Founder Reflection: 10 Common Offer Challenges I’ve Seen from 20+ Years as an Entrepreneur
I’ve been surrounded by offers for more than two decades — long before I ever became a coach and offer strategist.
Back in my corporate days, I worked in the food industry at a sales and marketing organization. Our job as food brokers was to be the marketing and sales arm for dozens of specialty food companies. And it was fascinating — some products took off with very little effort, selling like hotcakes, while others struggled no matter how much energy we poured into them.
We’d hustle, pitch, and promote. But if the product didn’t meet real market demand, it simply wouldn’t gain traction. Eventually, we’d have to drop those underperformers from our roster. That was my first real lesson in offers: some click, some flop — and you need to know the difference.
Years later, when I stepped into my first entrepreneurial role as a certified life coach for moms, I saw the exact same thing play out. I created a variety of digital products and signature speaking presentations, always experimenting and listening closely to see what resonated.
I’ll never forget my best-seller: Guilt-Free Parenting. It was a talk and product that taught moms my signature process for reframing guilt and learning to release it. And it spread like wildfire. Why? Because guilt was the one thing every mom I met — including myself — was struggling with. I had hit on a problem they urgently wanted solved.
That’s when it clicked for me: offers live or die by how well they meet real, urgent needs. Some you create will soar with ease, others need to be retired quickly. That is the nature of the entire offer process.
Since those early days, I’ve spent 20+ years watching entrepreneurs wrestle with the same patterns. And through my own journey, I’ve come to see the common challenges that make or break an offer.
Today, I want to share the 10 most common offer challenges I’ve witnessed across two decades — patterns I’ve seen in myself, my clients, and my peers.
Because when you know what these pitfalls are, you can recognize them early and avoid wasting months (or years) spinning your wheels.
So let’s dive in.
Strategy Challenges
Every strong offer begins with strategy — clarity about what you do, who you serve, and the transformation you deliver. But this is also where I see entrepreneurs stumble the most. Without a solid foundation, even the most well-designed offer can fall flat.
Two of the most common struggles I’ve witnessed (and personally lived through) are: choosing a clear specialty to anchor your work and deeply understanding your audience’s real problems. These are the roots of a strong offer — and if they’re missing, everything else becomes harder.
Let’s look at each of these on a deeper level.
Offer Challenge #1: The Wandering Specialty
When I launched my first coaching practice, Momnificent!, I thought I had chosen a niche. After all, I wasn’t trying to coach everyone — I was coaching moms.
But here’s the truth: “moms” isn’t a niche. It’s a massive, diverse population with countless unique challenges. And instead of narrowing down, I spread myself thin. One day I was helping a mom with parenting struggles, the next with her marriage, the next with health, and sometimes even business.
I didn’t realize it at the time, but I had fallen into the trap of the wandering specialty — trying to be everything to everyone within a broad category.
Looking back now, I see the deeper issue. It wasn’t just that coaching was new to many moms, or that I had to work harder to explain what I did. It was that I never chose a clear specialty to anchor my work.
If I could redo that business today, I know exactly what I’d choose: I’d work with moms raising autistic children, helping them navigate the unique parenting and relationship challenges that come with special needs. That level of focus would have allowed me to build authority, attract the right clients, and create offers that solved a very specific problem.
Instead, my wide-open niche eventually led to burnout. I couldn’t gain the traction or financial independence I craved, and I had to let that dream go. It was a painful ending, but it taught me one of the most important lessons in the offer world: without a clear specialty, even the best intentions won’t translate into a sustainable business.
Offer Challenge #2: The Audience Blind Spot
I once worked with a client who wanted to launch a program called Healing with Seashells.
She was passionate about her idea. It felt unique, creative, and deeply meaningful to her. But from the very beginning, I couldn’t shake the quiet question in my mind: is there really a market for this?
As I dug deeper, the issue became clear. She wasn’t creating from audience insight — she was creating from personal passion. She had no data on who this offer was for, no clarity on the specific problem it would solve, and no understanding of whether people would actually pay for it.
The result? She struggled to gain traction. There was no clear audience searching for “seashell healing,” and without that connection to a real, urgent problem, the offer simply couldn’t stick. Eventually, she gave up on the idea.
This is what I call the audience blind spot — when we create something because we think it’s brilliant, without checking whether our ideal clients actually want it.
Here’s the truth: offers don’t succeed just because we love them. They succeed when they solve a problem our audience knows they have and is willing to pay to fix. Passion matters, but passion without audience research is a gamble that rarely pays off. Trust me, I know from personal experience.
