What happens when the title you have carried for decades suddenly disappears? How do you prepare for the emotional shift that comes after stepping away from your business?

In this episode, Dan Reese, CFP®, continues the business exit series by focusing on the personal side of transition. He explains why identity, routine, and purpose play such a critical role in life after a sale. Dan shares practical exercises to help business owners design their ideal week, align with their spouse, and prepare emotionally for what comes next. He also discusses research suggesting that many owners experience regret after selling and how intentional planning may help reduce the likelihood of regret.

Key takeaways:

• Why identity transition is one of the biggest hurdles after selling a business
• How routine and decision-making impact emotional well-being in retirement
• The importance of lifestyle design and structuring your ideal week
• Why spousal alignment and family communication matter before exiting
• How proactive exit planning strategies can help business owners prepare emotionally and financially for transition
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

Thinking about stepping away from your business someday? The real question is whether you are preparing to leave or preparing to grow.

In this episode, Dan Reese, CFP®, kicks off a multi-episode series on exit planning for business owners. He introduces the concept of value acceleration as a proactive alternative to traditional succession planning and explains why many owners may overestimate what their business is worth while underestimating how much they rely on it financially. Dan breaks down the three legs of the stool, business value, financial planning, and personal purpose, and outlines practical first steps that may help strengthen each area before making any exit decisions.

Key takeaways:

• Why value acceleration differs from simple succession planning for business owners
• How most owners misjudge business value and overlook financial blind spots
• The importance of recurring revenue, leadership depth, and reduced buyer risk
• Why personal planning is critical to help avoid dissatisfaction after exiting
• Practical first steps, including business valuation and financial planning review
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

Most people see one or two meetings a year and assume that’s the whole picture. But real planning is happening year-round, often when no one is sitting across the table.

In this episode, Dan Reese, CFP, pulls back the curtain on how an annual service calendar guides financial planning throughout the year. He walks through how winter tax planning sets the foundation, how spring portfolio reviews and tax strategies are handled, and why summer and fall are critical for scenario planning, insurance reviews, and year-end decisions. Dan explains how systems help avoid missed opportunities, reduce costly mistakes, and keep everything aligned across taxes, investments, and planning.

Key takeaways:

• Why organizing planning work by seasons helps prevent last-minute decisions and overlooked deadlines
• How early year tax planning supports smarter moves during market downturns
• What happens during spring investment reviews and ongoing portfolio alignment
• Why summer is used for deeper tax analysis and real-life scenario testing
• How insurance reviews and year-end planning help protect against gaps and outdated coverage
• And more!

Converting from a traditional IRA to a Roth IRA is a taxable event.

Resources:

• Carson Wealth Retirement Readiness Quiz
• 2026 Calendar: Key Tasks & Financial Dates

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese