That, in hindsight, may have been a mistake. I thought writing shorter articles might help you, but it’s starting to confuse me.

Anyway, here are the last two roadblocks.

One says don’t rush, the other says move faster.

I know, more confusion when you first see it, but it’s really valuable when you understand it.

6. Rushing to sell

I’m constantly telling my clients: “You can’t have a microwave mentality in a crockpot world.”

Coaches rush to get through the script and fail to communicate their offer because they are rushing to the end of the sales call. Not listening closely is like a doctor prescribing brain surgery when you come in for a rash on your legs.

Think about the DM pitch-fests you see on social media:

• “Hi [first_name], thanks for connecting. Join my group.”

• “Great to connect. Tell me what your goals are?”

• “Great to connect. Mind if I ask you 12 questions about your business since I don’t care about you as a person at all?”

Unfortunately, that creates more offer roadblocks. The old “it’s a numbers game” is accurate, but the clients I attract aren’t going to build a business that way.

My coaching is all about building a steady, sustainable business. Coaching isn’t a hobby for my clients. We are playing the long game.

I have a coaching method called the C4 Method, and the 2nd “C” is Cultivation. That means building real relationships with visitors, prospects, clients, and people who will never become clients, but who I can still help.

To wrap this up:

• Take your time when selling.

• Listen closely.

• Dig deeper into what the prospect has struggled with.

• Discover what they are afraid of now and in the future.

• Confirm they are genuinely a good fit for your program.

7. Not learning how to sell quickly

Wait! What? Didn’t you just say “Slow down”?

Let me explain. You must learn to sell, and learn to sell well, even though you will never be a professional closer. You are a coach AND a business owner.

“Nothing happens until a sale occurs.”

The better you learn to sell, the better your marketing becomes. The massive elephant in the room is that, like any profession, it takes time. New coaches often have never sold. They don’t have a massive flood of leads to practice on, and they don’t have a sales manager listening to their calls to guide them.

So, how do you get good, quickly?

“The Secret” is the application of knowledge. Applying that knowledge only comes from selling millions of dollars’ worth of services, or from practicing with someone who knows how to sell, how to be a good pretend prospect, and how to coach you through each step.

I sought out and found personal coaching. Personal coaching skyrocketed me past the learning curve.

That’s why I’m a massive Personal Coaching Advocate.

No sales pitch here to train with me. Just keep checking out the content I’m posting. I’m always trying to make them noteworthy.

Right about here, there should be a call to action to book a “free 15-minute strategy session.” I know I’m supposed to follow the Internet Illuminati rules and pitch you to get on a call with me after you read this.

But I hate conforming to the rules even if it costs me cash. So there aren’t any calendar links here. Take your time; get to know my content first.

Instead, I recommend watching one of my live events (held virtually for everyone’s convenience), which will be announced here in The Encore Society.

During those events, we spend a tremendous amount of time teaching real-world, helpful information and leave time for Q&A.

Until then. This is Coach Jim, wishing you many blessings and a peaceful path to success.

3. Not communicating a clear benefits-driven offer

Speaking of seeing clearly, the way you communicate your offer is often like a fine wine in your eyes. You can just taste how good it is.

It’s your masterpiece. You’ve worked on this for months, maybe even years.

However, when most coaches try to explain their offer to a prospect hearing the specifics for the first time, they get a glass of muddy water.

What’s wrong with them? Can’t they see how elegant, smooth, and perfect your offer is?

Your job is to figure out how to turn muddy water into fine wine.

The biggest challenge facing coaches is their excitement about all the video modules they spent weeks producing, the 73 pages of text-based courses, and the 5 hours of group calls they offer clients every month.

Videos and .pdfs and calls! Oh My!

How does that benefit your client? Those are features of the program, not benefits.

The prospect hears you describe all “the stuff” and is only thinking, “That’s a lot of work! I don’t know if I can go through all of that. How is all that going to help me achieve the desired result?”

When I work with my clients, we constantly evolve how they communicate their offers. We discuss emotions, analogies, stories, and vivid imagery, all centered on one focus: communicating the transformation the program delivers.

I'll brag on myself a little bit here, but this is where I have been asked by million-dollar sales teams and coaches alike to teach them how to better communicate their offer.

I often help a person see their offer in a way that actually sells them on their own program. The value they offer becomes so clear that they start to get excited about sales calls… I know, weird, right?

That is why I insist on 1:1 coaching for each of my VIP clients. That process will never be taught in a recorded format.

4. Not a high enough price

Now, if you’ve noticed, I’m not promoting my coaching as high-ticket coaching, like so many think they’ve discovered online since about 2005.

Let me tell you a story.

I was approached by a goof-ru in 2006 that was proclaiming himself as a big-time, high-ticket demigod. At the time, I was working with a company that marketed and sold international real estate, doing $250,000 to multimillion-dollar deals every week.

I liked what the goof-ru were doing online and wanted to learn from them. They called me directly and told me how they could teach me this new, high-priced, big-money-selling approach, rather than what many people were doing, selling $27-$297 courses.

The wealth wizard then presents the investment for his big-money, high-ticket program: $1,000.

The value of their program deflated dramatically. I was ready to hear $5,000 to $10,000. Just a couple of years before that, I was consistently selling twenty-one $5k programs each month, month after month. My brain was shocked when I heard that it was only $1,000. He was losing out on at least $ 3,000 –$4,000 per sale.

Today, most coaches struggle to sell coaching programs priced between $1,000 and $2,500.

You must learn what you are offering and how it benefits the future client. Next, you must sincerely believe you are delivering a program worth five, six, or even seven figures.

Your mission is to Create Value Worthy of a 5-figure Investment. (even if you only sell it for 4-figures or less)

Once you have done that, you can now start increasing your prices.

Let’s look at the numbers again by going back to Part 1 of this series. (We started with the idea of you having a $3k offer and making 2 sales/week.) So the original is 104 sales per year at $3k or $312k/year.

If you only increase your coaching fee by $2,000 (less than double) on that $3,000 offer we mentioned earlier, and you make 3 sales a week instead of 2 as mentioned in Part 1 of this series, the numbers look like this:

• 156 total sales times $5,000 = $780,000/year.

• Don’t let the math mess with you; that’s the challenge with separating the 7 Roadblocks into different parts. I’ll do a few live calls in June to help you out with your numbers.

You more than doubled your income without even doubling your fees or the number of sales per year. You just made more offers, resulting in 1 more sale per week. With a slight price increase, you doubled your annual income.

Consider what happens when you start selling 25% or 30% of your calls... which brings us to the next roadblock.

5. Fear of speaking

I have a tough time believing people would rather be in the coffin than deliver the eulogy, but that’s what I’ve heard for decades. The psychiatric world calls it glossophobia, and it can affect up to 75% of all people.

This report isn’t to teach you how to overcome that fear but to explain that when you do, the world of possibilities opens up to you almost as much as when you learn to sell.

By “speaking,” I mean speaking to larger audiences, not just one person at a time: Webinars, FB Lives, YouTube Lives, virtual events, workshops, or in-person seminars.

Speaking is a leveraged skill. It allows you to market your business, build yourself up as an authority, help people bond with you, and sell to more than one person at a time.

The beautiful thing about speaking to a larger audience is that you don’t have to be a great salesperson. You don’t have to “close from the stage” at all.

Examples of how this has worked for me personally:

• I presented a webinar to only two people. We pitched at the end and closed both. 1 hour of speaking, two sales, $6,000 in the bank.

• Did a 15-minute coaching session with another coach’s group by invitation. I never pitched. Just coached. Three people reached out to me to discuss my $30k program.

• Held in-person events in a hotel conference room each month for over a year. No website. No internet marketing. We limited clients to 21 per month at $5,000 per person. We sold out every month with a waiting list. That’s $105k/month for 4 hours of speaking.

• Did a small seminar for 12 people and presented a simple internet marketing service. Creativity on my feet turned that $8,000 sale into a $55,000 contract, plus a new vehicle from the client!