Ecosystem Challenges
Once you’ve got your core strategy in place, the next step is to think about how your offers work together. I call this your offer ecosystem — the big-picture flow of how someone can move through your world, from their very first freebie all the way to your most transformational program.
When your ecosystem is working, it feels seamless. Each offer naturally leads to the next, giving your clients a clear journey and giving your business more stability and scalability.
But when your ecosystem is not working, it feels scattered and disjointed. Clients don’t know what to do next, and you feel like you’re constantly starting from scratch. Over the years, I’ve seen two challenges come up again and again in this area: disconnected offers that don’t link together, and the missing middle that leaves big gaps in the client journey.
Offer Challenge #3: Disconnected Offers, Disconnected Clients
I’ve worked with many entrepreneurs who treat their offers like a grab bag — random freebies here, a service there, maybe a workshop tossed in for good measure. On the surface, it feels productive. You’re creating! You’re launching! You’re putting things out into the world!
But underneath, the problem becomes clear: none of the offers connect.
I’ve seen this play out most often with lead magnets. A coach will create a freebie they’re excited about — but it has nothing to do with their core offer. Then they wonder why their funnel isn’t working. The truth is, if your freebie doesn’t naturally lead someone to your next step, you’re building a dead end.
I once worked with a writing coach who tried to solve this problem by launching a brand-new offer every single month. She wanted consistent income, but instead, she ended up with a collection of low-ticket programs that required enormous energy to create and even more energy to sell. None of them built on each other. And eventually, she burned out.
Disconnected offers don’t just drain your energy. They confuse your clients and keep you stuck in a cycle of reinvention instead of building sustainable momentum.
Offer Challenge #4: The Missing Middle
Another pattern I’ve seen repeatedly — especially in the coaching world — is what I call the missing middle.
A lot of high-ticket business coaches will tell you to run a free webinar and then pitch a $5k–$10k program to cold prospects. And while it sounds great in theory, in practice it’s one of the hardest strategies to pull off.
I’ve seen health coaches and leadership coaches alike struggle with this. They had incredible signature programs that stretched over six months or more, but with no mid-tier offer in place, selling those big-ticket commitments to brand-new leads felt like pushing a boulder uphill.
One leadership coach I worked with couldn’t get traction with her long-term program — until we introduced a one-month option at $1k. Suddenly, the door opened. Clients who weren’t ready to jump straight into a $5k program could dip their toe in. And once they had a taste of the transformation, it was much easier for them to say yes to the full experience.
When you don’t have stepping stones in your ecosystem, you end up asking too much, too soon. Adding that missing middle creates an easier path for your clients — and a much more sustainable business for you.
Structuring Challenges
Once you know who you serve and how your offers fit together, the next hurdle is structuring those offers so they actually work — for your clients and for you. This is where questions about format, delivery, and pricing come into play.
I’ve seen so many entrepreneurs stall here: they either pack their offers with too much and overwhelm everyone involved, or they freeze up when it comes to setting the price. Structuring is where clarity turns into reality, and if you miss the mark, even the best idea can start to wobble.
Offer Challenge #5: Overstuffed & Overwhelming
I once worked with a leadership coach who poured her whole heart into creating a year-long program. On paper, it looked incredible — course materials, guest speakers, group coaching, masterminding, and more. She wanted to equip entrepreneurs with everything they could possibly need: marketing strategies, brand presence, mindset work, systems, visibility, leadership development.
Her intentions were pure. She genuinely wanted to give her clients the most comprehensive support possible. But there was one problem: it was simply too much.
Clients began checking out. They skipped course modules, ignored bonus sessions, and focused only on what they truly valued — the community and masterminding. The rest of the “extras” became noise.
And it wasn’t just overwhelming for her clients. By month nine or ten, she herself was exhausted. The delivery demands were relentless, and though she loved the people she was serving, the joy drained out of the program.
Eventually, she pivoted. She designed a shorter, 6-week offer focused on her true passion — equipping leaders with the confidence they need to thrive. That shift brought her excitement back and gave her clients a focused transformation they could actually finish and celebrate.
The lesson? An overstuffed offer doesn’t serve anyone. When you try to give everything, you risk diluting the very transformation your clients are looking for — and burning yourself out in the process.
Offer Challenge #6: Pricing Paralysis
If there’s one question I hear more than any other when clients launch a new offer, it’s this: “What should I charge?”
On the surface, it seems like such a simple question. But pricing is rarely straightforward — it’s emotionally charged. Will someone actually pay this much? Should I lower the price so it’s easier for people to say yes? What if I charge too much and people complain? What if I charge too little and people don’t take it seriously?
