Mr. Stillman's Opus

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

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment

☎️ 919-391-3446

Trump Accounts may offer families a valuable new way to save, but they are not automatically the right solution for every goal. In this episode, John and Jake explain how these accounts work, where they may fit, and why careful planning still matters. Tune in to find out whether this new account type deserves a spot in your financial toolbox or should be left on the shelf.

Here’s what we discuss in this episode:

🆕 How It Works: Understand how Trump Accounts work

⚠️ Use Caution: Outdated information can create confusion

🎯 Start With Goals: Match each account to its purpose

🧾 Tax Considerations: Different accounts carry different tax treatment

📲 Getting Started: Setup is easier than expected

Resources for this episode:

https://trumpaccounts.gov

Connect with us:

Web: https://rosewoodwealthmanagement.com/

Phone: 919-391-3446

Schedule a Meeting: https://www.rosewoodwealthmanagement.com/schedule-an-appointment

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

John addresses the obvious right away: it’s not just him anymore, and everyone should get used to seeing Jake because he isn’t going anywhere. In this episode, John welcomes longtime friend Jake Doser as the newest partner and Financial Advisor at Rosewood Wealth Management. They share how the partnership came together and how the move creates new opportunities without changing the personal experience clients have come to expect. Plus, Jake offers an update on the whirlwind family journey from Connecticut to North Carolina.

Here’s what we discuss in this episode:

🛣️ Jake’s Journey and Background

🏀 Jake learns quickly about Carolina’s “different shades of blue”

🤝 Client Interaction and Team Dynamics

👶 Personal Updates and Family News

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

After 40+ years in the same home, the idea of packing up and moving somewhere new—like Florida—can feel both exciting and overwhelming. The tax savings might look great on paper, but there’s a lot more to consider than just the financial side. Today, John walks through the real questions you should be asking before making a move in early retirement. It’s all about making a decision that works not just financially, but for your day-to-day life.

Here’s what we discuss in this episode:

🌴 Tax Savings: No income tax has advantages

🌦️ Weather Reality: Florida summers hit different

📦 The Big Move: Downsizing takes time and effort

🏡 Housing Tradeoffs: Size, price, and location shift

🧭 Lifestyle Fit: Daily life may change more than expected

⚖️ Whole Picture: Money is only part of the decision

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