Speaking not only allows me to make more offers but also improves my communication skills for my 1-on-1 sales presentations. It eliminates most sales calls and objections because you answer them while you talk!

I’ll have roadblocks 6 & 7 up together in a few days, then in June I’ll be teaching on all of these with live one-on-one sessions for those who are interested.

• False

• Expectations

• Appearing

• Real

They expect that to mean something when you actually have to speak with a prospect on the phone and close a sale. The fear is real, I acknowledge that. I’m not going to brush it off and tell you it isn’t.

The reason you may be struggling with fear is more about the expectations you place on yourself:

• “I gotta close this sale.”

• “I can’t afford to waste another lead.”

• “If I don’t start making money from this, I’m going to have to go get a job I hate.”

• “What’s my family going to think if I don’t make a million dollars this year?”

Even when it’s your first couple of years in business, that pressure has been hypnotically placed into your brain by too many overly hyped promises and social media mavens pretending to be something they are not.

Just as roadblock #1 has a close cousin in roadblock #6, roadblock #2 has a close relative in roadblock #7.

Here’s what you need to know: You have to stop thinking of the “Hollyweird” portrayals of salespeople in sitcoms and movies.

You do need to start doing what you are already good at. (At least I hope you are if you’re a manager, coach, trainer, teacher, digital marketer, or info-product producer.)

That thing you’re good at already is listening.

Just have a conversation with the prospect. Pay attention. Listen closely without worrying about what you have to say next because someone gave you their super-duper seven-figure sales script, and you think you’re trying to get through a checklist to close a sale…

You are not. Have a conversation. Quit trying to close a sale.

The person on the other end of the phone, in a Zoom meeting, or across the table just wants to be heard and to know whether you can help them.

I recently coached approximately 750+ entrepreneurs and coaches every month for 3 years in another business.

When I get an opportunity to listen to their calls, I always hear at least 2 to 3 instances where the coach glides right past a vital comment from the prospect. Each time it happens, the coach is trying to move the prospect through the sales machine they’ve been trained on.

Fear can be controlled best when you decide to have a conversation and quit focusing on the sale. (Roadblock #7 will reveal how you can control those emotions with the proper coaching.)

Bonus Micro-Training: The 3-Headed Objection Monster and How to Tame It

The shadowy characters looking to attack you during your pitch aren’t real. Objections are often just gaps in knowledge.

In my 40+ years of selling, there are basically three objections:

1. Price

2. Decision maker

3. Certainty

The average business owner thinks that answering objections means they have to get “Pushy”.

When Objections #1 and #2 come up, I always say something like:

“No problem. Just to be clear, if money or having to talk to your spouse wasn’t a concern, do you feel that the program would help you get the results you want?”

Too many times to count over the years, I have heard hesitancy in their voice or seen them become overly agreeable.

“On a scale of 1-10, where are you?”

If they aren’t answering 9.5 or 10, then it’s Objection #3 that has to be addressed. They just aren’t sure your program is a fit for them.

You need to get them as close to a ten first. When you do, the other two objections will be much easier to handle, and you’ll never feel pushy.

I used to think of all that fear I carried with me on each call as walking into a dark room.

If I don’t turn on the lights, I never discover that my prospect may just be someone in the room who needs some assistance.

Help them see clearly, and don’t be afraid to give them some assistance to understand exactly how you can help.

Look for me to go live to ask any questions or comment below.

If a guy who was too shy to ever ask a girl out can sell millions and millions of dollars across multiple industries over the years, then I know you can.

You’ve already created a newsletter, a course, a coaching program; now you only have to help people know you have something that can help them and how you can help.

Roadblock 1: Not enough offers

Roadblock 2: Fear of Selling (think coffee date conversation, not selling)

I’m not one for lengthy introductions and spending three pages bragging about myself before getting to the details you came for, so let’s dig right in.

1. Not enough offers

Many, if not all, coaching programs start by telling you to focus on one niche, develop one product, and use one marketing channel to make sure your offer is valid and you can sell it.

Makes all the sense in the world. I agree.

The challenge most coaches face when learning from the goof-rus (my term for gurus) is that they continue down that path for months or even years.

If the new coach stays in the “Group Training Model” of learning (really not a fan of group coaching as a longtime investor in learning and as a client), they hear the same, monotonous droning about focusing on one thing… being told to the NEW Coaches.

If you have even a few sales and you know your offer is good (good enough to make some sales), then you have to start getting the word out on more channels, more often.

(I’ll describe one of the fastest, most leveraged ways to make more offers in roadblock #5 below.)

But consider the math: If you have a 20% closing ratio on calls with prospects, and you go from 10 calls per week to even 15, you go from 2 sales/week to 3 sales/week.

Do that math for one year. That’s 52 more sales per year!

Assuming you have a lower-end coaching program, say, only $3,000/sale, you’ve added $156,000 to your income from only five extra calls per week!

Cast a wider net!

Too many people spend time focusing on the niche and perfecting an offer, then cast a single line into the water and hope and pray someone will bite.

If you started letting more people see your offer in different places, then you are fishing with a net.

Easy to understand, but if the offer isn’t good, throwing a net into the water that ends up feeling like throwing a net into a sandy desert.

We discuss this often here.

Good offer and good marketing, but…

If you are learning to grow a steady, sustainable business by maintaining a set of marketing systems that will sustain it, that won’t be a problem.

You’re casting a net into a good fishing spot.

The challenge is that each person has a different net, a different spot to fish, and their marketing may have gaping holes in that net that they weren’t aware of.

I share that kind of information/guidance/coaching on my Substack and YouTube Channel every week (yeah, I know, I’m lazy with YouTube, but I’m fixing that hole in my net now. LOL!).

When fishing for business, it’s better to cast an “offer net” than to fish with a single line with your competitors standing on the same deck as you.

Part two coming very soon.

A masterclass in pricing your coaching programs, courses, and services, from your very first $5 offer to your first $25,000 package, without losing your mind, your clients, or your self-respect.

Let me tell you something that will either comfort you or irritate you, depending on where you are today: almost every coach, consultant, and course creator I have ever worked with has had their pricing backward.

The beginners charge too little and apologize for it.

The experienced ones charge too much and wonder why nobody’s buying.

And the ones who’ve been sucked into the guru-sphere, bless their hearts, are convinced they need to hit $25,000 a month by Tuesday or they’ve failed at life.

None of them is right.

And after years of helping businesses rethink how they package and price what they know, I can tell you this with complete confidence: your price is not the problem.

Your clarity is.

Stick with me, because we’re going to walk through the whole thing, from your very first tentative $5 workshop to a robust, confident, premium fee structure.

We’ll talk about the psychology of pricing, the mechanics of value, the lies the gurus told you, and why a real estate company I once worked with went from $500 courses to $5,000 programs and sold out every single month within 90 days.

(Spoiler: they didn’t change their program. They changed how they talked about it.)

THE CORE PRINCIPLE

The clearer the result, the greater the prospect’s confidence, and the higher the price the market will gladly pay. Pricing is a communication problem dressed up in a spreadsheet.

Part One: The Value-Clarity-Confidence Triangle

WHY YOUR PRICE IS ACTUALLY A PROMISE

When a prospect looks at your price, they are not calculating whether the content is worth it. They are asking themselves a single question, usually subconsciously:

Will this work for me?

That question has three layers.

• First, does this person actually know what they’re doing? (Credibility.)

• Second, do I understand exactly what I’m going to get? (Clarity.)

• And third, can someone like me really achieve this result? (Confidence.)

  Every pricing problem I’ve ever solved, and I’ve solved hundreds of them, comes down to a failure in one of those three layers.

Here’s the triangle.

Value sits at the top. Below it are two pillars: Clarity of result and Certainty of success. The bigger those pillars, the taller the triangle, and the higher the price you can sit at the peak without anyone blinking.

Knock one of those pillars down, and the whole thing tips over, no matter how brilliant your content actually is.

This is why two coaches can teach identical material: one charges $297 and the other charges $4,997. The content didn’t change. The communication of what the content produces changed everything.

