Productivity, High Performance, and the Realities of Business Ownership

Productivity, High Performance, and the Realities of Business Ownership with Charlie Gilkey

Hey there everyone. It is Tara Newman from The Bold Money Revolution Podcast. I’m really excited today. I’m here with my friend, Charlie Gilkey. He is really in the top 10 of my favorite people in the world. He is the owner of Productive Flourishing and he is an author. He’s got books called The Small Business Lifecycle and Start Finishing. Charlie and I have decided he is gracing me with his presence very generously to bring you some bold truths that I think are very much needed.

Prior to recording this, we decided that we’re not going to be lobbing any softballs at you today. We are ripping the band-aid off. We are going to talk to you like we talk to each other, right Charlie?

Charlie Gilkey: That’s pretty much it. That’s the truth.

Tara Newman: So welcome, Charlie.

Charlie Gilkey: I am so honored to be here. You said gracing you with the time and I’m like, “I’m honored to be here.” For all the listeners who don’t know me, what I will say is if you’re anything like Tara, and you probably are, 100% respect how much of a powerhouse you are and the great work that you’re doing in the world. If we throw a spiritual punch, it’s not to make you smaller, it’s just to be honest and let’s just have that conversation because dodging the truth, as you know, does not benefit you, it does not benefit your work, and it does not benefit the folks around you. I’m just going to start it out that way.

Tara Newman: I have so many questions for you because I’m like, “Ooh, I got him captive, he’s my captive audience, he’s going to answer my questions, I’ve got things.” First of all, if you don’t know Charlie, he’s in the small-business coaching productivity space, he is a dynamo in his own right, he’s got the most amazing energy, he’s a kind soul. Would you like to add anything about your awesomeness into that?

Charlie Gilkey: Yeah. Well, the thing about it is, and this is one of those things we’re working on at Productive Flourishing, while a lot of people know me for my work in entrepreneurship and small business, I actually do a lot of work in corporate as well. Same energy, same vibe. I just have to put the LinkedIn tie on. It’s really walking into a situation being like, “There’s a whole lot of halls and barriers going on here so let’s level set and let’s get this going.” That’s the only thing I’d add to that.

Tara Newman: Yeah. Awesome. I love that. Corporate needs more folks like you as well. I love walking into corporate just to be a disruptor.

Charlie Gilkey: Yeah. It’s helpful when you can walk in the corporate and be okay with being fired. That’s the trick when you’re like, “You know what, I could speak what’s going on. We can have a real conversation and y’all could not like me and that’s fine,” because that’s the dance you get into in corporate is that if you’re working there, unless you really, really love your job—and let’s be real, that’s like 20% of the people based upon most statistics—a lot of times you’re like, “There’s a lot of things I want to do but if I do it the way I want to do it, if I say the thing that needs to be said, I may not have a job,” and so I take that into what I’m doing. I’m like, “You know what, the best service I can be is to speak the truth and make the changes happen that the people who feel like they can’t do.”

Now, obviously, I know that sounds like the whole white knight thing and that’s problematic but I’m just like, “But look, I can be fired and be okay. But what about that mom of four kids, it really does need this job, it needs a change to happen, I’m here to make that shift happen.”

Tara Newman: Yeah. I go in and I say “I’m here to say the things that you can’t.”

Charlie Gilkey: Yep. So you have questions and that wasn’t one of them, or I answered like eight other questions you didn’t ask.

Tara Newman: Yeah. Okay, so here we go. I’m a productivity person, you are a productivity person. I find that I’m personally very triggered by the anti-productivity movement. I understand that we have misunderstood productivity in this country for the most part, and actually, that’s one of the reasons why I left corporate, but I want you to tell me and tell my listeners why productivity is important, and what it means to you.

Charlie Gilkey: Yeah. I’m hella curious about the threads of anti-productivity movement, which there are several going on between the neurodiverse community, between the anti-capitalist movement, between all those different elements of them coming up between the multi-potential, I think, no shade on Emilie, but just some of what pops up there, but from my perspective, productivity is simply doing the things that enhance your thriving or that advance you towards your thriving.

I have been frustrating and confusing for a lot of people the whole time I’ve been doing this because you cannot separate productivity and personal development. People who try to do so end up with very systems and ideas that don’t work in the real world and just make people worse off either way. Look, I have not met a person really worth, ooh, that sounds bad, really about something that doesn’t care about people’s thriving, that doesn’t care about their own thriving, that doesn’t care about doing their best work and being their best self in the world. Their best self could be being the best parent, being the best sibling, like a whole full spectrum of people, that is important.

Seventeen ways to hack a damn shoebox, no, that is not important. That is just productivity prawn that we read to feel like we’re doing something. But there are different levels of doing the work in productivity. The first level is like that 17 ways to hack a shoebox things, like you’re just learning tips, you’re learning different ways of working. At a certain point, you’ll start redesigning your workflow, then at a third point, you’ll start redefining your life, and then at the fourth point you realize you have no idea what the hell is going on and you’ll be stumped for a while.

