If you have ever looked at your accounts and wondered, “Should I start pulling back the risk in my investments?” this episode is for you. Michael, CFP®, EA unpacks portfolio de-risking.

We look at what happens when your time horizon shrinks, why the often forgot about sequence of returns risk can quickly wreck a person's plan, and how to think about shifting from growth mode to enjoy your savings mode. JFK shows up with a surprisingly useful quote, football metaphors sneak into the conversation, and we explore that tension between wanting more and protecting what you've already built.

You will walk away with a clearer understanding of how de risking works and how you may want to think about things like stocks, bonds, cash, options, alternatives, diversification, and the spicy annuity conversation. It is all about taking calculated risk.

Topics:

💭 Why sequence of returns risk is a silent retirement killer

💭 When to maybe start planning for risk adjustments

💭 How stocks, bonds, cash, and alternatives can work together

💭 Why too conservative can hurt just as much as too aggressive

💭 What to know before considering annuities

💭 How to think about “winning the fourth quarter” of your retirement plan

If you have ever wondered how to balance growth and safety on the doorstep of retirement, this episode gives you a roadmap to start thinking it through.

Chapters:

00:00 Risk vs Reward in Retirement

00:41 Opportunity vs Crisis

02:16 Reassessing your partnership with risk

03:01 New Planning Pieces When Nearing Retirement

03:48 What does de-risking look like?

04:29 Why is De-Risking Important?

06:03 Bonds and alternatives for potential portfolio changes?

06:52 What Type of Equities we May Consider

08:23 Thoughts on Annuities?

09:50 How Much De-Risking Should I Consider?

11:05 Role of Taxes on Your Plan

11:50 Is There an Easy Button?

12:34 Let's Win the Fourth Quarter

𝐖𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐡𝐞𝐫𝐞?

We’re here to make retirement planning feel less intimidating by helping people think through their strategies and plans through clear relatable financial topics!

💬 Questions or Want to Connect?

🌐 𝐖𝐞𝐛𝐬𝐢𝐭𝐞: www.custerfinancialadvisors.com

📧 𝐄𝐦𝐚𝐢𝐥: custerfinancialadvisors@lpl.com

Disclosures:

Harborfront Financial Group is a Registered Investment Advisor registered with the Securities and Exchange Commission (SEC). Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority.

The information contained in this material is intended to provide general information about Harborfront Financial Group and its services. It is not intended to offer investment advice. Investment advice will only be given after a client engages our services by executing the appropriate investment services agreement. Information regarding investment products and services are provided solely to read about our investment philosophy and our strategies. You should not rely on any information provided on our web site in making investment decisions.

Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Harborfront Financial Group, a Registered Investment Advisor. Harborfront Financial Group and Custer Financial Advisors are separate entities from LPL Financial.

This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. All investing involves risk including loss of principal. No strategy assures success or protects against loss.

In this episode, Michael and Jacqueline welcome a special guest: Michael’s grandpa Larry. Long before Dave Ramsey made his financial classes famous, Larry was already living it.

He stretched a teacher’s salary to provide for his family, steering clear of debt like it had fangs, and had the foresight to invest early with a long‑term mindset.

They discuss:

💭 Larry growing up in a low income family where every penny had a job

💭 He joined the Navy Reserves and used his military paychecks to build his first savings pile

💭 Budgeting his $4,100/year income

💭 He was running envelope budgets before it was cool, even convincing his wife to join the system

💭 He refused to buy anything on payments except this home

💭 He saved for his kids college before most people he knew even said the word investing

💭 He quietly set his family up well for generations by planning years ahead

💭 And yes, there is a family story about cash flying out the car window on the highway

His story shows that steady discipline and choices has been a secret of the American Dream. And according to Larry, the two big lessons are simple: think ahead and marry the right women!

If you love hearing real life wisdom from someone who quietly lived out these philosophies decades before the personal finance world turned them into slogans, you are going to enjoy this one.

Stay curious.

Chapters:

00:00 Larry's Upbringing

01:33 His Gift of Foresight

02:40 His time in the Navy

04:18 Life after the Navy

05:27 Newly Married and Setting Up Finances

07:30 Cash Flying Out the Window?

08:49 Having long-term thinking key for Larry

12:44 Planning How to Help His Grandkids

18:26 Larry Doesn't Like Debt

19:32 Home Price vs Income

22:00 Change Anything About Tax Planning?

