End of Year Checklist for Your Taxes, Points and Miles

Key takeaways

Understand whether to take the standard deduction or itemize based on your financial situation.
Use charitable giving effectively to maximize deductions, especially focusing on appreciated asset donations.
Take advantage of capital gains strategies by understanding loss harvesting before year-end.
Complete retirement account contributions before year-end to maximize savings and tax benefits.
Keep track of credit card perks and points to ensure no benefits are left unused before the calendar year ends.

Summary

Tax Strategies for Year-End Planning

In the episode, Chris discusses various strategies around taxes that can lead to savings before the end of the year. He emphasizes the importance of deciding whether to take the standard deduction or itemize deductions. Chris breaks down the new adjustment for the state and local tax (SALT) cap and suggests strategies for pre-paying property taxes, making adjustments to charitable giving, and utilizing deductions related to mortgage interest to navigate these tax options effectively.

Optimizing Charitable Giving

A significant portion of the episode is dedicated to charitable giving strategies. Chris discusses the different ways to give—cash vs. appreciated assets—and highlights the benefits of donating stocks to avoid capital gains taxes. He explains the advantages of using Donor-Advised Funds (DAFs) as a way to manage charitable giving over the years while discussing changes to charitable deductions coming in 2025.

Investment and Capital Gains Strategies

Listeners are guided on capital gains and loss harvesting with actionable tips on how to minimize tax liabilities on investments. Chris explains how capital losses can offset gains and discusses the importance of being aware of the wash sale rule in investment strategies. He further emphasizes capital gain harvesting for those in lower income years to avoid higher tax brackets.

Retirement Accounts and Contributions

Chris outlines crucial deadlines for retirement account contributions, discussing the benefits of both traditional and Roth IRAs. He emphasizes the Mega Backdoor Roth as a strategic tool for high earners and explains the importance of completing contributions before the end-of-year deadline. Additionally, he covers specifics on contributions for HSA accounts and the associated benefits.

End-of-Year Financial Checklist for Points and Miles

The episode wraps up with a checklist for managing credit card points and miles before the year ends. Chris details various strategies to earn status through travel, reiterating the importance of tracking points expiration and maximizing annual benefits from credit cards. He provides specific points on how to use up credits and hints at ways to net additional bonuses via spend.

Show notes

#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

Hotel Mattress Run

CardPointers Pro (50% off here)

Use Your Credits

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

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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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