Then later on you realize that the problem was you thought life had to be lived a certain way, you thought all these things work out. That being said, when the anti-productivity movement comes up, I’m like, “But then what are you about?” Anti-brands don’t last. That’s the thing you gotta know. If you’re on a thought leadership journey, you’re like, “D*mn whatever. D*mn Marie Kondo. D*mn Brene Brown. D*mn whatever.” At a certain point, your audience is going to look at you and say, “But yes, what are you about though? We’re tired of just being angry, frustrated, and anti. We need to be going somewhere.”

If you can’t present a positive view of going somewhere, which is going to look like you’re having the productivity conversation, at a certain point, people are going to find someone else who actually has gone through that anti-journey. They can say, “Okay, and now here’s how we go forward in a way that makes sense for you, that makes sense for your family, that makes sense for our society.” You start having those conversations, you’re in the productivity conversation again. Welcome back.

Tara Newman: Yeah. My background’s in high performance and I always say that high-performance strategies are really a lot about self-love, about caring for yourself. There’s a difference between being a high achiever and a high performer and it’s a spectrum. High performers double down on the things that high achievers think are meaningless, unproductive, or pointless, like getting more sleep, creating more space, and practicing a lot. High performers practice more than they compete, things like that.

I’m always curious I think because I’ve been so in it for so long and I’m not tainted by the hacks,  the tidbits, the tips, and the tricks because I’ve studied it at a different level that I’m always like, “Oh, but I wish you really understood,” so thank you for sharing your perspective on that as somebody who is an expert.

Charlie Gilkey: Thank you. What I like about the difference between high performance and high achievement in the way that you said it is high performance is functional. You do the things that help you perform well, that solve some specific goal that matters. The problem with high achievers is that achieving becomes the goal, not what achieving does for your life. You win all the things and lose at life. Guess what, you’re not winning.

Tara Newman: Correct. I have another question. I consider myself a truth-teller. You’re a pretty candid straightforward person. I think we both have that in common, transparency. Do you think that truth-telling, candor, and transparency are being weaponized in our current marketing culture, or do you think that we can still claim the truth-telling?

Charlie Gilkey: We can claim the truth-telling, it’s your intent. I’ve seen non-violent communication weaponized way more than about any other framework that I’ve ever come across, which is funny. You got to think any communication framework, any paradigm like that can be weaponized. The culture of radical authenticity can absolutely be weaponized because there are some people who can be authentic because their authenticity lines up with society’s aspirational lines, whereas other people’s authenticity does not. You can be authentic if you’re norming if you’re reinforcing the norms, whether it’s the norms of Insta, whether it’s the norm of TikTok, whether it’s the norm of whatever thing that you’re into.

Anytime I see something like that and when I do communications, coaching, communication with myself, I’m like, “What is the intent?” Even in this conversation itself, like that in the green room, the question I asked here is like, “Well, are we going to land this truth softly or it’s going to speak clearly?” Because there’s an intent behind that. If we were just here to, and [Sam] and I talked about this yesterday, I’ll give this example and I will pull it back around, I promise you, Tara, we were talking about—and this will be a public podcast soon—but we were talking about the way events can be designed, there are multiple different ways.

You can design suffering in a crucible and all sorts of things in there to break people, and you can do that from a manipulative point of view that makes them codependent and subservient to you and the paradigm and things like that. Or you can just create experiences that have people confront their own things naturally and organically. They’re still going to struggle but you’re not doing it in a manipulative way, you’re not doing it in a way that makes the process, your process, or you, the real center point. It’s them and what they’re going through.

I think it’s very similar to any of these things. If you’re really doing it to push people in really thinking about what you want them to do and where you want them to go, you got to be careful about that. If you’re creating a container that helps them go where they most want to go, you’re probably going to be on the right line of that.

Tara Newman: Thank you. I was checking in, I was writing some copy or whatever, and I was talking about like who this thing was for and I’m like, “Well, this is for people who value this type of conversation. This is for people who value truth, who value candor, honesty, ambiguity, and the nuance that comes with that. I said today in my program, somebody was really rumbling with something and I said, “Hey, listen, entrepreneurship is a high-contact sport, the high-contact team sport with a greater propensity for risk and injury. It’s basically rugby.”

When we can accept that, we can let it go and we can move on with greater ease. But if we’re going to continue to fight hard, it’s going to make it harder. But if we can accept what is a challenge and say, “Okay, this is challenging, and this,” and I know that you were actually when we started this, you were talking about people’s attachment to their own struggle and that being a part of their identity and how they put forth a lot of cognitive emotional and spiritual labor for that struggle, and I’m going to add that there are people who are wanting to see that manipulated and continued.

Charlie Gilkey: Yeah. I’ll bridge the conversation here. This is often why, and this was a very coachy thing, very writer thing, very philosopher thing, to look at words and the words that we use. I am very careful about when I use hard, like that’s hard work. Hard invokes a struggle, it invokes emotional, and unfortunately in our society, we get attached to the hard. I will say, “Look, this is a difficult thing to do.” Difficulty doesn’t necessarily come with the emotional. No. This is just a difficult task. We have to stand up and be prepared to do this task but we don’t have to be like, “Oh, it’s hard so I’m either going to shy away from it or I’m going to do it because it’s hard.”

You do the work because the work is necessary to achieve some end. If the work is difficult, you do the difficult work and you figure out how to make it less difficult. But there’s not a big story about it being hard.