23:22 Best Advice He's Ever Gotten

25:10 Thoughts on Moving to Retirement Community?

30:00 Financial Values He Hopes to Pass Along?

30:32 Try to Marry Up!

𝐖𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐡𝐞𝐫𝐞?

We’re here to make retirement planning feel less intimidating by helping people think through their strategies and plans through clear relatable financial topics!

💬 Questions or Want to Connect?

🌐 𝐖𝐞𝐛𝐬𝐢𝐭𝐞: www.custerfinancialadvisors.com

📧 𝐄𝐦𝐚𝐢𝐥: custerfinancialadvisors@lpl.com

Disclosures:

Harborfront Financial Group is a Registered Investment Advisor registered with the Securities and Exchange Commission (SEC). Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority.

The information contained in this material is intended to provide general information about Harborfront Financial Group and its services. It is not intended to offer investment advice. Investment advice will only be given after a client engages our services by executing the appropriate investment services agreement. Information regarding investment products and services are provided solely to read about our investment philosophy and our strategies. You should not rely on any information provided on our web site in making investment decisions.

Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Harborfront Financial Group, a Registered Investment Advisor. Harborfront Financial Group and Custer Financial Advisors are separate entities from LPL Financial.

This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. All investing involves risk including loss of principal. No strategy assures success or protects against loss.

In this episode Michael CFP®, EA tackles one of the most emotional and confusing decisions in personal finance. Should you buy a home now with a higher interest rate or wait and hope for a lower rate later? Our listener is looking at a payment that could be 42% of their income today but if rates came down would be a smaller amount of their income.

We talk through how to think about this without the noise of social media predictions and without betting your future on something none of us can control.

Inside this episode we explore:

💭 Why 42% might feel tight depending on your lifestyle and income

💭 How the size of your income may change what percent of income your home may be

💭 The problem with planning your life around a forecast of three percent rates

💭 How mortgage rates connect to the federal funds rate

💭 Why the ultra low rates after the Great Recession were the exception not the rule

💭 What inflation and unemployment have to do with potential future rate cuts

💭 The impact of layoffs in tech and the race for artificial intelligence

💭 Why a higher rate today with a refinance option later can sometimes make sense

💭 How slower housing markets and price cuts may work in your favor

💭 Why assuming rates will drop soon can be dangerous for your long term plan

If you are wrestling with the buy now or wait question, this episode gives you a grounded way to make your decision with more confidence and less stress.

Chapters:

00:00 Can I Afford the Home?

01:41 Wait Until Rates Come Down?

02:57 How Could We See Interest Rates Come Down?

04:12 What Would Michael's Current Gameplan Look Like?

05:34 Potential Downside to This Strategy?

05:53 Wouldn't Assume Int. Rates Going to 3% Now

06:36 Interest Rate Cuts Potential Effect on Bond Market?

𝐖𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐡𝐞𝐫𝐞?

We’re here to make retirement planning feel less intimidating by helping people think through their strategies and plans through clear relatable financial topics!

💬 Questions or Want to Connect?

🌐 𝐖𝐞𝐛𝐬𝐢𝐭𝐞: www.custerfinancialadvisors.com

📧 𝐄𝐦𝐚𝐢𝐥: custerfinancialadvisors@lpl.com

Disclosures:

Harborfront Financial Group is a Registered Investment Advisor registered with the Securities and Exchange Commission (SEC). Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority.

The information contained in this material is intended to provide general information about Harborfront Financial Group and its services. It is not intended to offer investment advice. Investment advice will only be given after a client engages our services by executing the appropriate investment services agreement. Information regarding investment products and services are provided solely to read about our investment philosophy and our strategies. You should not rely on any information provided on our web site in making investment decisions.

Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Harborfront Financial Group, a Registered Investment Advisor. Harborfront Financial Group and Custer Financial Advisors are separate entities from LPL Financial.

This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. All investing involves risk including loss of principal. No strategy assures success or protects against loss.

Welcome back to Common Curiosities: Retirement where this time of year means two things in our house: Sports season is in full swing, and so are the financial questions popping up on social media.

In this sporty moments episode, Jacqueline shows up repping LSU beach volleyball, Michael shows up repping his undefeated 8th-grade basketball squad, and together we break down a viral financial “hack” you’ve probably scrolled past:

Does paying your mortgage every other week actually save you money?