THE VOCABULARY OF VALUE

There’s a word that I’ve used in boardrooms and kitchen-table coaching sessions alike, and it changes everything when people finally get it: transformation.

Not the word information.

Transformation.

People do not pay for what you know. They pay for who they will become, or what they will have, after spending time with you.

A $47 course on how to write better emails is priced correctly when that’s all it is.

But a program that helps a real estate agent go from six figures in debt and losing listings to having a waiting list of buyers? That’s worth considerably more than forty-seven dollars.

The information might overlap. The transformation does not.

When you can describe, specifically, vividly, in the exact words your clients use, what life looks like on the other side of working with you, your price stops feeling like a barrier and starts feeling like an investment. And people invest in things they believe will give them a return.

Part Two: The Case of the $500 Course That Became $5,000

A REAL STORY. A REAL RESULT. A REAL LESSON.

CASE STUDY

The Real Estate Training Company That Found Its Voice

A real estate training company approached me about selling a $500 course. Good content. Experienced instructor(s). Modest results. They had been running it for two years and couldn’t figure out why sales were sluggish and referrals were rare.

I quickly identified the issue: they were selling the what and not the so what.

Their marketing said things like “learn lead generation strategies” and “master the art of rentals.” All true. All boring. All completely abstract to someone who’s staring at their mortgage statement at 11 pm, wondering how they’re going to make rent.

What their graduates were actually experiencing, and what nobody was talking about in the marketing, was transformational: agents going from 4 deals a year to 18, a woman who landed her first million-dollar listing three weeks after finishing the program, a burned-out agent in Arizona who rebuilt his pipeline in 60 days and finally took a vacation with his family for the first time in four years.

None of that was on the sales page.

We rebuilt the offer around the real outcomes.

We tightened the language to mirror what actual graduates said during our interviews.

We restructured the delivery into a program model with accountability built in, not because the content changed, but because a structured program signals commitment and produces better results. And we priced it at $5,000.

They were nervous. I was not.

Okay, yes, I was This was early in my career, and I was testing out what I learned in different industries and from my mentor.

Within three months, they were selling out every cohort and clearing over $100,000 a month.

The content didn’t change. The confidence in communicating the result changed. The clarity of what a student could expect changed. And when both of those shifted, the pricing power shifted with them… by a factor of ten.

Now, you might be thinking: “Great story, but I don’t have a warehouse full of successful graduates.

I’m just starting out. My content hasn’t been tested yet.

I can’t charge $5,000 for something I’ve never delivered.” And you know what? You’re absolutely right.

Which brings us to the part nobody in the guru world ever honestly talks about.

Part Three: It Is Completely Fine to Charge $5. Start There If You Need To.

THE CASE FOR THE HUMBLE BEGINNING

I want to say something that might get me expelled from the Online Business Influencer Hall of Fame: starting small is not a character flaw.

It’s a strategy.

And for many people, especially those of us entering coaching, consulting, or teaching later in life, starting small is the wisest, most efficient path to getting started at all.

Here’s what a $5 course actually is: it’s a live-fire conversation with your market.

It’s a way to get real people, people who cared enough to pull out a credit card, to show up, engage, and tell you what they actually need.

It removes the terror of “what if nobody signs up” because at five dollars, the bar to entry is low enough that people say yes just out of curiosity.

And that’s fine. Because you’re not trying to build an empire this week. You’re trying to learn to speak your client’s language.

PERMISSION SLIP

You are officially allowed to start with a $5 workshop, a $17 guide, a $27 live training, or a $97 introductory course. Nobody is going to revoke your coaching license. The priority right now is to talk to real prospects as often as possible and learn what they actually want.

When you get a group of real people into a room (virtual or otherwise), and you start teaching what you know, something magical happens.

They ask questions.

And those questions?

That’s your market research, your curriculum guide, your marketing copy, and your product roadmap, all delivered to you for free, in real time, in the exact words your next client will use to describe their problem.

THE TWO-SIDED GIFT OF TALKING TO CLIENTS EARLY AND OFTEN

I’ve watched coaches spend four months building a twelve-module program, invest in a beautiful course platform, hire a video editor, design a logo, and launch, only to discover that the thing their clients desperately needed was in module seven, and nobody was sticking around long enough to get there.

Talk to clients first. Teach small and live first. Learn first. Build the big thing second.

And here’s the glorious bonus: when you discover that your clients don’t actually need, or want, certain material you had in your outline, you don’t throw it away.

You set it aside. You package it. And later, when the time is right, you introduce it as a surprise bonus. “I wasn’t going to include this, but because of how hard you’ve all been working, I’m going to add this module on X at no additional charge.”

Their value perception shoots through the roof. They rave about you. Your testimonials become magnetic.

Content they didn’t know they needed, delivered as an unexpected gift, hits entirely differently than content crammed into a syllabus.

This is not a trick.

It’s good teaching.

And good teaching creates good stories, and good stories sell programs.

Subscribe now

Part Four: The Full Pricing Ladder — From First Dollar to Five Figures

YOUR CONFIDENCE GROWS, YOUR PRICE FOLLOWS

Let me walk you through a complete pricing architecture.

This is not a rigid formula; it’s a map.

Your journey may skip some rungs, hover on others, or double back.

That’s fine. The point is that there is a logical progression, and you do not need to sprint to the top. Every rung has its purpose.

STARTER $0–$27 The Conversation Opener - Free workshops, $5–$9 mini-trainings, $17–$27 guides or resource packs. The goal here is not revenue. The goal is contact. You’re learning to describe what you do in a way that makes real humans nod and say, “Yes, that’s exactly my problem.” This stage is priceless; treat it like market research, because that’s what it is.

ENTRY $47–$297 The Proof-of-Concept Course - Your first real self-paced course, a recorded workshop series, a workbook + video bundle. At this price, you’re beginning to package your knowledge with intention. You have some early testimonials, some language that resonates, and you’re starting to see which problems your audience cares most deeply about. Results at this level begin to seed your case studies.

MID-TIER $497–$2,000 The Group Program or Live Cohort - Now you’re adding live interaction, community, or accountability. You have enough confidence to stand in front of a group and say, “Here’s how we’re going to do this together.” You’ve tested your content, you know which pieces land, and you have at least a handful of success stories. This is where most coaches should be after 6–12 months of active work.

PREMIUM $2,500–$10,000 The Signature Transformation Program - This is the real estate company’s territory. You have documented outcomes. You have a clear process. You can articulate, without hesitation, exactly what your client will be able to do, have, or become at the end of working with you. You’ve eliminated the filler, amplified the impact, and built in enough support that the result feels nearly guaranteed. This is not for beginners. This is where consistent investment in your craft takes you.

ELITE $10,000–$50,000+ The VIP, Mastermind, or Retainer - High-touch, high-access, high-accountability. One-on-one intensives, annual masterminds, executive coaching retainers. The price is justified by proximity, your time, attention, and expertise applied directly to one person’s specific situation. At this level, you’re not selling a program. You’re selling a partnership. The person across from you isn’t buying your curriculum. They’re buying you.

Every single one of these tiers is legitimate. Every single one of them serves a purpose. And the idea that you should skip straight to the top because some weekend webinar told you that “small offers aren’t scalable” is, and I say this with affection, absolute nonsense (I try not to use bad words or I would right there, LOL!) that has cost more talented coaches their momentum than any other single idea in the industry.

Part Five: Let’s Talk About the Gurus for a Minute

A LOVING BUT COMPLETELY HONEST INTERVENTION

The online coaching industry has a problem. Several, actually, but let’s focus on the one actively preventing good people from helping others: the mythology of the instant empire.

You’ve seen the ads. You may have bought the program. Maybe more than once. The promise goes something like this:

“I went from zero to $25,000 a month in 12 weeks, and so can you! Join my group program, follow my proven system, scale to six figures, and build your dream life”!

There’s usually a Lamborghini somewhere in the background, casually parked in front of what may or may not be their house.

