Your financial planning isn't always about saving more. Sometimes it's knowing when to adjust your savings, plan taxes, and use the accounts you have more strategically.

In this episode of Common Curiosities: Retirement, Michael Custer, CFP®, EA, and CSS™, works through two detailed Reddit questions about finances.

The first looks at a 28 year old living in New York City who is trying to balance high living expenses, retirement savings, and a future home purchase. The second explores parents approaching retirement who want to begin gifting to their children while being thoughtful about taxes, investments, and estate planning.

Topics include:

💭 Reduce your 401(k) contributions to spend more now?

💭 What accounts to prioritize

💭 Roth versus pre tax contributions for someone living in a high tax state

💭 How diversification may go beyond simply owning the S&P 500

💭 Can parents gift cash or investment shares more tax efficiently?

💭 Why gifting appreciated investments may shift the capital gains tax to the recipient

💭 How the step up in basis may affect taxable investments and inherited real estate

💭 Why placing bonds and dividend focused investments in certain account could create unnecessary taxes

💭 Should retirees stop reinvesting dividends?

💭 Roth conversions, Required Minimum Distributions, and the potential tax impact after one spouse passes away

💭 Qualified Charitable Distributions and gifting appreciated investments to charity

💭 Why families should be careful before transferring real estate to children during their lifetime

These questions show why financial planning rarely comes down to one investment or one tax strategy. Income, spending, account types, retirement timing, taxes, gifting goals, and estate planning should all work together.

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.

Many people spend decades saving for retirement, but the biggest questions often show up right as retirement begins.

In this episode of Common Curiosities: Retirement, Michael CFP®, EA, CSS™ walks through three retirement planning questions. From deciding whether to use Roth savings later in your career, to evaluating if an annuity fits your fear for a down market, to determining which accounts to spend first in retirement for tax planning purposes. This episode explores practical strategies retirees often wonder about as they transition from saving to spending.

Topics include:

💭 Should you contribute to a Roth 401(k) or a Roth IRA if most of your savings are pre tax?

💭 What annuities may help solve and what questions to think through before purchasing one

💭 Why "market like returns without losses" deserves a closer look

💭 How retirement income planning differs from accumulation

💭 Which accounts retirees often spend first and why withdrawal order matters

💭 How taxes, Medicare premiums, and future RMDs can influence retirement decisions

💭 Strategies for balancing Roth, pre tax, taxable, and cash accounts

Whether you're approaching retirement or already retired, understanding how your accounts can work together may help you make more informed financial decisions!

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

Chapters:

00:13 Football Season is Here and Question Overview

03:00 Switch to Roth 401(k) or Roth IRA?

03:13 Tax Diversification Strategies

07:51 Keep Less in My Bank Account Now?

08:51 Annuity a Good Fit For Me?

15:01 What Accounts to Spend First In Retirement?

21:59 Michael's Attempt at Being a Trophy Husband

#RetirementPlanning #RothIRA #Roth401k #RetirementIncome #Annuities #TaxPlanning #RetirementTaxes #financialplanning

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.

Many people approaching retirement find themselves asking the same question: Do I have enough to retire, or do I need to work a few more years?

In this episode of Common Curiosities: Retirement, Michael CFP®, EA, CSS™ walks through a retirement case study of a couple in their early 60s who hope to retire at age 65. Using retirement planning software, Michael explores how what accounts to use these final years, retirement expenses, Social Security timing, healthcare costs, and tax planning decisions may influence the likelihood of your retirement goals.

Topics include:

💭 Can this couple retire with roughly $700,000 in a few years?

💭 Why healthcare costs can significantly impact retirement plans

💭 How retirement spending assumptions affect success rates

💭 Roth 401(k) versus Traditional 401(k): which may make more sense near retirement?

💭 Why current and future tax brackets matter when deciding between pre-tax and Roth contributions

💭 Why keeping too much cash in the bank may create unintended tax consequences

💭 Understanding Monte Carlo simulations and retirement probability analysis

If you're wondering whether you're on track for retirement, this episode provides a practical look at the tradeoffs between working longer, spending differently, and making more tax-efficient planning decisions.

