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Charlie Gilkey

67 Podcast Episodes

Latest 8 Dec 2022 | Updated Daily

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3 Strategies to Start Finishing What Matters Most with Charlie Gilkey: From the 2019 archive

Entrepreneurs on Fire

From the archive: This episode was originally recorded and published in 2019. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. Charlie Gilkey helps people start finishing what matters most. He's the founder of Productive Flourishing and the author of two books, the latest being Start Finishing: How to Go from Idea to Done. Top 3 Value Bombs: 1. Remember that failure is not a character trait. Own your success more than you own your failure. 2. There are things that you don't like to do. Don’t create too much of a story around it; just get it done. 3. The more people start finishing the stuff that matters, the more they find their success. But more importantly than that, the more they find their happiness and they set themselves up to thrive. Reserve a copy of Charlie's book, Start Finishing: How to Go from Idea to Done! - Start Finishing Sponsors: HubSpot: A platform that’s easy for your entire team to use! Learn how HubSpot can make it easier for your business to grow better at Hubspot.com! ProsperSpark: Anything and everything you can imagine in Excel, ProsperSpark can create and deliver it for you! Book a free project call today at ProsperSpark.com/fire! Mention Entrepreneurs On Fire to receive a 10% discount up to $1,000 on your project or service agreement!


11 Sep 2022

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From the Military to Mentoring With Charlie Gilkey


We’re super excited to be introducing some fresh new formats to the mix here on the SPARKED podcast. Our new Hot Takes segments, which we just launched last week, tackle hot topics in conversation with expert guides from the SPARKED Braintrust. And, today, we’re sharing a fun new episode format we’re calling SPARKED Stories, where we spotlight the experience of one person and explore how they’ve built a living and life that honors, celebrates, and centers the parts of themselves that truly make them and their work come alive. That sparks what they do, and who they are.And today, we’re going to start with a spotlight on the story of someone our listeners have come to know and appreciate, but you likely didn’t know about the stories and experiences that got him where he is. I’m talking about SPARKED Braintrust member, Charlie Gilkey. Now you may know Charlie's work. He runs a company called Productive Flourishing, which is all about helping people get things out of their heads and figuring out how to actually take the actions to produce the things that they so deeply want to make real in the world as a maker myself. His work has resonated so profoundly with me, which is why he’s a part of the SPARKED Braintrust.But, Charlie also has a really powerful background. He came out of the military where the decisions that he was making, the systems and processes that he was building, the advising and mentoring and coaching, and leading that he was doing very often had extraordinary stakes. Life and death stakes. If he chose wrong, lives were at risk in a part of the world that was very far from where he grew up. He's since written a fantastic book called Start Finishing, which is all about his methodology. As we sat down to dive into Charlie’s Sparked Story, I wanted to understand what were his deep impulses for the things that he's done and what have been the through lines. And, of course, along the way, he shares his Sparketype profile and we dive into how that has informed the different types of work he’s said yes and no to, the way that he has stepped into them, and what he's learned along the way about how he makes decisions that better aligned with that. SPARKED STORY GUEST: Charlie Gilkey | WebsiteCharlie is a strategic advisor and executive coach, founder of the Productive Flourishing consultancy, and author of the multi-award-winning book, Start Finishing.YOUR HOST: Jonathan FieldsJonathan is a dad, husband, award-winning author, multi-time founder, executive producer and host of the Good Life Project podcast, and co-host of SPARKED, too! He’s also the creator of an unusual tool that’s helped more than 650,000 people discover what kind of work makes them come alive - the Sparketype® Assessment, and author of the bestselling book, SPARKED.So what is your Sparketype? Turns out, we all have a unique imprint for work that makes us come alive, this is your Sparketype. When you discover yours, everything, your entire work-life- and even parts of your personal life and relationships - begins to make sense. Until you know yours, you’re kind of fumbling in the dark. How to submit your question for the SPARKED Braintrust: Wisdom-seeker submissionsMore on Sparketypes at: Discover You Sparketype | The Book | The Workshop | The WebsitePresented by LinkedIn.


1 Sep 2022

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Finishing The Stuff That Matters wtih Charlie Gilkey

The Happiness Hunter Podcast

Charlie Gilkey helps people start finishing the stuff that matters. Charlie is the founder of Productive Flourishing, a company that helps professional creatives, leaders, and changemakers take meaningful action on work that matters. He is the author of the book and and host of the Productive Flourishing podcast. Before starting Productive Flourishing, Charlie worked as a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy.Start FinishingThe Small Business Lifecycle, Through actionable guidance grounded in thought-provoking theory, Charlie helps you take meaningful action on the stuff that matters in both life and work. I was so delighted to have Charlie join me on this episode of the podcast. I was first introduced to his work several years ago, specifically his approach to time blocking, and my mind was blown by such a simple concept. Charlie’s philosophy around living our best lives, productivity and his time blocking method was a game-changer for me, and I share his teachings with all of my clients. In this episode of the podcast we cover a lot of ground, from: Charlie's background in military logistics Living intentionally The overwhelmed brain Why to-do lists will frazzle your brain The concept of time blocking Understanding focus, admin, social and recovery blocks How to communicate your time blocking preferences with others Not all time is created equal Factoring in invisible activities and SO MUCH MORE I hope you enjoy this episode and take what you learn to start to get stuff done.See omnystudio.com/listener for privacy information.


22 May 2022

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091: Quarterly Planning with Charlie Gilkey

Free Time with Jenny Blake

“I’m always stumping quarterly planning for business owners. It’s the Goldilocks horizon for strategy execution, project scoping, and team alignment.” Today I’m talking with Charlie Gilkey about why the quarter is an ideal time unit for strategic planning, how to apply his stepwise Momentum process to mapping projects and goals, and striking the balance between visioning and planning. Charlie also had an interesting response on why tracking metrics matters . . . and it’s not what you might think.More About Charlie: Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing (2019) and The Small Business Lifecycle (2012), founder of the new Momentum app, and host of the Productive Flourishing podcast. Before starting Productive Flourishing, Charlie worked as a Joint Force Military Logistics Coordinator while simultaneously pursuing a Ph.D. in Philosophy. He lives with his wife, Angela, in Portland, Oregon.🌟 3 Key Takeaways: 18 months is a typical “now” horizon for established businesses, whereas three years can get mysterious. There’s a difference between your visioning horizon and your planning horizon; when deciding what to work on, consider cash flow, visibility, and opportunity. When you hit a strategic, urgent, recurring logjam, ask: “What experiments can I try?” instead of obsessing over numbers. It’s so that we can build alignment with the team and take pressure off of the owner to be the Chief Prioritization Officer. 📝 Permission: Drop at least one project that does not create cash flow, opportunity, or visibility.✅ Do (or Delegate) This Next: Identify the next two quarter-sized projects that will move you toward your biggest 18-month business goal.📘 Books Mentioned: Free Time: Lose The Busywork, Love Your Business Pivot: The Only Move That Matters Is Your Next One Start Finishing: How to Go from Idea to Done The Small Business Life Cycle: The No-Fluff Guide to Navigating the Five Stages of Small Business Growth The Road Less Stupid: Advice from the Chairman of the Board Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality 🔗 Resources Mentioned:  Charlie on the Web, Instagram, Twitter, Facebook, LinkedIn Charlie’s podcast: Productive Flourishing podcast App: Momentum App Free Planners: Momentum Planners Article: Cashflow, Opportunity, and Visibility: The 3 Goals of Any Business Activity Related Podcast Episodes: 035: The Long Game with Dorie Clark, Pivot 136: Start Finishing—Pricing, Projects, and Momentum Planning with Charlie Gilkey❤️ Enjoying the show? The best way to thank us is by leaving a rating or review. Consider becoming a podcast BFF and you’ll get access to a monthly Q&A call with Jenny, a private feed, and access to a community forum with fellow Heart-Based Business Owners.💌 Subscribe to the Time Well Spent newsletter: http://itsfreetime.com/join🛠 Get instant access to the Free Time Toolkit: http://itsfreetime.com/tools 💬 I’d love to hear what’s on your mind! Take the Free Time listener survey🗣 Submit a voice question or comment for future episodes: http://itsfreetime.com/ask🎧 Make sure you’re subscribed wherever you listen to podcasts📝 Check out full show notes and links from this episode and share it with a friend! https://itsfreetime.com/episodes/091 Learn more about your ad choices. Visit megaphone.fm/adchoices


10 May 2022

Most Popular

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EP 52: Charlie Gilkey: Leading With What Matters Most

The Unburdened Leader

When you are not clear on what truly matters most to you, how you decide to use your precious time can leave you feeling overwhelmed and lost. And even your sense of time and what you can get done gets skewed by the tyranny of the urgent. Or comparison to how others are doing life and work. Striving and grinding is still the norm in so many spaces. The message is still suck it up, chin up, get it done. And falling or failing is on you and you alone.This mindset is deeply problematic as many are pushing back on these approaches to how we use our time and the expectations around how we do work recognizing how culture and many of the systems we work in contribute to burdening our sense of time. Boundaries around your time mean disappointing people. So if you are focused on over-delivering and making everyone happy, things can get messy, fast.  If what matters most means meeting metrics that are set by others, burnout and disillusionment are inevitable.These dangerous messages have us chasing something we think will give us relief when in fact, we only feel worse when we put this kind of pressure on ourselves My guest today has an approach and a philosophy to time and getting things done that has transformed my relationship with work, time, and my calendar.Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing (2019) and The Small Business Lifecycle (2012), and host of the Productive Flourishing podcast. Before starting Productive Flourishing, Charlie worked as a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon.Listen to the full episode to hear:Why our problems are with expectations, not time managementHow we need to shift our relationship to productivity to prioritize values, self-awareness, and compassionHow we end up with so much of what Charlie calls project debt, and how to dig ourselves out of itWhy we need to stop reinforcing the narrative of the busy partyWhy leaders need to stop playing the hero or the martyr to their teamsLearn more about Charlie Gilkey:Productive FlourishingTwitter: @CharlieGilkeyInstagram: @productiveflourishingFacebook: @ProductiveFlourishingConnect with Charlie on LinkedInStart Finishing: How to Go from Idea to DoneThe Small Business Life CycleLearn more about Rebecca:rebeccaching.comWork With RebeccaSign up for the weekly Unburdened Leader EmailResources:White Supremacy Culture, Tema OkunZone to Win: Organizing to Compete in an Age of Disruption, Geoffrey A. MooreThe Ten Equations That Rule the World: And How You Can Use Them Too, David SumpterNahko And Medicine For The People - “Skin In The Game”Star Trek: DiscoveryIndiana Jones and the Temple of Doom

1hr 8mins

6 May 2022

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Finishing What Matters Most, Stumbling Toward Genius with Charlie Gilkey

Stumbling Toward Genius

Do you have an unfinished project you’ve been working on for months, years, or maybe even decades? You know, the one you keep putting on the back burner for “some” day. But that day never seems to come? Today, we’re talking with Charlie Gilkey, author of the book Start Finishing about what happens to us when we don’t finish the projects we start, and how we can “start finishing.” Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing (2019) and The Small Business Lifecycle (2012), and host of the Productive Flourishing podcast. Before starting Productive Flourishing, Charlie worked as a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon. I’m excited to share our conversation with you. Charlie has been a tremendous influence in my life and on my creativity. Listen to hear the insight Charlie shared with me a few years ago that challenged me to think differently about the days of the week and dare to try something new. Charlie says, “It’s really hard to go and look at this other thing that no one is asking for except your inner self and prioritize it.” And yet, through his planners, books, and Momentum app (coming soon) he’s found a way to help people finish the projects that matter most. Listen as he shares: Why we’re all asking the wrong questions when it comes to our projects and how to ask the right ones The secret to planning your creative time to get the best energy The value of focusing on fewer things—how hustle culture, grinding, and head trash are keeping us from finishing and how to align your (limited) time, energy, and attention towards the things that matter most. Why not everything is meant to be finished Plus he’ll tell us more about the Momentum app and his new book, Workways coming in 2023.