I’ve seen entrepreneurs discount their offers into the ground because they were afraid of hearing no. I’ve seen others freeze entirely, unable to move forward because the “right price” felt impossible to find. And yes, I’ve also seen programs that overcharged and underdelivered — which only fuels the fear that no price is ever “safe.”
The truth is, pricing taps into so many layers of our inner world: self-worth, money stories, cultural conditioning, even the economy. It’s no wonder it makes entrepreneurs second-guess themselves.
And I’ll be the first to admit I’m not immune. When I was pricing the OfferMojo Squad itself, I went back and forth with Kate — The Offer Builder — more times than I care to admit. At one point, I suggested a price so low it made no sense at all (because I saw someone else charging it). Kate stopped me in my tracks. She challenged my mindset, reminded me of the value the Squad was actually delivering, and helped me land on a price that felt fair, sustainable, and in full alignment with the transformation it provides.
That’s the key: pricing isn’t about pulling a number out of thin air. It’s about finding the intersection of value, sustainability, and alignment. When you do that, you stop spinning and start selling with confidence.
Messaging Challenges
You can have the most aligned specialty, the perfect ecosystem, and a beautifully structured offer — but if you can’t communicate its value, none of that matters. Messaging is where so many entrepreneurs stumble.
I’ve watched offers fall flat, not because the idea was bad, but because the way it was explained didn’t connect. Sometimes the language is too vague or filled with buzzwords. Other times, the message just doesn’t resonate with the right people, leaving confusion instead of clarity.
This is the heart of Theo’s work — helping entrepreneurs find the words that move people. And over the years, I’ve seen two common pitfalls emerge again and again: language that sounds impressive but doesn’t actually communicate the transformation, and messages that get lost in the noise because they simply don’t land.
Offer Challenge #7: Lost in Translation
The marketing industry is notorious for this one: using fancy, insider terms that don’t mean much to the average business owner. I can’t tell you how many times I’ve heard acronyms like TOFU, MOFU, and BOFU tossed around — short for top, middle, and bottom of funnel. Here’s the thing: most business owners don’t even fully understand what a funnel is, let alone the different “layers” of it.
And this isn’t unique to marketing. Other industries do it too — especially ones rooted in science. Neuroscience, health, fitness, therapy… so many use language that makes sense to practitioners but flies right over the heads of the very people they’re trying to help.
Take health coaching as an example. I’ve seen countless offers around “gut health.” But what does that actually mean to the average person? Even as someone who’s studied wellness for years, I sometimes find myself asking: Do I have gut health issues? How would I know? Does it mean stomach aches? Digestive problems? Something else?
And if you do solve my “gut health issues,” what will that actually do for me? Will I be able to eat the foods I love again? Will I finally sleep through the night? Will I lose the stubborn belly fat that frustrates me? Those are the outcomes people actually care about — the ones they talk about and complain about in everyday language.
When your offer gets lost in translation, it doesn’t matter how powerful it is. If people can’t connect the dots between your language and their lived experience, they won’t see the value. The lesson? Speak to the transformation in words your audience already uses — not the jargon you were taught in school.
Offer Challenge #8: The Muffled Message
Not long ago, a colleague reached out to me because she was struggling to talk about her offer in a way that made sense. And I could see why — her offer was broad and undefined: she was selling “systems” setup for entrepreneurs and companies.
The problem? Systems can mean just about anything. Are we talking operating procedures? Software platforms? Financial systems? Marketing systems? Client delivery? Without specificity, her message got muffled.
And that’s the trap so many entrepreneurs fall into. They know their work is valuable, but when they try to explain it, the language is vague, general, or too broad. Instead of clarity, the audience hears noise.
The real key is getting specific:
What kind of system (or service, or solution) are you really providing?
Why does your audience care about that system?
What will their life or business look like after it’s in place?
If the audience can’t see the gap between where they are now and where your offer can take them, they won’t connect with it — no matter how good it is.
I see this in my own work, too. If someone doesn’t believe they have a problem with their offer process, I could talk about it all day and it wouldn’t land. The truth is, you can’t sell to someone who doesn’t think they need what you’re offering. And if your message is muffled, they’ll never recognize themselves in your solution.
Visibility & Sales Challenges
Even with a strong strategy, a connected ecosystem, clear structure, and solid messaging, there are still two critical pieces that can make or break your success: visibility and sales. These are the stages where your offers actually meet the world — where people discover what you do and decide whether to say yes.
And yet, this is where so many entrepreneurs hesitate. Some stay hidden, hoping word of mouth will be enough. Others skip the sales process altogether, assuming a great offer will somehow sell itself. But visibility and sales aren’t optional — they’re essential.
