The Strategic Entrepreneur
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)
The Strategic Entrepreneur
257: Measure Backward to Move Forward: The Progress You're Missing
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-step Quarterly Gain Review system that changes everything
- 7 CEO Dashboard metrics to track weekly (takes 10 minutes)
- How one entrepreneur discovered 47 wins she couldn't see
- The four gain categories most businesses miss
- Year-end review framework for seeing your full transformation
- How to build next quarter's plan on actual momentum, not arbitrary goals
- The confidence compound effect of documenting evidence
Perfect for: Entrepreneurs feeling stuck despite working hard, anyone frustrated with not hitting goals, business owners planning their year, and leaders wanting tactical measurement systems.
Key insight: "When you only measure forward, you're literally working with incomplete information."
Join 1,500+ entrepreneurs getting tactical strategies weekly in Cindy's newsletter, or go deeper with the Growth Collective's group gain reviews (prices increasing soon).
Resources mentioned:
- The Quarterly Gain Review Framework
- CEO Dashboard Weekly Metrics
- Annual Mega Review Process
Stop feeling stuck. Start seeing your gains. Your progress is hiding in plain sight.
💌 Join 1,500+ entrepreneurs receiving weekly strategic insights and business clarity frameworks - sign up now! https://cindygordon.myflodesk.com/countmein
Connect with Cindy Gordon -
- Website: ExclusivelyCindy.com
- Instagram: https://www.instagram.com/exclusivelycindy/
- YouTube: https://www.youtube.com/@cindygordon
last week I had a one-to-one call with a client she'd been in business for a year and felt like she had made zero progress. She said, I'm exactly where I was last January. Maybe I'm just not cut out for this. I asked her one question, what couldn't you do in January that you can do now? 20 minutes later, we had a list of about 62 items. Yes, literally 62. She launched three new services, automated her onboarding, raised her prices twice, spoken on multiple podcasts, built an email list of over 500 people. But she couldn't see any of it because she was measuring forward against her goals and not backwards against her starting point. Hi, I'm Cindy Gordon and you are listening to The Overwhelmed Entrepreneur. Today is inspired by Dan Sullivan's Gap and Gain concept, and i'm gonna give you the exact quarterly review system that reveals the progress that you are missing and builds unstoppable momentum. Most entrepreneurs feel stuck even when they're growing and it's because you are measuring wrong. You set a goal, you work towards it all quarter, and then you look at how far you still have to go instead of how far you've come. And with the end of the year approaching, this gets even worse. You are looking at all of those annual goals you set in January. Seeing the gap and feeling like a failure, but you're missing the gain. All of the progress that's happened along the way. This isn't just feel good mindset work. This is about accurate data. When you only measure forward, you are literally working with incomplete information. You are making decisions based upon what hasn't happened yet instead of what has actually occurred. Imagine trying to navigate using only your destination, never checking where you are or where you've been. That's what forward only measuring does to your business. So let me give you the exact system I use and teach. This isn't about journaling or gratitude. This is strategic tactical business measurement that changes everything. every Quarter I conduct what I call a gain review. So here's the framework. Step one, you get a baseline shot. You pull out where you were 90 days ago, not your goals, your actual reality, revenue list, size, service offers, prices, systems in place, skills you had. Step two, the current reality. So I document where I am in those categories. Just facts, no judgment. Step three, this is the documentation List. Every single thing that's different, not better, not worse, just different. New skills, new connections, new systems, new knowledge, new anything. Step four, the progress patterns. Look for the patterns in your progress. Where did you gain the most? What type of progress came the easiest? This tells you where your natural strengths are. Step five, momentum map based upon what actually happened. Not just what you planned, but map the next 90 days. Building on actual momentum and not theoretical goals, but here's the key. You can't just do this quarterly. You truly need weekly data points to make the quarterly review powerful, and this is where the CEO dashboard comes in every Friday. I track these seven metrics, and it can vary by business, but this is what I track. I track revenue, actual money that came in. I track leads, so these are new potential clients. I track conversations. These are leads to clients. I track deliverables. This is what I produced. I track systems. What did I improve or automate? I track connections. These are relationships built and I track capabilities. These are skills or knowledge that I gained. This takes me 10 to 15 minutes a week, but by the end of the quarter you have 12 weeks of data