No spreadsheets! I keep a simple Word document and track all ongoing income sources (SS, annuity, investments, etc.) and required RMD amounts for the current year, as well as all expected deductions (I'm an itemizer), together with my safe harbor amount from the previous year's filing.
I am averse to seeing my SS or annuity payments dinged by withholding, and since the IRS credits tax payments from RMDs at the end of the year as though made throughout the year, that's when I settle up. Same goes for Estimated Payments: Why pay early what I can pay later? For me, RMDs have the feel of "found money," even when our Uncle has taken his share before I get what's left. I agree with others about hitting the safe harbor as essential in all these transactions.
For sure, but sometimes one gets the impression that some folks would rather give anyone $100 rather than give the govt $24 or whatever the marginal rate is. I don't like paying taxes either, but lowering my RMDs by giving away my "surplus cash"...guess I've a way to go for that to make sense.
Since I don't know the amounts involved, perhaps you need the management, but if significant sums are present, paying the surcharge seems reasonable to access bundles of cash that allow you to pay without any stress. I'll be paying higher IRMAA whether I sell my stock winners or not, which might explain spending my time doing something besides yet more tax management.
It seems odd to me that you've made 90% on these stocks, but fear a very manageable (and fair) IRMAA surcharge or extra percentage on your tax bill, when you've killed it in the market.
Comments
So, the flip side would seem to be that ALL that those not like us do not have ARE Curses.
Post: Americans and their credit cards
Link to comment from August 25, 2026
No spreadsheets! I keep a simple Word document and track all ongoing income sources (SS, annuity, investments, etc.) and required RMD amounts for the current year, as well as all expected deductions (I'm an itemizer), together with my safe harbor amount from the previous year's filing.
Post: If Retirement is Getting Close
Link to comment from August 19, 2026
I am averse to seeing my SS or annuity payments dinged by withholding, and since the IRS credits tax payments from RMDs at the end of the year as though made throughout the year, that's when I settle up. Same goes for Estimated Payments: Why pay early what I can pay later? For me, RMDs have the feel of "found money," even when our Uncle has taken his share before I get what's left. I agree with others about hitting the safe harbor as essential in all these transactions.
Post: If Retirement is Getting Close
Link to comment from August 19, 2026
For sure, but sometimes one gets the impression that some folks would rather give anyone $100 rather than give the govt $24 or whatever the marginal rate is. I don't like paying taxes either, but lowering my RMDs by giving away my "surplus cash"...guess I've a way to go for that to make sense.
Post: Risk and Taxes
Link to comment from August 8, 2026
Since I don't know the amounts involved, perhaps you need the management, but if significant sums are present, paying the surcharge seems reasonable to access bundles of cash that allow you to pay without any stress. I'll be paying higher IRMAA whether I sell my stock winners or not, which might explain spending my time doing something besides yet more tax management.
Post: Risk and Taxes
Link to comment from August 8, 2026
I am always puzzled by this strategy to give away money to lower a tax bill that will cost much, much less.
Post: Risk and Taxes
Link to comment from August 8, 2026
It seems odd to me that you've made 90% on these stocks, but fear a very manageable (and fair) IRMAA surcharge or extra percentage on your tax bill, when you've killed it in the market.
Post: Risk and Taxes
Link to comment from August 8, 2026
Indeed! A "cool" winter in Key West delivered those three weeks without the units humming away. Rather a different story right now!
Post: The Price of a Cool Pillow
Link to comment from June 25, 2026
See above on my timeline and how I simply shifted to Starbucks when they took over a coffee space I was patronizing already in the 1980s.
Post: Dickie and his magic beans
Link to comment from May 7, 2026
Wait until they start putting dirt in there and I just mindlessly brew that!
Post: Dickie and his magic beans
Link to comment from May 7, 2026