Tara Newman: That’s the thing. Once you do the difficult thing, the hard thing, the challenging thing, whatever we want to call it, the thing that’s causing us some kind of strife or strain, it’s not that way anymore.

Charlie Gilkey: Yeah. It’s something you’ve done and you know next time it’s still going to probably be difficult. But to what we’re talking about here, we live in a society founded by the Protestant work ethic. I know I’m going to sound like the anti-productivity people but give me a second, I’m going to get my way out with this.

Tara Newman: I’m with you though. I’m on it. I’m with you.

Charlie Gilkey: We attach moral value to hard work. We attach moral value to the struggle because of the foundations of our society. Unfortunately, it becomes unfathomable for us for something to be great work that’s not hard, that doesn’t struggle. Where that really messes this up, three or four clicks up is like as entrepreneurs and as small business owners, we want to charge the most for the things that are the easiest for us.

I’ll say that again for the thing in the back. We want to charge the most for the things that are easiest for us. But because hard work is valuable, we oftentimes will attach the price point thing to the thing that’s the hardest and then we set up ourselves with a no-win scenario that if we get the high-priced thing, we have to do this hard work. But what we really want to do is this easy thing but nobody pays us for it. Well, that’s because that’s where you place the value on it. We assume that it’s valuable to me because it’s hard for me but it doesn’t mean for your customer, your client that its difficulty for you creates value for them. It’s actually noise.

Tara Newman: Correct. Actually, the more difficult it is for you, the less value it’s going to create for your client, in my opinion. This comes up a lot with people who are looking to leverage and scale services because leverage feels too easy, leverage to me is I work once, I deliver many times. One of the things that we’ve been working on leveraging, scaling, whatever is some productized offers. We’ve built out some pretty cool productivity boards behind the scenes that would allow people to run a support ticket, like customer experience and it’s automated and it’s in a Monday project management board. We’re going to be rolling some of that stuff out.

I had a moment where I was like, “Oh. What am I charging for this?” Then I was like, “Well, let’s think about this. This is literally 20 years of experience. This is my education. This is the countless hours that I have put into learning Monday, tweaking Monday, evolving it, improving upon it, making sure it works, clarifying the result, capturing the data, but it’s going to be really easy to sell that. I don’t have to do any more work to it.” But all of those other things have gone into that.

Charlie Gilkey: Absolutely. I’m working on my next book called Team Habits. Largely, when I do my work, I’m at synthesis as opposed to this person that comes up with like the one cool idea that no one’s ever thought about. My background is a trained philosopher, I’m like, “The odds of my coming up with an idea no one’s ever thought about are really stinking low, but we’re in an abundance of ideas anyways. We need more sense-making and execution on those ideas, so why am I going to hold on to that?” Anyway, that’s a whole different story.

But the reality is anytime you buy a book, you’re not just buying the amount of time the person spent writing the book. Most authors worth their salt are distilling 100, 200 different books like different things into that, so sure, you can go read all of those and maybe come up with the same insights or you have the shortcut that frames that it makes it sense for you in the same way that yours does.

I’ll give another example of this. It took me way too long to figure this one out too. Something that’s actually pretty simple and easy for me to do is to walk into a room full of a bunch of people running all over the place and get them aligned and pointed toward the same goal and going in the right direction, really easy. I’m like, “This is just what people do.” It turns out, not so much. I was like, “Oh, this is a unique skill.” The other one that I have is I’m a good endnoter and I thought everybody was a good endnoter.

The key thing about being a great endnoter in an event is you have to be able to weave together all of the different conversations, pull out the ones that matter, get a sense of the room, and then do that almost on the fly to create an end cap that bookends the thing. I’m like, “Everybody can do that.” It’s a rare skill turns out. I had to have that reinforced multiple times because I was like, “This is just easy for me.”

You have to think like your idea of what’s easy doesn’t actually matter when it comes to marketplace value, it’s what result does that give for people who don’t have that trait, attribute, skill, or expertise, and then focus on that piece.

Tara Newman: Yes. How do you think or what have you seen helpful in helping people work through that addiction to struggle? You touched on the Protestant work ethic and I have been, in the last couple of years, just so deeply present to how conditioned we are, but not just how conditioned we are, but how our conditioning is being continually reinforced even more so than before through things like social media, and we’ll go there in a bit because I do want to touch upon that, but these messages that we’re picking up almost daily that continually reinforces, how do we start to unring this bell?

Charlie Gilkey: Alright. I’ll start where you said we’re going to get to, just be conscious of what you’re getting through social media and other sources. You think you have control of those messages, you do not. This stuff creeps in and it’s reinforced and it’s reinforced and stuff that you were taught when you were four to six years old. I want to give people a chance to let themselves off the hook at the same time they don’t want them to stay on the hook.

Here’s the place where you get yourself off the hook. This is neurological priming. What fires together wires together. If you’ve been told the same story for decades, those neurons, that’s just the story, that’s just what they recreate every time. Once that thread starts, the rest follows. That’s what learning is. That’s what socialization is. That’s the place where you’re off the hook.

Now where you’re not off the hook is you can stop receiving those messages. I want to pause here. This is going to sound like from a productivity perspective, people confuse distractions and interruptions. Don’t make that confusion. Don’t make that conflation. An interruption is like a being, whether it be four-legged or two-legged, whatever, coming to your space knocking on the door, or with some analogy of that, and claiming your attention in that moment. That’s an interruption.

A distraction is what you allow yourself to do. YouTube does not interrupt you. Instagram does not interrupt you. You allow yourself to be distracted by YouTube. How do I know that? Because you can stop that. Without a lot of negotiations, you can’t stop your child from knocking on your door to get your attention. Those are fundamentally different things. That is within your power to choose not to do, that’s within your power to choose to do, it’s an Aristotle quote, but if you can make that choice, then it’s your responsibility on that point. I’ll start there. The second thing is to stop participating in the social behaviors that propagate those stories. Very specific.

Tara Newman: Oh my God. Please, we might have to get heated here. Stop participating.

Charlie Gilkey: Stop participating in the behaviors that advance that story. Notice how common it is for us all to get together and complain about how busy we are and notice how awkward it is if you’re the person that’s just like, “Actually, I had a really great day. I took a Wednesday matinee. I left work early. I had a good exercise,” there is no space in so many conversations for that so your choices are to do the socially-acceptable thing, which is to pile on about how busy and hard your life is, and then that’s what your group does, that’s what your friends do. In other words, this is how you’re prioritizing spending your time together, i.e. This is what you value. Think about that for a second.

Tara Newman: Yeah. I remember being in some early psych classes in college and the professor said, “Misery doesn’t love company. Misery loves miserable company. Struggle loves struggling company. Distraction loves distracted company.”

Charlie Gilkey: The flip side of that’s true though, that’s the key thing. Happy people love being in the company of happy people. Chill folks love being in the company of chill folks. Successful folks love being in the company of successful folks. We’re likely going to end up talking about forming relationship, exiting relationship, management at some point, if not today, then later, Tara, but the thing that we don’t realize is the single biggest vector of change that we have is not necessarily ourselves but changing who we’re with.

We can’t dictate where and how we were born, what class we were in, what our skin color is, how we present to the world, all those things we were born with. However, we can choose who we associate with. If you associate with the people and continue the pattern of getting together and talking about how busy you are and how much suffering you’re going through, I want to be clear here, there’s a lot of power and bonding in talking about the real struggle of your life. If you come from an oppressed community and you need to be with your people who can talk about it and understand that, I’m not saying we can’t talk about that. But I’m talking about for the trivial busy that we glorify, the trivial stuff.

When I say stop participating in that behavior, have the courage and the boldness to be like, “Hey, I’m just wondering if today we can talk about maybe the good things going on in our life?” Interrupt that pattern and it’s like, “No, I want to complain, then you know what you’re getting here.” That’s what this group is about. But most of the time, if you take that leadership moment, that personal self-leadership moment to say, “You know what, in this very precious time that we have together, let’s do something that really matters with each other, and complaining about the trivial is not it.”

Tara Newman: Well, more than one thing can be true at the same time. We can be challenged by some things, struggling with something, grieving something, exhausted about something, and want to be moving forward, have a goal, and be ambitious. I hear from women a lot around like, “Oh, I need to heal. I need to heal. I need to heal.” I’m always like, “Yes, we can heal and work. We can heal and move forward. We can heal and make money. We can do both of those things.”

Charlie Gilkey: Yeah, and I want to be clear here that I’m not advocating for just the toxic positivity that exists in our society and in our workplaces. That’s not really what I’m talking about. I’m not trying to force people to be happy in a bright side and all that jazz. But I’m just saying if we want our minds and conversations to shift, someone has to introduce the shift. If we understand that all of our storytelling about struggle is reinforcing the value of struggle, the necessity of struggle, and all that, we’re going to keep getting what we’re getting.

I’m not saying at all that you can’t talk about the hard, I’m not going to go the whole toxic positivity thing, but life is more than the struggle. Life is more than hard and it’s more than the tyranny of the urgent. How are you going to bring that to your people so that you start talking about it?

Tara Newman: Yeah. I think about this a lot with small-business ownership and with entrepreneurs because I think we sell entrepreneurship as something that’s very sunshine, rainbows, easy, and path to riches, and it can be those things and it also can be a lot of pressure, it can be stressful, it can be murky, it’s not always like a clear path, it’s not comfortable. For me, it’s like let’s just say that the way it is this is a huge learning curve for some people. This has an element of stress. It has an element of uncertainty. It has all of those things. It has an element of complication. Okay, great, yes.

Because the less time I spend trying to tell myself it’s something different, the more time I can spend on moving forward and moving out of that place in that moment that it’s like, “Where do I want to put my energy?” When I say, “Yeah, this is a struggle. Small-business owners have mental health challenges. This isn’t always the path to riches,” it’s to say yes and now let’s just get on with it and do the things that are going to lead us to a better place. It’s like when you see the cage, are you going to leave the cage or are you going to stay in the cage?

Charlie Gilkey: And to what degree are you going to own the parts of the experience that is the cage that you made?

Tara Newman: Oh, yeah. What was that? I think that was in Michael Singer’s, gosh, I’m going to forget his book, but he talks about that you’re decorating, he has his book that you’re decorating the cage.

Charlie Gilkey: You’re in the decorating cage. I think it’s a Remy quote of like “Why do you allow yourself to stay or why do you keep yourself locked in the cage when you have the key?”