showing you your actual progress trajectory. You can literally see your business growing week by week, so let me make this a little bit more real with some actual data from the one-to-one client. And yes, she did give me permission to share in January. Her baseline had no email, so nobody on her email list. She was trading time for money. She had three services with super unclear on her pricing. Zero systems working about 50 hours a week. So her current reality, which is just about 12 months later, she has 500 email subscribers. She has passive income coming from templates that she created. She has two clear packages with set prices. Onboarding and invoicing has been automated and best of all, she's working about 35 hours a week. She couldn't see this because she was so focused on not hitting 10 K months yet, but look at those gains. Her revenue is up and her hours are down, plus passive income and an audience has been built. When you're doing a quarterly review, make sure that you're measuring gains in all categories and not just revenue. So let me go through and give you some examples of all the different types of gains in the categories. So we have tangible business gains, so that's revenue increases, new clients list growth, new products or services, systems created or time saved, then we have the capability gains category. So in here we're measuring new skills, learned problems you can solve Now, software you've mastered, strategies you understand, and most important mistakes you won't repeat. Then we have the relationship gains category. These are connections made, partnerships formed, mentors found, team members added and community built. Then we have the category of confidence gains. These are the prices you charge now, the opportunities you now pursue, the conversations you now have, and the decisions you now make quickly, most people only measure that first category, but the other categories are what make the first category possible. Since we're approaching the year end, let's talk about the annual version of this same process, but looking back at all the four quarters of gains, and here's what it might reveal. Quarter one, you are learning and building foundations. Quarter two, you were testing quarter three. You found what works and systematized. Quarter four, you scaled what works. When you see this pattern, you realize you weren't stuck. You were building. Each quarter had its purpose in the bigger picture. Now pull out your calendar from January and look at what scared you then. Look at what felt impossible. Look at what you didn't even know existed that distance. That's your real progress. Here's where measuring backward becomes a strategic advantage. When you actually see the gains you can build on them intelligently. Instead of setting arbitrary goals, you can set goals. Based upon proven momentum. If you gained 10 clients per quarter, aim for 12 to 15 next year. If you raised prices by 20% successfully, try another 20%. If you launch one project per quarter, maintain that pace. If systems saved you about five hours weekly, what other systems could you build in? This is how you create sustainable, predictable growth instead of boom bust cycles. So let's talk about confidence and momentum When you document your weekly gains and review them quarterly, you build evidence of your capability, not hope, not affirmations, but actual evidence, actual data. This evidence changes how you show up. You find yourself pitching with more confidence because you have proof of results. You raise your prices easier because you see your value increasing. You take bigger swings because you can handle challenges. You worry less because you see, you always figure it out. One of my clients started doing this and said, for the first time, I can actually see that I am a successful business owner and not someone trying to become one I want you to remember that you are making more progress than you can see, but if you don't measure backward, you will never know it. You'll keep feeling stuck when you're actually growing. You'll keep doubting yourself when you should actually be celebrating. The entrepreneur who measures backwards has a massive advantage. They are working with complete data. They're seeing what's actually working. They're building real momentum. They make decisions with confidence and not fear. This week, even before the quarter ends, do a mini gain review. Look back at the last 30 days list, 20 things that were different from a month ago. I guarantee you, you will find them and now you have the system to prove to yourself and every single quarter what your gains are.
Speaker:Thanks for spending these few minutes with me today. Remember, overwhelm isn't permanent. It's simply your brain's way of saying pause and take a little reality check. If you got value in today's episode, please share it with another entrepreneur who needs that reminder. If you're loving the show, I'd be so grateful if you could leave me a quick review. It helps other overwhelmed entrepreneurs find us. Make sure you hit subscribe so you never miss your weekly dose of clarity. For more resources and to connect with me, visit exclusively. Send. d.com. Until next time, remember, you've got this.