Decision Season Begins: Why September is the Perfect Time to Start Your Exit Planning Journey

Decision Season Begins: Why September is Perfect for Exit Planning

There’s something about September that makes business owners start asking the big questions.

Maybe it’s the shift from summer’s relaxed pace to fall’s focused energy. Maybe it’s the approaching year-end that creates natural reflection. Or maybe it’s just that back-to-school feeling that makes us think about new beginnings and fresh starts.

Whatever the reason, September consistently marks the beginning of what I call “Decision Season” for business owners across Texas and beyond.

The September Shift: From Summer Thinking to Strategic Planning

After nine years of helping business owners navigate their exits, I’ve noticed a clear pattern. September is when the phone starts ringing more frequently. It’s when business owners who have been “thinking about it” for months (or years) finally decide to get serious about understanding their options.

The conversations usually start the same way:

“I’ve been thinking about this for a while, but I don’t know where to begin.”

“I’m not ready to sell tomorrow, but I want to understand what I’m working with.”

“My CPA mentioned I should start thinking about exit planning. What does that actually mean?”

Sound familiar? If you’re reading this in September 2025, you’re probably having similar thoughts.

Why September is Strategic Timing for Exit Planning

There are practical reasons why September is the perfect time to begin your exit planning journey:

1. Q4 Financial Clarity

By September, you have a clear picture of your year-to-date performance. You can see trends, identify strengths, and spot areas that need attention before year-end. This financial clarity is essential for accurate business valuation.

2. Tax Planning Opportunities

Starting your exit planning assessment in September gives you and your CPA time to implement tax strategies before December 31st. Whether you’re planning to sell next year or in five years, optimizing your current tax position strengthens your eventual exit.

3. Buyer Activity Cycles

The M&A market follows predictable patterns. Buyers are most active in Q4 and Q1, making fall the ideal time to begin preparation if you’re considering a sale in the next 12-24 months.

4. Natural Planning Season

September feels like a natural time for strategic planning. It’s when budgets get finalized, goals get set, and long-term decisions get made. Your exit planning fits naturally into this rhythm.

5. Time for Thoughtful Preparation

Starting in September gives you the full fall and winter to prepare thoughtfully rather than reactively. You can address weaknesses, strengthen systems, and position your business optimally—all without the pressure of an immediate timeline.

The Cost of Waiting: Why “Someday” Becomes “Never”

Here’s what I’ve learned from working with hundreds of business owners: The ones who achieve their ideal exit outcomes are the ones who start preparing 2-3 years before they’re ready to sell.

They don’t wait until they’re “ready to go.” They get ready while they’re still building.

The business owners who wait until they’re emotionally ready to sell often find themselves in reactive mode. They’re dealing with:

Rushed preparation that leaves money on the table
Limited buyer options due to poor timing
Stress and anxiety from uncertainty
Suboptimal deal structures because they lack leverage

But the owners who start their exit planning journey in “Decision Season”? They have time to:

Clean up financial records systematically
Build management depth and reduce owner dependency
Optimize operations for maximum value
Develop relationships with potential buyers
Structure deals that meet their personal and financial goals

What “Decision Season” Really Means

Decision Season isn’t about deciding to sell immediately. It’s about deciding to get clarity on your options.

It’s the difference between wondering “What if?” and knowing “What’s possible.”

When you complete a comprehensive exit planning assessment, you gain:

Financial Clarity: What is your business actually worth in today’s market? Not a guess or a multiple you found online—a real assessment based on your specific business, industry, and market conditions.

Readiness Assessment: How prepared is your business for a potential sale? What are your strengths, and what areas need attention?

Timeline Guidance: Based on your goals and current readiness, what’s a realistic timeline for your exit? What preparation steps should you prioritize?

Option Awareness: What exit strategies make sense for your situation? Sale to a strategic buyer? Financial buyer? Management buyout? Family succession? Each path requires different preparation.

Confidence Building: Perhaps most importantly, you gain the confidence that comes from having a plan instead of just hopes.

The September Assessment Advantage

Business owners who complete their exit planning assessment in September position themselves for success regardless of their timeline:

For 2026 Exits: You have 12+ months to address any preparation gaps and position your business optimally.

For 2027-2028 Exits: You have time to implement systematic improvements that can significantly increase your business value.

For Long-term Planning: You establish a baseline and can track progress over time, making strategic decisions with your eventual exit in mind.

Real Stories from Decision Season

Let me share two recent examples that illustrate the power of September decision-making:

Sarah’s Story: Sarah owned a successful landscaping company in Austin. She completed her exit planning assessment in September 2023, thinking she might sell “someday.” The assessment revealed her business was worth more than she expected, but also highlighted some owner dependency issues. She spent 18 months systematically addressing these issues. When an unexpected buyer approached in early 2025, she was prepared. The result? A sale at 15% above her original assessment value.

Mike’s Journey: Mike ran an HVAC company in Dallas. His September 2024 assessment showed strong value but messy financials. Instead of rushing to market, he spent six months cleaning up his books and documenting processes. By spring 2025, he had multiple buyer offers and the leverage to negotiate terms that met both his financial and personal goals.

Both Sarah and Mike started their journeys during Decision Season. Both achieved outcomes that exceeded their expectations because they had time to prepare strategically.

Your September Action Plan

If you’re feeling that familiar September urge to get clarity on your exit options, here’s your action plan:

Week 1: Complete Your Assessment

Start with our comprehensive exit planning assessment. It takes 15-20 minutes to complete and provides immediate insights into your business value and readiness. You’ll receive detailed results within 24-48 hours.

Week 2: Review with Key Advisors

Share your assessment results with your CPA, attorney, or other trusted advisors. Get their perspective on the findings and recommendations.

Week 3: Identify Priorities

Based on your assessment, identify the top 3 areas that would most impact your business value or exit readiness. These become your focus areas for the coming months.

Week 4: Create Your Timeline

Develop a realistic timeline for your preparation activities. Whether you’re planning to exit in 18 months or 5 years, having a timeline creates accountability and momentum.

The Questions That Start Everything

As September 2025 begins, ask yourself these questions:

If I couldn’t work in my business for 30 days, what would break first?
Do I know what my business is actually worth in today’s market?
What would need to change for my business to be attractive to buyers?
What are my personal and financial goals for my eventual exit?
Who should be on my exit planning team?

If you don’t have clear answers to these questions, you’re not alone. Most business owners don’t—until they decide to get clarity.

Decision Season is Here

September 2025 marks the beginning of another Decision Season. The question isn’t whether you’ll eventually exit your business—every business owner does, one way or another. The question is whether you’ll be prepared when that time comes.

The business owners who achieve their ideal outcomes are the ones who start preparing during Decision Season, not during crisis season.

They get clarity while they have options, not when they’re out of time.

They build value systematically, not frantically.

They create the exit they want instead of accepting the exit they get.

Your Decision Season starts now. What will you decide?

Ready to Begin Your Exit Planning Journey?

If you’re feeling that September urge to get clarity on your options, we’re here to help. Our comprehensive exit planning assessment provides the insights you need to make informed decisions about your business future.

Take the first step: Complete your confidential exit planning assessment today. It takes 15-20 minutes, provides immediate insights, and includes a detailed review within 24-48 hours.

Start Your Assessment →

Questions about the assessment or exit planning process? Contact Joshua Carnes directly at Lion Business Advisors. We’ve helped hundreds of Texas business owners navigate their exit planning journey with confidence and success.