Welcome to another episode of The Retirepreneur Podcast. I'm your host with this week's executive summary for busy entrepreneurs building their second-act business. Today's episode is designed for maximum impact in minimum time.
So let's set the scene, because I think a lot of people listening are going to recognize this moment. You've just stepped away from a 30-year career. You've got the plaque on the wall, you've got the severance package, or maybe you've just decided it's time. You sit down in your home office ready to start that consulting business or that online course everyone's been telling you to build.
And you open a blank document. Just silence. It's just you. No team, no assistant, no crisis to manage. Just a blinking cursor. And you freeze.
It's the blank screen syndrome, and believe me, it hits senior professionals harder than anyone. And it's not because they don't know enough. It feels like the opposite problem. It is the opposite. It's like standing in a Costco warehouse of your own memories and trying to figure out which single box someone actually wants to buy. You're just overwhelmed by your own experience.
Exactly. When you've spent decades in the trenchesâmaybe you're a CFO, director of operations, something like thatâyou've built up so much tacit knowledge. The stuff you just know without thinking. And you can't separate the valuable insights from all the day-to-day noise. You know too much to be simple.
And that really is the mission for this briefing. We are breaking down the 3-Circle Method. It's a strategic framework designed specifically to help you slice through that fog and find the one topic that's actually sellable, sustainable, and frankly, enjoyable.
I like enjoyable. We definitely forget that part. But okay, before we get into the circles, I need to play devil's advocate for a second. I talk to a lot of people in this demographicâ55, 60 plusâand there's this lingering fear that the online course ship has sailed, or that consulting is a young person's game now. Is there really space for a Boomer or a Gen X expert in a digital market?
Well, the data actually suggests the complete opposite. The global e-learning market is heading toward $450 billion by 2026. But here's the stat that really matters for us: the Kauffman Foundation found that adults aged 55 to 64 are starting businesses at higher rates than younger folks, and they're failing less. Much less.
And it's because of what the Harvard Business Review calls the wisdom economy. In a world that is flooded with AI-generated content and generic advice, deep, battle-tested human judgment is becoming a premium asset. You're not competing with ChatGPT. You're selling the wisdom that prevents a $2 million mistake. That's what we're banking on today.
Okay, that makes a lot of sense. So let's get into the framework. I'm picturing a Venn diagramâthree overlapping circles. We're trying to find that sweet spot in the middle. Let's start with Circle 1.
Deep expertise. And we need to be really careful how we define expertise here. This isn't something you researched last weekend. We are looking for skills where you have solved real, expensive problems for at least a decade.
A decade feels like a high bar, but I get it. We're selling mastery, not just knowledge. But here's the issue I see all the time: the boring skill paradox.
Oh, this is a big one. I have a friendâlet's call him Dave. Dave was a logistics manager for 30 years. To him, his job was just moving boxes from A to B. He literally thinks it's the most boring thing on earth, and he assumes everyone knows how to do it.
Exactly. That is the curse of knowledge. To Dave, supply chain optimization is like breathing. But to a small business owner who's losing 20% of their margin because they can't manage inventory, Dave's a wizard.
So how does Dave find out he's a wizard?
He needs to look for pattern recognition. That's the key. Can he look at a warehouse floor plan or a spreadsheet and just immediately spot the disaster before it happens? That's the skill. It's the ability to see around corners.
Okay, but let's get specific. Is there a test? Because feeling like an expertâthat can vary from day to day. Some days I feel like a genius, other days an imposter.
I know. The imposter syndrome never fully goes away. But the litmus test is financial. Just ask yourself this: Would I confidently coach someone one-on-one on this topic for $200 an hour?
$200 an hour? If you hesitate, if you think, "I couldn't look them in the eye and charge that," then you don't have the conviction to build a course on it.
Why is that?
Because a course is just your coaching methodology scaled up. If it's not worth $200 an hour live, it's not worth scaling.
That's a tough reality check, but a good one. Now, usually people jump straight from here to "Is there a market?" But you want to go to Circle 3 nextâteaching stamina. Why skip the market step for now?
Because you can find a huge market for something you absolutely hate doing. And at this stage of life, the goal isn't just revenue, it's purpose. Circle 3 asks: Can you obsess over this topic for the next two to five years?
This is the six-month test, right?
That's it. Can you wake up every single morning for the next six months, write about this topic, teach it, andâthis is the really hard partâanswer the same basic beginner questions over and over again without losing your mind?
