly know to fix. And so we’re like, “What do we do?” And then we get back distracted and we don’t do it. So I gave people a project because the projects, especially best work projects, they’re both mirrors and bridges. They’re mirrors because they reflect back to us what’s going on in a world, and what’s going on in our lives. And so the second you commit to doing the best work project, all sorts of stuff start coming up for you. And guess what? It’s not the project, it’s you. It’s what’s actually going in the world.

And so I want to have that frame so that actually did unfortunately experienced that discomfort because that’s the reality of things. But they’re bridges because they’re what helps us build that life that we want to live. So the whole reason I say that is because I apply success pack to a specific project, but you can apply it to your broader life. Now, there are four types of people who you want to be in your success pack. First off, who you don’t want in your success pack are naysayers. We spent a lot of time unfortunately trying to make the naysayers agree with us and try to make them a complete and utter distraction. Right?

Tara Newman: Yip.

Charlie Gilkey: And you’re never going to get a naysayer to be a yea-sayer. Like haters going to hate. Drive on. So your success pack is full of the yea-sayers that actually want you to be successful, believing you’re successful. Yea-sayers are those people that when you start talking about an idea, they don’t question if you’re going to be successful, they question how you’re going to make that success happen. And that’s a big distinction. Four types of people that you want in your success pack. They are your guides, which are the people that are little bit ahead of you or actually a lot ahead of you. And they’ve walked the road a little bit longer. They’re your Yoda, your Morpheus. They say cryptic things like, “Use the force.” Or, “Trust yourself.” You like, “What the hell does that mean?” It never means anything until the moment you need it. So those are your guides. Your peers are your people that are down at your level of accomplishment or perspective. They’re side by side, but they’re not working in the project with you.

So these might be your mastermind buddies. These might be that friend that you get together with once a month and you talk about what’s going on, and you help each other out. But you’re not instrumentally involved in the project. They’re your supporters, which are the people that are in your project or are in the work with you. And then lastly, they’re your beneficiaries. And I want to hang out with the beneficiaries a little bit, because I think they’re one of those superpowers once you really lean into it. When we talk about beneficiaries, if you’ve ever done … On the business side, if you’ve ever worked with a marketing consultant, like “Who’s your avatar?” Then you end up with some sort of weird 44 year old woman living in Indiana, she’s got three kids. And we list in demography, but we don’t actually say, “Do I know that person? Do I have a friend.” We want your beneficiaries to be people you actually know, whose world will be better off because of the work that you’ve finished. Right?

Whose lives will be changed. You’re either going to solve a problem or you’re going to deliver a delight. That’s the only two ways that we can do. Sometimes we do both. But having your beneficiaries in mind gives you two things. One, when you get stuck and you don’t know what to do and whether your project is working, you can ask that person, “Hey, I made a thing. Does it work for you or not?” And that’s scary, but it’s way better to get that answer sooner than to spend three years working on something and figure out it doesn’t work. The second thing, and this is really goes for a lot of us who are service minded and compassionate is, it helps you remember that in that moment that you don’t want to do the work. You’re stuck, you’re thrashing, you’re ready to give up, that you’re not just quitting on yourself, you’re quitting on that other person too. If you don’t finish your work, that person’s not better off. They’re going to not have some benefit, or they’re not going to have some delight that only you can create.

Somebody else can make a close copy, but it’s not going to be your work. And so for a lot of people who when you’re stuck, you’re like, “You know what? I’m done. I can’t. It’s just about me, I need to move on.” Actually, it’s not about you. It’s about this planet, this community, this network that you’re in and how you’re making that better at the same time that you’re making yourself better and having enjoyment while doing it.

Tara Newman: Yeah. I talk about this as putting your mission over your money. Sometimes people will really think I’m crazy. It really triggers their scarcity mindset, but I have bills to pay kind of a thing. But for me, it’s very … And I appreciate that for everybody who it’s not motivating. But for me, that’s a very motivating way for me to complete projects, and to really stick with the long haul that it takes to do your best work in the world.

