This is some good, common-sense points on how to think about our Roth Conversion Wagers. And I mean wager--since we are betting on several unknowns, such as tax rates, tax code structure, the mood of Congress, not to mention our own (unknowable) plethora of personal circumstances. As you state, converting in the lower (10-12%) brackets is fairly low-risk. But as rates rise, and potentially more ancillary taxes are piled on, the risk of overpaying also rises--substantially.
A Roth account is a wonderful thing to have, but take care that you don't pay too much for it.
"I bet on import taxes creating havoc for the balance of the year,..." My feeling is--and I freely admit, I could be wrong--those taxes ARE creating havoc, but just not in the predictable way or within the precise time frame that you were expecting. My reaction wouldn't be "I told you so dummy", but something like "you ought to know better by now."
As others have stated below, there will be ample buying opportunities at some point. But patience may be required; if it helps any, just pretend that it's September 2021, and you're sitting on a big pile of cash. Maybe it is, and maybe it ain't, but at some point it will be. Hang in there!
To me, the Four Percent Rule is similar to the Pirate's Code, in that they're not really hard and fast rules; they're both more like...guidelines (lol). It's a good place to start when trying to determine a rough expectation of how much lifetime income a portfolio might be capable of generating, and then adjusting your needs, expectations, and enhancements from there.
"On the federal tax form, how could a state or states NOT “conform”?" By not allowing the new federal changes to "flow through" to any particular state's income tax form. For example, several states tax capital gains, even though they may not be taxed on the federal form; similarly, many states have their own formulas for setting a standard deduction that's different than what's used on the federal return, and so on.
I confess, I find the subject of purchasing individual TIPs on the secondary market to be a somewhat confusing endeavor, and something I hesitate to recommend. But since durations of some issues have gotten more attractive in the last few years, it might be worth the effort, if one is willing to put in the time to do some research. I definitely feel there is more potential for satisfactory performance with individual issues, as opposed to TIPs funds.
Good discussion! To that list of total bond market funds, corporates, treasuries, and municipals, I'd add CD's, Multi-Year Guaranteed Annuities (think: CDs from insurance companies), and if you have access to one--a stable value fund (think: G-fund for the federal Thrift Savings Plan). This last can simplify your life considerably, especially when you are in the draw-down phase of your retirement.
Also, another important distinction: One's overall bond allocation should be broken down to include both short-term and long-term holdings, especially when one is taking account distributions. For example, funds like BND might not be the best for the short-term bucket, but generally can fit pretty good in longer-term holdings. I also tend to avoid most anything with a duration of longer than 10 years, since within recent memory I don't feel investors are being adequately compensated for the (considerable) risk that entails. And of course, muni's should generally be avoided for retirement accounts, as their tax advantages are mostly negated there, and their generally lower return doesn't usually make up for that.
When I was in the fifth grade, I worked for a teen-age acquaintance of mine. He hired me to deliver the weekday edition of the Wichita Eagle-Beacon; I'd go pick up the papers at the drop spot every week day, and walk the route on foot for $6 a week. It took a few hours, I could get it done before dark after school. Payday was every Friday; I'd take my $6 cash earnings, stop at the local laundromat, have the dollar-bill changed to quarters, and play the old (mechanical) Eight-Ball pin ball machine. What a blast! I'd usually take the fiver home and save it for a "rainy" day.
A good life lesson about earning, spending and saving for an elementary age kid, I always thought later.
"Wouldn’t she have effectively drained the original $200K in the Roth, while converting $125K?" That's the way I see it as well. This would effectively get her to the same place as just taking a taxable distribution out of her 401(k) up to the amount of the standard deduction, and then taking the rest of her income needs from her Roth.
IMO, neither of these options make much sense to me. If it were me, I'd rather just take my income needs from my 401(k) until I was ready to draw Social Security, and save my Roth accounts for later. If she really wants to get fancy, she might even convert an additional amount to her Roth up to the limit of the 12% bracket in excess of her income needs, up until the year she starts Social Security. Then forget about Roth conversions, take her income needs from the 401(k)--whatever she needs in excess of SS. Once SS starts, Roth conversions are paying extra tax--just to be paying extra tax, and might actually be doing more harm than good. Then, when RMD's start, maybe spend a little more, or just save more in her taxable account. Or make a QCD, or...?
Then, in years she when may need a little extra cash in excess of her RMD+Social Security, take a "tactical" Roth distribution, both to supplement her income, and to help control her tax bill.
My personal opinion--I don't think in this case, it's going to matter much financially when she starts Social Security, although I'd like to see her wait at least a year or two if she can. Just start SS whenever it feels right, and then forget about Roth conversions, as they're not going to make much difference one way or the other, and only complicate her finances at this point. KISS.
Thank you for your thoughtful-- and deeply personal--article on what can often be a difficult, painful subject. Communicating effectively with our own children can at times feel like the hardest thing in the world--and I have yet to figure out why. I'm still trying to figure it out, and I fear my quest is far from complete.
Comments
This is some good, common-sense points on how to think about our Roth Conversion Wagers. And I mean wager--since we are betting on several unknowns, such as tax rates, tax code structure, the mood of Congress, not to mention our own (unknowable) plethora of personal circumstances. As you state, converting in the lower (10-12%) brackets is fairly low-risk. But as rates rise, and potentially more ancillary taxes are piled on, the risk of overpaying also rises--substantially. A Roth account is a wonderful thing to have, but take care that you don't pay too much for it.
