Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Ryan goes over a few today that he thinks are worth asking. None of these questions are really about money. That's kind of the point. Sometimes the best way into a financial conversation is to start somewhere else entirely.

Here’s what we discuss in this episode:

🧠 Beyond Math: Look past numbers alone

🕙 Tuesday Morning: Picture everyday retirement life

🧞 Money Problems: Identify your biggest financial concerns

❤️ Passions: Define what gives life purpose

🔙 Past Lessons: Learn from previous money mistakes

🪣 Bucket List: Put timelines around big goals

🧭 Lifestyle Planning: Build real life into the plan

Visit us online: https://blackoakam.com/

Phone: (470) 508-0508

Get in touch with the Black Oak team: https://blackoakam.com/contact-us/

Schedule a call with Ryan: https://speakwithryan.com/

Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc

Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

There's a 7-minute animated short that got nominated for an Oscar this year called Retirement Plan. It's free on YouTube, narrated by Irish actor Domhnall Gleeson, and it follows a middle-aged man named Ray who spends his days listing everything he plans to do once he finally retires. Ryan uses the short as a jumping-off point for a bigger conversation about the expectations we build around retirement and the life we’re living right now.

Here’s what we discuss in this episode:

💵 Pension Planning: Why understanding your retirement benefits matters before making permanent decisions

✈️ Travel Goals: Turning “I’ll travel more someday” into an actual financial plan

❤️ Giving Back: Using retirement assets strategically when charitable giving matters to you

⚖️ Life Balance: Saving for the future without sacrificing everything you could enjoy today

🕰️ More Time: Learning how to say yes—and no—when retirement gives you greater control of your schedule

🌅 Present Living: Why the film’s message about being “aggressively present” hits especially hard

📝 Your Own List: Using the short film as inspiration to think about what you want retirement to look like

“Retirement Plan” (2026 Oscar Nominee) | The New Yorker -

https://www.youtube.com/watch?v=2Mqa4zfJdx4

Visit us online: https://blackoakam.com/

Phone: (470) 508-0508

Get in touch with the Black Oak team: https://blackoakam.com/contact-us/

Schedule a call with Ryan: https://speakwithryan.com/

Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc

Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

Worrying about future tax rates can make retirees feel like they need to act before the rules change. In this episode, Ryan explains why taking extra money out of an IRA simply out of fear may create new problems if it isn’t part of a larger strategy. He looks at the importance of understanding how one tax decision can affect the rest of your financial plan. Don’t guess where tax rates are headed, make intentional decisions with the options available today.

Here’s what we discuss in this episode:

⚖️ Withdrawal Strategy: The difference between taking what you need and pulling out extra money

🔄 Roth Conversions: Why converting excess IRA dollars may be more efficient than simply withdrawing them

📈 Reinvesting Funds: What to consider if extra withdrawals are moved into a taxable brokerage account

🛍️ Spending Risk: How easier access to cash can make it more tempting to spend

📊 Tax Brackets: Why current deductions and tax thresholds matter when deciding how much to withdraw

🧩 Full Plan Impact: How one tax move can affect income, investments, and other planning decisions

Visit us online: https://blackoakam.com/

Phone: (470) 508-0508

Get in touch with the Black Oak team: https://blackoakam.com/contact-us/

Schedule a call with Ryan: https://speakwithryan.com/

Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc

Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI