What does it take to be an Entrepreneur? Join us as Charlie Gilkey shares his Entrepreneurial mindset and an inside glance at his journey of becoming a successful Entrepreneur.
Charlie helps people and businesses focus on what matters, and then executes it. His company’s website, ProductiveFlourishing.com, is one of the top websites on the Web for planning, productivity, and team development.
- “One worthwhile task carried to a successful conclusion is worth half-a-hundred half-finished tasks.” ~ Malcolm Forbes
- Charlie put his heart and soul into a speech and knocked it out of the part. So how did he fail? His disconnect with his audience was HUGE.
Entrepreneurial AHA Moment
- Charlie tells great stories, and his AHA moment is no different.
- Charlie is in the midst of writing a book that I am personally very excited to read… listen and hear why you will be too!
Small Business Resource
- GoToMeeting: Work can happen anytime, anywhere
Best Business Book
- Innovation and Entrepreneurship by Peter F. Drucker
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John Lee Dumas: Okay. Let’s get started. I am simply overjoyed to introduce my guest today, Charlie Gilkey. Charlie, are you prepared to ignite?
Charlie Gilkey: I’m always ready to ignite, but yes, right now, I’m still ready to ignite!
John Lee Dumas: My man! Charlie helps people in businesses focus on what matters and then executes. His company’s website, Productive Flourishing, is one of the top websites on the web for planning, productivity and team development.
I’ve given Fire Nation a little overview, Charlie, but take it from here. Tell us who you are. We want to know about you personally. And then tell us about your business.
Charlie Gilkey: Alrighty! So I’m Charlie Gilkey. I live in Portland, Oregon, which is both the weirdest and one of the most awesome cities on the planet. And I will say that it was that way before I moved here, just in case you think I’m egocentric about that.
John Lee Dumas: [Laughs]
Charlie Gilkey: So the easiest way to understand me is to imagine three overlapping circles with one being a Military Logistics Officer, another circle being a trained academic philosopher, and then the third circle being someone who’s acquired an experiential MBA. I just have learned a lot about starting businesses and growing businesses not through getting a traditional MBA. And so I bring a lot of that to bear in the work that I do with individuals and organizations, and as John mentioned earlier, it’s really about focusing on what matters and then executing on it because as I get out there and talk to people, we see a lot of people with a lot of ideas, and a lot of really great ideas, that stumble and fumble on getting it done. And so that’s what we show up and help people do, focusing a lot on planning, productivity and team development because that’s how we make it happen, folks. So that’s me. Did that answer the question, John?
John Lee Dumas: That totally answered the question, Charlie. Thank you for taking the time to do that. One thing I love about these interviews, I don’t always know everything about my interviewees, and Charlie, I had no idea that you were a Military Logistics Officer. That’s something that we have in common. I was actually an Armor Platoon Leader in the US Army, and then I moved over to the Transportation Corps/Logistics for a couple of years. So that’s pretty cool stuff!
Charlie Gilkey: That’s very cool stuff, and thank you for your service. We’re recording this, what? Two days after Veterans Day?
John Lee Dumas: Yes. Yes, right after. So thank you, kind sir, for your service as well. So Charlie, we’re going to move now into our first real topic, which is our success quote, because at EntrepreneurOnFire, we love getting the motivational ball rolling for this awesome content that you have to share with us today. So what do you have for us, for Fire Nation, for your success quote?
Charlie Gilkey: Alrighty. This was from Malcolm Forbes, and it says, “One worthwhile task carried to a successful conclusion is worth half a hundred half-finished tasks.”
John Lee Dumas: That is a very insightful quote. Now tell me how you actually apply that to your mentality or to your business.
Charlie Gilkey: The way that I apply that is – well, I could give you another quote from Lao Tzu. So you’re going to get two quotes today, and I warned John ahead of time.
John Lee Dumas: He did.
Charlie Gilkey: That this might happen. But there’s a line, I think it’s from Chapter 63 or so of the Tao Te Ching, that it basically says if people were as careful at the end as they are in the beginning, then they would never come to failure. But because they are not as invested and careful at the end as they are in the beginning, then they fail. The idea is, is that a lot of times we start a lot of things, but we don’t do the thinking, the planning, the work and the follow-up it takes to actually finish it. And so the way that I apply that both in my life and in my business is one, to only really start the things that I know I can complete well, and two, as I’m in the process of completing things, to not ride on necessarily what’s happened before, but to continually stay vigilant to make sure that we’re meeting our success matrix, that we’re doing it the most effective way possible, and that really we’re showing up with the intention to serve and to get that impact. And so those are the things that guide those actions. So it’s not necessarily a hyper-minimalism, which is trending right now, right? To do fewer things and just focus on 100 items and stuff like that. That’s not what it’s so much about, but it’s about that continual, conscious focus on doing the stuff that matters and doing it well and sticking with the process until it’s completed.
John Lee Dumas: I love that. One acronym that I always come back to that really rings true here, and that’s FOCUS, which is “Follow One Course Until Success.” And that “Until Success” part is what you’re talking about until completion. So that just really rings true. I love both of those quotes that you shared with us and how you actually apply it to your mentality. That’s so meaningful and so insightful. We’re going to use that, Charlie, to transition to our next topic, which is failure. As entrepreneurs, our journey is riddled with failure on every single level. We have obstacles we need to overcome, we face challenges every single day. Share with EntrepreneurOnFire, take us down to the ground level of a failure that you encountered at some point in your journey, of a challenge that you had to overcome, and walk us through that.
Charlie Gilkey: Alrighty! So I think we are blessed with failures at times and we are blessed with a particular type of failure that I call a “defining failure,” something that you did that was so identity-shifting and course of action-changing that you could not just overwrite it. The thing about a defining failure is if you understand that you’re in the presence of one and you respond with openness and respond with a sense of detachment, you can actually define a better new you. And so if I had to look at the defining failures that I’ve had in my life, one of the last defining failures didn’t come from business. Actually, it came from one of my old jobs. I was the Assistant Director of the Ethics Center at the university I was teaching and I gave a really powerful presentation, really well-researched, but not only that. It looked like a TED Talk, and it was an epic failure. It was an epic failure because I completely lost track of who my audience was and what they wanted and my ability to show up and serve them. It was so defining in the sense of it woke me up and said, You know what? This is something. I was so on fire to do this. I had done all the preparation. I had spent six weeks putting this thing together. I was proud of it. But it didn’t match the community that I was in. This might sound really cocky, but I knew at that time that I was in the wrong community.
And so that last defining failure is what precipitated me actually leaving the academia and starting – well, I had already started Productive Flourishing, but me going all in and building it up because I knew that I could craft the community that would really value what I was putting on the table, but I would also value working with that community because we saw enough things the same that we can have meaningful conversations, but we saw enough things differently that there was still a point to talk.
John Lee Dumas: Can you share with us the message that you were trying to portray and the specific disconnect that you had with your audience?
Charlie Gilkey: The specific message that I was trying to convey was actually around applying ethics in all the different classes that we were teaching. So the audience was made up of faculty from across disciplines. And so we were talking about what ethics was and how to apply more ethics into their classrooms. When you’re talking to scientists and engineers, getting them to sprinkle more ethics in there that it kind of seems like what’s the point of that, and I don’t want to pick on them because we had lawyers and business professors there at the same time. And so really, it was one showing the ways in which ethics could be used in their classrooms, but it also didn’t apply a lot of the case study methodology, which is used oftentimes in those branches to teach ethics as much more than like normative ethics which is what you would learn from a philosopher about different ways of thinking about ethics versus different case studies to look at and try to find ethical stuff going on. Again, it was just largely around application but applying – well, in the academic community I would say I would say it was about praxis, which is the application of knowledge in a very practical way versus theory or just sort of baseline application, and it didn’t fit.
So here’s a sneaky secret, and I guess since I’m saying this in a public broadcast it’s not a secret, a lot of what we do in Productive Flourishing is cross-purpose philosophy and cross-purpose sort of my military background to come up with this interesting combination and useful combination in the world that we live in. And so I knew I had the right approach. I just was in a community that wasn’t ready for that approach and it wasn’t the right fit. So did that answer the question, John?
John Lee Dumas: That totally answered the question. It’s actually a perfect lead in to our next topic, which is on the other end of the spectrum, Charlie. That’s the aha moment. As entrepreneurs, we absolutely have to deal with failure on many levels, but we also get to deal with these little aha moments every single day that inspire us, that encourage us to move forward or pivot or change directions. Take us back in your journey at some point you’ve had a great aha moment. How did you apply that aha moment and turn it into success?