Here’s what we dig into with the goal of helping you understand the moving parts:

🏀 Why bi-weekly payments might shave 4–6 years off a 30-year mortgage

🏐 How paying earlier could reduce your interest paid

🏀 The sneaky reason bi-weekly = 13 payments a year, not 12

🏐 What not to do we=hen trying this strategy

🏀 Why this idea can work well for some but others wouldn't like it

🏐 Would this idea works for student loans, cars, credit cards, and more?

It’s all curiosity-first, judgment-free, and sprinkled with just enough sports talk to make November feel right.

If you’re wondering whether this mortgage move fits your playbook, this episode may give you a clearer lens.

Stay curious. 🏀📚💭

Chapters

00:00 Sporting Season

01:40 Biweekly Mortgage Pay Hack?

03:30 Will My Bank Allow Bi-Weekly Payments?

03:49 Checking if Payments Go Right to Principal

04:27 Who May or May Not Want to Do Bi-Weekly Payments?

06:02 Would Paying Early Help Other Types of Loans?

𝐖𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐡𝐞𝐫𝐞?

We’re here to make retirement planning feel less intimidating by helping people think through their strategies and plans through clear relatable financial topics!

💬 Questions or Want to Connect?

🌐 𝐖𝐞𝐛𝐬𝐢𝐭𝐞: www.custerfinancialadvisors.com

📧 𝐄𝐦𝐚𝐢𝐥: custerfinancialadvisors@lpl.com

Disclosures:

Harborfront Financial Group is a Registered Investment Advisor registered with the Securities and Exchange Commission (SEC). Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority.

The information contained in this material is intended to provide general information about Harborfront Financial Group and its services. It is not intended to offer investment advice. Investment advice will only be given after a client engages our services by executing the appropriate investment services agreement. Information regarding investment products and services are provided solely to read about our investment philosophy and our strategies. You should not rely on any information provided on our web site in making investment decisions.

Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Harborfront Financial Group, a Registered Investment Advisor. Harborfront Financial Group and Custer Financial Advisors are separate entities from LPL Financial.

This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. All investing involves risk including loss of principal. No strategy assures success or protects against loss.

Should you pay off your medical school loans ASAP or stretch them out? This is an especially important question for medical professionals, with many factors to consider!

From different repayment options, to loan forgiveness programs, to tax implications. Not to mention the emotional satisfaction of making quicker progress on your debt. Which plan is right for you? Jacqueline, is currently in medical school so Michael has done a lot of research into this with other experts.

They discuss thoughts on their own repayment strategies based on listener's question. What should you consider when making this decision?

This applies to more than just Medical school loans too. From student loans to mortgages to car loans, Michael CFP®, EA and Jacqueline break down when it actually may make sense for some people to keep loans around and use the resources another way, while others may want to pay them off as soon as possible!

Discussion topics:

🤔💭 Why paying the loans off even if the math says different isn't such a bad idea for many

🤔💭 What is “cheap money” and when may it be wise to use your resources in other ways than pay off the loans

🤔💭 Medical School loans and navigating the repayment and forgiveness options

🤔💭 How emotion and discipline may shape your financial success

🤔💭 Are you the type of person that may be okay keeping low interest debt?

🤔💭 Why some people don't rush to pay off a mortgage

🤔💭 What do ice baths have to do with staying calm when the market drops?!

It’s not just math, it’s mindset.

Want to ask a question? We love answering questions that are helpful to you!

Chapters

00:00 Introduction to Listener Questions

00:30 PAYOFF MED SCHOOL LOANS VS INVEST

01:36 LOW MORTGAGE RATE PAYOFF THOUGHTS?

03:38 IBR, PSLF, Refinancing Loans

06:06 Loans vs Cash Type Returns vs Investment Returns?

06:50 Are you someone that can handle market volatility?

11:30 Do taxes impact our decision?

12:23 The Psychology of Debt Repayment

13:22 Any science behind the ice bath benefits?

15:04 What types of loans do you have

𝐖𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐡𝐞𝐫𝐞? We’re here to make retirement planning feel less intimidating by helping people think through their strategies and plans through clear relatable financial topics!

Disclosures: Harborfront Financial Group is a Registered Investment Advisor registered with the Securities and Exchange Commission (SEC). Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority. The information contained in this material is intended to provide general information about Harborfront Financial Group and its services. It is not intended to offer investment advice. Investment advice will only be given after a client engages our services by executing the appropriate investment services agreement. Information regarding investment products and services are provided solely to read about our investment philosophy and our strategies. You should not rely on any information provided on our web site in making investment decisions. Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Harborfront Financial Group, a Registered Investment Advisor. Harborfront Financial Group and Custer Financial Advisors are separate entities from LPL Financial. This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. All investing involves risk including loss of principal. No strategy assures success or protects against loss.