Charlie Gilkey: Well, it’s motivating. But I want to be … A little bit of science here helps. We have mirror neurons that activate when we experience the emotions of other people. So if someone else is smiling and starts to activate things in your brain, they make you more likely to smile. All sorts of other moods work like that. Emotional contagion is a real scientific thing. And so part of what’s going on here is when you have a beneficiary and you’re sharing that work with them, and they’re smiling, or they’re happy, or they’re excited, they’re thankful, it triggers those same emotions within you. Whereas when you just focus on that scarcity mindset, you only get a negativity spiral in that mindset, “I need money, so I’m going to do the thing. If it works great …” A lot of times it doesn’t work. That’s part of the trick. It doesn’t work or doesn’t work on the timeframe that you want it to. So, “It didn’t work, I need money. So I got to do it. Didn’t work, I need money.”

So you end up in a negativity spiral that keeps you there, as opposed to a positive or positivity spiral that keeps you focused on other things. And so it really is quite primal. And unfortunately, I think we fail to recognize that we are organic beings driven by primal urges, and that we can hack those and use those to become better humans. As opposed to try to pretend that they’re not there like we’re some rational robot that can just do things when we’re scared, or tired or, hungry, or anger, or lonely, or depleted and do it at the same level as if we weren’t. And that’s just fundamentally not true.

So the more that you can introduce success packs to your work, the more you can talk to beneficiaries, the more you can do things that lights you up and help you live from the inside out, the more you create these positivity spirals that keep you doing that, and keep you from being stuck in these sort of spirals where it’s like, “Ah, I gotta do the thing because I got to make the money. And if I don’t make the money, then I don’t get to do the thing.” And how helpful is that?

Tara Newman: I really appreciate you when you said the word “robot” because it reminded me of just something I want to acknowledge you for because this book is not written as if we should all be productivity robots. As a matter of fact, you address it and you say, “Books on productivity, creativity and personal development, often, oddly tend to make people feel bad about themselves. So I want to be clear up front, you aren’t uniquely defective, you aren’t constitutionally wired to struggle, and you aren’t fated to be unable to get your shit together.”

Charlie Gilkey: Yeah, that’s the thing, man.

Tara Newman: You acknowledge everybody’s humanity and your humaneness in that moment, and that we do struggle with these things like productivity. Or I was saying to you that I want to talk about boundaries on here, because probably creating boundaries around my work is one of the hardest places that I create boundaries.

Charlie Gilkey: Why is it so hard for you?

Tara Newman: Because it’s so funny. There’s something about doing my most important work in the world that feels oddly selfish to me. And I know that that’s the opposite of true, that’s my head trash. So there’s something about carving out boundaries around my work that it starts to feel like I’m not approachable, which is also more head trash that I’m working on. Or that I’m not accessible to people, that it’s not inclusive of me. When really that’s the way for me to do my best work and to be the most inclusive, is to draw those boundaries.

Charlie Gilkey: Yeah, I totally get that. I totally get that. And there’s this weird mental loop that we get into. Super strange. I’m going to say it. Unlike most of the things I say in the book, when I say it, it sounds absurd. But it’s what we actually do. When it turns out that you enjoy doing your best work, it’s harder to set boundaries for it because it’s something you benefit from it, and it makes you happy. And you’re denying other people something that they want just to do your own thing. It’s this weird thing where like, if you didn’t enjoy it as much, you would probably have an easier time setting a boundary to do it.

Tara Newman: Yeah, I feel like my work is my guilty pleasure sometimes.

Charlie Gilkey: Yeah, yeah. So the guilty pleasure, sort of whatnot. So part of it is, I’m trying to get on the philosophical train, and then get off of it very quickly, sometimes. But see, here’s the thing that we have Tara, is like many of us struggle with letting our own happiness and pleasure being good enough. It has to be constructive. It has to be for some purpose. It can’t just be that we’re happy, and we like it. And that’s why we do something. And that’s it. We don’t need any further explanation. Whether you’re talking about sex, whether you’re talking about money, whether you’re talking about work, there’s a thing that we can’t acknowledge. That our own internal pleasure and happiness is something valuable in and of itself, and that we don’t have to justify that.

Tara Newman: Yeah. You actually said it in your dedication, “For my mom who places so many people’s thriving above her own.”