Charlie Gilkey: I’ve had a lot of aha moments. It’s interesting. This is going to be a side note here. As an entrepreneur, it’s very important that you celebrate and deconstruct your successes. The reason I say that is we talk a lot about failures and we try to deconstruct what happen when things go wrong, but we don’t do nearly as well at looking at what went right and deconstructing and celebrating that. And so your journey as an entrepreneur is going to be filled with a lot of ups and downs and some of them aren’t going to be the defining type failures that I just talked about. They’re going to be the more like you tried an offer out and you had a goal of selling 100 units and you sold 20. Okay, there’s a lot to learn there, but it’s not really defining in a lot of different ways. Just remember that it’s really important that you counteract the negativity bias that we as humans have, but especially that’s really promulgated throughout our society and that you celebrate and deconstruct success.
Now the aha moment I had actually came in the earlier days of PF and most of them were accidental. The biggest aha moment I had was when I wrote a post called “How Heatmapping Your Productivity Can Make You More Productive.” What I had done here is I had basically used a clock analogy to explain heatmapping, which is the concept of looking at different energy or activities across a different known set of data to apply where important insights were happening, but I applied it to productivity and schedules. To me, I came up with that diagram and it was a way to explain the concept, but it wasn’t really about the diagram, right? That took off. It took off in a major way, and it was a completely throwaway idea. As you write and as you produce stuff, what you’ll notice is sometimes your throwaway ideas are the things that get the most traction, largely because you haven’t attached so much damn attention to it and you haven’t made it harder than it needs to be.
But that took off, and so I kind of stayed in that space and played with it a while and developed a few other ideas around there, but that eventually led to our very popular planners that we have on our website because it kept applying those concepts that resonated in different ways, that resonated with hypercreative, proactive leaders, change makers and creative. So yes, that was the first of a series of major ahas that came. Yes, I’ll leave it there. Otherwise, I can list other ahas and we’d go on for a long time.
John Lee Dumas: Absolutely! That was such a great aha moment for a lot of levels because as entrepreneurs, we really sometimes overthink things when really just simplicity wins the day. So thank you for sharing that thought in general. We’re actually going to use that to move into our next topic, which you already alluded to, and I know we’re on the same page because you have brushed upon this topic, but the direct question to you, Charlie, is, have you had an I’ve made it moment?
Charlie Gilkey: No. Here’s the odd thing, right? The things that we teach are sometimes the hardest to accept. I’ve had plenty of I am making it moments, but not so many I’ve made it moments. I’m currently working on a book right now. Maybe when that comes out I’ll say I’ve made it, but I think I’m skeptical about my own personality to say that there will be a point where I’ve ever made it. I’ll have made a lot of different things, but in that grand sense of it’s done and over and not so much – I think when we really pursue excellence in our lives and careers, you can’t say that I’ve made it because you know that tomorrow presents another opportunity for you to hone in and do what you do. Either continue doing it, which itself is a success, right? If you have an epic level of success and you manage to do that over and over again, that itself is pretty huge, or you have the opportunity to take it one step further. I know that sounds like a paradox, on the one hand, really celebrate and deconstruct success, but on the other hand, to wake up in the morning and say, “You know what? Yesterday was awesome. Last week was awesome. Today is going to be awesome too and how am I going to make it so?”
So yes, I don’t know. Ask me in 10 years, ask me in 10, 20 years if I’ve ever made it, and I might have a different answer, but I had a really great career as a Military Logistics Officer, I had a pretty good career – not excellent career – as an academic for reasons that I just mentioned earlier, and I’ve done a lot of great things, but I don’t know that I’ve made it in that epic sense.
John Lee Dumas: Nope. Charlie, that’s why I love this question, because every entrepreneur looks at it differently. For me at EntrepreneurOnFire, it’s all about the journey, and in some ways, “I’ve made it” denotes that you’ve reach the destination, where in reality, we’ve never reached that destination till the end. We set these goals and we drive forward and we reach these goals, and then we just continue to raise the bar in our entrepreneurial minds to that next level to keep driving forward. For me, it’s about celebrating those milestones we’re hitting, which is what you’re talking about about deconstructing successes and appreciating them. That’s so important to appreciate those milestones and those successes because it’s part of the journey, and that’s what entrepreneurs, we need to learn to celebrate. So I understand completely where your head’s at. I’m on the exact same boat. I don’t know if I’ll ever have an I’ve made it moment because like I said, to me that kind of denotes the end, where to me it’s more I’m making it. I like how you phrase it. I’m going to go with it and we’re going to use that to move into our next topic, which is your current business. You have a lot of cool things going on right now with Productive Flourishing. You’ve talked about a couple of them. But break it down for Fire Nation. Share with us one thing that’s really exciting you about your business right now.