Post: Contrarian Thinking About Roth Conversions
Link to comment from October 16, 2025
"I bet on import taxes creating havoc for the balance of the year,..." My feeling is--and I freely admit, I could be wrong--those taxes ARE creating havoc, but just not in the predictable way or within the precise time frame that you were expecting. My reaction wouldn't be "I told you so dummy", but something like "you ought to know better by now." As others have stated below, there will be ample buying opportunities at some point. But patience may be required; if it helps any, just pretend that it's September 2021, and you're sitting on a big pile of cash. Maybe it is, and maybe it ain't, but at some point it will be. Hang in there!
Post: Told Ya So Big Dummy
Link to comment from September 27, 2025
To me, the Four Percent Rule is similar to the Pirate's Code, in that they're not really hard and fast rules; they're both more like...guidelines (lol). It's a good place to start when trying to determine a rough expectation of how much lifetime income a portfolio might be capable of generating, and then adjusting your needs, expectations, and enhancements from there.
Post: Are you actually using the 4% rule?
Link to comment from September 20, 2025
"On the federal tax form, how could a state or states NOT “conform”?" By not allowing the new federal changes to "flow through" to any particular state's income tax form. For example, several states tax capital gains, even though they may not be taxed on the federal form; similarly, many states have their own formulas for setting a standard deduction that's different than what's used on the federal return, and so on.
Post: New 2025 Tax Deductions
Link to comment from September 20, 2025
I confess, I find the subject of purchasing individual TIPs on the secondary market to be a somewhat confusing endeavor, and something I hesitate to recommend. But since durations of some issues have gotten more attractive in the last few years, it might be worth the effort, if one is willing to put in the time to do some research. I definitely feel there is more potential for satisfactory performance with individual issues, as opposed to TIPs funds.
Post: Best Bond Funds for Your Portfolio: Treasurys, Corporates, and Municipals Explained
Link to comment from September 20, 2025
Good discussion! To that list of total bond market funds, corporates, treasuries, and municipals, I'd add CD's, Multi-Year Guaranteed Annuities (think: CDs from insurance companies), and if you have access to one--a stable value fund (think: G-fund for the federal Thrift Savings Plan). This last can simplify your life considerably, especially when you are in the draw-down phase of your retirement. Also, another important distinction: One's overall bond allocation should be broken down to include both short-term and long-term holdings, especially when one is taking account distributions. For example, funds like BND might not be the best for the short-term bucket, but generally can fit pretty good in longer-term holdings. I also tend to avoid most anything with a duration of longer than 10 years, since within recent memory I don't feel investors are being adequately compensated for the (considerable) risk that entails. And of course, muni's should generally be avoided for retirement accounts, as their tax advantages are mostly negated there, and their generally lower return doesn't usually make up for that.
Post: Best Bond Funds for Your Portfolio: Treasurys, Corporates, and Municipals Explained
Link to comment from September 20, 2025
When I was in the fifth grade, I worked for a teen-age acquaintance of mine. He hired me to deliver the weekday edition of the Wichita Eagle-Beacon; I'd go pick up the papers at the drop spot every week day, and walk the route on foot for $6 a week. It took a few hours, I could get it done before dark after school. Payday was every Friday; I'd take my $6 cash earnings, stop at the local laundromat, have the dollar-bill changed to quarters, and play the old (mechanical) Eight-Ball pin ball machine. What a blast! I'd usually take the fiver home and save it for a "rainy" day. A good life lesson about earning, spending and saving for an elementary age kid, I always thought later.
Post: My Money Memories
Link to comment from August 7, 2025
"Wouldn’t she have effectively drained the original $200K in the Roth, while converting $125K?" That's the way I see it as well. This would effectively get her to the same place as just taking a taxable distribution out of her 401(k) up to the amount of the standard deduction, and then taking the rest of her income needs from her Roth. IMO, neither of these options make much sense to me. If it were me, I'd rather just take my income needs from my 401(k) until I was ready to draw Social Security, and save my Roth accounts for later. If she really wants to get fancy, she might even convert an additional amount to her Roth up to the limit of the 12% bracket in excess of her income needs, up until the year she starts Social Security. Then forget about Roth conversions, take her income needs from the 401(k)--whatever she needs in excess of SS. Once SS starts, Roth conversions are paying extra tax--just to be paying extra tax, and might actually be doing more harm than good. Then, when RMD's start, maybe spend a little more, or just save more in her taxable account. Or make a QCD, or...? Then, in years she when may need a little extra cash in excess of her RMD+Social Security, take a "tactical" Roth distribution, both to supplement her income, and to help control her tax bill. My personal opinion--I don't think in this case, it's going to matter much financially when she starts Social Security, although I'd like to see her wait at least a year or two if she can. Just start SS whenever it feels right, and then forget about Roth conversions, as they're not going to make much difference one way or the other, and only complicate her finances at this point. KISS.
Post: 100% Base Pay Replacement: What Does It Mean?
Link to comment from July 23, 2025
Thank you for your thoughtful-- and deeply personal--article on what can often be a difficult, painful subject. Communicating effectively with our own children can at times feel like the hardest thing in the world--and I have yet to figure out why. I'm still trying to figure it out, and I fear my quest is far from complete.
Post: Family Dynamics, Part 2: Supporting Adult Children
Link to comment from July 22, 2025
Agreed, having a trustworthy advisor is a valuable asset, and should give you another layer of both advocacy and protection.
Post: Pig Butchering
Link to comment from July 21, 2025