Ever feel like there are way too many retirement account names to keep straight? It’s almost like alphabet soup for your retirement planning.

In this episode of Common Curiosities: Retirement, Michael, CFP® and EA is joined by his wife, who asks the questions many people may secretly have. Like what to do with extra money now, what about extra money I don't need now, how do these different accounts actually work, and who can (or can’t) fund a specific account?

Along the way they cover:

💬 What's different between traditional IRA from a Roth IRA outside of just the taxes and who the heck is “Mr. Roth” anyway?

💬 Why are there so many types of accounts? 401(k)s, 403(b)s, and IRAs (and how they connect with one another)

💬 Who can open or contribute to a Roth IRA (even if you’re under 18)

💬 Why earned income matters (and what the IRS really means by that)

💬 The “Starbucks app” version of paying taxes now vs. later

💬 Plus, a little “girl math” and TJ Maxx logic to keep things grounded

It’s an easygoing, real-world conversation for anyone who’s ever looked at their 401(k) form or Roth contribution limits and thought, “Wait, which one is this again?”

👉 Subscribe to Common Curiosities: Retirement for more episodes that make complex financial topics feel like normal conversations.

Chapters

00:00 Understanding IRA vs Roth IRA

00:51 What to do with a little extra money?

01:53 Do we treat checking and savings similarly?

02:30 Potential pros and cons of HYSA or MM

05:03 Money left after your TJ Maxx budget?

07:26 Who the heck is Roth?

09:01 Tax management like the Starbucks app?

09:48 Tax differences on Roth vs Trad. IRA

10:48 If I'm young which account should I consider?

11:42 When can you start retirement savings?

12:40 Have earned income but who can fund an IRA?

13:56 Is there a stage you can't use a Roth IRA?

14:40 Income restrictions for IRA and Roth IRAs?

15:52 How many different type of retirement accounts are there?!

18:39 Are there auto investments in 401ks or IRAs?

19:32 Why so many different retirement accounts types!?

21:10 Youtube Disc. TN & Words.mp4

𝐖𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐡𝐞𝐫𝐞?

We’re here to make retirement planning feel less intimidating by helping people think through their strategies and plans through clear relatable financial topics!

💬 Questions or Want to Connect?

🌐 𝐖𝐞𝐛𝐬𝐢𝐭𝐞: www.custerfinancialadvisors.com

📧 𝐄𝐦𝐚𝐢𝐥: custerfinancialadvisors@lpl.com

Disclosures:

Harborfront Financial Group is a Registered Investment Advisor registered with the Securities and Exchange Commission (SEC). Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority.

The information contained in this material is intended to provide general information about Harborfront Financial Group and its services. It is not intended to offer investment advice. Investment advice will only be given after a client engages our services by executing the appropriate investment services agreement. Information regarding investment products and services are provided solely to read about our investment philosophy and our strategies. You should not rely on any information provided on our web site in making investment decisions.

Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Harborfront Financial Group, a Registered Investment Advisor. Harborfront Financial Group and Custer Financial Advisors are separate entities from LPL Financial.

This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. All investing involves risk including loss of principal. No strategy assures success or protects against loss.

Ever wonder why your tax refund may change so much from year to year or why making a little more money doesn’t always feel like it pays that much extra?

In this episode of Common Curiosities: Retirement, Michael CFP® and EA breaks down how our progressive tax system actually works, using everyday language (and a few buckets of water).

We walk through side-by-side examples of a married couple earning $120,000 and $200,000 to see how their tax bill may look, what tax deductions they may get (or not get) and even look at planning around certain tax credits.

You’ll learn:

💧 How each “bucket” of income gets taxed differently

💡 The difference between marginal and effective tax rates

👶 How credits may reduce your tax bill (and when some begin to phase out)

💭 Why tax planning can be valuable and should align with your investment and retirement planning

It’s a practical, down-to-earth look at how the numbers actually stack up hopefully understandable as well.

Because good financial planning isn’t just about investing… it’s about knowing how taxes, savings, and long-term goals all fit together like ingredients in a recipe that works for you.

Stay curious. 🧠

Chapters

00:00 Why is it important to understand your taxes?

