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

Retirement tax decisions often feel simple on the surface, but the ripple effects can last decades. The real question is not whether taxes will be paid, but when, how, and by whom.

In this episode, Dan Reese, CFP®, walks through how Roth conversions, a taxable event, can fit into a broader retirement and estate plan for high-income earners. He explains when conversions may help manage future tax exposure, Medicare premiums, and inherited IRA issues. The conversation also covers market downturns, early retirement gap years, state tax differences, and why scenario planning is essential before acting.

Key takeaways:

• How Roth conversions can affect heirs, estate plans, and long-term family tax outcomes over multiple generations
• Why higher income does not automatically rule out conversions, and how added income can trigger hidden taxes
• How market downturns may lower the taxable cost of converting retirement assets
• Why early retirement gap years can create valuable planning windows before Social Security begins
• How moving between low-tax and high-tax states can change the timing and value of conversions
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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

Most business owners say they feel prepared to step away, but available data suggests gaps in readiness.

In this episode, Dan Reese breaks down insights from the National State of Owner Readiness Report and explains common areas where small and mid-sized business owners may lack preparation for a significant financial transition. With a large portion of many owners’ net worth tied up in their business, exit planning often involves business, personal, and financial considerations.

Dan walks through common elements often associated with readiness, including understanding business value, identifying wealth gaps, and planning considerations for life after the business following a transaction.

Dan discusses:

• The role small and mid-sized businesses play in the U.S. economy
• The commonly referenced three legs of exit planning: business, personal, and financial considerations
• The role formal business valuations can play in exit planning
• The wealth gap and how lifestyle expectations may affect a transition
• And more

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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

Online platforms surface a steady stream of financial content, often from influencers whose guidance is not tailored to individual situations.

In this episode of Ramp Up to Retirement, Dan Reese discusses the difference between broad online commentary and fiduciary planning, and how that gap can affect real retirement decisions. He walks through examples involving Roth conversions, Social Security timing, and investment choices that are sometimes framed too broadly in short-form content.

What to expect:

• How social algorithms can pull you into financial advice content
• Possible motivations behind influencer content
• What fiduciary standards require (and what they do not)
• How personalized planning can help you assess decisions and potential tradeoffs
• And more!

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

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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

Gold is in the headlines again.

Prices are higher this year, we see gold ads on TV, and fear-based marketing may be convincing more retirees to convert their savings into precious metals. But is gold truly as safe as it’s perceived to be, or are investors falling for glitter over substance?

Dan Reese delivers a calm, factual look at the emotional and financial realities of gold investing. From physical bars to ETFs, Dan explains the pros, cons, and costly surprises many people overlook, especially when they’re acting out of fear.

Here’s what to expect:

• The emotional appeal of gold and how it’s used in marketing
• Why physical gold may cost more than you think to buy, sell, and store
• How gold ETFs could offer a simpler, lower-cost option
• Why timing, taxes, and diversification matter more than hype
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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

Mark and Susan thought they did everything right: no debt, over a million saved, markets trending up. But one well-intentioned gift to their kids set off a chain of financial consequences they didn’t anticipate.

In this episode, Dan Reese is joined by Brent Oliver for a hypothetical case study exploring how using the concept of a financial “postmortem”, an exercise in looking back to uncover what went wrong and why. You’ll hear how early retirement optimism, overconfidence, and lack of a coordinated plan may result in unexpected taxes, reduced income, and potential long-term challenges.

Here’s what to expect:

• Why starting strong doesn’t always mean finishing strong in retirement
• How a single decision can derail your entire income plan
• The hidden dangers of IRMAA and tax bracket creep
• How to rebuild confidence with structure, buckets, and stress testing
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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

Connect with Brent Oliver:

• Avery Wealth
• LinkedIn: Brent Oliver, CFP®

About our Guest:

Brent Oliver is a Wealth Manager at Avery Wealth, Inc. He focuses on providing wealth management solutions to retirees and pre-retirees in the Mid-Michigan Area. Brent helps affluent clients address their five biggest concerns: preserving their wealth, mitigating taxes, taking care of their heirs, ensuring their assets are not unjustly taken and charitable giving.

Brent has been with Avery Wealth, Inc. since 2013 where he uses a consultative process to gain a detailed understanding of his clients’ deepest values and goals. He then employs customized recommendations designed to address each client’s unique needs and goals beyond simply investments.

Successful individuals and families work with Brent to:

• Develop and implement a comprehensive wealth management plan to help them reach their financial dreams.
• Make smarter decision in today’s uncertain political, economic and social environment.
• Obtain an independent second opinion from a top financial advisor in their community.

Previously, Brent owned and operated Midwest Wireless Communications, LLC, a successful business, in the Jackson Area. He hosts a weekly radio show/podcast, The Retirement Café, which focuses on educating listeners on a wide variety of financial planning and investing topics. He is currently a Trustee on the Western School Districts Board of Education.

Disclosure:

The scenarios discussed are hypothetical and for educational purposes only. They do not represent actual clients or guarantee future results. Investment involves risk, including possible loss of principal.