Ah, the beginner questions. That's the killer. "How do I log in? What is a spreadsheet?" If you're teaching an intro to finance course, you are going to explain what a P&L is a thousand times. If that thought makes you want to retire again, pick a different topic.
This brings up the shiny object trap. I am seeing this everywhere with AI right now. Everyone wants to be an AI consultant because it's hot.
It's the danger zone. If you are learning the topic at the same time you're teaching it, you're building on sand. You might have the stamina because it's new and exciting, but you lack that Circle 1 expertise. The moment a student asks a nuanced question that isn't in your notes, your credibility just evaporates. Stick to what you've lived, not what you've just read about.
So we've got deep expertiseâthe boring stuff you're actually great at. We have staminaâthe stuff you can tolerate talking about forever. Now we get to Circle 2: market validation. Because as we always say, passion plus expertise without a market is just an expensive hobbyâor expensive therapy.
So let's validate. You have a CFO approach to this. No guessing, we're auditing. You have three methods. Let's walk through these because I think this is where people get stuck.
Method one: the Udemy search. Go to Udemy.com, a huge marketplace for courses. Type in your topic. Let's say "project management for construction."
Okay, I type it in and I see 50 courses. My stomach drops. I'm thinking, "It's saturated. Too late. I'm going home."
And that is exactly the wrong reaction. You should be celebrating. Saturation in this context is a myth. Competition is proof of life.
Proof of life. I like that.
If there are 50 courses and the top ones have thousands of students and recent reviews, that is a verified market. People are already spending money to solve this problem.
So silence is the real enemy here.
Correct. If you search for "underwater basket weaving for accountants" and you find zero courses, you haven't found a blue ocean. You found a graveyard. Do not try to educate a market that doesn't exist.
Okay, so we want competition. That's actually a relief. Now, method two is my favorite because it's so sneaky: the Amazon 3-star review method. Walk us through this.
So you go to Amazon, you find a bestseller in your niche, and what you do is you ignore the 5-star reviewsâthey're fans, they're friends. You ignore the 1-star reviewsâthose people are just angry at the world. You go straight to the 3-star reviews. These are the reasonable people who spent money, wanted the solution, but were let down.
Okay, give me an example.
So let's go back to our HR director. She's looking at a book on employee retention. She finds a 3-star review that says something like: "The author explains the theory of retention perfectly and the psychology is great, but I'm a manager with a crisis today. There were no scripts, no templates for the stay interview, no checklist for onboarding. I left feeling inspired but empty-handed."
Boom. That's your product roadmap right there.
It is exactly your product roadmap. You don't write another book on theory. You create the Manager's Retention Toolkit with the scripts, the templates, and the checklists that were missing. You're not guessing what they want. They're literally screaming it at you in the reviews.
That is just incredible leverage. You're letting your competitors do all your market research for you. Okay, third method: price tolerance check.
This one's simple. You need to verify that people in this space pay between $50 and $500 for solutions. If the only things you can find are $19 eBooks, run away.
Why? Why not sell 1,000 $19 eBooks?
Because you're a solopreneur. You don't have the marketing machinery to sell at that kind of volume. You need margin. You need a customer who values the outcome enough to invest real money. If the market is just bargain basement, it's very hard to build a second-act business that replaces a corporate income.
Got it. Avoid the race to the bottom. Okay, so we have the three circles: expertise, stamina, market. If you hit the center, you have a business. Now, execution. This is where the rubber meets the road, and this is where I see people self-sabotage all the time.
They decide on a topic and then they lock themselves in a room for three months to record 40 videos. Please, for the love of everything, do not do that. That is the old way and it is the fastest way to burn out.
So what's the alternative? I mean, you need a product to sell, don't you?
No, you don't. You need an offer. We advocate for the beta strategy: sell the course before you build it.
That sounds terrifying. You want me to take people's money for something that doesn't exist yet?
Well, it exists as a curriculum. It exists as a promise. You sell a live cohort. You just say, "Starting November 1st, I'm teaching this 4-week framework live on Zoom."
But what if nobody buys? I mean, really, if I send the email, I post on LinkedIn, and... just crickets. Isn't that humiliating?
It stings. Yeah, of course it stings. But let's look at the alternative. You spend three months recording videos, editing them, building a website, and then nobody buys. Now you've lost three months of your life and your confidence is shattered.
Okay, good point. If you launch a beta and nobody buys, you've lost whatâa week of planning? You've learned the most valuable lesson there is: the offer wasn't right. You pivot and try again.
