Shows
The Strategic Entrepreneur262: How to Know If You're Actually Being Productive How to Know If You're Actually Being ProductiveYou worked 10 hours, completed 23 tasks, yet your business is exactly where it was last week. Business strategist Cindy Gordon reveals the difference between motion and progress, and why most successful entrepreneurs are professionally busy but not actually productive.In this episode:The difference between real productivity and motion productivityWhy perfectionism on low-impact tasks steals from high-impact decisionsHow to identify what actually changes your business trajectoryThe warm audience reality check you need to hearThree tests to audit your actual productivityThe u...
2026-01-2008 minThe Strategic Entrepreneur261: The Identity Crisis Nobody Talks About When ScalingThe Identity Crisis Nobody Talks About When ScalingYou could do that task in 30 minutes. The VA would take 2 hours and do it 80% as well. So you do it yourself while strategic planning waits another week. Business strategist Cindy Gordon reveals the identity evolution required when scaling demands you multiply yourself, not just work harder.In this episode:Why delegating feels like betraying what got you hereThe difference between perfect overwhelm and imperfect leverageHow to multiply your voice without losing itWhy knowing every detail becomes impossible at scaleThe identity shift...
2026-01-1508 minThe Strategic Entrepreneur260: The Strategic Pause: Your Most Underused Power ToolThe Strategic Pause: Your Most Underused Power ToolYou're action-oriented, decisive, quick to execute - exactly what built your business. Now those same strengths sometimes create complexity. Business strategist Cindy Gordon reveals how successful entrepreneurs naturally evolve to use the strategic pause as a power tool for major decisions.In this episode:Why the pause is a natural evolution at your level of successHow to use strategic pausing for offer decisions, partnerships, and hiringWhy successful CEOs build pause into their decision processThe difference between "this could work" and "this is...
2026-01-1309 minThe Strategic Entrepreneur259: The CEO Energy Reset: Stop Managing Your Business, Start Leading ItThe CEO Energy Reset: Stop Managing Your Business, Start Leading ItYou're the highest-paid employee in your own business, not the CEO. In this strategic episode, Cindy Gordon reveals the CEO energy reset that saved her business when she was running 5 websites with 11 contractors. Learn the weekly CEO Dashboard practice, daily CEO habits, and the data-driven approach that stops you from second-guessing every decision.In this episode, you'll discover:The difference between CEO energy and employee energy (it's not what you think)The CEO time block that transformed Cindy's businessThe...
2026-01-0513 minThe Strategic Entrepreneur258: The Year-End Review That Actually Feels Good (Your Hidden Wins Revealed)The Year-End Review That Actually Feels Good (Your Hidden Wins Revealed)Your year was better than you think. In this transformative episode, Cindy Gordon teaches the Gain Review Framework that reveals all the small wins you're dismissing - the ones actually driving your growth. Learn how consistency compounds, why boring discipline beats dramatic sprints, and how to build next year on what's already working.In this episode, you'll discover:Why traditional year-end reviews feel terrible (and what to do instead)The 4-part Gain Review Framework that reveals hidden progressHow small...
2025-12-3110 minThe Strategic Entrepreneur257: Measure Backward to Move Forward: The Progress You're MissingMeasure Backward to Move Forward: The Progress You're MissingYou're making more progress than you realize - you're just measuring wrong. In this tactical episode, Cindy Gordon reveals the quarterly gain review system that uncovers hidden progress and builds unstoppable momentum. Learn the exact CEO Dashboard metrics to track weekly and how to turn backward measurement into forward momentum.In this episode, you'll discover:Why measuring against goals keeps you stuck (even when growing)The 5-step Quarterly Gain Review system that changes everything7 CEO Dashboard metrics to track weekly (takes 10...
