💼 Business Sale Readiness Checklist

You’ve worked hard to build your business — now it’s time to protect what you’ve built.
Selling isn’t just a financial transaction; it’s a major life transition. The choices you make before, during, and after the sale can shape how much you keep, how long your money lasts, and how smoothly you move into retirement.

This checklist covers the essentials — from cash flow and taxes to investments and your next chapter — so you can turn years of work into lasting wealth, security, and confidence.

💵 Cash Flow & Exit Prep – Know Your Numbers Before the Sale

✅ I know my business’s current net profit and monthly cash flow
✅ I have a current business valuation (formal or estimated)
✅ I’ve separated personal and business expenses in my books
✅ I know how much income I’ll need post-sale to maintain my lifestyle
✅ I’ve reviewed debt, leases, and contracts that could affect the sale price
✅ I’ve identified any other financial or operational issues that could impact valuation

✅ I’ve met with a CPA or tax pro about capital gains on the sale
✅ I understand my options for structuring the sale (asset vs. stock sale)
✅ I’ve explored tax deferral or mitigation strategies (installment sales, trusts, etc.)
✅ I’ve reviewed how the sale could impact Social Security or Medicare premiums
✅ I’ve updated my estate plan to reflect the coming liquidity event
✅ I’ve addressed any other legal, tax, or compliance matters tied to the sale

📈 Investment & Retirement Plan – Replace Your Paycheck

✅ I have a plan for turning sale proceeds into sustainable income
✅ I know how much to keep in cash vs. invest immediately
✅ I’ve identified accounts (IRAs, brokerage, annuities) for post-sale investing
✅ I’ve considered inflation, market risk, and healthcare costs in projections
✅ I’ve mapped out the first 12 months post-sale to avoid rushed decisions
✅ I’ve reviewed other unique financial opportunities or risks related to my windfall

🔐 Insurance & Risk Management – Protect the Nest Egg

✅ I’ve reviewed liability protection until the business transfer is complete
✅ I’ve checked health insurance coverage post-sale (private, COBRA, Medicare)
✅ I’ve evaluated long-term care insurance options
✅ I’ve updated life insurance needs based on reduced debt and new assets
✅ I have a cybersecurity and fraud protection plan for my new liquidity
✅ I’ve considered other risk protections (umbrella liability, property, etc.)

📂 Organization & Next Chapter Planning

✅ All sale documents, contracts, and financial statements are organized
✅ I have a trusted advisory team (attorney, CPA, financial planner) in place
✅ I’ve set reminders for tax deadlines tied to the sale
✅ I’ve created a “Next Chapter” budget for the first few years of retirement
✅ I’ve clarified my post-retirement purpose (travel, hobbies, volunteering, part-time work)
✅ I’ve addressed any other personal, family, or business wrap-up tasks

🔎 Readiness Score

Count your ✅:
20–25: You’re well-prepared to maximize your sale and step confidently into retirement.
14–19: Solid foundation — focus on your weakest category before listing your business.
Under 14: You could be leaving significant money on the table — the right prep now can protect your retirement and boost your net proceeds.

💼 Want help reviewing your checklist and creating a retirement income plan? Schedule a no-pressure strategy call — free, confidential, judgment-free today.

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Disclaimer: The information provided on this site and its blogs is for educational and informational purposes only. It does not constitute financial, legal, or tax advice. Always consult with a qualified professional for guidance tailored to your individual circumstances. The examples, illustrations, and sample checklists are intended for general reference and are not meant to reflect any individual or family's specific needs or outcomes. They are provided to demonstrate concepts and do not guarantee future results. All investing involves risk, including possible loss of principal. Past performance is not indicative of future results.