It's failing fast. It's the lean startup method applied to a consulting career.
Exactly. And if 10 or 15 people do buy, now you are literally paid to build it. You show up every week, you teach live, you see their faces, you see where they get confused, and you refine the material in real time. It makes the course infinitely better than if you just recorded it in a vacuum.
And what about pricing? We don't charge full price for this, right?
The rule of thumb is about 50% of your target price. If the course is eventually going to be $300, the beta is $150. And you're transparent about it. You tell them, "You are getting this half off because you're founding members. In exchange, I want your feedback, I want your questions, and if you love it, I want a testimonial."
So it's a trade: discount for data.
Precisely. Now I have to address the elephant in the room. I can literally hear the heart rates of our listeners going up. I was talking to a former VP of sales the other day, a guy who closed multi-million dollar deals, and he told me the idea of setting up a payment processor made him want to lie down.
It's a massive psychological barrier. It really is. When you were in the C-suite, you had an IT department, you had a marketing team. Now you are the IT department, and that identity shift is painful.
So how do we solve it? Do we need to learn to code? Do I need to hire a developer?
Absolutely not. Do not build a custom website. That is like building a house from scratchâpouring the foundation, wiring the electricityâjust to sleep in it. You want a furnished apartment. And these furnished apartments are platforms like Kajabi, Teachable, Podia. They're all-in-one platforms. They handle the website, the credit card processing, the email list, the video hosting. You pay a subscription, usually $50 to $150 a month, and the tech just works.
But is it actually easy? Be honest.
It's user-friendly, but sure, there's a learning curve. The bar I always set is this: If you can send an email with an attachment and you can create a PowerPoint presentation, you have the technical skills required. The rest is just clicking buttons.
Okay, but what if I really, truly hate it? What if I am just completely tech-phobic?
Then you use the producer model. Find a younger collaboratorâmaybe a digital native, a smart VA, or even a college student. You make a deal: I provide the wisdom and the face, you handle the tech and the uploading, and you split the money. Usually an 80/20 or 70/30 split. You keep the lion's share because you own the IP and the audience. They get a cut for handling the headache. It's a fantastic way to bypass that tech fear entirely.
That's a great workaround. Focus on your zone of genius, outsource the frustration. Now before we wrap up, we have to talk about something specific to our audience: money and the government. Specifically, Social Security.
Yes. This is a critical compliance note that often gets overlooked in all the excitement of starting a new business. Break it down for us. When does making money become a problem?
Well, it depends on your age. If you've started collecting Social Security benefits but you have not reached your full retirement ageâwhich is usually 66 or 67, depends on your birth yearâif you're under that age, there's an earnings limit, and that limit is pretty low. For 2024, it's $22,320. If your net business income goes over that, the government deducts $1 from your benefits for every $2 you earn above the cap.
Ouch. That's effectively a 50% tax on your benefit.
It is. So you could accidentally earn enough to penalize yourself. But, and this is the good news, the moment you hit that full retirement age birthday, the cap just vanishes. You can make a million dollars in your consulting business and collect your full Social Security check.
So the strategy is: check your birthday, check the cap, and plan your launch accordingly.
It's just another variable in the business plan. You just don't want it to surprise you.
We've covered a massive amount of ground today: the 3-Circle Method, the beta launch, the tech anxiety. Let's just boil this down to the absolute essentials. What are the three things our listener needs to do this week?
Okay. Number one: mine your boring skills. Look for the things you've done for a decade that feel like breathing to you. That pattern recognitionâthat's your product. Don't dismiss it because it's not sexy.
Number two: validate before you build. Be a detective. Search Udemy, search those Amazon 3-star reviews. Find the gap between theory and practice that your competitors are missing.
And number three: pre-sell the beta. Do not record a single video until you have a paying customer. Launch a live cohort, charge 50%, and co-create the course with your students. It lowers the risk and guarantees you're building something people actually want.
I love it. It turns a mountain into a series of small, climbable hills. Here's the question I want to leave everyone with today. It's a question to ask yourself on your next walk: If you were forced to earn your living for the next year teaching only one specific skill, and your pay was based entirely on your students getting a measurable result, what would you teach?
If you can answer that question, you've found your center circle.
That's your executive briefing for this week. If you found value in these insights, share this episode with fellow retirepreneurs and subscribe to the Retirepreneur newsletter at retirepreneur.com. Follow us for weekly strategic insights and remember, your most successful chapter is just beginning. Until next week, keep building.
