End of Year Checklist for Your Taxes, Points and Miles
All the Hacks: Money, Points & Life
Wash Sale Rule and Loss-Pairing Options
Chris covers the 30-day wash sale rule, using non-identical ETFs to harvest losses, and crypto exceptions.
#257: We break down essential tax and financial decisions to make before year-end. Learn how to maximize deductions, optimize charitable giving, manage investment gains and losses, and take advantage of retirement and home-improvement credits. We also run through all the credit card, points and miles deadlines to hit before 12/31.
Link to Full Show Notes: https://chrishutchins.com/end-of-year-financial-checklist-2025
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Resources Mentioned
Chris' End of Year Checklist for Taxes, Points & Miles
Carry Solo 401k
Kick (20% off your first year of bookkeeping with code CHRIS20)
Invest America Kids Savings & Investment Accounts
CardPointers Pro (50% off here)
ATH Podcast
- Chris’ Best Cards Page
- Ep 144: Leveraging Tax-Advantaged Accounts to Maximize Your Wealth with Katie Gatti Tassin
- Ep 243: Smarter Strategies for Retirement, Wealth Building, and Taxes with Michael Kitces
- Leave a review: Apple Podcasts | Spotify
- Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com
Full Show Notes
(00:00) Introduction
(01:03) Standard Deduction vs. Itemizing
(03:02) The New SALT Cap & Property Tax Strategy
(05:02) Pass-Through Entity Taxes for Business Owners
(06:07) Smart Charitable Giving Strategies
(07:07) Donating Appreciated Assets
(09:18) Using Donor-Advised Funds (DAFs)
(14:16) Why 25-26 Changes Matter for Charitable Giving
(16:14) New Car Loan Interest Deduction
(18:19) Deduction for Qualified Tips & Overtime
(18:34) New Senior Deduction
(19:12) Shifting Income to Optimize Your Tax Bracket
(20:48) Capital Gains: Loss & Gain Harvesting
(22:02) Understanding the Wash Sale Rule
(25:11) Advanced Tax Moves to Ask Your CPA
(25:42) Key Retirement Deadlines & Contribution Limits
(31:01) Roth IRA & Traditional IRA Rules
(34:18) Backdoor & Mega Backdoor Roth Contributions
(35:18) ISOs & Alternative Minimum Tax
(36:16) FSA Essentials: Use It or Lose It
(38:57) HSA Strategy & Triple-Tax Advantage
(42:13) Home Efficiency & Solar Credits for 2025
(43:14) 529 Plans, Gifting Rules & Education Savings
(47:37) The New “Trump Account” for Kids
(48:14) Funding a Child’s Roth IRA Through Earned Income
(50:29) EOY Tax Moves for Business Owners
(55:51) EOY Checklist for Points & Miles
(01:00:32) Credit Card Annual Credits & Benefit Resets
(01:03:57) Calendar-Year Credits to Use Before January
(01:14:55) Final EOY Checks for Airlines, Hotels & Credit Cards
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