Category Archives: Taxes

A retirement planning expert dives into the Big Beautiful Bill

Posted on July 9, 2025 by Tipswatch

By David Enna, Tipswatch.com Just to give you an idea of how complicated taxes are: For my last post, discussing the tax on Social Security benefits, I made 27 edits and revisions within a day of publishing as I received … Continue reading →

Posted in Retirement, Social Security, Taxes | Tagged , , , , | 7 Comments

No tax on Social Security benefits? Not quite true.

Posted on July 5, 2025 by Tipswatch

By David Enna, Tipswatch.com I sometimes watch too much CNN (stop me!) and on Thursday I heard Republican members of Congress repeatedly state that the just-approved Big Beautiful Bill would eliminate the tax on Social Security benefits, fulfilling a campaign … Continue reading →

Posted in Medicare, Retirement, Social Security, Taxes | Tagged , , , , | 77 Comments

My schedule, and what’s coming next

Posted on February 9, 2025 by Tipswatch

Plus, a few other thoughts on a changing Treasury market. By David Enna, Tipswatch.com Long-time readers of this site know what that headline signals: I am on the move. Over the next 3+ weeks I will be traveling in Argentina … Continue reading →

Posted in Federal Reserve, Inflation, Investing in TIPS, Medicare, Retirement, Social Security, Taxes | 18 Comments

The unique serenity of holding TIPS at TreasuryDirect

Posted on February 2, 2025 by Tipswatch

By David Enna, Tipswatch.com Want to find your happy place? Sometimes you have to go your own way. The consensus advice is to buy individual Treasury Inflation-Protected Securities in a tax-deferred account, most likely a traditional IRA. These bonds pay … Continue reading →

Posted in Cash alternatives, Inflation, Investing in TIPS, Retirement, Taxes, TreasuryDirect | 36 Comments

TreasuryDirect tax forms: How to find the 1099s, decipher them

Posted on January 26, 2025 by Tipswatch

By David Enna, Tipswatch.com If you are an account holder at TreasuryDirect, one of your “duties” each January is to go on a hunt for your 1099s, the extremely important (and ruthlessly obtuse) tax forms the Treasury hides away deep … Continue reading →

Posted in EE Bonds, I Bond, Investing in TIPS, Savings Bond, Taxes, Treasury Bills, TreasuryDirect | 45 Comments