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The Strategic Entrepreneur helps female business owners and women entrepreneurs move past strategy fatigue to decision precision. Hosted by Cindy Gordon, business strategist and coach who built and sold four digital businesses, this podcast delivers pattern recognition frameworks and data-driven clarity for entrepreneurs ready to stop second-guessing every move.
Whether you're a solo entrepreneur drowning in strategies that aren't working, a small business owner managing 1-4 contractors who needs to cut through the noise, or a woman in business tired of collecting advice without implementing it, each episode gives you strategic business coaching backed by real data, not assumptions.
You'll discover what's worth refining versus releasing in your business, how to make confident business decisions using your actual numbers, and practical frameworks for operating from clarity instead of overwhelm. From business mindset and strategic systems to data-driven growth and cutting through false urgency, every episode of this entrepreneur podcast helps you distinguish between tweaks and pivots so you can make revenue-generating decisions with confidence.
Perfect for female entrepreneurs and women business owners who are done with strategy collection and ready for strategic action. No more second-guessing. No more paralysis. Just clear business strategy guidance for what to do next.
Ready to operate from clarity? Your strategic breakthrough starts now.
Formerly: The Overwhelmed Entrepreneur (originally Thrive in 5)
259 Episodes
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The CEO Energy Reset: Stop Managing Your Business, Start Leading It You'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 emp...
How to Know If You're Actually Being Productive You 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 ...
The Identity Crisis Nobody Talks About When Scaling You 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 you...
The Strategic Pause: Your Most Underused Power Tool You'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 hiringW...
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 (an...
Measure Backward to Move Forward: The Progress You're Missing You'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...
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...
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 opportun...
The 5 Life Domains That Fuel Your Business Your 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 sabotagi...
Stop Trading Time for Money: The Systems That Build Wealth While You Sleep Millionaires 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+ hour...
The Moment I Realized I Was Measuring My Success All Wrong - The GAP and the GAIN Feel 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 be...
You Don't Have to Choose: Both-And Success for Overwhelmed Entrepreneurs Stop 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 ...
Episode 250: The Evolution of the Reality Check Method In 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 che...
Broke-Ass Decisions vs. Million-Dollar Decisions: What You Choose Daily Every 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 episo...
Black Friday Special: Shopping Your Own Business First Before 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 di...
Pre-Thanksgiving Special: The Permission Slip You Need This Holiday Feeling 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 exha...
Thanksgiving Week Reality Check: Gratitude Without the Guilt Gratitude 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 ...
Holiday Business Boundaries: Protecting Your Energy for What Matters Holiday 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. M...
The 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...
From Survival Mode to CEO Energy - Real Talk for Overwhelmed Entrepreneurs Are 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 busi...
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