Mr. Stillman's Opus

Finding Opportunity in a Market Crisis

When the market takes a dive, most people panic. But the most successful investors often see downturns differently. Being able to recognize opportunity in the middle of market uncertainty can help you make critical decisions during difficult market environments. Let’s talk about what steps you can take to strengthen your plan while others sit on the sidelines.
We'll cover four smart strategies that can work during volatile periods, including increasing savings, timing Roth conversions, reallocating investments, and using the experience as a wake-up call to build a more resilient plan. No matter what stage of life you’re in, taking the time to pause, think, and respond with purpose instead of fear will help you emerge stronger.
Here’s what we discuss in this episode:
🔁 Roth conversions during a downturn
💡 Rebalancing when some sectors fall harder
🧠 What panic reveals about your plan
🧾 Learning now to prepare for the next time
 
0:00 – Intro
1:28 – Buying more (if you can)
3:42 – Roth Conversions
5:49 – Investment Strategy
7:37 – Create a buffer
 
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

Key 2025 Tax Breaks & Adjustment Opportunities

Tax season is here, but did you know that filing your 2024 return is only part of the equation? With the 2025 tax changes in place, John breaks down key areas where you may be able to reduce your tax bill. With increased standard deductions and higher retirement contribution limits, now is the time to evaluate how you can plan smarter and potentially put more money toward your future.
In this episode, we dive into the major tax changes for 2025 and discuss how smart planning now may save you a lot of money and stress later. From updates to the standard deduction to misconceptions about catch-up contributions, John explains what really matters for pre-retirees and retirees.
Here’s what we discuss in this episode:
📊 Most people won’t need to itemize, instead they’ll take the Standard Deduction
💡 Catch-up contributions aren’t “free money,” they require planning
🏥 The HSA might be your most powerful retirement savings tool
💸 Adjusting paycheck withholdings can avoid surprise bills or big refunds
 
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

How Should You Pay for That Home Renovation in Retirement?

Once you’re on a fixed income in retirement, it can be difficult to open the checkbook to pay for major expenses. Emotion and logic both play into the decision, and many spouses can feel apprehensive about spending large sums of money without a paycheck still coming in. So how do you determine if you can afford that home renovation you’ve always wanted and what’s the best way to convince your partner it’s going to be okay long-term?
We’ll highlight three potential scenarios regarding that cause someone to have reluctance to spending: emotional resistance, logical miscalculations, or a valid conclusion that the expense isn’t feasible. We want to approach these discussions openly and honestly, ensuring that both partners feel heard and understood. So let’s walk through the process for determining whether the concern is justified and show how knowing the numbers can help alleviate fears and make informed decisions.
Here’s what we discuss in this episode:
0:00 – Intro
2:51 – Logical reasons
4:53 – How we help
 
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

March Market Update: What’s REALLY Happening with Social Security, DOGE & Tariffs

There’s a lot of anxiety out ​there ​right ​now ​about ​the ​market ​and ​the ​current ​economy ​that ​we're ​experiencing. ​People are concerned about the uncertainty surrounding Social Security, DOGE, tariffs, and more. So ​I ​wanted ​to ​get ​on ​here ​and ​try to ​dispel some of the ​myths, ​talk ​about ​what's ​actually ​happening, ​and ​then ​drill ​down ​specifically ​to ​what ​you ​should ​be ​doing ​yourself.
Here’s some of the things we’ll cover:
📉 Market Volatility Explained – What’s really causing the recent swings?
🗳️ Political & Economic Factors – Tariffs, policy shifts & investor panic
💰 Social Security Myths – Why it’s likely not going away anytime soon
🚀 Managing Market Anxiety – Why less news = better financial health
 
0:00 – Intro
1:31 – Social Security fears
3:27 – DOGE
4:52 – What’s causing the volatility
7:16 – What should you be doing?
 
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

What’s the Best Age for Retirement?