Charlie Gilkey: And unfortunately, when you place other people’s thriving above your own long enough, you become resentful, you become frustrating or frustrated. You become that martyr that no one actually likes to be around where, “I do all this for other people, and I never get to do my own thing. And no one ever comes for me.” Because the reality is … And sometimes this happens, but it happens so rarely that I’m okay with saying it never happens. It’s not like the world is one day going to wake up and be like, “You know what? It is our day to focus on Tara’s priorities. It’s our day to make sure she gets what she wants. And we’re going to stop all of our requests against her time. We’re going to stop asking that she gets involved in our own project, we’re just going to focus on her.” Never going to happen. Right? So in this case, yeah. It’s a guilty pleasure. And that’s I think, when you know that you’re doing your best work, is when you feel like you’re cheating.

You feel like … Like when I started doing this work, I felt like someday someone was going to figure out that I loved it so much and stop paying me as much as I could get paid to do it. “Oh, you actually enjoy this so I don’t have to pay you as much.” Just pro tip, as an entrepreneur, the more you enjoy the work and the more native it is to you, or more genius you have at it, the more you should charge. So anyways, moving on. Yeah, setting work boundaries is super hard. But here’s the thing, if you look at it from what’s going to matter in two weeks, and what’s going to matter in two months, two quarters, two years, two decades, a lot of the times you notice that you have to make those positive and negative boundaries for you to do those things.

And that in some, more people are going to be happier and the world is going to be better when you focus on those things that may require you to set some boundaries than if you remain unboundaried and end up that accidental misanthrope who really just need some time to go work through their creative constipation, and get some things out in the world so that they can show up in a place of generosity. So there’s this weird tension between boundaries and generosity. I know I’ve got there in a roundabout way. The more boundaried you become, the more generous you can be.

Tara Newman: This is true.

Charlie Gilkey: Right. And it’s the other way around. The less boundaried you are, the less generous you can be. Now, you can be generous in speech. You can commit to a lot of things, you can tell people you’re going to be there, you can do that with your mouth. But it turns out when it comes time for you to actually be there, you won’t be because you’re too over committed. Your body might be there, but your mind is somewhere else thinking about something else that you’ve committed to and trying to figure that out. So the more that you can figure out what your right yeses are and what your right nos are, the more that you can focus on that and be generous in the moments that you need to be. So there’s this weird sort of thing because boundaries … I’ll talk a bit more about it in the book, but boundaries always seem to be that exclusion. “I’m pushing people away. I’m telling people I don’t want to be around them.” So and so forth. That is legit one way of thinking about it.

They’re positive boundaries, where you’re making space for the things that matter most to you. And when you really think about that, it actually allows you to be more generous with the right set of people. We talked a little bit about online entrepreneurship, we talked about the digital web and things like that. But one thing I want to slide in here real quick, is we are 20 years in to one of humanity’s biggest experiments, that is the internet and being connected the way we are. Our wiring is not made for the type of social context that we’re in. We’re made for much smaller environments, much fewer … knowing fewer people.

Remember back … I mean my age, I’m nearly 40 now. But I remember when there was you had your friends and friends meant something, and then there wasn’t digital friends. There weren’t people you knew online. There weren’t people that you’re following, or friending, and things like that. And my whole point of bringing that up is there was a much smaller, tighter, warmer group of people that we’re used to being in relationships with that as technology has connected us with more people, we’ve assumed that our capacity to be in relationships have caught up with it. And they have not, and they will not.

Tara Newman: Correct.

Charlie Gilkey: So the fact of the matter is, we have to be more boundaried now, this is because we have more exposure to more people than we’ve ever had in human existence. So if you’re struggling with relationship these days, again, you’re not uniquely defective. It’s just that you might be immersed in technology that has outpaced your ability to be the type of human in relationship that you actually want to be.

Tara Newman: Yeah. I read a great book. I’m sure you’ve read it, Margin?

Charlie Gilkey: Yeah.

Tara Newman: And that book really stirred stuff up for me and made me question what my social capacity actually was, because I felt like it was being dictated to me via social media, and that like that was a falsity. And I had to really start to define my social capacity for myself.

Charlie Gilkey: Absolutely. Swenson. That’s what’s great about that book is when it was written, it was so prescient, that it was just talking about where we are now. But if you want to read a modern book, that is more like Cal Newport’s Digital Minimalism.

Tara Newman: Yip, that’s a great book.

Charlie Gilkey: It’s a really great book to read. And it will make you really think about the benefits and the cons of this sort of digital immersive experience that we live in.

Tara Newman: Yeah, it’s always helpful to read books where you believe what the author believes because it’s confidence building. And when I read that book, it built a lot of confidence for me to really step away from social media and the distractions that it was causing.

