Common Curiosities: Retirement

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 b...

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...

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...

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 ty...

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 the...

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 m...

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 confid...

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 navigatin...

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 p...

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?...

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 rea...

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 l...

A lot of retirement withdrawal advice is simple: Something like 1.) Spend your brokerage account first, then 2.) Use our pre-tax accounts, and 3.) save the Roth assets for last. But when you really study it, does that always make the most sense? In this episode, Michael Custer CFP®, EA walks through a different way to think about retirement income. Instead of following a rigid order, this conversa...

Homeowners do have access to valuable tax deductions and strategies but most people only know about one or two of them. In this episode, Michael Custer CFP®, EA explores some of the most common tax planning tools available on your primary home. 𝐖𝐡𝐚𝐭 𝐘𝐨𝐮'𝐥𝐥 𝐋𝐞𝐚𝐫𝐧! 💭 The mortgage interest deduction: Who qualifies, the limits, and why many people don't use it. 💭 Property tax deductions, inc...

In the previous episode, we broke down what IRMAA is and why it catches so many retirees off guard when it comes to Medicare surcharges. Now it's time to actually see it in action. In this episode, Michael Custer CFP®, EA pulls up real retirement and tax planning software tools and walks through a live scenario — showing how Roth conversions, IRA distributions, and even paying off your home co...

Are you doing Roth conversions without checking this first? If you're not factoring in Medicare surcharges (IRMAA), you could accidentally be paying more for Medicare without even finding out until two years later. In this episode, Michael Custer CFP®, EA breaks down one of the hidden cost of "blind" Roth conversions he sees often. Why could converting too much trigger an Medicare su...

When it comes to investing, a lot of the terminology can feel confusing. What is active vs passive investing? What does alpha actually measure? And what happens if you want to get out of an annuity but there is a surrender charge involved? In this episode of Common Curiosities: Retirement, Michael CFP®, EA walks through three questions that came up. Topics include: 💭 The difference between active...

We find that many people heading into retirement aren't aligning their own life with their investment portfolio and they don't even know it! The investment industry has often placed people in specific investments based upon their age, but why may you want to build a custom investment portfolio based on your life and instead of your age? Here's what we cover: 💭 Why your life and goals — not your a...

What do your taxes actually look like right now and what might they look like in retirement? In this episode, Michael CFP®, EA walks through a listener question from a couple earning $250,000 who wanted to understand their tax picture today, if their 401k contributions are actually helping them much, and what retirement might look like if they plan to spend $100,000/year. This is a step by step wa...

There are so many types of retirement accounts out there… and let’s be honest, most people have no idea what any of them really mean. Whether you’re self‑employed and choosing a plan for your business or trying to learn about the one your employer offers, this episode should help. Jac brings a list of retirement accounts she recently came across and puts Michael CFP®, EA on the spot with a rapid f...

Is there really something magical about having $100,000 invested? Or is it just a shiny milestone that gets a little too much hype? In this episode Jacqueline and Michael unpack the idea of the “$100K magic number” and why it feels so powerful emotionally even though nothing actually flips a switch in your investments overnight. They talk through why the first $100,000 often feels like the hardest...

Budgeting has a reputation for being boring… but does it really have to be? Are there simpler, more flexible ways to manage your money than the old-school method? Instead of pushing a one size fits all spreadsheet, we walk through two very different approaches to budgeting. 1.) The traditional line by line method and 2.) A reverse budgeting system Michael likes to use. Topics include: 💭 Tradition...

How do you actually spend more in retirement? It's not typically by letting the IRS quietly become your biggest business partner via taxes without a plan. In this episode of Common Curiosities: Retirement, we unpack a few of the most overlooked ideas aimed at helping you spend more in retirement. The quiet, low tax years right after retirement feel great… until RMDs, Medicare surcharges, Social Se...

Most people don’t lie awake thinking about Restricted Stock Units (RSUs). Until they have some and then tax time hits. Then suddenly… curiosity shows up quickly. RSUs aren't the most complex form of equity compensation but they can be tricky. RSUs often sneakily behave like a cash bonus for people and if you don’t plan for them properly, they can quietly create tax surprises, risk concentratio...

Are leveraged ETFs a smart move or a hidden risk? What does “negative yield on cash” actually mean? And how should you think about investing when markets fall? In this episode Michael CFP®, EA breaks down leveraged ETFs, market downturn strategy, and negative yields in plain language so you can understand what may make sense for you and your plan! Topics covered in this episode: 💭 Ideas you may c...