Mr. Stillman's Opus

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com
☎️ 919-391-3446
 
Long-term care is one of those retirement expenses nobody exactly looks forward to planning for, but ignoring it can leave your nest egg exposed if the bill eventually lands in your lap.
In this episode, John and Jake walk through the different ways retirees can prepare, and some strategies that may help keep a major care event from shipwrecking the rest of the plan. The right answer depends on how all the pieces of your retirement fit together and which financial levers you have available to pull. You may not need long-term care insurance, but you absolutely need a plan for how you’ll handle the cost if the need arises.
 
Here’s what we discuss in this episode:
 
🏥 Care Planning: Prepare before the need
💰 Self-Insurance: Know what assets can cover
📄 Insurance Options: Compare different coverage types
⚖️ Tradeoffs: Understand costs and risks
🏡 Alternative Strategies: Use assets intentionally
✅ Bottom Line: Have a payment plan 
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://www.meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com
☎️ 919-391-3446
 
Most people don't think about taxes until they're sitting down to file, and by then, most of the best opportunities are gone. The moves that actually lower your tax bill usually have to happen before December 31. Here's what's worth tackling now. The best tax planning rarely happens in April. It happens months earlier, while there's still time to do something about it. If you haven't looked at this year's picture yet, now's the time.
 
Here’s what we discuss in this episode:
 
🧾 Q4 Planning: Make decisions before deadlines arrive
❤️ Charitable Giving: Use generosity more strategically
💼 Self-Employment: Explore additional retirement plan options
🏥 Tax Tools: Take advantage of overlooked accounts
📅 Year-End Review: Adjust plans while there’s time 
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://www.meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com
☎️ 919-391-3446
 
It's spooky season. And while most people are thinking about haunted houses and horror movies, a lot of pre-retirees have scarier things on their minds: running out of money, or a market crash at exactly the wrong time.
Today, Jake shines a flashlight on five of the biggest financial frights and how to prepare for them. Most of what scares people about retirement isn't the event itself. It's not knowing what happens next. A plan won't make the unknowns disappear, but it can make them a lot less frightening. Happy Halloween.
 
Here’s what we discuss in this episode:
 
💸 Running Out: Know what you can safely spend
📉 Market Risk: Match investments to actual needs
🏥 Healthcare: Prepare for rising medical expenses
🩺 Long-Term Care: Discuss difficult possibilities early
❤️ Losing Spouse: Prepare for life-changing transitions
🧭 Clarity: Replace uncertainty with informed planning
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://www.meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com
☎️ 919-391-3446
 
Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Jake 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:
 
🧞 Financial Constraints: Identify worries holding you back
❤️ Purpose: Define what matters beyond money
🔙 Past Regrets: Learn from previous financial choices
🧠 Money Mindset: Recognize habits shaping retirement decisions
🪣 Bucket List: Turn future dreams into goals
📅 Retirement Stages: Plan around changing life seasons
 
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://www.meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com
☎️ 919-391-3446
 
Roth conversions can sound simple on the surface, but the decision can become much more nuanced once you look at the full picture. In this episode, John and Jake explain why the bigger issue is not simply whether to convert, but how taxes, family goals, flexibility, and timing all fit together. They also explore why the answer can change depending on what the money is ultimately meant to accomplish. The best Roth conversion strategy is the one that makes sense within the entire financial plan.
 
Here’s what we discuss in this episode:
 
👨‍👩‍👧 Generational Wealth: Considering heirs in the strategy
🛡️ Tax Defense: Creating flexibility against future changes
🏥 Medicare Costs: Watching income-related premium impacts
💍 Surviving Spouse: Preparing for future filing changes
⏱️ Conversion Timing: Why age and timing matter
⚠️ Implementation Risk: Avoiding costly conversion mistakes
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://www.meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL

Ready to grow your wealth with confidence?
Let’s talk! 👉 http://www.meetwithrosewood.com
☎️ 919-391-3446
 
Spoiler Alert: There’s no single “best” age to claim Social Security because the right answer depends on far more than the size of the monthly check. In this episode, John and Jake explain why Social Security should be viewed as one piece of a larger retirement plan, with other key factors all influencing the decision. They also unpack several common misconceptions that can push people toward claiming too early or waiting too long.
 