2025-12-1909 minThe Strategic Entrepreneur256: Why Your Competition Should Be Your Collaboration (The Abundance Revolution)Why Your Competition Should Be Your Collaboration (The Abundance Revolution)What if the people you see as competition are actually your key to growth? In this game-changing episode, Cindy Gordon shares how a travel blogger mastermind taught her that collaboration beats competition every time. Discover the "hype woman method" for turning competitors into collaborators and why supporting others multiplies your own success.In this episode, you'll discover:Why competition is a scarcity mindset keeping you smallThe rising tide principle that grows all businesses fasterHow supporting "competitors" led to 60% of new...
2025-12-1710 minThe Strategic Entrepreneur255: The 7 Money Mindset Myths That Keep You Playing Small (And Broke)The 7 Money Mindset Myths That Keep You Playing Small (And Broke)Your money mindset is sabotaging your success - and you probably don't even know it. In this breakthrough episode, Cindy Gordon exposes the seven money myths programmed into you before age 10 that are keeping you undercharging, over-delivering, and staying broke. Inspired by Jen Sincero's badass approach to wealth, discover how to rewrite your money story.In this episode, you'll discover:Why you turn down high-paying opportunities (it's not modesty, it's programming)The "money is hard" myth that makes you...
2025-12-1511 minThe Strategic Entrepreneur254: Why Your Life Is Draining Your Business… and How to Fix ItThe 5 Life Domains That Fuel Your BusinessYour business doesn't fuel your life - your life fuels your business. In this paradigm-shifting episode, Cindy Gordon reveals the five interconnected life domains that determine business success: Physical Energy, Mental Clarity, Emotional Resilience, Relational Wealth, and Spiritual Alignment. Discover why treating business as separate from life is killing your success.In this episode, you'll discover:Why your lowest-scoring life domain is sabotaging your business growthThe Domain Audit that reveals what's really holding you backHow neglecting any domain creates a downward spiral in...
2025-12-1211 minThe Strategic Entrepreneur253: Stop Trading Time for Money: The Systems That Build Wealth While You SleepStop Trading Time for Money: The Systems That Build Wealth While You SleepMillionaires don't work harder than you - they work differently. In this paradigm-shifting episode, Cindy Gordon exposes the hustle lie and reveals the five systems that actually build wealth. Inspired by Rachel Rodgers' approach to million-dollar businesses, discover why systems, not schedules, create sustainable wealth.In this episode, you'll discover:Why hustle culture is keeping you broke despite working 60+ hoursThe wealth equation that has nothing to do with working harderReal comparison: $75K hustling vs. $250K with systems...
2025-12-1011 minThe Strategic Entrepreneur252: The Moment I Realized I Was Measuring My Success All WrongThe Moment I Realized I Was Measuring My Success All Wrong - The GAP and the GAINFeel like you're never doing enough even when you're crushing it? In this transformative episode, Cindy Gordon reveals why high-achieving entrepreneurs feel constantly behind and how to shift from measuring against impossible horizons to celebrating actual progress. Inspired by Dan Sullivan's gap and gain concept, discover the neuroscience of success measurement.In this episode, you'll discover:Why you feel behind even when you're winning (the measurement trap)The neuroscience of measuring backward vs. forwardHow gap...
2025-12-0810 minThe Strategic Entrepreneur251: You Don't Have to Choose: Both-And Success for Overwhelmed EntrepreneursYou Don't Have to Choose: Both-And Success for Overwhelmed EntrepreneursStop believing the lie that success requires sacrifice. In this game-changing episode, Cindy Gordon reveals how to create "both-and" success instead of exhausting either-or choices. Inspired by Steve Houghton's rich routines philosophy, discover how to have business success AND personal fulfillment without the guilt.In this episode, you'll discover:Why either-or thinking is keeping you exhausted and guiltyThe both-and framework that successful entrepreneurs secretly useHow to create "rich routines" that feed multiple life areas simultaneouslyPractical swaps to turn either-or choices...