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

Chapters:

00:13 Introduction to Retirement Analysis

01:08 Understanding Financial Position and Goals

03:03 Evaluating Retirement Expenses and Income Needs

03:30 Monte Carlo Simulation and Probability of Success

05:15 Strategies to Improve Retirement Outcomes

08:10 Could Save On Taxes & Reinvest for Final Years?

10:36 Should I Reduce My Checking Account at This Point?

12:46 Final Thoughts and Ideas

#RetirementPlanning #Retirement #FinancialPlanning #TaxPlanning #RothConversion #401k #SocialSecurity #RetirementIncome #CFP #RetireAt65

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.

Many people entering their final working years find themselves with more cash flow. The question then becomes: Where should those extra dollars go to try and strengthen your retirement future?

In this episode Michael CFP®, EA, CSS™ walks through a case study of a couple in their early 60s who are trying to make the most of their final working years. The discussion explores how different account types, tax brackets, and retirement contribution strategies could impact both current taxes and future retirement income.

Topics include:

💭 Why the years just before retirement can be a tax planning sweet spot

💭 Should extra savings go into a brokerage account, Roth IRA, or pre-tax retirement account?

💭 How the age 59½ age can change savings decisions

💭 Why taxable interest and dividends may create hidden tax drag

💭 The difference between marginal and effective tax rates

💭 How pre-tax 401(k) contributions could potentially lower your tax bill

💭 When it may make sense to target specific tax brackets

💭 A strategy for combining pre-tax and Roth contributions

💭 How capital gains tax rates can change based on taxable income

💭 Common mistakes pre-retirees make with excess cash flow

If you're within a few years of retirement and wondering how to try and make your savings work more harder for you, this episode provides several planning ideas to consider with your financial and tax professionals!

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

Chapters:

00:13 Where to Put Dollars In Final 3-5 Working Career

02:30 $140k Income Example

03:31 Different Taxes On Type of Investments

04:34 Marginal and Effective Tax Rates

05:35 Impact of $15k Tax Deduction?

08:02 Wait, Spend Down My Savings Before Retirement?

08:47 Tax Ideas for Retirement Savings

10:59 Combine Roth & Pre-Tax Savings?

13:35 This Even Matter and Help?

14:17 Final Ideas & Considerations

#RetirementPlanning #TaxPlanning #401k #RothIRA #RetirementIncome #FinancialPlanning #PreRetirement #RetirementTaxes #PersonalFinance #cfp

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.

Retirement planning gets complicated fast, so we’re discussing four common areas retirees and pre‑retirees wonder about. From planning for future Required Minimum Distributions, tax‑smart giving ideas, to how large IRA withdrawals could impact your Medicare costs. Michael a Certified Financial Planner™, Enrolled Agent, and Certified Social Security & Medicare Specialist™ helps walk through these key concepts.

Topics include:

💭 What happens if you don't need your Required Minimum Distributions?

💭 Qualified Charitable Distributions (QCDs) and how they may be able to help your taxes and charitable giving plans

💭 How Roth conversions may help reduce your future Required Distributions

💭 Why large IRA withdrawals may trigger added Medicare costs

💭 Does it make sense to split up large purchases?

💭 Why gifting investments instead of cash might make sense

💭 How to think about Roth conversion decisions

💭 Why inheritance goals should impact your Roth conversion planning

💭 The difference between asset allocation and asset location

💭 Common retirement tax planning mistakes people may want to avoid

Retirement planning is rarely just about investments. Taxes, Medicare, charitable giving, Social Security, spending strategies, and account structure all work together to build your plan. Understanding how these pieces interact may help create more flexibility and efficiency throughout your retirement.

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

Chapters:

00:13 Trying to Limit Medicare Costs, Tax Smart Giving, Required Distribution Planning

01:00 How Could I Limit Required Distribution Issues?

04:22 Reduce RMDs with Roth Conversion?

05:45 Changing Where I Own Certain Assets

06:37 Medicare Surcharge Concerns

07:55 Split a Large Purchase for Taxes & Medicare?

10:07 Can We Gift More Tax Efficiently?