Tara Newman: Yeah. The Untethered Soul is the name of his book.

Charlie Gilkey: Yeah. Here’s the other thing that we’re going to say, yeah, I’ll speak to both truth, in this moment, maybe this morning, I don’t know if I feel like it right now but this morning, I got a few buddies that have recently gotten some really great jobs and I’m like, “Man, it’d be so cool to have that job right now. There are so many things I’m thinking about right now that I’d just rather not. I don’t want to be having some of these conversations.”

Tara, we’re recording on Friday, on Monday, I am a month out from turning in my manuscript from Team Habits. We’re building Momentum, which is our software-as-a-service productivity app, we got some other things going on, there’s just a lot. I was like, “You know what, it’d actually be really good not to think about all these founder owner things for just like a minute, maybe six months, maybe three years of not selling, getting the money, managing the money, managing people, hiring, letting people go, onboarding, integrating, training folks, managing, coaching, all the things you do, I could just do the thing for a little bit.” That’s real.

I can speak to it because it’s not like I’m going to go get a job tomorrow, and if I did, that would be freaking okay. But I know that job is going to have things that are going to be a pain in the ass, like someone can tell me to be somewhere at a certain time in the morning and I can’t negotiate my ass out of it, all those different things that come with it. But I think people don’t let themselves really be like, “You know what, this thing that I’m doing is difficult right now. I’m going through a bit of a crucible. I’d rather not be doing it.” All those different things. I don’t like it.

I have a post on Productive Flourishing called like “I am pro-entrepreneurs but not pro-entrepreneurship,” for this very reason. When someone has made the commitment to start their own small business and they start their own startup or whatever it is, let’s do the best we can to support them in that dream and vision. But can we please, for just a freaking second, stop pretending that as a creative person, this is the one way you can live your life, and if you don’t start your own business that you’re somehow less than? Because if you were a real entrepreneur, you’re a real creative person, then you would start your own business. Like, “No, I know so many wonderful creative professionals that are doing fantastic work in organizations.”

Let’s be real, especially with the way technology is, we have a good five, some of us will have six working decades, we are going to float in and out of owning our own business, being an advisor here, working for someone else, doing this other thing. The whole question that I would want people to think about when it comes to their economic arrangement, whether they’re employed, part-time, whatever, is in this moment, in this season of my life, is this vehicle of economic sustenance working for me, or is there something that would work better?

It would be foolish of me to turn down an opportunity to do the work that I do in a much broader scale and get paid much more just because I would have to go work for someone else. That’s not enough to keep me from doing that. Just like it would be foolish for me to throw in the towel because it’s hard today for other reasons. The main question is not like “Are you an entrepreneur? Are you an employee?” or any of those random labels, does this economic arrangement work for your mission, for your values, for this season of your life?

I say the season of your life because let’s be real, part of the reason we get stuck with these attachments and these identity attachments is because we made a decision five years ago, that made sense five years ago, and we’re still working through the projects that have come from that decision without asking the question of “Does that decision make sense for me now?” Yes, that made sense when I had three kids in high school, but they’re all gone to college and doing their own thing now. Maybe, just maybe, I could work part-time. I don’t need this bullshit. Maybe I could do all sorts of other things. I know I’m on a rant here, Tara.

Tara Newman: No. I think it’s timely too because I always joke around, I have this joke that I have the secret recession indicator and it’s peaking right now, that business owners start increasing talk about going back to a traditional nine-to-five, they talk about going and being a barista at Starbucks, they talk about being a yoga teacher. They start to fantasize about relieving the pressure of ownership in that way, especially when we have the added catalyst of the geopolitical economic environment that we have.

We are having a lot of conversations with people around “Is that what you want to do? Is that the right choice for you right now? My husband and I have definitely made those decisions. He went back to work for somebody else after closing a business and now he’s back in his own business again. Because we blew out all our finances and he needed to just go earn a steady paycheck and not have the stress and needed to recoup so I totally get that.

I think that’s really timely and it’s a necessary conversation because I don’t think we’re talking about that. I find the people that I talk that I work with, it’s not even that they’re looking to be entrepreneurs, they’re told that they should be entrepreneurs, it’s they don’t really want to be small-business owners, that feels like a lot of work and heavy. Freelancer doesn’t feel significant enough. Really what it comes down to is that people, at some point in their life, they’ve decided that they want to earn income independent of an employer. We need to stop labeling.

Charlie Gilkey: That’s the funny thing. I was in the coffee shop today and one of the guys that we talk sometimes, he’s like, “Hey, so how’s it going today?” I was like, “Man, I’m happy this Friday.” He’s like, “Cool, what’s making it? You’re not accountable to anybody, are you?” Because he knows I own my own small business, he’s like, “You’re not really accountable to anybody.”

Tara Newman: “Oh, yeah, we’re just swinging the breeze over here.”

Charlie Gilkey: Right? I was like, “That’s such a weird way of thinking about it.” I guess that’s one frame, I don’t have a boss in that traditional way, but I’m in constant collaboration with a whole bunch of other people. I’m not just going to be like, “Ah, it’s Friday. I don’t feel like working today. Screw Tara and this podcast, whatever.” We’re always accountable to somebody. If you’re a small business owner or startup, whether we talk about Productive Flourishing, which is much more services and coaching-focused, or Momentum, which is product-focused, we are accountable to our customers and someone’s got to pay the bill somewhere until we get to the point to where we can make money off money, we’re on that journey but we’re not there yet.