Charlie Gilkey: The thing that’s got me the most excited – John, you can see a trend here. You ask me one thing and I give you five.
John Lee Dumas: [Laughs]
Charlie Gilkey: The thing that’s got me most excited today is the book that I’m working on. The working title is “Start Finishing: A Guide for Completing the Stuff That Matters.” What excites me about that so much is when you look at the journey I’ve been on in the last couple of years with writing different book concepts and getting headways into them and saying, “You know what? That wasn’t it.” That journey and looking at this one and saying, “You know what? Everything is right about this one for me. I’m the right person with the right message with the right time,” and so on and so forth. So that’s got me super excited because writing a book, I’ve got a friend and colleague here in Portland named Todd Sattersten who wrote a small book called “Every Book is a Startup.” I love the book and I love the concept. I love Todd too. You got to know Todd Sattersten. But he’s so right in the sense of writing a book is a startup, or to use language that John and I are more familiar with, it’s a damn tour of duty, right?
John Lee Dumas: [Laughs]
Charlie Gilkey: You sign up for it and it’s like three to five years of you messing around with this book. So when you start to see it come to fruition and start to see all of the wind get behind you rather than in front of you, it starts to really open up a lot of options for you. So that’s the thing that’s got me most excited because not only does it galvanize and sort of streamline a lot of the content that we already have on Productive Flourishing, it gives me the opportunity/challenge to go and do some of the hard work and tying them together and coming up with those concepts that are the bridging concepts that make it all hang together. As an entrepreneur, and especially if you do a lot of content marketing – and by the way, every business today is a content marketing business, so get used to it. As you do more and more content development and marketing, you’ll notice that the things that you can be best in the world at can sometimes be the hardest for you to write.
So it turns out for me, writing about planning is incredibly hard to do. I could write about marketing and strategy and things like that for a long time, but actually, the process by which you develop plans, not so easy. So that’s one of the key things of this book, is that I’m really happy to sit down and do the hard work at making planning simpler to do, more accessible for a lot of people, but really results-driven so that you don’t get stuck into overplanning land, but you also don’t stay stuck in shooting from the hip land.
John Lee Dumas: Awesome! Well, Charlie, I look forward to sharing the release date with Fire Nation when that time becomes available because it seems like just a great fit for our listeners, for our audience, so definitely keep me updated on that.
Charlie Gilkey: Will do.
John Lee Dumas: So Charlie, we’ve now reached my favorite part of the show. We’re about to enter the Lightning Round. This is where I get to ask you a series of questions and you come back at us, Fire Nation, with amazing and mind-blowing answers. Does that sound like a plan?
Charlie Gilkey: It sounds like a plan. Well, let me say, you can ask the question. I’m not so sure about that amazing and mind-blowing answer, but we’ll see what works here.
John Lee Dumas: [Laughs] What was one thing that was holding you back from becoming an entrepreneur?
Charlie Gilkey: Thinking that I had to learn more to start. I came from an academic background. And so in that world, and in the military world, it’s the same way. Like you learn before you start doing. So when I started this, again, I don’t have an MBA, I had no formal business training. I just had a whole unique set of skills. I just sound like Liam Neeson from Taken, right?
John Lee Dumas: [Laughs]
Charlie Gilkey: I had a unique set of skills that I used to become an entrepreneur, but what was holding me back was seeing that I didn’t need to know more to start. I just needed to start and fix it on the fly.
John Lee Dumas: What is the best business advice that you ever received?
Charlie Gilkey: To think in terms of scalability. Let me explain that. Because I have a service-based business that also sells products – and a lot of people start with service-based businesses or they start with products, but they don’t necessarily have a scale plan in place. What happens is as businesses grow – this is a line from Peter Drucker, and it turns out to be true – “for every time you double your revenue, you have to change your capital base.” You have to change who your customers are, you have to change who your market base is, you have to change where you’re getting money from. You’ve got to have a scalability plan. And so it might be taking one product and figuring out how to get it to sell 10x. It might be taking one service and determining at which point it can scale and which point it can’t, and so on and so forth. So I think the best bit of business advice is really around thinking in terms of scale because when you think in terms of scale, you automatically have to think in terms of strategy, you automatically have to think in terms of marketing, you automatically have to think in terms of operations and you have to think about the financial piece as well, which are the four key dimensions of business.
John Lee Dumas: So Charlie, what is something that’s working for you or your business right now?
Charlie Gilkey: We’re laser-focused on engaging with the community, engaging with prospects and clients and things like that. I think a lot of times what happens is when our businesses start kind of tethering a little bit or kind of going off-course, it’s because we’ve lost focus with the customers and community that we’re serving. And so really staying engaged with their needs, their wants and their journey is really what fuels a lot of our journey. I mean, I approach our business from the perspective of a leader and a teacher, and my particular viewpoint on those is that when you’re a leader and a teacher, you’re there to serve the people that you’re leading and who are learning from you. So I think if ever you’re having great success in your business, you could probably track it back to ways in which you’re engaging your audience, and if you’re ever having some trying times, again, you could track it back to the ways you’re engaging with your audience and customers.
John Lee Dumas: Do you have an Internet resource like an Evernote that you’re just in love with that you can share with Fire Nation?
Charlie Gilkey: Actually, of all things, it’s probably GoToMeeting or GoToWebinar. Why I love GoToMeeting and GoToWebinar is again, it’s simple, a simple way to meet different people and an operating system and specific whatever to jump on and have productive meetings and productive conversations with people. I like to look at business activities in terms of create, connect and consume, or basically all of our activities – create, connect and consume. To me, at times we’re either stuck in create mode or consume mode, but most of your insights are going to happen from connecting with the right people. Right now, that particular set of software is really helpful for our business and team to just jump on and make stuff happen.
John Lee Dumas: What business book would you recommend for Fire Nation?
Charlie Gilkey: It’s a hard one, but if you’re really serious about entrepreneurship, you’ve got to read Peter Drucker’s “Innovation and Entrepreneurship.” It really encapsulates a lot of thinking on entrepreneurial strategy, what makes them work and not work, so on and so forth. It’s the precursor to things like “The Innovator’s Dilemma” and there’s a few others that I can throw in there, but I would definitely start with Innovation and Entrepreneurship.
John Lee Dumas: So Charlie, this next question is the last one, but it’s my favorite. So take your time and digest it because it’s definitely a tricky one. Imagine you woke up tomorrow morning in a brand new world, identical to earth, but you knew nobody. You still have all the experience and knowledge you currently have right now, your food and shelter is taken care of, but all you have is a laptop and $500. What do you do in the next seven days?
Charlie Gilkey: Find three to five hubs with creative people and talk to them, because if you do that, you’re going to find the framework of what’s going on in your world, where the possibilities are and where the challenges are, and you’re probably going to not necessarily be stuck in trivialities of how the weather is and so on and so forth. Those are important trivialities, but still. So if I had to start again, it goes back to a lot of intelligence training, to be honest, is just find the nodes and the hubs where people are and immerse yourself there to learn what’s going on and then take your next steps from there.
John Lee Dumas: What are some hubs that you can share with Fire Nation?
Charlie Gilkey: Well I live in Portland so I’m going to have to say coffee shops. Coffee shops, universities, business networking events sometimes. It really depends on the context of where you are in a lot of those things, but you can learn a lot by hanging out at a coffee shop. You can learn a lot by hanging out at the social area of your local library and you’re going to find the people there to talk to that are going to be in the know about different things. And so it’s not just necessarily an elitist – like I’m not saying go find the intelligent people. I’m saying find the people that are out there creating the possibilities for tomorrow, wherever they are, and talk to them to see what the current reality is and what the next adjacent possible is.
John Lee Dumas: Awesome, Charlie! That is just actionable advice and you’ve given us actionable advice this entire interview and we are all better for it. Give Fire Nation one parting piece of guidance, then give yourself a plug, and then we’ll say goodbye.
Charlie Gilkey: Okay. So one parting piece of guidance is the core premise of this entire interview is really take something that’s really lighting you on fire or something that has meaning and importance to you and start finishing it. Start working on it, on that thing, and let a lot of the other would’ve, could’ve, should’ve, this might be cool go to focus on completing that one thing. You will be better off for it. So that’s my one bit of advice.
The plug, I’m always bad at plugs, but if you want to really learn more about planning and how to make it work, especially for creative, change-makers and proactive thinkers, definitely check out our planners. We have free versions available at ProductiveFlourishing.com/freeplanners that will get you hooked up and ready to go.
John Lee Dumas: Awesome, Charlie. I will link all these up in the show notes – EntrepreneurOnFire.com/95. Thank you again for your insights and your generous sharing of your knowledge. Fire Nation, we salute you, literally and figuratively, and we’ll catch you on the flipside.
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