11:01 Gift Your Investments?

11:54 Trying to Raise Your Basis for Taxes

14:47 Worth the Tax Now for Maybe Less Later?

16:15 Who All Are You Tax Planning For?

19:21 Future Tax Thoughts?

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.

When you approach retirement and prepare to cross the work finish line, you are flooded with conflicting opinions on how to actually spend the money you worked your entire career to save. But the reality is that every withdrawal strategy comes with pros and cons. Two neighbors with the exact same net worth might want completely different income structures based on their goals and how they handle market volatility.

In this episode, Michael CFP®, EA, CSS™ aims to help you learn about four common retirement income approaches. Navigating the distribution phase of wealth is rarely a black-and-white math problem; it's about understanding the gray areas so you can try to build yourself an efficient stream of income that fits your retirement goals.

📘 What We Analyze In This Episode:

💭 Annuities: The mechanics of giving money to an insurance company to generate retirement income.

💭 Dividends: Pros and cons of living off dividends

💭 The 4% Rule: The origin of this framework, its modern updates, and why sticking to it may actually cause you to underspend!

💭 The Guardrails Approach: A more dynamic spending framework

💭 Behavioral Volatility: How your personal emotional relationship with market ups and downs may dictate your withdrawal strategy.

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.

You’ve hit the million-dollar mark and retirement is finally in sight! But is it actually enough to stop working now without running out of money later? Shifting from a working mindset to turning those savings into an income stream can be incredibly nerve-wracking.

Welcome back to Common Curiosities: Retirement. Today, we’re trying to help a couple navigate this exact transition so they may confidently step away from work and start enjoying their retirement.

In this episode of Common Curiosities: Retirement, Michael CFP®, EA, CSS™ walks through a few pieces of a retirement planning case study for a couple in their early 60s trying to decide whether they can retire now or if working one more year may dramatically improve the outlook. The episode explores how spending, Social Security timing, investment allocation, healthcare assumptions, and tax planning can all change retirement projections.

Topics include:

💭 Is $1 million enough to retire in your early to mid 60s?

💭 How retirement income projections are tested using planning software

💭 Why “probability of success” does not need to be 100%

💭 Sequence of returns risk and why early retirement withdrawals can feel stressful

💭 Whether delaying Social Security may improve long term retirement income

💭 Why healthcare cost assumptions can dramatically impact retirement projections

💭 Situations where Roth conversions may not make sense

💭 How investment allocation and withdrawal strategy plan may improve retirement flexibility

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

Chapters:

00:13 $1 Million Saved. Do We Have Enough?

01:05 Case Study: Madonna and Frank's Retirement Planning

04:17 Cash Flow Analysis

06:27 Simulation Thoughts

08:12 Does One More Year Matter?

09:06 What Adjustments Could We Make Instead?

09:49 S.S. Now Or Wait?

11:30 Roth Conversions: Pros and Cons?

13:14 Health Costs and Their Impact on Retirement

14:08 Don't Automatically Assume Working Longer is the Only Option

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.

Finishing your degree, landing that first “real” job, and finally getting the paycheck you worked years for can feel incredible… until the student loans, retirement decisions, taxes, and benefit elections all show up at once.

In this episode of Common Curiosities: Retirement, Michael and Jacqueline sit down with Alyssa, a recently graduated Speech Language Pathologist looking for help on navigating her first year in practice while trying to plan for her future.

Instead of turning this into a lecture filled with jargon and spreadsheets, this episode walks through the real questions many early career professionals are quietly asking themselves but often don't get help with.

Topics include:

💭 Understanding the tradeoffs between PSLF and aggressive student loan payoff strategies

💭 Breaking down how you're taxed now that you landed your job

💭 Why keeping too much cash in a traditional savings account may quietly work against you

💭 How SIMPLE IRAs, 401ks, employer matches, pensions, and workplace benefits work

💭 How beginners often get started

💭 Trying to balance living today while still building flexibility for the future

A lot of strong financial habits begin during the messy transition period between school and full professional life. This episode is designed to help make those early decisions feel a little less overwhelming and a little more approachable.

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.