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Small Business Survival Guide

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.

Woman business owner reviewing floor plan documents on desk

The Five Risk Zones Every Entrepreneur Must Watch

Think of these as your business dashboard. Monitoring these five risk zones allows you to spot warning signs early and stay on the growth path.

1.Market Fit

Even great offerings lose traction when client needs evolve.

Ask yourself:

Has my target market changed since I launched?
Do my current services still solve the correct problems?
Which clients or industries deliver the highest ROI?

Strong market fit comes from curiosity. Interview your clients, ask for feedback, and adapt before competitors do.

2. Cash Flow

Cash flow is the heartbeat of your business. Without it, even high revenue can’t sustain operations.

If things feel tight, review your expenses from the last 60 days. Cancel non-essential subscriptions. Negotiate vendor contracts. Ask your most loyal clients for introductions to others they care about, so that you can explore ways to help them, too.

Cash is oxygen. Monitor it daily, not monthly.

3. Team & Leadership

Whether you lead one assistant or a whole team, leadership determines your capacity to succeed.

Are you delegating effectively? Providing clear goals and feedback?

As a Business Coach, I often see owners stuck doing $30/hour tasks while neglecting $300/hour strategy work. Effective delegation frees you to focus on leadership and growth.

4. Business Model

Is your business scalable, or does it depend entirely on you?

If every sale relies on your direct involvement, growth will eventually plateau.

Revisit your offerings. Identify your most profitable services that align with your Pinnacle Gift™; the work that you do best and that has the greatest impact. Then systematize the rest.

That’s how small business owners move from self-employment to true entrepreneurship.

5. Marketing Visibility & Adaptability

Even a strong business can fade into obscurity. Visibility is your brand’s lifeline.

If your marketing has gone quiet, it’s time to re-engage:

Ask three loyal clients for testimonials and introductions to others you can help.
Share one genuine story of growth or challenge from this year.
Highlight the results your clients have achieved. Authenticity builds credibility.

Consistent visibility builds trust and opportunity.

Group of young business professionals smiling and shaking hands

The Success Boosting Prevention Check

Don’t wait until January to assess your business health.

Take your Success Boosting Prevention Check now. It's a simple five-minute self-audit that reveals where you should focus before year-end.

Rate yourself from 1 (struggling) to 5 (strong) in each risk zone:

Market Fit
Cash Flow
Team & Leadership
Business Model
Marketing Visibility

Then, choose one area to focus on strengthening over the next six weeks.

This week: Take one concrete step.

Next week: Take another!

If cash flow is your weak spot, review your expenses today and trim the unnecessary costs.

If marketing is lagging, reconnect with past clients and ask for referrals.

Momentum is built one decisive action at a time.

This simple exercise, repeated quarterly, is how small business owners stay proactive instead of reactive.

What Successful Founders Do Differently

After years of Executive Coaching, one pattern stands out:

The founders who thrive beyond year three are those who intentionally step out of the day-to-day to work on their business.

They build success by design.

Here’s how they lead differently:

Track progress weekly, not yearly.
Review key metrics, including revenue, leads, and margins, every week to identify trends early.
Delegate tasks that drain energy.
View delegation not as an expense, but as a growth strategy.
Align every decision with their Pinnacle Gift™.
Focus on the work that makes the most significant difference and build systems for everything else.
Build repeatable processes.
Templates, checklists, and automation create consistency and scalability.
Reflect and reset regularly.

Quarterly or year-end reviews give them clarity, confidence, and direction.

These aren’t massive changes; they’re habits. Small, consistent shifts compound into significant growth.

That’s where leadership maturity emerges, and where Executive Leadership Coaching often has its most significant impact: helping founders lead with calm confidence instead of constant urgency.

Summary: Turn Reflection into Momentum

The final six weeks of the year are your best opportunity to design a stronger 2026. The economy will continue to move forward, but you can step into it with renewed clarity and strategic intent.

Start with your Success Boosting Prevention Check.

Know your numbers. Know your risk zones. Know where to focus next.

Six Week Success Sprint

And if you’re ready to move from reflection to results, the Six Week Success Sprint is designed for precisely this season.

In this focused, results-driven coaching sprint, you’ll:

Choose one high-impact initiative (revenue, delegation, or systems)
Complete a 90-minute strategy session to design your plan
Meet weekly for accountability and support
Finish with clarity, measurable progress, and momentum

The Six Week Sprint isn’t about adding more to your plate; it’s about removing what’s in the way of growth.

If you’re a small business owner or executive ready to step into 2026 with confidence and structure, this program is your starting line.

Because small business success isn’t luck: it’s clarity, strategy, structure, and execution.

And the best time to begin is now.

Businessman holding target with an arrow in the bullseye.

Book time with me here

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5 Steps to Reclaim Your Time and Build Lasting Business Success

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.

How to Transform Your Freelance Business to CEO Success and Reclaim Your Freedom

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.

Why 93% of Successful Business Owners Actually Embrace Innovation Before the Competition

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.

Why Successful Business Owners Love Our New Success Accelerator Program

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?

Navigating Change: How Resilient Businesses Stay Ahead in 2025

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.

Quarterly Power Moves: How to Review, Reset, and Reignite Your Business in Q2

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.

Scaling Your Business: When and How to Expand for Next Level Success

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.

Time Management Strategies for Business Owners That Absolutely Move the Needle

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?

Achieve Your Top Business Goals in 2025: A Guide to Success

By Kathleen Winsor-Games • January 29, 2025

As small business owners, we know the power of setting clear, actionable goals to drive success. Whether it’s boosting revenue, growing your team, enhancing customer experience, or innovating your products, every step brings you closer to realizing your vision. Let’s dive into how you can define, align, and achieve your 2025 goals with clarity and purpose. 1. What’s Your Top Business Goal for the Year? Every business journey begins with a clear goal. What’s your primary focus for 2025? Is it to increase revenue, expand your team, enhance marketing efforts, or streamline operations? Reflecting on these priorities helps you create a roadmap for success. Start by identifying the most pressing needs of your business and your aspirations for the year ahead. These priorities can provide clarity and direction for the decisions you’ll make. If you’re not sure where to start, consider breaking it down into categories: Increase revenue or profitability Expand your team or build leadership capacity Enhance marketing or customer engagement Innovate your products/services or streamline operations By identifying your focus, you’ll inspire and motivate yourself and your team to achieve great things this year. Remember, clarity is the foundation of progress.

Start 2025 Right: Do This One Surprising, Proven Thing Instead of Resolutions

By Kathleen Winsor-Games • December 23, 2024

After navigating the challenges and demands of 2024, many entrepreneurs and small business owners are feeling burned out by the idea of New Year’s resolutions. You’re not alone. Resolutions often fail because they’re vague, fleeting, and disconnected from what matters most. Instead of resolutions, I encourage you to adopt a proven strategy: set values-based goals that align with your Pinnacle Gift™—your unique talent and purpose. At Capstone Coaching Group, I guide entrepreneurs through the Pinnacle Success System, helping them clarify their gifts and use that clarity to set powerful, actionable goals. The result? Greater momentum, more fulfillment, and measurable success. Why Values-Based Goals Work According to a Harvard Business Study, only 3% of MBA graduates wrote down clear, actionable goals. Those individuals earned 10 times as much as the other 97% combined. Goals succeed where resolutions fail because they are intentional and specific. When grounded in your core values and purpose, they also build resiliency—a must-have for business owners facing today’s uncertainty. Clayton Christensen, renowned author and consultant, once said that committing to a goal 100% is easier than 98% commitment. Why? Because 100% eliminates decision fatigue. Once you’ve fully committed to a meaningful goal, setbacks won’t derail you. You’ve already decided to stay the course.