Now, I’m not saying those results are impossible. I’m saying they are the lottery ticket, not the business plan. And when you build your expectations… and your timeline… around the lottery ticket, you set yourself up for a very specific kind of paralysis.

GURU MYTHS VS. ACTUAL REALITY

X Myth: You need a group program right away, because 1-on-1 doesn’t scale. Reality: The person who thinks, “What if I only get 1 or 2 people?” and never launches a group because of that fear will sit frozen for months. One client is infinitely better than zero clients. Start with one.

X Myth: You need to hit $25,000/month in 90 days. Reality: When you’re at week 9 of a 12-week program and still haven’t figured out your offer, people typically don’t push harder; they quit. The deadline was always the enemy. The momentum was always the goal.

X Myth: Low-priced offers devalue your brand. Reality: An offer that gets people into your world, serves them brilliantly, and converts them into raving fans and higher-tier buyers is not devaluing anything. It’s called a business funnel. It’s been working since before the internet was a thing. Same ‘goof-rus’ that have 2 dozen ‘free lead magnets’ and tell you to share everything for free, and then charge 5-figures to start.

X Myth: You need everything automated before you launch. Reality: The most successful coaches I have ever met started by personally emailing five to ten people they already knew and asking if they wanted to work together. Automation is for volume. Volume comes after traction. Traction comes from conversations.

✓ The truth they never tell you: Most of those gurus took 3–7 years to build what they’re showing you in a highlight reel. They’re not lying about the destination. They’re just dramatically misrepresenting the journey.

The specific damage that “you must have a group” creates is profound, and I’ve watched it up close more times than I care to count.

A coach builds out a beautiful group program. They’re excited. They’re ready. And then the thought creeps in: But what if only one person signs up? Then it’s not really a group, is it? What do I do then? Do I refund them? Do I postpone? What if they’re weird?

And so they don’t launch. Not because the program isn’t good. Not because there’s no demand. But because the guru planted a flag that said “group or nothing.”

Now the coach can’t move forward without a crowd.

Here is my official position: one client is a program. Two clients are a cohort. Three clients are a sold-out group. The label is your invention. The momentum is what matters.

Part Six: Building Pricing Confidence as Your Business Confidence Grows

THE INSIDE GAME OF CHARGING MORE

There is a version of this article that focuses solely on tactics, positioning frameworks, objection-handling scripts, and price anchoring strategies. And all of that has its place. But I’ve been doing this long enough to know that the biggest barrier to charging what you’re worth is not strategic.

It’s emotional.

When I ask coaches why they’re charging $297 for a program that delivers $30,000 worth of results, the answer is never “because the market research told me to.”

The answer is usually something like: I don’t know if it’ll work for everyone. What if they’re disappointed? What if I can’t deliver? What if they ask for a refund and tell everyone I’m a fraud?

That is not a pricing problem. That is a confidence problem masquerading as a pricing problem.

And it is extraordinarily common, especially among those of us who were raised to believe that talking about money is crass and asking for what you’re worth is arrogance.

So let me offer you this reframe: when you charge too little, you are not being humble. You are being irresponsible.

A client who pays $47 for transformational coaching treats it like a $47 experience: don’t do the work, and come back six months later to say it didn’t work.

A client who pays $5,000 (often) shows up differently. They do the homework. They ask questions. They implement. And then they get results. And then they tell everyone they know. (There is a referral strategy that should be built into your program that I coach on in the VIP level here in Encore Society.)

Your price sets the expectation for how seriously your client will take the work. Price accordingly.

THE CONFIDENCE PRICING SEQUENCE; WORK THROUGH THESE IN ORDER

1. Run a free or near-free workshop for 5–15 people you already know or can easily reach.

2. Listen obsessively. Write down their exact words. Ask follow-up questions like “what would it mean to you if you could solve this?” and “what have you tried before?”

3. Build a small, simple paid offering around the single most common and urgent problem you heard. Price it so that saying yes feels easy.

4. Deliver it exceptionally. Over-serve. Ask for feedback. Collect testimonials. Learn what worked and what didn’t.

5. Take the results you now have and rewrite your offer description using your clients’ actual words, not your internal jargon.

6. Raise your price by 30–50%. Deliver again. Repeat.

7. When you can describe, in one or two sentences, the specific, believable transformation someone will experience, raise your price significantly. Test the ceiling. You’ll know you’ve hit it when you get surprised-but-still-saying-yes, not “let me think about it and never email you back.”

WHEN YOU KNOW IT’S TIME TO RAISE YOUR RATES

There are four signs that your current price is too low. First: you’re fully booked and turning people away.

Second: clients routinely under-invest in the process because the price didn’t create sufficient commitment.

Third: you’re slightly resentful of what you’re delivering for what you’re charging, even if only a little.

Fourth: your best clients keep telling you that you changed their lives, and they couldn’t believe you charged so little.

Any one of those is a green light.

All four of them are a neon billboard.

And when you raise your price, something counterintuitive often happens: your conversion rate stays the same or actually improves. Because clarity and confidence have both increased. Because your testimonials are stronger. Because you’re showing up to the conversation as someone who knows the work is worth it…

And that energy is contagious.

Part Seven: The Conversation Is the Product (At First)

WHY TALKING BEATS BUILDING EVERY SINGLE TIME IN THE EARLY DAYS

I want to end this piece where I probably should have started it, because it’s the thing I wish someone had told me before I spent six months building a course that seventeen people bought and four of them ever opened.

In the beginning, before the funnel, before the evergreen course, before the membership site, before the mastermind, before the virtual summit, before the podcast, before the seven-part email nurture sequence, before any of it, there is a conversation. A real one. With a real person who has a real problem.

Your entire job for the first ninety days is to have as many of those conversations as humanly possible. Not to pitch. Not to close a sale.

To listen. To ask: “What does your day look like right now? What’s the hardest part? What have you already tried? What would it mean to finally solve this?” And then to be quiet and hear the answer.

When you do this enough, and “enough” is usually somewhere between twenty and fifty substantive conversations, you will know exactly what to build, exactly how to price it, exactly how to talk about it, and exactly who to talk to.

You will not be guessing.

You will not be hoping.

You will be responding to a demand that you have personally verified exists.

And then, and only then, does the question of pricing become simple. Because by that point, you’ve heard what people are willing to pay. You’ve heard what they’ve already spent on inferior solutions.

You’ve heard the cost, financial, emotional, relational, of the problem going unsolved. You have all the data you need to name your price with conviction.

The conversation is free research. It is also free marketing. And it is, for many coaches, the entire product, right up until the moment it becomes the foundation for everything else.

The Short Version, For Those Who Scrolled to the End

(Yeah, I know who you are!)

If you made it this far, congratulations. You’ve essentially completed a mini-course in coaching and consulting economics.

Here’s your cheat sheet:

1. Price is a communication of value, not a calculation of content. The clearer your promised outcome, the higher your price can legitimately go.

2. Starting at $5 is not embarrassing. It’s smart. It’s research. It’s the first conversation in a very long and very valuable relationship with your market.

3. Talk to clients before you build anything big. Use their words to describe the problem. Eliminate what they don’t want. Rebundle it as a bonus surprise. Watch them love you for it.

4. There is a pricing ladder, and you are allowed to climb it at your own pace. One client is a program. Progress beats perfection every single time.

5. The gurus are selling you a highlight reel. The timeline they promise is aspirational rather than instructional. Build for momentum. Revenue follows momentum.

6. When your confidence in the result grows, your price follows. Your job is to do the work so well, so consistently, and so specifically that you would feel slightly embarrassed charging anything less.

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Yes, that is a real last name, and now you know why most people call me Coach Jim, instead of “Jim Uhmmmm, How do you say your last name?”

Oh, my first time on television was Romper Room! I was five. Had to show up for work every day for a whole week!

I asked about childhood memories yesterday, and completely forgot about that experience.

What do you say?

Many people panic and explain their entire business model, including the origin story and a detour about their pivot.

Eyes glaze.

The snack table wins.

