By December, they're exhausted, their teams are burned out, and January 1st arrives with no real plan in place - just good intentions and a growing pile of "we should have done this months ago."
Running my own tech firm taught me that September is the best time to set up Q4 success and build the foundation for next year's growth.
When I work with Ready Founders™, September is when we lock in their annual planning systems. Wait until "after the holidays," and you've already lost the game.
September brings back-to-school energy - the perfect mindset for getting serious about business fundamentals that will carry you through the final quarter and into next year.
You cannot wait until year-end to do your annual planning. Life happens. You want to be with your family during the holidays. Your team wants time off. Everyone's mentally checked out by mid-December.
Founders who dominate Q4? They use September to handle all the planning so October through December can be pure execution.
September is the ideal time to make meaningful tax adjustments for this year. By December 1st, most tax-saving strategies are off the table.
Review your tax liability projections now. Look at your entity structure - are you set up optimally? Check your compensation strategy. Are you missing R&D credits or other opportunities?
Review our tax planning guide to understand your options. If you discover you need to make changes, you have time to implement them. Wait until December, and you're stuck with whatever situation you've created.
Where do you stand against your budget for the year? What do you need to accomplish in Q4 to hit your goals?
This goes beyond revenue. Look at your cost structure, cash flow projections, hiring plans. If you're behind budget, what can realistically be saved? If you're ahead, how do you maintain momentum?
Create a realistic Q4 execution plan based on what's achievable, not what you hoped would happen back in January. Effective cash flow forecasting requires clean financial data and reliable systems to track it.
September is the perfect time to evaluate your business infrastructure before the new year:
Payroll and Benefits: If you need to change payroll providers, benefits administrators, or PEO relationships, January 1st is the clean transition date. Make these decisions now so your team gets a single W-2 with clean tax calculations. A solid payroll system builds trust with your team and ensures accurate financial records.
Management Systems: Are you using EOS, Scaling Up, or another operating system? September is when you recommit to the frameworks that will guide next year's growth. Align your financial fundamentals with your business systems for operational consistency.
Software and Tools: What's working? What's not? Plan your technology changes for January implementation. When reviewing your financial accounting infrastructure, ensure it matches your current growth stage.
I learned this lesson the hard way in my tech business. We switched payroll providers once mid-year. The result? Every team member got two W-2s, tax calculations were a mess, and our accountant spent weeks cleaning up what should have been a simple transition. Never again.
During September planning, ask yourself: What framework are you using to manage and understand your business?
Many founders wing it. They make decisions based on gut feelings, react to whatever crisis appears, and hope things work out. Ready Founders™ take a different approach.
They use proven frameworks for:
Customer Development: Are you following the lean startup methodology, business model canvas, or another systematic approach to validate and grow your business?
Financial Management: Do you have systems for cash flow forecasting, profitability analysis, and capital planning? Build your financial infrastructure with the right tools and guidance.
Operational Excellence: Whether it's EOS, Scaling Up, or another system, how are you creating predictable growth? Accurate financial data powers every effective operating system.
What I've noticed: Founders who follow frameworks consistently outperform those who don't. The framework provides discipline, accountability, and a roadmap for making decisions under pressure.
For veteran founders in defense and technology - my focus area - September planning carries even more weight. Government fiscal years end in September. Contract cycles are shifting. Security clearance requirements are changing.
Defense contractors who thrive know that Q4 sets up next year's opportunities. I've watched clients use September to review their compliance systems, assess their clearance needs, and ensure their financial house can withstand the intense scrutiny that comes with government contracts.
September is when you audit your US persons-only requirements, review your cybersecurity protocols, and make sure your financial systems can handle the complexity of government contracting. For defense contractors, strong financial fundamentals and compliance practices are non-negotiable.
The difference between founders who struggle and those who thrive:
Struggling founders spend December trying to plan for next year while closing Q4, dealing with holiday schedules, and managing family time. They start January behind and spend the first quarter catching up.
Ready Founders™ handle all their annual planning in September. October through December become pure execution months. They finish Q4 strong because they're not distracted by planning. January 1st arrives with clear goals, defined systems, momentum already building.
Complete your tax planning review by October 1st - Work with your accounting team to identify any final opportunities for this year. Maximize tax opportunities before the year closes.
Finalize your Q4 execution plan - Based on real numbers, not wishful thinking. Strong cash flow management requires knowing your numbers inside and out.
Audit your business systems - Payroll, benefits, management frameworks, technology. Plan any changes for January 1st implementation.
Document your frameworks - What systems are you using for customer development, financial management, and operations? If you don't have frameworks, choose them now.
Set your 2024 budget and goals - Complete, realistic planning for next year so January can focus on execution. Financial accounting fundamentals ensure your budget is built on accurate data.
Founders who plan in September consistently outperform those who wait. They finish Q4 stronger and start the new year faster, building momentum while their competitors are still figuring out their basic annual plans.
Ready Founders™ understand that September builds the foundation for next year's success. They know that the best time to plan is when you have mental clarity and operational space, not when you're in the middle of executing year-end pushes.
They recognize that frameworks and systems separate reactive management from strategic leadership.
They understand that annual planning done right in September creates the space for what really matters: executing brilliantly in Q4 and starting the new year with unstoppable momentum.
Ready to build your September planning foundation? Our Year-End Planning Assessment evaluates where your business systems stand and identifies what needs attention before Q4. Don't let another year end with scrambling and stress.
The Ready Founder™ is part of One Degree Financial's commitment to helping founders gain the financial clarity and confidence they need to scale successfully. Learn more at onedegreefinancial.com.
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About the Author: Rod Loges is CEO of One Degree Financial and host of the MILCOM Founders podcast, where he helps veteran entrepreneurs build businesses with strong financial foundations.