I think it’s great that people are like, “You know what, I need another type of funder for my life. I need to go back and get a job so there’s one person that’s paying me and not 17.” Okay cool, great, you’re still getting paid by somebody. I just want to break down that idea that somehow, you start your business and you are 100% autonomous for everything, can’t nobody tell you nothing. You can start that but you’ll find yourself 18 to 24 months into it looking for a job because it turns out long-term people will not want to work for you and pay you.

Tara Newman: Yeah. It’s really funny because I remember when I started this business eight years ago, and what was the tagline, do whatever you want whenever you want, that’s how it gets marketed, whatever you want, whenever you want, and I was like, “Oh, this is great. I’ll be able to do whatever I want, whenever I want.” I remember maybe a couple of weeks into that and I’m like, “Heck, this isn’t productive. Nothing’s getting done. I can’t just go for lunch with my mom in the middle of the day and then expect to come back and get stuck into deep work. There needs to be a plan here. Yes, I can go for lunch with my mom but it’s probably going to be on Fridays but it’s my less heavy day. Because the things still need to get done.”

That’s actually really funny because I can speak from my husband’s experience of having a business, going back to work for somebody else, and then coming back and having his own business again. When you have the predisposition, the bias toward ownership accountability, you take that wherever you go. He was like, “I’m owning a lot of stuff here and I am not the boss.”

I’ve said to him, “You’re not allowed to work for anybody else at this point because all you do is recreate ownership and accountability and let somebody else, who’s supposed to have the ownership and the accountability, off the hook but not get paid the way they’re paying themselves, they don’t get treated the way they’re paying themselves. You completely lose the autonomy but you do all the things. We’re not doing that anymore. That’s your assignment. You need to work on that if you want to ever go back and work for somebody else again.” I’m the same way. I’ve got a strength around responsibility. I like being accountable. I like the concept of ownership and so this works and I own whatever comes with it.

Charlie Gilkey: Yeah. Most people should be so lucky to have a partner like you that can just call them on that because a common path to suffering is being over-responsible for things that are just not things that you can control, influence, or have the authority to make any decisions. It wears folks out. Again, we’re talking about corporate, it’s a very big thing in corporate. But even in small businesses and entrepreneurship, you just own way more than you reasonably can. Now what’s interesting, Tara, is part of when we’re hiring on the market, we actually look for people who have started their own business and closed it down and don’t want to start another business.

Part of the reason we look for that is the team may have neutered this a little bit but on our job applications, it used to say “Would-be entrepreneurs need not apply,” because if your real goal is to learn how to start a business three years from now and do whatnot, then you’re in this for a different reason. We just said about it upfront because I can sniff that out. But why we look for people who have closed their own business and don’t want to start another one because one, they get the journey of being in a small business and startup. Sometimes they can have really good boundaries about things, other times they overreach what you’re talking about.

But three, they have the ability to be like, “You know what, things are a mess. We can figure this out.” It’s okay, they’ve learned that bit of resiliency but it’s not just like that pipe dream of like the other hard hire in the marketplace or the person like this is their first or maybe second job out of college, that’s a hard hire because there’s a big idea of what the world of work should be and they’re learning from you that the world of work is not what their parents have told them and what they’ve learned in college and so that tends not to work out for a lot of folks.

I think learning to get to the perspective of truly owning what you can be responsible for and letting go of the things you can’t, whether you’re talking about being an employee or an entrepreneur, is so valuable to do and it’s one of the hardest journeys of this life.

Tara Newman: Yeah. I will say that this is a big one for the folks that we work with, is really getting clear on what you’re responsible for, what you’re not responsible for, what you can control on this journey, what you can’t control on this journey because taking too much responsibility just leads to a lot of overdelivering, undercharging, and harm for your business, and I actually think that that’s being used in some of these business-building programs as a way to increase your “value” or everything in the kitchen sink goes into the offer so you can charge more rather than learning and understanding how to truly communicate your value and position what you do for a premium offer.

It’s like, “And I have a Facebook group and I have this. We do this and this and now they want this and now we’re giving them this.” It becomes really harmful financially, emotionally, all those things.

Charlie Gilkey: That, and it actually degrades your relationship with your customers and clients because then they feel like crap because you created this kitchen-sink experience, it’s got 18 different touch points in all the different ways and they can do 3 and so they’re like, “Well, I’m not getting the value because I can only do 3 of the things and I’m paying for 18 things.” How about you find the three things that are making the biggest difference to people, focus energy around that, and subtract the rest. But I think people don’t think about that.

How does it feel when you’re a customer and you’ve been run through a kitchen-sink thing and you’re not able to use it but you have told yourself because you’ve been told by them that this is where the value is. You feel like you’re not getting your money’s worth, when the fact of the matter is you might be getting your money’s worth out of like one, two, or three things and you can make peace with that. If we were being honest with and in true partnership with and things like that, we might be able to tell the product creator or the experience creators like, actually it was just those three things, and you might make people’s lives easier if you get rid of the rest because it’s just causing us overwhelming and it’s hard to keep up with.

Tara Newman: Focus.

Charlie Gilkey: Focus what creates value, not what creates work, not what creates an inventory of stuff.

Tara Newman: The illusion of value.

Charlie Gilkey: Yeah, what creates value, and do your customers and clients put value on that thing that you think creates value? If you get that figured out, work that, lean into that. You might find that there’s 80% of it, that’s just noise at a certain point.

Tara Newman: Yeah. I talk about this a lot and I just want to bounce this value, but I think the real work when it comes to running a business and earning income independent of an employer, the real maybe competencies are not what people think they are. I think the competencies are more around being able to focus, taking consistent action, and being an agile learner. I think there’s a difference between competency and skill, so you need to have certain skills but you need to have the competency or the ability to then focus, take action consistently, and be an agile learner.

Sometimes I find that the online business space is the antithesis of that and so I do want to first say, I will preface, I do really appreciate social media. I have met so many people, you being one of them, but I use social media very differently than a lot of people. I’m more of a listener. I’m more of a behind-the-scenes relationship builder, connector in that way. What would you say for business owners who are looking to the online business space for their business education and maybe getting caught up in this matrix of distraction faux work, any tips, any advice, any opinions? You could disagree with me. Have at it.

Charlie Gilkey: Yeah. Let’s do a little bit of framework hacky sack here. I would say what we’re always looking for is that difference between capacity and utilization. I think especially people listening, because you and I happen to know some of the folks in here, super high capacity, and the trick is sometimes they want to keep developing more capacity and that’s not their leverage point. Their leverage point is the utilization, which is where we started talking about. Focus is where we talk about like doing things. I’ve seen way too many people be in year-long sales programs to avoid having sales conversations.

Tara Newman: I wish you all just saw my face.

Charlie Gilkey: I pick on that because one, in our society at large, we don’t arm women with the skills of sales. In our societies, we make women the responders and not the initiators. You got to understand that sales a lot of times is about proactive initiation and we’ve unfortunately created the socialized damsels and people are asking the question and so women just don’t like, “Oh, I can actually choose who I want to work with me and then ask them and invite them to work with me?” Yes, that’s sales actually.

I see a lot of that going on because they’re like, “Well, I need to get more confident. I need to get more capacity. I need more tools.” It’s like, “Actually, you probably just need to be rejected about three to five times and learn that you’re going to be okay and fumble through it in a lot of different ways.” That’s over simplistic but at the same time, it’s not. When I’m working with really novice coaches and consultants like, “Well, I gotta work on marketing and I got to build the website.” I’m like, “What we’re going to do, let’s create a Google doc, this is what you do, and then we’re going to actually talk to people about what you do and ask them to do that with you.”

Like, “What about the website?” I don’t care about the website. I care about getting you paid and having you learn this thing. I think when you start going into the online sales space, understand that most of the ways in which they’re going to tell you how to grow your business, 80% are going to revolve around digital marketing, and here’s why it’s going to be digital marketing, because that’s how they’re getting you.

Now, how you might need to get your customers is probably not digital marketing because you’re going to be competing with them. You bought from them so why would people hide from you? So you end up in this weird circle to where you’re learning the tools that worked on you but there may not be enough more of you left over to use the tools that work for you. Understand that and understand that most early-stage business problems actually are not about marketing, they’re about positioning, they’re about sales, they’re about clients, effective service, and product delivery and transformation. That’s really what you should be focusing on much more so.

I hereby give you permission or challenge you to stop messing with the website, stop picking the 82 different social media platforms that you’re going to seed and feed, and maybe have a real conversation with a real person about what transformational journey you’re guiding them along, whether it’s a product or whether it’s a service, I don’t care. Have that real conversation and do the bold thing of asking a real person in real time to buy that thing. Please do that. You will one, make more money faster, but two, you’re going to learn what you need to learn in the earlier stages of your business journey.

Now once you get to the point to where you can’t sell anymore because you have so many clients or you just can’t make those phone calls, now, oh, you got me on a rant, Tara, you’re going to have to pull me off this rant.

Tara Newman: No, I’m not touching you. You keep going, man. I’m just sitting here eating the popcorn.

Charlie Gilkey: If another person comes to me and says, “Yeah, Charlie, but what you’re talking about takes a lot of time and I gotta grow my business,” and I’m like, “Okay, especially if you’re in a service-based business, it’s like in the earlier stages, you’re doing one of two things, you’re either selling or delivering. If you’re not delivering, you’re selling, and if you’re delivering to the degree that you can’t sell, then maybe you don’t need to do that.”

But if you’re not doing that and you’re looking at me, you’re like, “Oh, Charlie, that’s going to take a lot of time,” of course, it’s going to take time. What the hell else are you doing? Oh, you’re taking someone else’s course.

Tara Newman: I’m going to light a match and keep you going.

Charlie Gilkey: So much of your early-stage journey is not about that digital marketing-focused thing. Every channel currently, there are a few that have emerged over the last couple of years, but podcasting, incredibly saturated, I’m not telling you not to start a podcast, not saying that at all, understand that the people selling you how to start and grow a podcast probably started when it was easy. They started in 2010, 2012. I will tell you if you’re starting your podcast in 2022, it is a different landscape.