Charlie Gilkey: Yeah. Have you read The End of Absence?

Tara Newman: No.

Charlie Gilkey: You got to read The End of Absence. You totally have-

Tara Newman: All right friends. You’re getting a great book list, I hope you’re taking notes.

Charlie Gilkey: Here’s the context of The End of Absence. He writes … Michael Harris, I believe is his name. He writes about the fact that … so I’m 40, I mentioned that earlier. I am one of … That generation or that people that lived about then are the last generation that will know what it’s like to not be connected to the internet 24/7. We know that period of time … Remember when we used to go and sit on hills, and sit in parks, and we didn’t have to do it to get away from the internet. We didn’t have to do intentional unplugging, we didn’t have to put our phone on airplane. We were disconnected as a way of natural way of life. And now, we’re connected as the natural and default way of life. And he draws that there are some stark changes to our society and our persons because of that, because of the end of absence.

Tara Newman: I’m going to read that. We just sent my kids to sleep-away camp. And one of the biggest benefits to sending them was that it was technology free for the amount of time that they were there, which was a significant amount of time for two kids. Post millennials living in this day and age. And they come home tomorrow, so I’m excited to hear their experience from not having their phones and everything on them. Something that really coincides with all of this is the whole concept of routines. Like, what are your routines? What are your routines for taking yourself out of some of these spaces and putting yourself into more productive spaces? So besides morning routines, which I think we’re all familiar with, what other routines help people get started and keep the momentum on their projects?

Charlie Gilkey: We can talk a long time about this. I love routines.

Tara Newman: Me too.

Charlie Gilkey: Before I jump into which, I’d like to talk about why they’re so important real quick. One of the things that routines do is that it lowers the amount of decisions that you have to make every day. Okay? And with the world that we live in, with all the micro decisions we have to make: what we’re going to eat, where are the key, am I going to do this? So on so forth. The more that you can remove those decisions and make them automatic, the more that you can free up your bandwidth to focus on the things that matter most. And I want to say both mental and emotional bandwidth. I think we’ve all been in that situation to where we haven’t figured out what dinner is, and it’s like four o’clock. And we figure out, we’re in that space until like 6:30, until we finally decide what we’re going to do. That’s two and a half hours of thinking and deciding that you don’t have to do. There are different ways around that.

So routines are really important because: one, they lower decision fatigue. And two, they spur us to find flow in our days, whether that’s at work, or whether that’s at home. And so, I’m going to go through three routines, which I think are really critical for people. I know you mentioned morning routines. But I want to be specific here because sometimes we have a morning routine, that’s when we get up in the morning and what we do first thing. But I also love pre work routines. What you do to trigger yourself to be in a good productive space. Yes, I’m going to, say, shut off notifications, don’t check email first. That’s kind of a standard advice. But I want people to be intentional about, “What are the four or five things I can do every morning or every time I’m going to start the day?” I’m Corona type friendly, meaning that if you’re a night owl, or you’re an afternoon emu, I’ll love you too.

So your beginning, let’s say it might be an afternoon or at night. But whatever the beginning of your work period is, what are the three to five steps that you can take that would make it set up so that you’re in flow? So pre work routines, killer. Post work routines, also very, very good to be able to gracefully … I sometimes think that what we do at work is like the way that Navy fighters land on aircraft carriers. Okay, people aren’t in the military so you don’t know this. There’s a very rapid descent and a very hard break once they hit the aircraft carrier because they don’t have as much runway. Okay, it’s not like landing the big jumbo planes where they have all the runway in the world. Well, we’re sort of those Navy fighter pilots when it comes to our work sometimes. It’s like we’re at work, and then boom, five minutes later we’re at home. And your mind and your body and your heart, all those things don’t have time to adjust for that. So post work period helps you extend that runway.

Helps you figure out what you’re going to do so that you don’t go from a busy commute till the garage door opens … if you have a garage, to walking in and the kids are on your leg and you haven’t had a space to really ground yourself. That’s critical. Bedtime routines also super critical. Now what I’ll say about this, and it’s going to issue a challenge to your listeners here. If you want to sleep really well, and you want to get up earlier in the morning, here’s what you do, no screens two hours before you want to go to bed. So if you want to go to bed at ten o’clock, no screens. And I mean no screens except for maybe a Kindle Paperwhite, I allow it in because that’s essentially reading. But none of the smartphones, no computers, no TVs, anything two hours before you go to bed. I promise, most people when I coach them through doing that for a week, they notice that, “Wait a sec, I can sleep and I get up rested.” Right?

