Episode 13: Your Mid-Year Financial Checkup
Summertime is for flip-flops and financial tune-ups. In this episode, Greg and Tom walk you through a four-part mid-year checklist: taxes, insurance, estate planning, and retirement savings. You'll hear practical tips on everything from saving money on your car insurance to gifting appreciated assets to your kids, plus what to ask your tax advisor now (not next April).
00:30 – Why Summer Is Checkup Season
Fewer distractions, more advisor availability, and time to prep for year-end
Start with insurance policies, wills, trusts, and directives
01:24 – Taxes: The Most Underrated Planning Tool
Think ahead, not backwards. April is too late
Get your tax professional on the calendar this summer
02:58 – Understanding Retirement Taxes
Different income types mean different tax rules
Why retirement taxes deserve a game plan
03:44 – TikTok Claims: $121K with No Capital Gains?
Greg fact-checks the viral claim
True for some, but it depends on AGI and filing status
04:42 – Tax-Loss Harvesting Basics
Pairing gains with losses to reduce taxable income
Why waiting until December could cost you
06:11 – The Clock Is Ticking
Charitable giving, rebalancing, and conversions must happen before December 31
Plan now so you don’t scramble later
07:04 – Bucket Planning Breakdown
The importance of having all three types: pre-tax, Roth, and taxable
Too much in pre-tax? It's time to rebalance
09:05 – Smart Gifting Strategies
Gift appreciated assets to lower-income family members
Annual gifting limits and avoiding capital gains
10:35 – Use Your Tax Return as a Planning Tool
Bring last year’s return to your advisor
What’s changed? What needs updating?
12:21 – Stewardship and Strategic Planning
Financial awareness means taking care of your family
Being a good steward isn’t just biblical, it’s practical
12:51 – Insurance Savings Are Hiding in Plain Sight
Why you might be overpaying for homeowners and auto
The power of comparison shopping
14:19 – To-Do List: Simple Summer Assignments
Pull your tax return and insurance declarations
How to request quotes quickly (and without phone calls)
16:30 – Hidden Gaps in Coverage
Roadside assistance, deductible surprises, and other things people miss
How a five-day waiting period nearly caught Tom off guard
18:35 – Are You Underinsured on Life?
Your coverage should grow with your income
Update policies to match today’s needs, not yesterday’s salary
19:42 – The Big Three Estate Planning Documents
Will, power of attorney, and medical directive
Make sure they’re signed, updated, and accessible
20:45 – Are You on Track for Retirement?
Mid-year is the perfect time to check savings goals and projections
Use our 60-point checklist to make sure you’re covering all the bases
21:56 – Sometimes the Win Is Avoiding the Loss
Avoiding catastrophe is just as important as growth
A small change could prevent a big problem
22:21 – Final Thoughts
Enjoy your summer, but make time for your financial checkup
You’re the manager of your resources. We’re here to help