Social media, the same. Webinars, the same. Email marketing, the same. All the things that you’re going to get from social media and online, a lot of those channels have already been optimized. What hasn’t really changed much, and actually your opportunity here, is most of the people who’ve learned how to do stuff that way don’t know how to sell and have a real conversation with people. That is actually your edge, and if you’re listening to the podcast, I’m imagining that you’re actually really good at that if you gave yourself a chance to do it.

Tara Newman: Just like do my job for me, Charlie, thank you. Thank you. Drop that mic. The longer you resist what Charlie is saying, which is essentially what I’ve been saying but sometimes you need to hear from a different person in a different way, and mad respect to Charlie and what he has built in this world, mad respect, the longer you resist doing that, the longer you are going to be lost in the sea of what social media channel should I use, what digital marketing strategy, what course should I take.

Charlie Gilkey: Yeah. I know I threw it in probably about the first third of that, to get good at some of these things in the early stage, some of these things, I’ll be more specific, at sales and getting to a yes in a conversation, you will learn along the way, if you don’t already know it, that you are not your work, you are not your promise, you are not all those things. Someone can say, “No, that does not feel like a fit for me right now,” and it does not mean you suck and I’m mad at you and how terrible of a person are you that you put this thing in front of me and ask me to buy it, those are different conversations.

Just like you’ve had plenty of wonderful heart-based, really thoughtful sales conversations, you might not have known you were in it, but I’ve gotten to the end of it, it’s like, “You know what, I don’t think that’s for me right now,” but I still like that person, I still am engaged in the conversation with that person. I’ll just say that because I think that that’s one of the barriers that earlier stage folks have is they’re like, “Oh, if they say no to this thing, then I’m not worthy.” No. People got stuff going on. You will get better, and to get better, you have to break that identification with you and your work or you and what you’re selling.

Tara Newman: There is a difference between your identity and the entity of the business.

Charlie Gilkey: There we go.

Tara Newman: Alright, Charlie, I’m going to tee you up in your zone of genius to end notice.

Charlie Gilkey: Ooh, when it’s somebody else’s thing but I’ll start here, look, so much of this bold money journey that you’re going to be on is learning to see a challenge and see that it’s difficult, and instead of finding all sorts of ways to get around the said challenge, actually start walking towards it. Because if you don’t, at some point, you’re going to be right back where you are dealing with the same challenge. We don’t have to make it harder than it needs to be but we do want you to take focused action toward that thing that challenges you, and the thing that challenges you the most might be that it doesn’t have to be hard.

Tara Newman: I always define bold as doing the thing you’re most unwilling to do, and not in a way that it bypasses your values or anything like that but in the way that you’re unwilling to do it because it’s uncomfortable. That’s how I tend to define bold. Charlie, thank you so much for coming by. You’re actually here with me, one day you will be. Tell them where to find you, tell them what you have going on. I know you have a new book coming out. That’s still a ways away, yes?

Charlie Gilkey: It’s still a ways away, yes. To this day, all roads still lead to If you like anything that I’ve said here or you’re curious about how Momentum can be a productivity coach in your pocket, you can learn more about that at as well as updates about Team Habits and when that’s coming out, or Start Finishing, which really does help people do what it says it does.

Tara Newman: Start Finishing is a great book. I had somebody quote it to me the other day and I was like, “Oh, Charlie’s book, he’s coming on my podcast, yay!” Yeah, it’s a great book. I also just want for everybody to say look, how simple he made that. Productive Flourishing, where it’s always been, focus, consistency, one thing.

Charlie Gilkey: Yeah. One thing, and it’s probably going to be there for quite a while just because why change it if it’s working?

Tara Newman: I adore you. Thank you so much for coming by.

Charlie Gilkey: Thanks for having me, Tara.

Tara Newman: Do you want to know the most stressful part of being a business owner? Want to know what that is? It’s making sure you get paid for your expertise, experience, and effort. Most service providers have no idea how much revenue they need to keep the business going and to keep you going. Pay yourself too little, and entrepreneurial poverty kicks in real quick. Pay yourself too much, and you don’t leave enough money in the business for growth and a cash cushion.

When you worked for someone else, things were easy peasy. You met job requirements, and each week, money appeared in your bank account like clockwork. Now, it’s a little more complicated than that so it’s normal to be confused. After all, how many of us actually got a financial degree at the same time we were starting a business? From my experience working with micro business owners like you, setting a revenue goal is so difficult. Most avoid it completely and just hope they bring in enough. It’s also why you might feel like you’re working way too hard for what you actually take home.

Does this sound like you? I hear from women all the time that navigating their numbers and spreadsheets just isn’t their jam and can even be incredibly intimidating at times. That’s why I’ve made it super simple, easy for you to calculate a clear revenue goal so you’re able to pay yourself more than enough and to run your business with financial clarity, confidence, and competency, a clear line of sight will make it so much easier to manage your money and build wealth.

This Revenue Goal Calculator is programmed based on my work as a Profit First certified consultant, which means you will know exactly how much money you can afford to pay yourself, how much money you will need to save for taxes, and how much money you can put toward the running of your business. All you need to do is key in a few numbers and you’re off the starting blocks. 

Grab your Revenue Goal Calculator right now to get started paying yourself more