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How to Go Beyond Your “Why” and Capitalize on Your Pinnacle Gift™ in 2026

Kathleen Winsor-Games • January 16, 2026


People often ask, “What’s your why?” It’s a fair question, and an important one.


But I ask something different:
What is your Pinnacle Gift™?


Your
why matters. Purpose matters. Values matter. I learned the hard way, though, that purpose without clarity can still lead to burnout.


Unless your why is paired with your Pinnacle Gift (the unique, high-value work only
you are meant to do) you can stall, even when you’re deeply committed to meaningful work.


What Do I Mean by Pinnacle Gift™?

Your Pinnacle Gift goes beyond strengths, skills, or even “unique genius.” It’s why you are on the planet. It’s the work that:

  • Comes most naturally to you and gives you energy.
  • Creates the greatest impact for others.
  • Generates the highest value.
  • And feels most aligned with who you are.


It’s the intersection of contribution, clarity, and confidence. And discovering it changes everything.


I Had to Learn This the Hard Way

Before I ever helped others through the maze of entrepreneurship, I had to navigate it myself. When I launched my first coaching practice, I felt that familiar rush of possibility, and then, shortly after, the wave of overwhelm.


On the surface, things were going well. Clients were coming in. Momentum was building. Ironically, that’s when the pressure really hit.


I had entered that universal phase of business ownership:
You don’t know what you don’t know.

And in business, what you don’t know can cost you time, money, confidence, and sometimes the business itself.


I made mistakes not because I wasn’t capable, but because I didn’t yet have the clarity or structure I needed. I was working hard, just not always wisely. To make things worse, I carried a quiet belief that I
should be able to do it all.

Marketing. Operations. Sales. Finances. Strategy. Delivery. I thought that being a business owner meant being self-sufficient in every area. That belief was exhausting and heavy.


The Shift That Changed Everything

Everything began to change when I clarified my Pinnacle Gift™,   the specific, high-value work that only I could do, and paired it with the Pinnacle Productivity™ process.


For the first time, I clearly understood:

  • What I should personally focus on.
  • What I needed to offload.
  • What could be delegated.
  • And where support would multiply my results instead of diminishing my value.


I also saw something uncomfortable, but important. In my overwhelm and effort to do it all, I was unintentionally
commoditizing my coaching practice.


My energy was depleted. My message sounded like everyone else’s. I had lost sight of what made my work truly different.


And here’s the truth I learned the hard way:

Asking for help isn’t a weakness. It’s essential to lasting success.


Once I embraced support as a strength and built my business around my Pinnacle Gift, everything shifted. The business grew, but more importantly, it became sustainable and aligned.


That experience became a core reason I coach today: To help others avoid the costly, heartbreaking lessons I had to learn by running into every wall myself.


The Pattern I See Over and Over (You May Recognize This)

Nearly every entrepreneur I work with has walked some version of this path:

  1. The Energy Phase: Excitement, creativity, and belief.
  2. The “Oh Wow, This Is a Lot” Phase: Realizing that being good at your craft isn’t enough.
  3. The “I’ll Just Work Harder” Phase: The trap. More effort without better structure.
  4. Decision Fatigue: Hundreds of choices, little context.
  5. Isolation: Feeling alone, even when support exists.
  6. Doubt: Wondering if you’re really cut out for this.
  7. The Fork-in-the-Road Moment: Do you build sustainably, or retreat to “safety”?


I’ve watched too many capable, values-driven people choose the latter, not because they lacked talent, but because they lacked clarity, tools, and support.


The Myth of “Safety” in a Full-Time Job

Let’s pause here.


Many entrepreneurs return to a job believing they’re choosing safety. Yet later, I hear:

“I miss building.” “I miss dreaming.” “I miss the freedom.”


A job may
seem to offer predictability, but for entrepreneurial thinkers, predictability without fulfillment becomes its own form of discomfort. Once you know you’re meant to build something meaningful, you can’t unknow it.


