The 5 Biggest Retirement Tax Mistakes Made at Filing Time (And How to Avoid Them) [Ep 45]

How to Talk to Your Aging Parents About Their Money [Ep 49]

Is talking openly about money with aging parents really necessary — or can it wait?  In this episode of Navigating Retirement, Certified Financial Planners Brad Lineberger and Matt Callahan share what happens to families who skip this conversation, and give you a clear framework for having it before it's too late. They cover why a will alone still sends your assets to probate, how to confirm a trust is actually funded, why beneficiary designations on IRAs and life insurance override everything in the trust, and why any trust written before 2010 needs an immediate review. Plus — why naming a child as executor sets families up for conflict, and how LastPass, Keeper, and the "when I die binder" keep your family safe from getting locked out. TIMESTAMPS   (0:00) Why Talking Money with Aging Parents Can Save Your Family (0:38) Why Aging Parents Won't Talk About Money (1:19) The Real Cost of Silence: Families Torn Apart (1:48) The Cost of Aging: Don't Get Caught Off Guard (2:22) Messy Accounts, Wrong Beneficiaries, Hard-to-Unwind Estates (2:44) How to Approach the Conversation: Love, Grace, Role Reversal (4:32) How to Open the Dialog: Gratitude First, Grandkids Second (5:50) What to Walk Away Knowing: Assets, Location, and Wishes (6:55) Wills vs. Trusts — Why a Will Alone Leads to Probate (7:33) Is the Trust Actually Funded? (9:05) The Conduit IRA Trust — And Why Pre-2010 Trusts Need a Review (10:21) Beneficiary Designations Override the Trust — And Become Law (10:47) Choosing an Executor — Why Naming a Child Is a Mistake (11:17) The Case for a Professional Fiduciary (12:44) Wills Are Public Record — Trusts Keep Your Estate Private (13:00) Probate Costs 2–6% — Here's How a Funded Trust Prevents It (13:29) Scattered Accounts: Clean Up the Mess Now (14:35) Power of Attorney and Trusted Contacts (15:04) Passwords and the "When I Die Binder" (16:33) The Bottom Line: Just Do It (17:06) Expenses, Bills, and Mom and Dad's Full Financial Picture (17:48) What the Non-Financial Spouse Needs to Know (19:22) How Seaside Helps Families Have the Hard Conversations More episodes & free consultation: https://www.seasidewealth.com/podcasts [https://www.seasidewealth.com/podcasts]

Should You Downsize Your Home in Retirement? [Ep 48]

Is selling your home and downsizing in retirement actually a smart move — or a costly mistake? In this episode of Navigating Retirement, Certified Financial Planners Brad Lineberger and Matt Callahan break down the real pros, cons, and tax consequences of downsizing, so you can make the right call for your financial future and your quality of life. They cover the Section 121 capital gains exclusion (up to $500,000 for couples), how home improvements affect your cost basis, the hidden tax traps, including net investment income tax and IRMAA Medicare surcharges, and why the step-up in basis at death could save six figures in taxes. Plus — why renting first before committing to a new city might be the smartest move you make. TIMESTAMPS  (0:00) Is Your Home an Asset or a Liability in Retirement? (0:45) Pros and Cons of Downsizing: The Big Picture (1:26) Before You Sell: Why You Should Rent First (3:25) The Community and Connection Risk Most People Ignore (3:45) Section 121 Tax Exclusion Explained (4:54) Why Your Home Improvement Receipts Could Save You Thousands (5:46) Capital Gains Rates, NIIT, Medicare IRMAA, and AMT (7:03) Moving Out of State: Property Tax Surprises (7:51) Real Example: Walking Through the $1M Home Sale Math (10:16) Should You Pay All Cash for Your Next Home? (10:58) 1031 Exchanges: What Applies to Primary Residences (12:27) The Advanced 1031 Strategy for Rental Property Owners (13:12) The Section 121 Exclusion Isn't a One-Time Deal (13:31) Downsides of Relocating: HOA Fees, Lost Community, and the Grandkid Study (15:08) Pros of Downsizing: No Mortgage, Aging in Place, Less Upkeep (17:30) The Step-Up in Basis Strategy — When NOT to Sell (19:22) Final Thoughts: Make This Decision Inside a Plan More episodes & free consultation: https://www.seasidewealth.com/podcasts [https://www.seasidewealth.com/podcasts] #retirementplanning #downsizinginretirement #sellyourhome #retirementtaxes #homeequity #section121 #capitalgains #realestateretirement #medicarepremiums #irmaa #1031exchange #stepupinbasis #retirementincome #financialplanning #certifiedfinancialplanner #navigatingretirement #seasidewealth #retirementstrategy

3 Ways To Make RMDs Work For You [EP 47]

Are required minimum distributions creating tax bills you weren't expecting in retirement? In this episode of Navigating Retirement, Certified Financial Planners Brad Lineberger and Matt Callahan break down three strategies to lower your RMDs, reduce your lifetime tax bill, and stop overpaying the IRS. They cover Roth conversions in the gap years, QCDs for tax-free charitable giving up to $111,000 in 2026, and investing RMD proceeds in a taxable account — plus the inherited IRA 10-year rule and why converting at today's tax rates could save you significantly down the road. More episodes & free consultation: https://www.seasidewealth.com/podcasts [https://www.seasidewealth.com/podcasts] #retirementplanning #requiredminimumdistributions #rothconversion #taxplanning #navigatingretirement #seasidewealth

What Happens to Your Retirement Plan If You Get Divorced? [EP 46]

Is a late-life divorce putting your retirement at risk? In this episode of Navigating Retirement, Certified Financial Planners Brad Lineberger and Matt Callahan break down the financial moves you need to make — and the costly mistakes to avoid — when divorce happens after 50. They cover how a QDRO lets you split a 401(k) without triggering a tax bill, when to keep assets in a 401(k) versus rolling to an IRA, how to claim Social Security spousal and survivor benefits from an ex-spouse (without them ever knowing), the Section 121 exclusion that can shield up to $500,000 in home sale gains, post-2018 alimony tax rules, COBRA and health insurance gaps, and why updating beneficiaries across every account is the single most important action step after a divorce is finalized. Whether your split is amicable or contentious, this episode gives you a clear, practical framework to recalibrate your financial plan and keep your retirement on track. More episodes & free consultation: https://www.seasidewealth.com/podcasts [https://www.seasidewealth.com/podcasts] #graydivorce #retirementplanning #socialsecurity #navigatingretirement #seasidewealth

The 5 Biggest Retirement Tax Mistakes Made at Filing Time (And How to Avoid Them) [Ep 45]

Are you unknowingly handing the IRS more than you owe? In this episode of Navigating Retirement, Certified Financial Planners Brad Lineberger and Matt Callahan walk through the five biggest retirement tax mistakes made at filing time — covering tax gain harvesting at the zero-percent capital gains rate, the Social Security tax torpedo, IRMAA Medicare thresholds, qualified charitable distributions, and how to optimize your tax brackets year-round with Roth conversions and smart IRA distributions. Whether you're already retired or approaching it, this episode gives you a practical, forward-looking tax planning framework to keep more of your money — and stop giving it to Uncle Sam. More episodes & free consultation: https://www.seasidewealth.com/podcasts [https://www.seasidewealth.com/podcasts] #retirementtaxplanning #rothconversion #socialsecurity #navigatingretirement #seasidewealth