Over the years, I’ve seen two common challenges surface here: entrepreneurs who remain invisible even though they have amazing expertise, and those who build an offer but never create the sales system to support it.
Offer Challenge #9: Invisible Expertise
I recently spoke with an experienced health coach who specialized in mindful eating. She came to me frustrated because her offers weren’t selling. At first glance, nothing seemed obviously wrong. Her ecosystem had flow. Her messaging was clear. Her offers themselves were sound — though I did caution her that relying solely on courses (a delivery method that’s been losing traction) might be limiting her reach.
But as we dug deeper, the real issue surfaced: visibility.
She had only just started posting on LinkedIn. She’d lost touch with the doctors who used to refer clients her way. She wasn’t attending networking events or actively expanding her reach. In short, her expertise was invisible.
We shifted our focus to reigniting her visibility. She created a new program for women using GLP-1 medications, which gave her a reason to reconnect with prescribing doctors. She also joined networking groups to broaden her audience.
The results? She sold her new offer — and with continued visibility efforts, I’m confident she’ll sell more of her programs.
The lesson here is simple but crucial: it’s not enough to have a great offer if no one knows about it. Visibility isn’t a nice-to-have; it’s the lifeline that keeps your offers alive.
Offer Challenge #10: The Silent Launch
For years, I lived in the camp of “build it and they will come.” And for a while, it seemed to work. I was great at publishing content, staying visible, and generating enough leads to keep my business afloat.
But as the online space grew more saturated, that approach stopped being enough. I realized the uncomfortable truth: I hated sales. I avoided it like the plague. And no amount of content could make up for the fact that I didn’t have a real sales system in place.
That’s when I met my former business and sales coach, Matt Biggar. He didn’t sugarcoat it. He looked me straight in the eye and said: “If you don’t learn sales, you’re going to keep struggling. We’ll be right back here in the same place a year from now.”
It was a hard pill to swallow. But he was right.
Not only did I have to face my fears around sales, I had to find a way of selling that felt natural to me. I’m not a pushy person — and as a Human Design Projector, I thrive when I wait for the invitation. But that didn’t mean I couldn’t create opportunities to introduce people to my offers.
I learned how to have natural DM conversations, thanks to another amazing coach, Tracy Beavers. I started networking and scheduling coffee chats in ways that felt good for my introverted personality. I even embraced soft launching — something I had historically avoided.
The bottom line? In today’s trust recession, you absolutely need a sales system. You need to build relationships. You need to practice, even if it feels uncomfortable at first. Because the more you practice, the easier it becomes. And here’s the truth every entrepreneur has to face: there is no business without sales.
Final Reflection
After more than 20 years of watching offers rise and fall, here’s what I know for sure:
You need to be willing to dive deep into the offer process. If you skip the work, you risk wasting months — even years — trying to force traction that never comes.
If you feel disconnected or burned out, there’s an alignment issue. It’s not just exhaustion. Something in your strategy, structure, or delivery is out of sync — and realigning is worth the scary step.
If your offer isn’t selling, look deeper. Chances are, one of these 10 challenges is at play. The sooner you identify it, the faster you can course-correct.4
Don’t go it alone. The offer process is both an art and a skill. It takes clarity, strategy, and sometimes the outside perspective of a specialist.
You are not alone. Every business owner — no matter their stage or level of success — has wrestled with offers. So don’t hide behind your computer. Seek support, ask questions, and find the solutions you need.
This is exactly why I created the OfferMojo Squad. It’s the only AI-powered, end-to-end system that covers the entire offer process — from strategy to sales. It’s cost-efficient, designed for DIY entrepreneurs, and delivers both high-level strategy and soulful support.
And here’s the best part: if you ever get stuck, I’m still here. Real human guidance is always available alongside the Squad.
The waitlist for the OfferMojo Squad closes on September 28th. It’s the only way to receive beta access — and 50% off.
So if you’ve been struggling with your offers — if you’re tired of second-guessing and ready to finally build an ecosystem that works — now is your time.
Because the truth is this: your offers are the heartbeat of your business and the ticket to growing revenue and impact.
Take the step. Join the waitlist. And let’s build offers that don’t just sell, but sustain you.
Lori Young is a certified business coach and offer strategist who helps coaches, wellness pros and soulful subject matter experts build clear, aligned offers that sell sustainably. With 20+ years spanning corporate marketing and entrepreneurship, she blends soul-led insight with practical strategy to turn scattered ideas into clean, compelling ecosystems. She’s the creator of the OfferMojo Squad—an AI-powered, end-to-end system that guides founders from offer strategy to sales with clarity and confidence.