An elevator pitch isn’t about cramming everything in. It’s about saying the one thing that makes someone lean in and say, “Wait, tell me more.”

That’s it.

One moment of genuine curiosity.

That’s your entire job.

Below are seven proven pitch frameworks that my clients and I have used over the years.

Each one is built around the same core idea: lead with what they care about, not what you do.

Read them all.

Pick one that fits your personality and your moment.

Then actually practice it out loud.

Why? Because saying “I’ll just wing it” is how people end up describing their LLC structure to a stranger at a wedding. 🤣

The 7 Templates

1. Classic one-sentence USP

Best for: social media bios, email subjects, quick intros

TEMPLATE

“I offer [your specific product/service] to [target audience] that [unique benefit/outcome] so you can [desired result], all for [clear price or investment] without [common pain/frustration].”

WORKED EXAMPLE

“I offer AI-powered email automation to busy e-commerce founders that cuts inbox management time by 80% so you can focus on sales, all for $299/month without needing a tech team.”

WHY IT WORKS

It hits every note (who, what, outcome, price, and relief) in a single breath. Concise doesn’t mean vague; this template proves it.

2. Problem → Solution → Benefit

Best for: in-person networking, cold emails

TEMPLATE

“Most [target audience] struggle with [main pain point]. I help them [your solution] so they can [key benefit/result] without [common frustration].”

WORKED EXAMPLE

“Most busy e-commerce founders struggle with drowning in customer emails. I help them automate everything with AI so they can focus on sales and growth without needing a tech team or spending hours every day.”

WHY IT WORKS

Starting with “Most [people like you] struggle with...” is like handing someone a mirror. If they recognize themselves in the problem, they’re already listening for the solution.

3. Question-led hook

Best for: starting conversations, video pitches

TEMPLATE

“Have you ever [relevant struggle]? What if you could [desired outcome] simply by [your solution], all for [price] without [frustration]?”

WORKED EXAMPLE

“Have you ever felt buried under customer emails while trying to run your store? What if you could reclaim 80% of that time simply by using AI automation, all for $299/month without hiring extra help?”

WHY IT WORKS

Questions create a tiny pause in someone’s brain - they can’t help but answer internally. That moment of self-reflection is you. In their head. Rent-free. That’s the goal.

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4. Results-first (credibility-focused)

Best for: sales calls, when you have strong proof or metrics

TEMPLATE

“I help [target audience] achieve [specific impressive result] in [timeframe]. With my [offer], you get [key deliverable] for [price] so you can [desired result] without [frustration].”

WORKED EXAMPLE

“I help busy e-commerce founders achieve an 80% reduction in email management time in just one week. With my AI automation, you get full setup and training for $299/month so you can focus on sales without needing a tech team.”

WHY IT WORKS

Lead with the number. Real, specific metrics do more heavy lifting than any clever wordplay. “80% reduction in one week” is a claim people can’t ignore - if you can back it up, use it up front.

5. Vision / future-oriented

Best for: investors, visionary audiences, creative industries

TEMPLATE

“Imagine [vivid positive future state]. That’s exactly what my [offer] delivers for [target audience], [unique benefit] in [timeframe] for [price] without [frustration].”

WORKED EXAMPLE

“Imagine having your inbox run itself while you focus on growing your business. That’s exactly what my AI email automation delivers for busy e-commerce founders, 80% less email time in one week for $299/month without needing a tech team.”

WHY IT WORKS

“Imagine” is a magic word. It invites people into a future they want to live in before you’ve asked them to spend a cent. Pair it with a vivid, specific picture, not a vague abstraction.

6. Mini-story / relatable scenario

Best for: storytelling cultures, longer networking conversations

TEMPLATE

“When [similar person/situation], they faced [pain]. After using my [offer], they [transformation]. You can too, for [price] without [frustration].”

WORKED EXAMPLE

“When Sarah, an e-commerce founder like you, was spending 4 hours daily on emails, she faced burnout and lost sales time. After using my AI automation, she cut that by 80% and doubled her focus on growth. You can too, for $299/month without needing a tech team.”

WHY IT WORKS

Humans are wired for stories, not statistics, though you can slip both in. “Sarah” makes the result feel real and achievable. Just make sure Sarah is a real person, not a made-up archetype with suspiciously round numbers.

7. Bold 15-second power version

Best for: elevator rides, trade shows, attention-grabbing openers

TEMPLATE

“[Target audience] are losing [time/money/opportunity] on [pain]. I fix that with [offer] in [timeframe] for [price], [unique benefit] guaranteed.”

WORKED EXAMPLE

“E-commerce founders are losing 20+ hours a week on emails. I fix that with AI automation in one week for $299/month, 80% time saved guaranteed.”

WHY IT WORKS

Three sentences. No fluff. This one earns its confidence - “guaranteed” only works if you mean it, but if you do, those six syllables hit harder than a paragraph of explanation.

Four Rules That Apply to All of Them

Templates get you 80% of the way there. The other 20% is delivery.

Here’s what separates a pitch that lands from one that trails off into “...so, yeah, that’s sort of what I do.”

Which template fits your offer?

Drop your product, your audience, and the main benefit in a comment, and I’ll work with you to create a version customized to your exact situation.

This content will be moving behind a paywall soon.

Ask your questions while it’s still free, or join the Paid Tier for full access, live workshops, and a first look at everything new.

P.S. Here is my Encore Mini-story version.

When executives and professionals over 50 came to me, tired of the grind myths, they had the wisdom but no clear path. After joining The Vault, they got my $100M frameworks, videos, and templates, and launched real Encore businesses. You can do the same for $97/year, or go all-in with VIP and get 1-on-1 coaching every month at $997.

This is a time to relax and share as much as it is a time to launch a Legacy business and earn enough play money to spoil a few grandkids and travel…well, the world and maybe even space pretty soon.

If you want to know the number one biggest secret that people who have spent tens of thousands of dollars on courses, coaches, and crap…

It’s that they don’t need to rush to create an offer and sell it yesterday!

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The rush comes from the urgency and deadlines to buy now or else, and then you are thrown into a 10-week group that rushes you to figure it all out so you can earn back your $10,000 investment.

At our stage of life, we’ve got time. Try enjoying the process of getting all of that wisdom out of your brain and onto paper, video, a newsletter, or a podcast.

I’m not telling you to wait 20 years, but come on, go from idea to a good offer, to a full presentation, to mastering sales, especially if you hate sales, all in 10-weeks.

Sure, and I’ve got some great swampland to sell you in Florida…no gators, bugs, or humidity. 🤣

Relax, share, and you will be surprised how the pieces start to fall into place.

I’m here for you,

Jim

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Sort of like people trying to come up with unique selling propositions that sound more like fantasy novels written in a foreign language!

Based on the “Your Offer” structure, which focuses on a clear one-sentence promise, a specific timeframe, and removing a major pain point, here are five more fun and varied templates tailored for coaches and entrepreneurs over 50: (okay, anyone could use them, you don’t have to be over 50, LOL)

To clarify, I used these as templates for my offer, but the structure is laid out for you.

Copy and paste into your own document and change it.

The Titles are my Encore Society ‘attitude with a smile’ headlines.

I’m making these videos and openly coaching everyone in April, so if you have questions, comment below, and we’ll work on them together.

1. The “Wisdom Over Hustle” Template

This template leans into your audience’s experience and maturity, positioning your offer as the “grown-up” alternative to common industry burnout.

• The Hook: “If I showed you how to [Achieve Specific Result] using the wisdom you already have...”
  
  

• The Timeframe: “...in just [Short Timeframe] of focused work...”
  
  

• The Benefit: “...so you can double your impact while reclaiming your weekends for [Family/Hobby]...”
  
  

• The “Without”: “...WITHOUT having to learn the latest TikTok dance or ‘hustle’ 14 hours a day...”
  
  

• The Closer: “...would you be interested in the details?”
  
  

2. The “Legacy Builder” Template

Designed for those looking to ensure their business thrives without being tied to a desk.

• The Hook: “If I offered to help you install a [System Name] over the next [Number] days...”
  