People trade possibility for predictability but lose fulfillment in the process. Watching that happen, watching potential go untapped, is a powerful reason I became a coach.


Entrepreneurship Shouldn’t Be a Guessing Game

People don’t fail because they lack passion. They struggle because they lack:

  • Clear priorities.
  • A working strategy.
  • Repeatable structure.
  • Perspective and support.
  • Accountability.
  • Confidence in their direction.


That’s why my work blends strategy, structure, values, emotional intelligence, and leadership.

Business owners don’t need more hustle. They need more clarity. More alignment. More support.


Success by Design, Not by Accident

My mission isn’t to motivate people with clichés or push them toward burnout.


My mission is simple:

To help small business owners build success by design, not by accident. To help them see the gifts they can’t see on their own. To help them stop trying to do everything alone and start leading with clarity and confidence.


When business owners define and articulate their
Pinnacle Gift™, everything changes.

·         They move away from commodity.

·         They move toward uniqueness.

·         They build businesses that are aligned, sustainable, and deeply fulfilling.


That journey begins with clarity.


As we look ahead to 2026, I want to invite you to pause before setting another round of goals.

Before you work harder. Before you commit to another strategy. Before you try to “do more.”

Get clear.


On January 23, 2026, I’m hosting an in-person Pinnacle Gift™ course designed to help you identify, articulate, and fully step into the high-value work only you are meant to do.


This isn’t about motivation or surface-level strengths.

It’s about uncovering the work that:

·         Gives you energy

·         Creates the greatest impact

·         Aligns with your values

·         Moves you out of commodity and into uniqueness

·         And gives you a clear lens for decisions, delegation, and growth


Every participant leaves with a clear, unique Pinnacle Gift Statement, and, more importantly, the confidence to build their business around it.


If you’re feeling the pull to build more intentionally in 2026, to work smarter, not harder, this may be the most valuable first step you take.


Give yourself the gift of clarity. It changes everything.


👉 Details and registration information are available here:

Learn more and register here.
By Kathleen Winsor-Games December 4, 2025
Here’s something I don’t talk about often. When I first became a Business Coach, I was the classic overwhelmed business owner. You know the one: trying to do all the things, all at once, all by myself. From the outside, it looked like everything was working. Clients were showing up, referrals were coming in, and my calendar was full. On paper, it was the kind of momentum new business owners dream about. But momentum without structure is a dangerous combination. And behind the scenes, I was running myself into the ground. I was drowning in decisions, working far too many hours, and living squarely in that phase every entrepreneur knows but doesn’t often admit: the “you don’t know what you don’t know” stage. It’s humbling, stressful, and, if left unchecked, it becomes a breeding ground for burnout. Looking back, I can see exactly what was happening. I was operating purely out of effort, not clarity. I was filling every gap in the business simply because it needed doing. And I was carrying the weight of every single role because I believed I should be able to. Let me repeat that: I believed I should be able to . This wasn’t a capability issue. It wasn’t a lack of intelligence or commitment. It was a mindset trap; one that many small business owners, leaders, and managers fall into without even noticing. As a Small Business Coach, I see this constantly today: capable professionals who confuse responsibility with self-reliance. We assume strong leaders “figure everything out.” We convince ourselves that asking for help signals weakness, when in reality, it signals self-awareness, maturity, and strategic discipline. I wish someone had told me that sooner. Instead, I learned the lessons the hard way, so my clients don’t have to.
By Kathleen Winsor-Games November 10, 2025
The Real Odds (and How to Redefine Them) The statistics can be sobering for small business owners. One in five small businesses doesn’t make it past its first year. By year three, nearly 40% have closed their doors. By year five, about half have failed. Yet most of these businesses didn’t collapse because their owners lacked skill, drive, or passion. They failed because no one showed them how to build success by design, not by accident. As a Business Coach and Executive Leadership Coach, I’ve seen this pattern repeatedly. Every entrepreneur begins with a spark; an exciting vision of freedom, growth, and a sense of purpose. But maintaining that momentum requires more than determination. It requires clarity, structure, and strategic focus. True success in the first three years depends on five essential pillars: A clear market need for your product or service. Healthy cash flow and margin awareness. A business model that can scale sustainably. The right team or partners to share the load. Consistent marketing visibility to attract your ideal clients. When even one of these weakens, cracks appear. Left unaddressed, those cracks can threaten everything you’ve built. The good news is that you can fix them, starting now. November is the ideal month to “failure-proof” your business for 2026 while you still have time to act strategically. Why Businesses Fail and How to Stay Standing Businesses rarely fail overnight. Decline begins quietly; a missed review, a delayed decision, a loss of focus amid busyness. The owners are working hard, but not necessarily on the right things. What separates those who thrive from those who falter is perspective. The most successful entrepreneurs know when to pause, step back, and evaluate objectively. They invest time in reflection, and when necessary, reach out for Executive Coaching or Small Business Coaching to gain outside insight. The goal isn’t perfection; it’s awareness. Once you clearly identify the risks, you can adjust your course before minor issues become major setbacks.
By Kathleen Winsor-Games August 29, 2025
If your business feels like it’s running in place, it’s not because you aren’t working hard enough. In fact, let’s be honest—you’re probably working too hard. The real problem? You’re stuck in the same gear, mistaking “busyness for progress.” Plateaus are normal in business. Staying there is optional. The difference between stagnation and breakthrough growth isn’t more hustle. It’s knowing when and how to pivot. Here’s the truth: working harder on the wrong things wears you out faster. Working smarter on the right things changes everything. That’s why in the Pinnacle Success System™, we start with clarity—aligning your business with your Pinnacle Gift™—and then focus relentlessly on high-impact actions. It’s not about doing everything. It’s about doing the right things and creating space to lead, innovate, and grow. Step One: Audit Your Time for Growth The simplest way to begin is by running a quick micro time audit. For one workday, jot down everything you do—every meeting, email, client call, or errand. At the end of the day, put a star next to anything that directly drives revenue or long-term growth. Those are your high-value activities. Circle the rest. That’s your low-value zone, the territory ripe for delegation, automation, or elimination. As a bonus, take note of which high-value activities actually energize you. These are clues to your Pinnacle Gift, the unique zone where you create the most significant impact. Scaling your business isn’t about grinding harder. It’s about shifting into growth mode by leveraging your strengths, refining your focus, and building systems that free you up to lead. This brings us to the second trap that holds back too many small business owners.
By Kathleen Winsor-Games July 25, 2025
