Common Curiosities: Retirement

Custer Financial Advisors
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Welcome to Common Curiosities: Retirement, where we explore financial questions many people ask as they prepare for retirement. By breaking down real world planning situations, we discuss retirement planning, tax strategies, investing, Social Security, Medicare, and other financial topics that may shape your retirement dreams. Our goal is to make complex ideas easier to understand so you could make more informed decisions and feel more confident about the retirement road ahead.

  1. 16h ago

    Key Retirement Planning Decisions | Taxes, Medicare Costs & Required Distribution Planning

    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.

  2. Aug 5

    4 Retirement Income Strategies | Pros, Cons & Finding Your Fit

    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.

  3. Jul 29

    Early 60s with $1 Million Invested... Think I Can Retire?

    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.

  4. Jul 22

    Landed Your First Career Job? Planning Around Loans, Housing, & Retirement

    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.

  5. Jul 15

    Physician Q&A: Disability Coverage, Target Date Funds, Roth or Pre‑Tax

    Being a physician often means years of delayed income, massive student loans, confusing benefit decisions, and suddenly jumping into a much higher tax bracket without much financial education along the way. In this episode of Common Curiosities: Retirement, Michael CFP®, EA, CSS™ walks through questions from physicians. Topics include: 💭 Own occupation vs any occupation disability insurance for physicians 💭 Why disability coverage may matter more for doctors with specialized skills 💭 When residents may prioritize investing or paying off student loans 💭 How student loan forgiveness strategies can change financial planning decisions 💭 Target date funds inside a 401(k) vs a non-retirement account 💭 Why taxes may matter more than many physicians realize when investing 💭 Roth vs. traditional retirement contributions for young attendings 💭 How future income, tax brackets, and retirement goals may shape savings strategies 💭 Why financial planning for physicians often changes dramatically between residency and attending years As always, this episode is focused on helping you think through the moving pieces, try to improve your money plans, and stay curious about how financial decisions fit into your overall plan. 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 Physician Planning Stages 01:03 Disability Insurance for Physicians 01:55 Own Occupation vs Any Occupation 04:13 Student Loans or Invest? 06:15 Evaluating Investment Options: Target Date Funds 09:40 Choosing Between Roth & Traditional Contributions 14:06 Why's Michael Proud of Himself? 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.

  6. Jun 26

    Reddit Q&A: Are 15 Funds Enough? 401(k) Taxes & Wills Explained

    In this episode Michael CFP®, EA, CSS™ answers four retirement planning questions found with Reddit to hopefully help answer people's questions! 𝐓𝐨𝐩𝐢𝐜𝐬 𝐢𝐧𝐜𝐥𝐮𝐝𝐞: 💭 Is having a will enough to avoid probate? 💭 Pros/Cons of putting retirement savings in a savings account? 💭 Do you owe taxes when selling investments in a 401(k)? 💭 Does owning 15 mutual funds mean you're diversified enough? 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 Reddit Questions Help 00:39 Does a Will Keep Us Out of Probate? 01:04 Putting Retirement Savings in Cash? 03:04 Owe Tax on Gain in 401k? 03:31 15 Funds. Am I Diversified Enough? 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.

  7. Jun 24

    Do You Actually Need Life Insurance? 5 Real-Life Scenarios Asked

    Is life insurance a necessary cost or are you paying premiums for coverage you’ve outgrown? Michael Custer CFP®, EA, CSS™ is transparent about his take on the industry. He doesn't love paying for insurance, but it's valuable when needed. So, when would he look at getting life insurance, and when would he pass? Also, what type of insurance does he lean toward? Today, he breaks down some real-world scenarios aimed to help you decide if coverage may be a good idea for you or may skip it! Here are the scenarios he explores in this episode: 💭 Term vs. Whole vs Variable Life 💭 What's laddering life insurance policies? 💭 The Young Family: How you may structure coverage for a single-income household with three kids. 💭 The Single Professional: Why he might skip the policy entirely 💭 The Small Business Owner: How you may use buy-sell agreements 💭 The Pre-Retiree with retirement savings but lost their job 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: 00:00 Thought on Life Insurance 00:56 Comparing Different Life Ins. Types 03:21 Stay Home Spouse & 3 Kids 04:38 What's Laddering a Life Policy? 05:42 Single and No Kids. Need Life Insurance? 06:10 Own Small Business. Need Life Ins.? 07:11 Business Buy-Sell Agreement? 07:40 65 & Laid Off. Keep Our Insurance? 09:28 Married & Have a Kid Now 12:55 Life Ins. Premium Disclosures .mp3 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.

  8. Jun 10

    Can You Get Social Security on an Ex‑Spouse? Ideas for an Annuity You Don’t Want & More! Q&A

    Turns out, a lot of people have the same questions sitting in the back of their heads. They just don't always know who to ask or are scared to ask! In this episode, Michael Custer CFP®, EA, CSS™ digs into four questions. The kind that sound simple on the surface but can get complicated when planning in depth. We're working through the tradeoffs, the gray areas, and the decisions that may look different for everyone. Also… a quick detour into Buc-ee's. Because apparently a gas station can have a great brisket sandwich?! Topics include: 💭 Social Security and divorce. When you can (and can't) claim off an ex-spouse 💭 What happens to Social Security when a spouse passes away 💭 Annuities. What to options there may be when you don't want it anymore. 💭 How to think about surrender charges and your options for getting out 💭 Should this couple stash cash, payoff the home, or invest to retirement more? 💭 Why the "best" financial move isn't always just about the math The goal isn't to hand out one-size-fits-all answers. It's to help you think a little more clearly about your own situation, your own tradeoffs, and what might make the most sense for you. Two people can make completely different decisions… and both can be on the right path. Stay curious our friends! 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.

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About

Welcome to Common Curiosities: Retirement, where we explore financial questions many people ask as they prepare for retirement. By breaking down real world planning situations, we discuss retirement planning, tax strategies, investing, Social Security, Medicare, and other financial topics that may shape your retirement dreams. Our goal is to make complex ideas easier to understand so you could make more informed decisions and feel more confident about the retirement road ahead.

Information

  • Creator
    Custer Financial Advisors
  • Years Active
    2025 - 2026
  • Episodes
    67
  • Rating
    Clean
  • Copyright
    © Custer Financial Advisors
  • Show Website
    Common Curiosities: Retirement

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