Here’s what we discuss in this episode:
 
⏳ Claiming Age: Why there isn’t one universally correct time to start Social Security
🧩 Bigger Picture: How Social Security fits into income, taxes, investments, healthcare, and legacy planning
🧾 Tax Strategy: Why delaying benefits can sometimes create room for Roth conversions or IRA withdrawals
💵 Income Needs: When taking Social Security earlier may help preserve other assets
📈 Delayed Benefits: Understanding the difference between a larger future benefit and an investment return
⚖️ Balancing Act: Avoiding the mistake of draining liquid assets simply to delay Social Security
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://www.meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com
☎️ 919-391-3446
 
“Safe” sounds simple, but in retirement planning, it can mean very different things to different people. Jake explains why feeling comfortable with your portfolio isn’t the same as having the right amount of risk for your actual financial situation. The goal isn’t to avoid risk altogether, it’s to make sure the risk you’re taking actually fits the life your money needs to support.
 
Here’s what we discuss in this episode:
 
💬 Client Perceptions: What people usually mean by “safe money”
⚖️ Risk Capacity: How much risk your plan can actually support
😴 Risk Tolerance: How much volatility you can emotionally handle
📈 Market Influence: Why strong markets can distort perception
🔍 Portfolio Reality: Why people often underestimate their risk
💵 Income Protection: Keeping retirement spending on track
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://www.meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL
 

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment
☎️ 919-391-3446
 
Many people plan to retire around 65, but new research shows a large percentage are leaving the workforce several years earlier—and often not by choice. Health problems, job loss, and rising healthcare expenses can suddenly force a retirement timeline to change. In this episode, Jake explains why those extra few years matter so much and how better planning can make an unexpected early retirement more manageable.
 
Here’s what we discuss in this episode:
 
📉 Early Retirement: Many leave sooner than planned
⚠️ Unexpected Exits: Health and jobs drive change
👨‍👩‍👦 Real-Life Impact: Family circumstances alter timing
💰 Income Differences: Flexibility varies by resources
🧮 Scenario Planning: Test earlier retirement dates
🔄 Flexible Plans: Adapt without losing direction
 
Resources for this episode:
Millions Are Retiring Earlier Than Planned. Do Advisors Need To Rethink Planning?
https://www.fa-mag.com/news/most-americans-retire-earlier-than-planned--here-are-the-top-reasons-87149.html
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL
 
 

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment
☎️ 919-391-3446
 
A simple parenting moment might be the clearest picture of what real financial advice should look like. Jake unpacks the “High Shoulders Theory” and how expectations and support shape your relationship with money and your advisor. You’ll see why “you’re fine” and “you’re doing it all wrong” both miss the mark, and what a true partner in your financial life actually does for you. Stick around to find out which quadrant your advisor falls into… and where you really want to be.
 
Here’s what we discuss in this episode:
🚫 Low Support: Little guidance or accountability
😌 Too Comfortable: Support without meaningful challenge
⚠️ High Pressure: Expectations without a plan
🤝 Ideal Relationship: Accountability backed by support
📋 Clear Plan: Priorities with specific actions
✅ Ongoing Support: Regular check-ins and follow-through
 
 
Resources for this episode:
The High Shoulders Theory 
https://www.sahilbloom.com/newsletter/the-high-shoulders-theory
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL
 

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment
☎️ 919-391-3446
 
Some people keep working because they love what they do. Others stay because retirement feels financially, socially, or emotionally uncertain. In this episode, Jake explores the different forces that can keep someone in the workforce longer than expected and why the real goal is understanding whether work is a choice or a necessity. A retirement plan should do more than tell you when you can stop working; it should help you prepare for what comes next.
 
Here’s what we discuss in this episode:
 
💼 Working Longer: People remain in the workforce for many different reasons
🤝 Social Connection: Leaving work can mean losing relationships, routine, and part of your identity
💵 Financial Necessity: A retirement income plan can help determine whether working longer is truly required
😟 Retirement Fears: Uncertainty can keep people working even when the numbers may support retirement
🏃 Semi-Retirement: Cutting back hours or changing careers can provide a middle ground
🗺️ Retirement Phases: A plan needs to account for decades of changing needs after work ends
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithrosewood.com
Check us out on YouTube: https://bit.ly/46RaLvL