  

• The Timeframe: “...that runs your lead generation on autopilot...”
  
  

• The Benefit: “...ensuring your business becomes a true asset that serves people for years to come...”
  
  

• The “Without”: “...WITHOUT you needing to be the ‘tech genius’ or the only person holding it all together...”
  
  

• The Closer: “...would you want to see the blueprint?”
  
  

3. The “Anti-Guru” Refresh

A direct and refreshing approach for entrepreneurs who are tired of high-pressure sales tactics.

• The Hook: “If I spent [Number] hours with you to map out a [Specific Goal] strategy...”
  
  

• The Timeframe: “...that you can start seeing results from in the next [Number] weeks...”
  
  

• The Benefit: “...that feels completely aligned with your values and integrity...”
  
  

• The “Without”: “...WITHOUT using any ‘ninja’ closing scripts or high-pressure psychological tricks...”
  
  

• The Closer: “...would you take me up on that?”
  
  

4. The “Second Act” Template

Perfect for coaches helping people transition into a new venture or level up their current one after age 50.

• The Hook: “If I helped you package your 20+ years of experience into a [High-Ticket Offer]...”
  
  

• The Timeframe: “...by this time next month...”
  
  

• The Benefit: “...that positions you as the undisputed authority in your niche...”
  
  

• The “Without”: “...WITHOUT you having to start from scratch or build a complicated 10-step funnel...”
  
  

• The Closer: “...would you be open to a quick chat about it?”
  
  

5. The “Invitation to Tea” (Low Pressure) Template

A softer, conversational approach that works well for building community and leads for your training.

• The Hook: “I’m looking for [Number] coaches who want to [Achieve Specific Milestone]...”
  
  

• The Timeframe: “...over the next [Number] days of working together...”
  
  

• The Benefit: “...so you can finally stop worrying about where your next client is coming from...”
  
  

• The “Without”: “...WITHOUT the stress of ‘launching’ or burning through an expensive ad budget...”
  
  

The Closer: “...would you like to join me for a virtual ‘coffee’ to see if it’s a fit?”

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Did a little intro, and discussed the current popular “Offer Template” that people are told to use.

It’s a great start, but it doesn’t teach you how to communicate your offer in a way you can build on.

Had some fun with a few mishaps and being new to the format…as you will notice, I don’t stress too much about mistakes, I quickly admit them, but I’m taking the coaching very seriously.

See you tomorrow for part 2, where we discuss how to communicate your offer and close sales without asking for them.

Blessings,

Jim

At the time, I had a business partner and was teaching/coaching about the real-world of high-ticket sales. The Good, The Bad, and The Ugly of it all.

Since the video below, my wife survived a second, different cancer, we are 31 years strong in our marriage, I’m completely silver-haired now, and back then I wasn’t yet a raving maniac about “OFFERS” yet. LOL!

• I was closing $30k sales from cold meetings

• Calling out fake “goof-rus” (my term for gurus that shouldn’t be teaching) with no real experience

• Explaining that courses are cute, but worth nothing if you don’t implement, and

• As recently as yesterday, getting agitated by coaches and mastermind groups that don’t know how to coach and just ask questions. Overpaid therapists basically.

That was then, but I still had ‘hang-ups’ and fear that prevented me from saying too much publicly.

Not fear of being mean, I wouldn’t do that, but fear of hurting some joint venture relationships (collaborations). I was right to bite my tongue back then.

Now!?!?

Here’s the video, “Real Life in The Real Coaching World.”

It’s actually a decent intro to who I am, a few bad jokes, and my attitude toward taking responsibility for doing the work, taking action, and not blaming the people you invested in for your lack of results.

You’re going to see multiple Lives here and on YouTube, where I’ll be sharing real-life marketing and sales for offline and online businesses.

I will also have fun with others who want to join me, chat, and let me coach them live.

If you’re up for it, message me.

No charge, no sale pitches, just me and you, talking about your offer, your sales process, your pets, your favorite foods, doesn’t matter.

Plenty of real-world coaching and as much fun along the way as we can have.

Oh yeah, if you are all about “Fun First, and Business Fast, please

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The short Post I wrote and referenced in the live is here.

Thanks to VIP Member Janna for commenting on that video and reminding me.

I’ve really got to start getting serious about YouTube, too.

Lots of Live Coaching here & on my YouTube channel coming very, very soon.

Blessings,

Jim

In an effort to avoid being 'salesy,' coaches have stripped their messaging of all substance, leaving them with a business that looks good but does nothing.

The epidemic is this: everyone’s marketing sounds wonderful, and nobody’s buying anything.

The emails are clean. The websites are polished. The social posts are thoughtful, balanced, and carefully worded so as not to offend, upset, or heaven forbid, pressure anyone into making a decision.

And the results? About what you’d expect from writing designed by committee and approved by lawyers.

Flat.

I’ve been in this industry for over thirty years.

I’ve written copy, coached copywriters, and helped businesses generate real sales with real words.

And the single most common problem I see in AI-generated content, in guru-approved templates, and in perfectly well-meaning business owners is the same one it’s always been.

They’re afraid to make a claim.

The Anatomy of Wimpy Marketing

Let me show you what wimpy marketing looks like, because you’ve almost certainly been on the receiving end of it.

Here’s the kind of headline you see everywhere right now:

Read that sentence again. Now ask yourself:

• What did you just learn?

• What problem does it solve?

• Who specifically is it for?

• What makes it different from the other fourteen thousand coaches who “help coaches and consultants”?

Nothing.

You learned nothing. You felt nothing. You’re going to click away in three seconds.

Now here’s what that sentence is trying to say, if it had any spine:

That bites a little, doesn’t it? Good.

That’s the point.

The difference between those two sentences is not creativity. It’s not talent. It’s not even experience.

It’s the willingness to make a claim, name a problem, and take a position.

That’s what marketing is supposed to do. It’s supposed to change the reader’s position, move them from “I’m vaguely aware this is a problem” to “I need to fix this today.”

Pleasant language doesn’t do that.

Only pressure does.

Why AI Keeps Making This Worse

Here’s the dirty little secret of AI-generated copy that the prompt engineers don’t want to admit:

AI is trained to be helpful, balanced, and safe.

That is not a bug. It’s the whole design.

The machine is naturally incapable of saying something that might ruffle a feather, because “ruffling feathers” looks a lot like “causing harm” to a system that can’t tell the difference.

• So it smooths everything, or it tries, at least.

• It balances what should be lopsided.

• It resolves tension before the reader has even felt the weight of the problem.

• It explains when it should sharpen.

The result is a bunch of words that sound like a very confident HR manual.

Let me show you the pattern, side by side:

AI Default: “Our coaching program provides a comprehensive framework to help you achieve your business goals through structured learning and ongoing support.”

Verdict: Zero stakes. Sounds like a brochure for a community college elective.

(By the way, some of the most popular names in the industry use that line almost word for word.)

What it should say: “You’ve been running the same offer at the same price for two years and wondering why it isn’t working. It’s not the offer. It’s that nobody believes you yet. Let’s fix that.”

Verdict: Now we’re having a conversation.

The difference is emotion.

Specifically, the second version understands that before someone will pay you, they need to feel the cost of not paying.

AI does not do this well.

• It will occasionally talk about creating urgency.

• It is very reluctant to actually create it.

And if you’re editing an AI copy without understanding this distinction, you’re usually just making the beige (I used that term for boring in retirement) a slightly warmer shade of beige.

You’re tidying up a sentence that was never going to work in the first place.

The “Goof-Ru” Industry and the Art of Selling Nothing

I want to spend a moment on the coaching industry specifically, because it’s become a master class in persuasive language that produces exactly zero results for the client.

You’ve seen the model.

• Large-ticket program.

• Impressive income screenshots.

• A promise of “seven figures” or “scaling to a million a month.”

You pay your $10,000 or $25,000 or $45,000, and what you get is:

• Access to a course library with 80 hours of video content (which no one finishes),

• A group coaching call staffed by a 23-year-old who has memorized a script,

• And a coach who no longer coaches because, as they’ll remind you proudly, they’ve “automated their delivery.”

• When you get stuck, and you will get stuck, the answer is always the same: “Go back through the courses.”

That’s not coaching.

That’s a filing cabinet with a monthly fee.

I call these people Goof-Rus.

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They’ve figured out that it’s easier to sell hope than to deliver results.

Also, they realized that as long as your marketing is emotionally compelling and your refund policy is quietly buried, you can run this model for a few years before people catch on.

Then you rebrand, relaunch, and resell the same people a new version of the same nothing.

The marketing that sells these programs is, ironically, excellent.

1. It’s emotionally charged.

2. It makes big claims.

3. It creates urgency.

4. It tells a compelling story.

5. It does everything I’ve been telling you wimpy marketing fails to do.

The problem isn’t the marketing. It’s that the marketing is selling a lie.

What I’ve found, and I mean this from speaking directly with hundreds of people, is that most coaches, consultants, and service providers don’t actually want a million-dollar month business.

1. They want to pay their bills comfortably.

2. They want to retire without financial anxiety.

3. They want to take a nice vacation and buy the grandkids something ridiculous.

4. That’s a $10,000 to $20,000 month.

5. That’s achievable. That’s real.

And the path to it doesn’t require a team, a funnel stack, or a Mastermind that costs more than a car.

It requires an honest offer, delivered to the right person, with copy that makes a clear claim.

Here’s proof. Three real clients. Three very different situations:

Amanda closed six figures in a single weekend, not because she had a complicated funnel, but because she stopped apologizing for her price and started explaining exactly what staying stuck was costing her clients.

Michelle started closing 80% of her $3,000 program. She wasn’t even asking for the sale. She was just having an honest conversation about the problem, and the close happened naturally because the desire was real and the offer matched it.

Brooke went from zero $10,000 programs sold to a $30,000 month. Not by working harder. By quitting the guru playbook, being direct about what her offer was and wasn’t, and letting the right clients self-select.

None of this involved a new tech platform.

None of it required 80 hours of courses.

All three of them changed the way they communicated.

(BTW, all 3 were in a ‘group coaching’ doom-spiral. All 3 came to me, got personalized coaching, and did more in a few sessions than years of groups and courses.)

That’s what this work is actually about.

Before You Keep Reading: A Quick Note on What’s Ahead

Everything above is the setup. The real work starts on the other side of this paragraph.

In the paid section of this article, I go deeper, and I mean considerably deeper.

We’re going to look at a specific offer I built that went from a 1% conversion rate to 25% and sold out month after month.

I’m going to walk you through exactly how that copy was structured, what claims it made, and why it worked, even though every “polished” version of that same offer had failed.

I’ll also give you three frameworks you can apply to your own offers today, not someday, not after you finish a course, today.

If you’re a paid member of The Encore Society, you already have access. Keep reading.

If you’re not yet a member, now might be a good time to fix that.

The paid tier includes the full article library, live workshops on sales, marketing, and coaching, and twice-monthly Q&As where you can bring your actual copy for an actual human who has been doing this for three decades to review.

It’s $97 a year. For that price, you can’t even get a decent dinner at an airport.

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The reason your prospects say “I’ll think about it” has nothing to do with price. It has everything to do with whether they felt seen when they read your offer.

A practical breakdown for coaches, consultants, and anyone tired of chasing people who “just need a little more time.”

Let me start with a confession.

For a long time, I thought the answer to a slow sales month was a better funnel. More automation. A slicker landing page. A pop-up that triggers at exactly the right scroll depth, as if that was going to be the thing that finally convinced someone to invest in themselves.

It wasn’t.

You know what I was actually doing? I was paying what one writer calls the Clarity Tax, the invisible financial penalty you rack up when you skip the hard work of sharpening your message and start throwing technology at the problem instead.

Funnel builders. Email sequences. CRM software that you’ve been meaning to “fully set up” since 2022. All of it is designed to amplify a message that, deep down, you knew wasn’t quite right yet.

Here’s the thing about amplifying a muddy message: you just get louder mud.

The real problem, for most entrepreneurs, and definitely for my clients, isn’t a marketing problem. It’s not a funnel problem. It’s not even a pricing problem.

It’s a clarity problem. Specifically: the inability to describe someone’s situation back to them with enough precision that they stop and think, “Wait. This person actually gets it.”

That’s the whole game. And it’s simpler than you’ve been told.

The reason “I’ll think about it” is actually useful feedback

When a prospect tells you they need more time, the polite interpretation is that they’re busy. The accurate interpretation is that something didn’t land.

Ninety percent of the time, “I’ll think about it” is a diplomatic exit. It’s the social equivalent of saying “we’ll see” to your kids when you mean no.

They’re not going home to mull over your offer with a cup of coffee. They’re going home relieved to be off the call. Am I right, or am I right?

But here’s the useful part: it tells you exactly where the breakdown happened.

They weren’t confused about the price. They didn’t have a scheduling conflict.

They simply didn’t feel certain enough.

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Certain that you understood their problem, certain that your solution was designed for someone like them, certain that this wasn’t just another thing that would sound great until implementation.

The fix isn’t a better rebuttal. (After 20 years of traditional sales training, I still laugh at the guy who tried selling me 346 sales rebuttals.) The fix is a better diagnosis, delivered before they even get on a call with you.

Most offers sell the solution. The ones that convert sell the diagnosis.

Think about the last time you went to a doctor with a vague concern. Maybe some fatigue, some headaches, a general sense that something was off. Now imagine the doctor walked in, handed you a brochure about a supplement, and said, “This works great. Most people see results in thirty days.”

You’d leave. Or at minimum, you’d be deeply suspicious.

What you want, what every patient wants, is for the doctor to listen, ask smart questions, and then say something that makes you think they’ve seen this before. That they know exactly what’s going on. That the prescription follows logically from a real understanding of your situation.

That’s diagnostic selling. And it works the same way in your business.

The shift is small, but it changes everything: instead of opening with your solution, you open with a description of your prospect’s problem so accurately that they feel like you’ve been reading their journal.

When someone reads your offer and thinks “this was written for me,” you haven’t just captured their attention — you’ve earned their trust before they’ve spent a dollar.

“The more clearly you can describe their pain back to them, the less you have to convince them of anything.”

That’s not a sales tactic. That’s just what it feels like to be actually understood.

Your audience’s pain runs three layers deep. Most offers only reach the first one.

Here’s where it gets interesting, and where most entrepreneurs leave a lot of conversions on the table. I have personally coached sales teams doing mid-six-figure annual revenue who didn’t know or understand what I’m about to share. (Oh, they went on to do mid-seven figures shortly after getting the sales team to follow through.)

When your prospect says they have a problem, they’re usually describing the symptom, not the wound. And the symptom is the least motivating part of the whole thing.

If you write an offer that speaks only to the surface-level complaint, you get a click. Maybe. But you don’t get a buyer.

Buyers come from the deeper layers. I’m not talking about the under $100, impulse buyer. I’m talking about the $2,000-$25,000 buyer.

For my audience, people over 50 who want to build real income without becoming content machines or learning seventeen pieces of software, the three layers look like this:

Layer 1 — Surface pain (what they’ll say out loud)

“I don’t know how to make money online. Everything I’ve looked at seems too complicated or too time-consuming.”

Layer 2 — Root pain (what they really mean)

“I’m afraid I’ve waited too long. I’m not a tech person, and I don’t want to look foolish trying. Everyone else seems to figure this out except me.”

Layer 3 — Identity pain (what keeps them up at night)

“I’ve worked hard my whole life. I shouldn’t have to watch my savings drain or feel like I’m becoming a burden. I want to still feel capable. Productive. Like I’ve still got something left to contribute.”

The surface layer gets a scroll-stop. The root layer gets real interest. The identity layer is what actually closes.

When your offer touches all three — in that order — you’re no longer selling a thing. You’re becoming the person who finally said what they’ve been carrying around in their head and heart and may not have realized it.