Tara Newman: Yeah.

Charlie Gilkey: If you really want to go, try a week with no screens after work. Super hard to do for a lot of folks, and the benefits are really there. To be clear, I’m not a Luddite. I do a lot of these experiments on myself and with other clients. I love technology and how it empowers our lives, but I … I think technology is like money. It can be a great slave, but a terrible master.

Tara Newman: Yeah, it’s about being intentional with how you use it. It’s not about eschewing it. It’s really just about being radically intentional about its purpose.

Charlie Gilkey: Absolutely. So no screens two hours before bed is a pre bedtime routine, but just think about what you do. And many folks luckily have a brushing their teeth, or they’re taking out their contacts. Or just something that you do in the bathroom a lot of times before folks go to bed. And if you really do what we like to call habit stacking, you can start layering another thing on top of that, and layer three to four things on top of that thing that you already do. And it might be a 15-30 minute ritual or routine before you go to bed. And I’m going to pause here because a lot of people are like, “Where am I going to find that 30 minutes?” Well stop watching TV.

Tara Newman: Not using your screens.

Charlie Gilkey: Not using the screens. It turns out that if you stop using screens, there’s a lot of time in the day. There’s a whole lot of time in the day. It’s like if you’re married, two things if you want to have really long days when your partner goes out of town, and especially if you don’t have kids or you arrange childcare for them, don’t have any screens for that weekend. It will be the longest weekend you have experienced in a long time because you don’t have kids, and pets, and things that you have to take care of. Or you could do the reverse. You can just leave and not have a screen with you. It makes really, really long days. So I want to be clear here, though. There is the whole like stop watching Lost and stop watching TV. I’m not going to go that far. I’m just going to say are the shows that you’re watching, or that you’re consuming, is it too much for what you actually need? And two, are you getting what you need out of it?

If watching The Bachelorette and Love Island just really gives you that sense of play and you just really need to do that, that’s fantastic. There’s nothing actually wrong with that. Do it, but do you need to watch four episodes in one night? Might one do well enough? So it’s like too much ice cream is a bad thing. A lot of these, especially the digital distractions that we allow ourselves to get into, fall under that sort of same principle. So it’s not that you can’t have any ice cream, it’s just are you having the right amount? And is it doing what it needs to do for you?

Tara Newman: We’ve been … and when I say “we”, my husband and I. We’ve both been doing a lot of research this year. We’ve dedicated this year to researching sleep. And we’ve been doing a lot of … I don’t want to say sleep hacking. But just really understanding what goes into having a good night rest and it’s not about the hours of sleep you get, there’s all these other factors that go in. But one thing that I’ve started doing and I’m encouraging my clients to do is making a KPI in their business around their screen time. Actually, if you have an iPhone, you can get that data right from there. And what’s possible for you when you really start pulling that screen time back, I mean, your brain … I feel like my brain gets its life back when I minimize my screen time. Like there’s something chemical that happens, and you can feel it when you are using too much screen time versus not too much screen time. So I’m with you on this.

Charlie Gilkey: Yeah, absolutely. And it is … to go back, it’s neurochemical. Sometimes what I’ll do with clients or when I’m teaching workshop, is I’ll say I’m like, “Okay …” so everyone listening, feel free to do this. “Clear your head for like 10 seconds. Okay, now what I want you to do is touch your smartphone.” As soon as people touch their smartphone, what happens is all the habit loops start firing off. You’re more likely to press the home button if you got a smartphone, but your fingers will start to gravitate towards those things that you click on the most. And I can literally see people doing this in workshop. And it’s infuriating for them because they’re not making the decision to do that. Their fingers … And there’s been some experiments, and there’s the monkey hammer experiment where they … It’s a graphic one it goes to show. But they remove the hands of monkeys and put a hammer on there anyways. All right, put a hammer on it. And it changed the neurology of the monkey’s brain such that that’s how the monkey understood to use that limb.

Unfortunately, I think smartphones have become the hammer that’s replaced our hand. And when it’s in our hand, our brain creates a feedback loop then we do the things that we do on the phone. And there’s also another great research or a great study that shows that the apps that we’re using on our phones the most are the ones that are making us the least happy. And the apps-

Tara Newman: Oh, I agree with that.

Charlie Gilkey: The apps that we use the least are the ones that make us the happiest. Very strange, it’s counterintuitive. So we’ve got this device, we touch it, we do the same things over and over again. But those same things are not making us happy. So we’re giving up on dopamine loop or we’re doing it more trying to get happy, trying to get happiness and it’s not working. Third study here show that even having a phone in the office is enough to lower your IQ points by five or 10 points. I don’t remember which one. So with some of these studies in hand, again, I do productivity experiments right now. Like right now in this moment, my phone is downstairs in its cubby, it’s on Do Not Disturb and it’s on constant Do Not Disturb.

I don’t bring it up in my office because what do I need it in my office for? Who besides robocallers call me. Right? I don’t have children, so if that might be another consideration. But I’ll pretty much figured out how to do that, or how I would make that work. But remember those times Tara were like we used to go to a phone that was on a wall or on a counter? We would make a call or check our voicemail messages, and then we’d go do other things?

Tara Newman: Yeah.

Charlie Gilkey: We’d get along just fine doing that. Right? So that’s what I’ve hacked again with my phone because I’m like, if I need to check my voicemail messages, I could walk my ass downstairs. I could check voicemail messages. Guess what? Nobody but robocallers called me just like yesterday, and the day before. And then I could go back to my business. I don’t need that device with me to do the work that I do, and I don’t need to be constant. The world can survive for two hours without me making sure everything was okay.

Tara Newman: Yeah. Oddly for me, my smartwatch, my Apple Watch has helped me because you would think that’d be, “Well, Tara that’s more technology.” But I actually use it like a flip phone. So I leave my phone away in my drawer or whatever. And then if somebody sent … when my phone’s not on Do Not Disturb, if my somebody sent me a text, it’s like really hard to respond via text via the Apple Watch. So it makes it like you’re going to be as short as possible and not sit there and really engage in long conversation. And the other thing is I set timers a lot because I’m a Pomodoro girl. And setting the timer on my watch, I don’t have to pick up my phone and be distracted by all the other things that are on my phone versus what’s on my watch. So yeah, I’ve been looking for ways around that as well.

Charlie Gilkey: Yeah. I’m currently with my Apple Watch in case you’re curious about this Tara. I found the same thing. But I’m currently also in timeout with my Apple Watch. And so Apple Watch is also where my phone is, and so I use it most of the same way. Or I take my watch if I’m going out more so. So it’s also I’m testing what it’s like to not even have that on me right now. I need to write about it. But it’s super fascinating. And that’s just what we’re talking about here is asking people to introduce and exclude different pieces of technology and different slices of time to see whether it makes them more focused, and engaged, and grounded, or not.

Tara Newman: And make space.

Charlie Gilkey: And space. Absolutely.

Tara Newman: I always like to leave my listeners with an action that they can take. And so I want to wrap us up here because you’ve given some really great action. They can try leaving screen time behind for the two hours before they go to bed. They can sit down and just look at how they’re using their phones, and things like that intentionally. And how they can really start to use that as a way to make space for some of these projects. Because in your book … I want to bring us back to the book. This is a great book, it’s very easy to read. It’s wonderfully laid out, and I think that was fairly intentional by you, Charlie. The way the book is laid out. I love the way that you don’t have to read it from cover to the back, so that you can pick it up at any place and really get value out of the book and really use it as reference.

Some of the chapters in here for everybody … because I really want them to go and actually get the book, that I really liked was around picking an idea that matters to us. So for all of you entrepreneurs who have all the ideas and need to figure out what matters most. Like we were just talking about, making space for your project. There’s a chapter in here around building your project roadmap, which I really like because Charlie doesn’t really give you a roadmap, he helps you build your own roadmap in here. And there’s one about building daily momentum. Looking at your schedule, and finishing strong. These are just some of the chapter. There’s more chapters, but those are some of the ones that I really appreciated. And there was value in every single chapter of the book, so I really want to encourage people to go and … I’m going to let Charlie tell you where you can find him, but I am going to tell you that the book is available.

The book, Start Finishing: How to Go From Idea to Done by Charlie Gilkey is on Amazon for pre order right now because it officially comes out September 24. Correct?