00:41 How the US tax system works

01:32 $120k income example

03:38 0% Tax on LTCG Possibly?

05:34 $200k Income Tax Example

06:17 Are bonuses taxed differently?

06:59 Am I trying to qualify for certain deductions or credits?

07:32 Balancing deductions and income to become eligible for tax benefits

09:41 Retirement contributions for deductions to get under tax credits and manage brackets

11:19 Roth IRA contribution mistake

11:33 Integrating tax planning with investment plans

13:20 Youtube Disc. TN & Words.mp4

𝐖𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐡𝐞𝐫𝐞?

We’re here to make retirement planning feel less intimidating by helping people think through their strategies and plans through clear relatable financial topics!

💬 Questions or Want to Connect?

🌐 𝐖𝐞𝐛𝐬𝐢𝐭𝐞: www.custerfinancialadvisors.com

📧 𝐄𝐦𝐚𝐢𝐥: custerfinancialadvisors@lpl.com

Disclosures:

Harborfront Financial Group is a Registered Investment Advisor registered with the Securities and Exchange Commission (SEC). Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority.

The information contained in this material is intended to provide general information about Harborfront Financial Group and its services. It is not intended to offer investment advice. Investment advice will only be given after a client engages our services by executing the appropriate investment services agreement. Information regarding investment products and services are provided solely to read about our investment philosophy and our strategies. You should not rely on any information provided on our web site in making investment decisions.

Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Harborfront Financial Group, a Registered Investment Advisor. Harborfront Financial Group and Custer Financial Advisors are separate entities from LPL Financial.

This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. All investing involves risk including loss of principal. No strategy assures success or protects against loss.

If you’re a Michigan school teacher, you only get 75 days from your first pay period to choose your retirement plan and that one decision may shape your financial future for decades.

In this episode, Michael CFP® and EA unpacks what those two options really mean. There's the Pension Plus 2 plan and the Defined Contribution plan. He discussed how they work differently when it comes to paychecks, matching contributions, potential taxes, early access, and even what happens to your money after you’re gone.

We’ll talk through questions like:

💭 How does the new Michigan Teacher pension formula actually work?

💭 What happens if you change careers or retire early?

💭 Why do newer teachers have such different benefits from those who started 20 years ago?

💭 What are the pros and cons to each option?💭 How do you know which plan might fit you best based on your goals, comfort level, and your long-term plans

If you’re a newer teacher, this episode breaks down the fine print into plain English to help you make a more confident, informed choice about your future.

🧠 Stay curious.

🎧 Listen to more episodes of Common Curiosities: Retirement wherever you get your podcasts.𝐖𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐡𝐞𝐫𝐞? We’re here to make retirement planning feel less intimidating by helping people think through their strategies and plans through clear relatable financial topics!💬 Questions or Want to Connect?🌐 𝐖𝐞𝐛𝐬𝐢𝐭𝐞: www.custerfinancialadvisors.com 📧 𝐄𝐦𝐚𝐢𝐥: custerfinancialadvisors@lpl.com 📬 𝐂𝐨𝐧𝐧𝐞𝐜𝐭 𝐰𝐢𝐭𝐡 𝐮𝐬: https://www.custerfinancialadvisors.com/contact-us-form

Disclosures:

Harborfront Financial Group is a Registered Investment Advisor registered with the Securities and Exchange Commission (SEC). Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority.The information contained in this material is intended to provide general information about Harborfront Financial Group and its services. It is not intended to offer investment advice. Investment advice will only be given after a client engages our services by executing the appropriate investment services agreement. Information regarding investment products and services are provided solely to read about our investment philosophy and our strategies. You should not rely on any information provided on our web site in making investment decisions.Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Harborfront Financial Group, a Registered Investment Advisor. Harborfront Financial Group and Custer Financial Advisors are separate entities from LPL Financial.This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing. All investing involves risk including loss of principal. No strategy assures success or protects against loss.This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor. The economic forecasts set forth in this material may not develop as predicted and there can be no guarantee that strategies promoted will be successful. All investing involves risk including loss of principal. No strategy assures success or protects against loss. Harborfront Financial Group will provide all prospective clients with a copy of our current Form ADV, Part 2A (Disclosure Brochure) prior to commencing an advisory relationship. However, at any time, you can view our current Form ADV, Part 2A at adviserinfo.sec.gov. In addition, you can contact us to request a hardcopy.