2025-12-0512 minThe Strategic Entrepreneur250: The Evolution of the Reality Check MethodEpisode 250: The Evolution of the Reality Check MethodIn this milestone 250th episode, Cindy Gordon shares the 10 reality checks that transformed her from an overwhelmed entrepreneur drowning in chaos to the creator of the Reality Check Method helping thousands bridge the gap from paralysis to action.Discover the three reality checks that started everything, the three that clients credit with changing their businesses, and the three Cindy still needs to hear daily. Plus, the one reality check that defines everything: "You've got this."In this special episode, you'll discover:
2025-12-0310 minThe Strategic Entrepreneur249: Broke-Ass Decisions vs. Million-Dollar Decisions: What You Choose DailyBroke-Ass Decisions vs. Million-Dollar Decisions: What You Choose DailyEvery decision you make is either keeping you stuck or moving you forward. In this raw, honest conversation, Cindy Gordon breaks down the difference between broke-ass decisions (based on fear and scarcity) and million-dollar decisions (based on strategy and abundance) - and why this matters even if your bank account isn't there yet.Inspired by wealth mindset principles from thought leaders like Rachel Rodgers, this episode will make you rethink every choice you make in your business.In this episode, discover:
2025-12-0110 minThe Strategic Entrepreneur248: Black Friday Special: Shopping Your Own Business FIRSTBlack Friday Special: Shopping Your Own Business FirstBefore you open your wallet this Black Friday, pause and ask yourself one question: Have you shopped your own business first? In this timely Black Friday special episode, host Cindy Gordon, creator of the Reality Check Method and execution coach for overwhelmed entrepreneurs, reveals why your next big win might not be in someone else's course - it might be in the Google Drive folder you haven't opened in months.In this episode, you'll discover:Why most entrepreneurs don't need another course...
2025-11-2807 minThe Strategic Entrepreneur247: Pre-Thanksgiving Special: The Permission Slip You Need This HolidayPre-Thanksgiving Special: The Permission Slip You Need This HolidayFeeling like you need to earn your rest before the holidays? This pre-Thanksgiving episode gives you the permission slip you've been waiting for - but probably wouldn't give yourself. Host Cindy Gordon, creator of the Reality Check Method and execution coach for overwhelmed entrepreneurs, reveals why rest isn't something you earn - it's something you require.In this episode, you'll discover:Why "earning rest" keeps you exhausted and resentfulThe 3 Permission Slips every entrepreneur needs this holiday seasonHow to rest without justifying...
2025-11-2609 minThe Strategic Entrepreneur246: Thanksgiving Week Reality Check: Gratitude Without the Guilt Thanksgiving Week Reality Check: Gratitude Without the GuiltGratitude without guilt for overwhelmed entrepreneurs. Cindy Gordon shares how to practice real gratitude during Thanksgiving week without performing or proving you're grateful enough.In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon breaks down why entrepreneurs feel guilty about gratitude - and how to practice gratitude without ignoring the hard stuff or faking cheerfulness you don't feel.You're allowed to be grateful AND exhausted. You can love your business and still feel tired. You can be thankful for clients and s...
2025-11-2408 minThe Strategic Entrepreneur245: Holiday Business Boundaries: Protecting Your Energy for What Matters Holiday Business Boundaries: Protecting Your Energy for What MattersHoliday business boundaries aren't selfish - they're essential. Cindy Gordon shares how to protect your energy during the busy season without burning out or letting your business suffer.In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon breaks down how to set Holiday Business Boundaries that actually work - so you can end the year feeling energized instead of needing a three-month recovery.Most entrepreneurs roll into November and December saying yes to everything: last-minute client projects, holiday sales, family o...
2025-11-2109 minThe Strategic Entrepreneur244: The 3-Minute Work Setup Routine That Doubles Your FocusThe 3-Minute Work Setup Routine That Doubles Your Focus (Works Any Time of Day)Struggling to dive into deep work after interruptions? You're not alone. Most productivity advice focuses on morning routines, but what about when you're starting work at 2pm after client calls, or 8pm after the kids are in bed? In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon reveals the 3-minute work setup routine that helps overwhelmed entrepreneurs double their focus, no matter when they sit down to work.In this episode, you'll discover:Why traditional morning...