If my July social media posts had a theme, it was this: Stop running your business like a one-person rescue mission. All month long, we explored one of the most powerful and overdue shifts a small business owner can make—moving from scrappy, overworked solopreneur to confident, strategic CEO. It’s a shift that unlocks growth, sanity, and sustainability—but only if you're willing to do the deep (and often uncomfortable) work. Let’s walk through the key lessons from this transformation, one powerful step at a time. 7 Signs You're Ready to Level Up Still calling yourself a freelancer? It might be time for an upgrade. There’s a big difference between being self-employed and being a business owner. One trades time for money. The other builds something that can grow without you. Here are seven signs you’re ready for the shift: Your calendar is full, but your income has plateaued You’re constantly putting out fires instead of planning ahead You dream about taking a vacation… but can’t unplug You’ve hit the limit of what you can do alone You’re attracting more opportunities than you can handle You’re doing high-level work and low-level tasks—daily You know there’s a bigger vision for your business… but you’re stuck in the weeds If even two of these hit home? You’re not just ready—you’re overdue for a change. Let’s talk about how to make that leap.
By Kathleen Winsor-Games June 30, 2025
Innovation Isn’t Optional Anymore Staying the same is a risk. After guiding business owners through multiple economic downturns, I’ve learned that innovation isn’t about flair or flash. It’s about survival—and relevance. Here’s the truth: What worked last year might stall this year. But here’s the good news—innovation doesn’t require a Silicon Valley budget. Sometimes, it’s as simple as improving your onboarding process, rethinking how you re-engage past clients, or packaging your expertise in a more scalable way. Start here: Choose one area—your offer, your delivery, or your customer experience. Then ask: What’s one experiment I can run this quarter? Small shifts often spark big momentum. Innovation Starts with You The best innovations don’t come from mimicking others. They come from alignment with what you do best. When you’re grounded in your Pinnacle Gift™—your unique brilliance—creativity flows naturally. If you’re forcing innovation, check your energy first. Review your calendar: What drains you? What lights you up? Double down on what energizes you. Let go—or delegate—the rest.  When your energy aligns with your genius, innovation becomes your natural next step.
By Kathleen Winsor-Games June 19, 2025
Because growth shouldn’t be a guessing game. At Capstone Coaching Group, we’ve spent years working closely with small business owners, supporting them through the highs, the lows, and the in-between moments when it’s not quite clear what the next move should be. Along the way, we started noticing a pattern. Clients who worked with us one-on-one consistently told us that coaching gave them something they hadn’t found anywhere else: clarity, accountability, and forward momentum . They left each session with a renewed sense of purpose and direction. Meanwhile, business owners who joined our Peer Advisory Boards found something equally powerful: a confidential community of fellow entrepreneurs. Here, they could solve real problems, speak openly, and feel supported—not judged. The feedback was clear. These collaborative boards were a game-changer, providing a much-needed relief from the isolation that often comes with entrepreneurship. Others went through our Pinnacle Success System™ courses, discovering their Pinnacle Gift™, learning how to structure their time and achieve Pinnacle Productivity™, designing their Pinnacle Offering™, and scaling their business by crafting their Pinnacle Process™. Every course led to breakthroughs. But then something bigger happened. Clients who engaged in all three—coaching, peer advisory boards, and the Pinnacle Success System™—saw exponential progress. The combination created a synergy that accelerated their growth far beyond what any single element could do alone. And just like that, the idea sparked: What if we built a program that delivered the whole experience—strategic coaching, powerful community, proven tools—under one roof?
By Kathleen Winsor-Games May 30, 2025
In today’s turbulent economy, one thing is crystal clear: standing still is not a strategy. Markets are shifting. Customer needs are evolving. Competition is fiercer than ever. If you’re a small business owner, reacting to change isn’t enough anymore—you need to lead it. Adaptability is no longer optional. It's the price of entry into a future where only the most resilient businesses thrive. Those business owners who anticipate and plan for change will stay in the game. Those who don't may find themselves outpaced, outperformed, or out of business. So how do you prepare for what's next without burning out or blowing up your business model? Let’s take a deeper look at what it takes to not only survive change—but use it as a competitive advantage. Adaptability as a Strategic Advantage Proactive change management is quickly becoming one of the most important business skills of our time. It’s not enough to be great at what you do—you must also be great at evolving when the market demands it. Ask yourself: How quickly can your team pivot when the unexpected hits? Do your systems empower change—or strangle it? Are you building a brand that stands out when others are shrinking back? Now is the time to review, refine, and rebuild with resilience at the core. Choose one process, product, or service this week and stress-test it: If the market shifted tomorrow, would this still work—or would we scramble? Small adjustments today can prevent big regrets tomorrow.