The formula for writing an offer that lands

Good news: this isn’t complicated. It’s just specific. And specificity is a skill, which means you can learn it.

Here’s the four-part diagnosis statement I use. Think of it as a mirror, not a pitch:

1. Name exactly who they are. Not “entrepreneurs” or “people who want income.” Try: “people in their 50s and 60s who are five to ten years from retirement and aren’t sure if there’s still time to build something.”

2. Name what they’ve already tried. This is the move most coaches skip, and it’s the most powerful one. When you reference the road they've already been down, the YouTube rabbit holes, the “too tech-heavy” courses, the programs built for caffeinated 24-year-olds, you prove that you understand more than just their goal. You understand their history.

3. Name the real fear underneath the surface complaint. Not “they want more money.” Try: "they've half-convinced themselves that this stuff works for other people, just not for them."

4. Name what they actually want, including how it should feel. Not “passive income.” Try: “a consistent, low-tech path that works with patience and persistence, not hustle and hype.”

Put all four together, and you get something that reads less like an offer and more like a letter from someone who actually paid attention.

The before and after. See the difference for yourself.

Same business. Same coach. Two completely different levels of connection:

Before = generic

“I help people create online income streams using a simple, proven system. No experience needed. Start earning in 30 days.”

After = diagnosis-first

"I help people over 50 create a steady, consistent income online, without posting on social media, without learning a stack of software, and without starting over from scratch. If you've tried this before and felt like everyone teaching it was speaking a different language, that's not a ‘you’ problem. That's a ‘them’ problem."

Someone who wants overnight results won’t read “steady and consistent” and feel excited about it. That’s a feature, not a bug. Good offers exclude the wrong people just as clearly as they attract the right ones.

The cold reader test: three questions before you publish anything

Before any offer goes live, email, landing page, social post, whatever, I run it through three questions (okay, I’m lazy sometimes, but the goal is to run it through the following):

• Could someone read this and immediately know it’s not for them? If your offer could apply to anyone, it converts no one. “I help entrepreneurs grow their business” is not an offer. It’s a LinkedIn bio from 2015.

• Does it reference something your audience has already experienced, not just what they want? Desire is common. History is specific. The moment you describe something they’ve already lived through, you go from salesperson to person who gets it.

• If you removed the promised result entirely, would the description of their problem still be compelling enough to keep reading? If yes, your diagnosis is doing the heavy lifting. If no, you’re leaning too hard on the outcome and not enough on the understanding.

Three yeses and you’ve got something worth publishing. Anything less, go back and add more specificity.

Why this market specifically rewards patience over flash

Let me say something about the 50+ income market that the hustle-crowd misses entirely.

This audience isn’t harder to sell. They’re harder to fool. That’s a real distinction.

They’ve been around long enough to recognize a pitch. They’ve heard “best-in-class,” “game-changing,” and “passive income machine” more times than they can count. The moment your offer sounds like something they’ve seen before, a mental filter kicks in, and they’re gone. Researchers call this “mental opt-out.” I call it wisdom.

What bypasses that filter isn’t more energy, better graphics, or a countdown timer in the corner of the screen. It’s specificity. It’s the moment where the offer sounds so precisely like their situation that they can’t dismiss it as generic because, well, it isn’t.

The 26-year-olds are winning (maybe) on volume and velocity. You win on resonance. They’re chasing the click. You’re earning the trust that turns a cold reader into a buyer who sticks around.

Consistency isn’t just your teaching; it’s your competitive advantage. The low-tech, low-drama, show-up-every-week approach that you teach is also the approach that builds a coaching business that doesn’t require you to go viral every Thursday.

Let them have the likes. You get the clients.

The full framework: name all three layers of pain → write the four-part diagnosis statement → run the cold reader test → lead with the diagnosis, not the solution. That’s it. No NASA-level funnel required.

P.S. If you read this and thought, “I need to rewrite my entire offer,” you might be right. But start small. Take your current bio or landing page headline and ask: Does this describe my person’s situation, or does it describe my solution? That one question will tell you everything.

Written for the VIP Coaching Members who are over 50 and starting or growing in the Coaching Market • Diagnosis-First Offer Framework

Being older is a competitive advantage.

I know.

In an industry obsessed with young Instagram influencers, 28-year-old”goof-rus,” I mean ‘gurus,’ and the perpetual mythology of the wunderkind entrepreneur, that’s a countercultural statement.

So let me say it again, more clearly: your decades of experience, the scar tissue you’ve earned, and the hard-won wisdom you carry around like it’s normal — that is your greatest marketing asset.

The problem isn’t that you lack the advantage.

The problem is that nobody taught you how to market it.

The Marketing Mistake Almost Everyone Over 50 Makes

When coaches over 50 try to ‘do marketing,’ most of them do one of two things.

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It was written by a brilliant woman, 22 years of executive coaching, a client roster that would make your jaw drop, and a gift for cutting through corporate nonsense that I’ve rarely seen matched.

She sent me her website copy for feedback. I opened it. I read the first paragraph. Then I looked at the URL again to make sure I was on the right page.

It sounded like a bank brochure.

Boring. A Yawn-Fest.

Phrases like ‘leveraging transformative synergies’ and ‘holistic methodological frameworks.’ Not a single laugh. Not a single human being in sight. She had somehow taken 22 years of warmth, wisdom, and hard-won real-world perspective... and sanitized every drop of it out.

Sound familiar?

Here’s the uncomfortable truth: most coaches over 50 write copy the same way they were taught to write in the 1980s. Formally. Distantly. Impressively. And unfortunately — invisibly.

Why Copywriting Is Just a Fancy Word for ‘Conversation’

David Ogilvy — the man who defined modern advertising, the patron saint of people who believe words actually matter — said something that I’ve carried with me for decades:

“The consumer isn’t a moron; she is your wife. You insult her intelligence if you assume that a mere slogan and a few vapid adjectives will persuade her to buy anything. She wants all the information you can give her.”

— David Ogilvy

What Ogilvy understood — and what most coaches miss entirely — is that copy is not a performance. It’s not a showcase. It’s a conversation with one specific human being who has a specific problem and is quietly wondering whether you understand them well enough to help.

When you write ‘I help high-achieving professionals unlock their potential,’ you haven’t written copy. You’ve written a LinkedIn headline that could apply to 400,000 coaches worldwide. Nobody reads that and thinks, ‘That’s exactly for me.’

When you write ‘If you’ve been the most capable person in every room for 20 years and still can’t figure out why you feel completely stuck — I know exactly why. And I know exactly what to do about it,’ now you’ve got somebody’s attention.

The Single Most Dangerous Word in Your Copy

That word is ‘I.’

Go look at your website right now. Count how many sentences start with ‘I.’

I’ll wait.

Done? If the number is above three, we have work to do.

Great copy is about your reader, not about you. Every time you write ‘I have 25 years of experience,’ your reader’s brain hears: ‘This is about me, the coach.’ Every time you write ‘You’ve spent 25 years becoming the expert — and nobody’s paying you like it,’ the reader’s brain hears: ‘This person gets me.’

This is not a small distinction. It is the entire game.

“The most important word in the vocabulary of advertising is TEST. If you pretest your product with consumers and pretest your advertising, you will do well in the marketplace.”

— David Ogilvy

Ogilvy was talking about testing ad campaigns. I’m talking about testing your copy on a simpler metric: read it out loud. If it sounds like something you’d never actually say to a real human being over coffee, rewrite it.

The Five Elements of Copy That Actually Converts

After 30+ years working with coaches, consultants, and sales teams, I’ve distilled great coaching copy down to five non-negotiable elements. Miss any of them, and you’ll write the kind of copy that gets ‘likes’ but no clients.

1. A Hook That Stops the Scroll: Your first sentence has one job: make them read the second sentence. That’s it. Don’t impress them. Do not explain your methodology. Just make them curious enough to continue.

That’s a hook. It creates tension, it asks a question, and it points directly at the person you’re writing for.

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