What’s the average age that people retire? While that question can give you an idea of what most Americans do, it’s best to understand why people choose the specific ages they do. This video will explain the key ages that influence retirement decisions to help you identify the factors that might affect your timeline.
We’ll tell you why the milestone ages begin at 59.5 and what ages are most important for Social Security and Medicare. Most of our clients at Rosewood Wealth Management tend to retire between the ages of 65 and 68, but there is a wide spectrum of retirement ages based on individual circumstances and goals. Plus, there’s a wildcard that you need to know about if you’re a state employee.
Here’s what we discuss in this episode:
0:00 – Intro
0:56 – Age 59.5
1:52 – Age 62
2:44 – Age 65
4:20 – Age 66/67
5:52 – Wildcard for state employees
7:11 – Our clients’ retirement age
 
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

Can a Will Override Beneficiaries from a Previous Marriage?

What happens when you get remarried and want to create a new will and estate plan with your new spouse? Do you have to change all of your previous beneficiaries or will the new will override those existing designations? That’s the question we’re answering in this week's show. 
 
Here’s what we discuss in this episode:
0:00 – Intro
0:51 – Beneficiaries override the will
2:32 – Estate planning challenges with second marriages
 
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

Financial Planning Trick or Treat

With Halloween on the horizon, we’re rolling out a themed edition of the show today by tackling some of the trick or treat decisions of the financial planning world. We’re going to present John with four different products that have risen in popularity recently and find out whether he would characterize them as tricks or treats.
 
Here’s what we discuss in this episode:
0:00 – Intro
1:20 – Home equity line of credit
5:18 – Infinite banking
8:12 – Buying gold
10:17 – No closing cost mortgage
 
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

I Was Laid Off at 61, Do I Need to Find a New Job?

Getting laid off or forced into retirement earlier than expected can be a big blow emotionally and financially, but it’s a life event that many people will have to navigate. If you find yourself in this position of no longer having a job before you were prepared to retire, should you go find another job or can you find a way to retire without it?
Today we’re answering a question we received recently from someone who is 61 and trying to determine if they need to go back to work. John will walk you through the factors that will impact this decision, like financial readiness and health insurance needs. Covering that gap until Medicare kicks in is often one of the biggest financial challenges for retiring early so we’ll share some options you could consider.
This is one of those situations where planning is critical for getting a clear answer that will allow you to move forward confidently, and we’ll give you a better understanding of the process we work through to help you develop that plan.  
 
Here’s what we discuss in this episode:
0:00 – Intro
1:32 – Withdrawing from retirement accounts
2:40 – Knowing where you stand in terms of retirement income
5:46 – Wanting to know the answer
 
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

Do I Need To Wait Until 70 To Take Social Security?

Social Security timing is one of the most crucial decisions you’ll make in your retirement planning journey. Should you wait until 70 to claim your benefits, or is it better to start earlier?
Today we’re going to answer a question from someone who planned to wait until 70 for Social Security so they didn’t leave money on the table, but now that they’re approaching age 68, they’re having second thoughts about waiting. So what’s the best path forward?
John breaks down the pros and cons of taking Social Security at different ages and why there’s never one answer that applies to every situation. He’ll also share practical examples of how Rosewood Wealth Management has helped clients make the best decision about Social Security within their overall income plan.
You want a well-thought-out retirement plan that takes your entire financial picture into account because Social Security is a decision need to get right.
 
Here’s what we discuss in this episode:
0:00 – Intro
0:44 – When to start taking Social Security benefits
 
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

Should You Purchase Long-Term Care Insurance in Your 50s?

As we age, one of the most pressing questions we face is how to manage long-term care expenses. What coverage will you need and what’s the best way to pay for that coverage? Today we answer a question about purchasing LTC insurance and whether it’s worth doing while you’re in your 50s.
John will discuss whether it is a necessary investment for those nearing retirement age and examine alternative options such as self-insuring and leveraging life insurance policies with accelerated death benefits. One significant drawback of insurance is the potential for premiums to increase over time, potentially pricing policyholders out just when they might need the coverage the most, which is why you want to know all of the options available.
Join us as we break down the pros and cons of different strategies to address long-term care expenses.
 
Here’s what we discuss in this episode:
0:00 – Intro
0:39 – LTC insurance at an earlier age can be a mixed bag
2:50 – Can you self-insure?
6:45 – Life insurance to pay for long-term care
 
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