1hr 4mins

27 Apr 2022

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BONUS EPISODE: Charlie Gilkey talks about Momentum

A Productive Conversation

On this bonus (and sponsor-free) episode of A Productive Conversation with Mike Vardy, Mike is joined by his good friend Charlie Gilkey of Productive Flourishing to talk about Momentum, the productivity app that he and his team are developing.Mike asks him why in the world we need another productivity app, what Charlie is hoping to see happen with the Kickstarter campaign for Momentum, and much more. This audio is from a livestream that Mike had with Charlie on his YouTube channel so it'll sound different than our regular episodes. (Not bad... just different.)You can check out the Momentum app Kickstarter campaign here.Want to watch the recorded livestream? Here you go.Want to support the podcast? You can subscribe to the show wherever you listen to podcasts. Click on any of the links below to make that happen.Spotify | Apple Podcasts | Google Podcasts | StitcherYou can also click on this link to paste the podcast feed into your podcast app of choice.Thanks again for listening to A Productive Conversation. See you later.


1 Feb 2022

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How to Get Unstuck & Finish What Matters | Charlie Gilkey [Best Of]

Good Life Project

Hosted on Acast. See acast.com/privacy for more information.

1hr 18mins

24 Jan 2022

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Charlie Gilkey on How to Get Things Done

The One You Feed

Charlie Gilkey is the author of Start Finishing: How To Go From Idea To Done. An Army veteran and near Ph.D. in philosophy, Charlie is the founder of Productive Flourishing, a company that helps professional creatives, leaders, and change-makers take meaningful action on work matters. He’s widely cited in outlets such as Inc. Magazine, Time, Forbes, The Guardian, Life Hacker, and more and his work will help you discover the path from the ideas in your head to the actions you take in your daily life and how to go about getting things done.But wait – there’s more! The episode is not quite over!! We continue the conversation and you can access this exclusive content right in your podcast player feed. Head over to our Patreon page and pledge to donate just $10 a month. It’s that simple and we’ll give you good stuff as a thank you!Charlie Gilkey and I Discuss How to Get Things Done and…His book, Start Finishing: How To Go From Idea To DoneHow kindness towards others often brings out the best in everyoneThe Tao Te ChingFocusing on your input and letting go of the resultsWe don’t just improve by thinking about things, we improve by doing themCreative constipation breeds toxicity We’re either creating something or destroying somethingWe don’t do ideas, we do projectsHow doing our best work is often really hardThe myth: if it’s meant to be for us, it’s supposed to be easyThe myth that if it doesn’t come easy for you, you shouldn’t do itDoing something until you’re good enough at it to decide whether or not you want to continue doing itThe 5 things that get in the way of doing our best workHead Trash: Doesn’t matter if a thought is true or not – it matters if we believe it or notThe problem with automatically believing our thoughtsHow discipline limits decision fatigueHow action expresses priorityCharlie Gilkey Links:Charlie’s WebsiteInstagramTwitterFacebookUpstart: The fast and easy way to get a personal loan to consolidate, lower your interest rate, and pay off your debt. Go to www.upstart.com/wolfIf you enjoyed this conversation with Charlie Gilkey, you might also enjoy these other episodes:Chris Bailey on Focus, Productivity, and MeditationDavid Kadavy on Getting StartedSee omnystudio.com/listener for privacy information.


21 Dec 2021

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Charlie Gilkey - Author with a ‘thinking edge‘ in business strategy

Thinking Edge

On this episode of Thinking Edge, we spoke with Charlie Gilkey. Charlie is the founder of Productive Flourishing, one of the top websites on the web for planning, productivity, and team development. They offer coaching, consulting, workshops, and products that help people start finishing the stuff that matters. He is also an author! He has written books such as "Start Finishing: How to Go from Idea to Done" and "The Small Business Lifecycle: A Guide for Taking the Right Steps at the Right Time." On this episode Charlie talks about ways to avoid burnout, tips for working better together as a team virtually, and the curse of the dreaded CC thread. You can connect with Charlie via his Linkedin. Find his books here: - Start Finishing: How to Go from Idea to Done: (https://www.amazon.com/Start-Finishin...) - The Small Business Lifecycle: A Guide for Taking the Right Steps at the Right Time: (https://www.amazon.com/Small-Business...) ----more---- Find out more about the podcast & watch the video version of this episode which includes helpful visuals here: https://linktr.ee/thinkingedgepodcast​​ Email us at thinkingedgepodcast@gmail.com ----more---- Music created by previous CTO and Cofounder of KAYAK.


24 Sep 2021