Charlie Gilkey: Correct.

Tara Newman: Yeah. So where can they find you if they want to learn more about you? I know is your website. And you’ve got really amazing templates on there too.

Charlie Gilkey: Absolutely. First, thanks so much for the feedback on the book. I’m loving it. And you’re right, there lot of intentional choices. I wanted to make this feel super accessible and feel more like a cookbook than a super wordy productivity book that no one really wanted to get into. So thanks for seeing that.

Tara Newman: Yeah, you nailed it.

Charlie Gilkey: Thank you. So if you’re interested in the book, go to, you’ll be able to download a free chapter. Chapter three, a lot of people dig that chapter. And you’ll be able to get more information. One thing that also say that makes me super proud about the book is it’s got some great contributions from folks like Seth Godin, and James Clear, Jonathan Fields, Susan Piver, Tod Kashdan. I’m going to forget names, I feel like a butt hole. But there’s a lot of really great-

Tara Newman: Chelsea Dinsmore.

Charlie Gilkey: Chelsea Dinsmore, Srinivas Rao, Jeffrey Davis. I was really happy to include their work because we’re all doing this work together, so they have some great features as well. So is where you can find out more about the book and get your free chapter. If you’re curious, Productive Flourishing is the place to check out. She’s right, we do have some great free planners that have been used by millions of people. They’re free free, meaning I don’t even ask for your email address. You can provide that for some bonuses, but you don’t have to. Really what I want … I probably should have said this at the beginning. Start Finishing it’s a bit of a Trojan horse, and let me explain why. It’s a Trojan horse because, yes, it’s about productivity. It’s about how to get your idea done, but it’s is really a book about thriving, and what you need to do to get there.

And if nothing else, take a couple of hours and think about your days, and how those days are going. And think about if it’s going towards the life that you most want to live. And if not, what project may start that path for you?

Tara Newman: Hmm, I love that. I think that I can really identify with that because that was when I started to … I was there and that’s when I started my business. That was my project. It’s a big one.

Charlie Gilkey: That’s a big one, and you’re still-

Tara Newman: That’s a big one.

Charlie Gilkey: … doing it. Right.

Tara Newman: So, Charlie, thanks so much for your generosity and your value that you gave to my audience today. Thank you for stopping by.

Charlie Gilkey: Thanks for having me. I’m pumped and hope to do it again.

Tara Newman: Thank you. Now, if this conversation was interesting to you and felt unique and a little different, I want you to do me a favor. I want you to take me up on my invitation to join The BRAVE Society. So if you’re a female, small business owner, this is likely your community if you’re resonating with this podcast and the things we’re talking about over here. Because they are very much the essence of how we talk about things in The BRAVE Society.

The BRAVE Society was founded on three basic principles.

One, community. How can we come together and become a marketplace of business owners where we can do business together, where we can open doors for each other, where we can collaborate with like minded credible business owners?

Two, nobody should ever short change their leadership development. I see too many times women spread thin making investments in their businesses as they grow and short changing their leadership development, and I’m here to solve that problem. You can make the investments that you need to make in, say, your marketing, or your branding, or your website and develop yourself as a leader.

And the third thing that we come together for is to really stand at the pinnacle of our leadership, which John Maxwell talks a lot about in his work. He says that we’re the pinnacle of our leadership when we are a leader who develops leaders who develops leaders. What I asked the women of the BRAVE Society to do is to take what they learn in The BRAVE Society and bring it into the world into their communities, into their families, into their, into their clients and their customers and to really continue to develop more leaders on this planet.

If this sounds interesting to you, I want you to go over to the show notes and click on the link or you can come find me on Instagram @thetaranewman and ask me any questions you need to about joining The BRAVE Society.

If you found this podcast valuable, help us develop more bold leaders in the world by sharing this episode with your friends, colleagues and other bold leaders. Also, if you haven’t done so already, please leave a review.

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Special thanks goes to Stacey Harris from Uncommonly More, who is the producer and editor of this podcast. Go check them out for all your digital marketing and content creation needs. 

Be sure to tune into the next episode to help you embrace your ambition and leave the grind behind.

Important links to share:

Productive Flourishing

Start Finishing: How to Go From Idea to Done by Charlie Gilkey

Listen in on CEO Debriefs and Get 10 BOLD Questions for your own debrief.

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