PodParley PodParley

Tax Return Red Flags

Episode 443 of the Retirement Starts Today podcast, hosted by Benjamin Brandt CFP®, RICP®, titled "Tax Return Red Flags" was published on March 9, 2026 and runs 21 minutes.

March 9, 2026 ·21m · Retirement Starts Today

0:00 / 0:00

Sheryl Rowling positions income tax returns as diagnostic tools — not merely a compliance document — and outlines four common red flags that suggest a client failed to take advantage of proactive tax strategies.

Here are "4 Tax Return Red Flags That Signal Poor Tax Planning":

  1. Very Low or Zero Taxable Income
  2. Charitable Giving After Age 70½ Without Using QCDs
  3. Donating Cash Instead of Appreciated Securities
  4. Holding Municipal Bonds in Low Tax Brackets

For our listener question: "I'm in a job I hate and would love to scale back to something that could pay less but be more enjoyable -- how can I evaluate if that is possible?". Most people think the first question is: "How much do I have saved?", but that's actually backwards. I share a calculation for cash burn that matters more than your portfolio balance.

And to wrap up the show in our "Retire to Something" segment, I'll share Jerry's story that shows us how retirement isn't about winding down — it's about doubling down on growth, adventure, and intentionally building an active, meaningful life. 

 

Resource:
Article by Sheryl Rowling on Morningstar: 4 Tax Return Red Flags That Signal Poor Tax Planning

 

Connect with Benjamin Brandt:

Get the book!
Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Follow Retirement Starts Today in:
Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

 

The Boldin Your Money Podcast Steve Chen Welcome to the Boldin Podcast — your trusted source for retirement planning, financial wellness, and purposeful living. Formerly known as NewRetirement, Boldin is on a mission to empower you to take control of your financial future. Whether you're nearing retirement, already retired, or just starting to plan, we cover what matters most: money, lifestyle, health, meaning, and how to retire smarter.Each episode features expert interviews and actionable insights on topics like retirement income strategies, Social Security planning, saving for retirement after 50, and creating a fulfilling life after work.Ready to start your journey? Explore the best free retirement planning tool and a library of financial resources at Boldin.com — and take the first step toward financial independence and a well-lived life. The Lifestyle Builders Podcast Tom and Ariana Sylvester This podcast is for you if you are looking to build the ideal lifestyle for you and your family. Tom and Ariana Sylvester are serial entrepreneurs who are passionate about helping others achieve success in business and in life. They have started and operate multiple businesses, from real estate investing to running a wine and liquor store to business strategy & entrepreneur coaching, they have done a little bit of everything. But it's not all about business here. Tom and Ariana are also married & parents to 2 young kids, so they share strategies and lessons for how to not only start and grow your business, but also how to create a great life for your family. From goal planning, time management, getting out of debt, getting your spouse on board, testing & validating your business idea, pushing past fears, systems & processes, increasing profitability, getting your time back, and practical ways to plan out & achieve financial freedom and early retirement, this podcast will give you e Mischief Improv David Escobedo Follow the start of an improv team in Chester, England. David Escobedo has been performing improv since 1995 and has directed/produced 100's of improv shows ranging from Long Form to Short Form, and from Street Performances to Happenings. This podcast will give you the Warm-Up's, Exercises and some of the challenges that arise from promoting, producing an improv team consisting of many people who have never heard of improv before! This documentation occurs as a requirement from his Master's Thesis from University of Chester and in conjunction with his internship at Storyhouse The Retirement Roadmap Podcast Glenn Mosseller Retirement Insights From Greensboro's Glenn Mosseller
URL copied to clipboard!