2025-11-1908 minThe Strategic Entrepreneur243: Why You're Stuck in Survival Mode Instead of CEO Mode (And How to Shift)From Survival Mode to CEO Energy - Real Talk for Overwhelmed EntrepreneursAre you running your business or is your business running you? In this conversational episode, Cindy Gordon explores the difference between operating from survival mode versus CEO energy, inspired by wealth mindset principles from thought leaders like Rachel Rodgers.Learn why you're stuck responding to every "urgent" email, undercharging for your services, and feeling like the emergency response team for your own business - and more importantly, how to shift into strategic CEO thinking even when you're overwhelmed....
2025-11-1709 minThe Strategic Entrepreneur242: Stop Task Switching: The Task Batching Method That Creates Business Momentum (For Overwhelmed Entrepreneurs)Stop Task Switching: The Task Batching Method That Creates Business Momentum (For Overwhelmed Entrepreneurs)How to stop task switching with task batching. Cindy Gordon shares the batch processing method for overwhelmed entrepreneurs who lose focus constantly switching between different types of work.In this episode of The Overwhelmed Entrepreneur, execution coach Cindy Gordon breaks down the task batching method - a way to group similar tasks together so you stop losing 23 minutes of focus every time you switch between activities.Overwhelmed entrepreneurs don't just have a productivity problem - they have...
2025-11-1407 minThe Strategic Entrepreneur241: The Momentum Stack Method: How to Build a Productivity Chain Reaction (Task Stacking for Entrepreneurs)The Momentum Stack Method: How to Build a Productivity Chain Reaction (Task Stacking for Entrepreneurs)How to use the task stacking method to build a productivity chain reaction. Cindy Gordon shares the Momentum Stack Method for overwhelmed entrepreneurs who know what to do but can't get started.In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon introduces the Momentum Stack Method - a way to turn small wins into unstoppable business momentum, even when you're feeling stuck and overwhelmed.Most entrepreneurs know what they need to do but can't...
2025-11-1209 minThe Strategic Entrepreneur240: How to Create a Productivity Power Hour That Actually Gets Results (The Entrepreneur's Focus Method)How to Create a Productivity Power Hour That Actually Gets Results (The Entrepreneur's Focus Method)In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon breaks down how to create a productivity power hour that actually gets results - not another productivity hack, but one protected focus hour where you work on what truly matters.Most entrepreneurs work 10-hour days but never find time for strategic work. Your calendar is full of meetings, your inbox is overflowing, and by the end of the day, you haven't worked ON your business - only IN it...
2025-11-1008 minThe Strategic Entrepreneur239: How to Do a Calendar Audit That Actually Frees Up Your Time (The 'Hell Yes or Not Right Now' Method)How to Do a Calendar Audit That Actually Frees Up Your Time (The 'Hell Yes or Not Right Now' Method)How to do a calendar audit that actually frees up your time. Cindy Gordon shares the Hell Yes or Not Right Now method to identify time wasters and eliminate tasks that don't move your business forward.In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon introduces the 'Hell Yes or Not Right Now' calendar audit method - a quick way to identify time wasters in your calendar and eliminate what doesn't...
2025-11-0707 minThe Strategic Entrepreneur238: How to Maximize Small Pockets of Time (Work Windows Method)How to Maximize Small Pockets of Time (Work Windows Method)Never have long time blocks to work? This episode reveals productivity for busy moms who need to maximize small pockets of time. In this episode of The Overwhelmed Entrepreneur, execution coach Cindy Gordon shares the Work Windows Method that helps entrepreneur moms get real work done in short bursts between life responsibilities.Discover how to maximize small pockets of time using strategic Work Windows, why short burst productivity works better than waiting for perfect time blocks, and the Reality Check Method for making progress even...
2025-11-0508 min