By Kathleen Winsor-Games April 30, 2025
The first quarter is behind you. But before you charge into Q2 full speed, let me offer this: pause with purpose. In the daily whirlwind of small business ownership, it’s easy to stay busy but miss the bigger picture. That’s where a strategic quarterly review comes in—not as a judgment session, but as a tool for clarity and course correction. Ask yourself: What did I plan? What actually happened? And most importantly—what do I need to shift now to move forward with greater focus, alignment, and momentum? In this article, we’ll walk through five critical areas every small business owner should assess at the close of Q1—financials, marketing, team, time, and tools. Use this as your reset ritual. You’ll come out sharper, stronger, and more prepared to lead the next 90 days with intention. Financials First—Are You on Track? Revenue, profit, and cash flow are the pulse of your business. That’s why we begin here. Start your Q1 review by looking at the numbers—not just how much you made, but what you kept, and how well your money moved. Even if you’re not a finance pro (I’m certainly not a CPA, nor do I play one on TV 😊), understanding your numbers is a non-negotiable leadership skill. Ask yourself: What was your gross revenue vs. net profit? Are your expenses aligned with your growth goals—or eating into margins? What do your receivables and payables say about your cash flow health? If the numbers aren’t telling a clear story, it’s time to clean them up. Don’t wait for tax season to find out where your profits went. Financial clarity builds confident decision-making—and that’s the foundation for a strong Q2.
By Kathleen Winsor-Games March 30, 2025
The Scaling Dilemma—Are You Ready to Expand? Scaling a business is exciting—but also nerve-wracking. You’ve worked hard to build momentum, and now you’re wondering: Is it time to grow? And if so, how do I do it without losing what’s already working? Many business owners hit a point where they’re turning down opportunities, struggling to keep up with demand, or sensing that their current model can’t take them further. Growth isn’t just about more revenue—it’s about building capacity with intention. Signs You’re Ready to Scale: You’re regularly turning down work because your plate is full. Clients are asking for additional services or support. Your systems (and maybe your sanity) are straining under the current load. If any of these sound familiar, you're likely at a crossroads. The good news? With the right strategy, scaling can actually bring more ease, not just more work. Let’s explore how to grow your business wisely—without burning out or getting overwhelmed. Hiring vs. Outsourcing—Which One Fits Your Growth Plan? One of the first decisions you’ll face is whether to bring on help—and if so, what kind. Hiring an employee may feel like a big leap. But so is continuing to do everything yourself. The key is understanding what kind of support will move the needle without bogging you down. Hire when: The role is critical to your core business operations. You need someone consistently and long-term. You want to build a cohesive team with shared values and vision. Outsource when: The task isn’t in your Pinnacle Gift™—your zone of genius—and doesn’t need to be done in-house. You need short-term or specialized expertise. You want to test a role before committing to a full-time hire. Think of hiring as building your foundation—and outsourcing as adding flexible scaffolding. Both support growth, but in different ways. 
By Kathleen Winsor-Games February 25, 2025
Rethinking Time What do we currently believe about Time? Let’s start by challenging common assumptions. Many of us treat time as though it’s equal—60 minutes of one activity must be as valuable as 60 minutes of another, right? Wrong. Truth bomb: All time is not equal. Some activities deliver exponentially more results, earnings, or success than others. Actionable Item: Perform a time audit this week. Track every activity you do for three days and categorize tasks as high, medium, or low impact. Use this data to identify which activities you can eliminate, delegate, or prioritize. As business owners, the secret lies in prioritizing the right activities. Imagine dedicating 20% of your time to high-impact tasks that generate 80% of your results. That’s the power of the Pareto Principle in action. In future blog posts, we’ll explore how to measure time against productivity and introduce strategies to amplify your effectiveness. Stay tuned for more on Pinnacle Productivity TM ! Time vs. Productivity All activities are not created equal. You’ve heard it before: “Work smarter, not harder.” But what does that actually mean? At Capstone Coaching Group, we emphasize a critical distinction: Time ≠ Productivity. Naturally, spending 8 hours on busy work won’t match the impact of 2 focused hours on strategic decision-making or relationship-building. What’s more, the good ole American standard of doing “more, better, faster” will likely get you marginal change in your results, plus longer workdays (and longer workweeks) . . . and is a sure path to burnout. Instead, ask yourself: Which tasks contribute directly to your long-term goals? Are you spending too much time on low-value activities? Pro tip: Start tracking your tasks for a week. Identify what generates the most meaningful results, then focus your efforts there. Small shifts in how you allocate your time can drive massive results. What’s one activity you plan to prioritize this week?