This is a great article. I didn’t realize a 4Q taxable event impacted the required estimated payments for the previous quarters. We have some ongoing withholding through the year, then when we get to 4Q we up it enough to cover either our expected tax liability or the safe harbor number.
Like DrLefty I’d also be wary and would probably take out a loan before raiding the Roth. I also agree with her that it depends on one’s own situation. You might start withdrawing from your Traditional accounts to build up cash in your taxable account for a purchase. You could withdraw some this year and some more next year for the same tax it would have cost you to convert that amount to Roth.
I hadn’t thought about that but you’re right, as I recall they’ve only become popular to talk about in recent years. I’m guessing for two reasons: one being the heightened inflation you mention, and the other being higher interest rates which make a TIPS ladder more attractive.
It’s a shorter trip to the Moray Coast where it’s been lovely through the heat wave. Windy today but still beautiful - and no problem for an Irishman. We were just saying the other day that even if we were to settle in a climate like the one here, or yours, that we would at least have AC in the bedroom. I'm also glad Andrew picked up on your main point; I confess I missed it as well.
When I read the first paragraph I was thinking being nomadic we hardly ever buy anything we can’t eat. I read further and realized this is about greeting cards. We’ve certainly spent on those, and have also spent to send them to the United States as we’re usually elsewhere. However we very recently took a subscription to an electronic greetings service. Now we can send as many as we want and have actually sent e-cards for occasions we might not have otherwise. No trees harmed and now they get there on time too.
We might stop selling assets, or we might still want to sometimes. For example, we might want a large sum, beyond monthly cash flow, or we might want to exit a taxable position. And regardless, we’d still want to be doing Roth conversions. If we did buy an annuity it wouldn’t necessarily be with after tax dollars. I Having that taxable account gives immediately accessible money without the same tax bite as we’d create taking a large sum from a Traditional IRA or 401(k).
Comments
This is a great article. I didn’t realize a 4Q taxable event impacted the required estimated payments for the previous quarters. We have some ongoing withholding through the year, then when we get to 4Q we up it enough to cover either our expected tax liability or the safe harbor number.
Post: Don’t Let a Roth Conversion Trigger a Penalty
Link to comment from July 9, 2026
Like DrLefty I’d also be wary and would probably take out a loan before raiding the Roth. I also agree with her that it depends on one’s own situation. You might start withdrawing from your Traditional accounts to build up cash in your taxable account for a purchase. You could withdraw some this year and some more next year for the same tax it would have cost you to convert that amount to Roth.
Post: Thinking of a possible reason to tap Roth earlier then planned
Link to comment from July 8, 2026
I hadn’t thought about that but you’re right, as I recall they’ve only become popular to talk about in recent years. I’m guessing for two reasons: one being the heightened inflation you mention, and the other being higher interest rates which make a TIPS ladder more attractive.
Post: What’s in your portfolio ?
Link to comment from July 4, 2026
A US total stock market fund, an international fund, and bond fund and a TIPS fund is still very simple.
Post: What’s in your portfolio ?
Link to comment from July 4, 2026
Assume you know that approach de-weights a whole lot more than just the Mag 7.
Post: What’s in your portfolio ?
Link to comment from July 4, 2026
It’s a shorter trip to the Moray Coast where it’s been lovely through the heat wave. Windy today but still beautiful - and no problem for an Irishman. We were just saying the other day that even if we were to settle in a climate like the one here, or yours, that we would at least have AC in the bedroom. I'm also glad Andrew picked up on your main point; I confess I missed it as well.
Post: The Price of a Cool Pillow
Link to comment from July 2, 2026
When I read the first paragraph I was thinking being nomadic we hardly ever buy anything we can’t eat. I read further and realized this is about greeting cards. We’ve certainly spent on those, and have also spent to send them to the United States as we’re usually elsewhere. However we very recently took a subscription to an electronic greetings service. Now we can send as many as we want and have actually sent e-cards for occasions we might not have otherwise. No trees harmed and now they get there on time too.
Post: Exercising true frugality
Link to comment from July 1, 2026
Congratulations. I’d at least like to be able to count my individual stocks on one hand; currently I can’t count them on two.
Post: Independence Day
Link to comment from July 1, 2026
I go through a similar drill later in the year.
Post: Automatic Income stream? How important to you?
Link to comment from June 28, 2026
We might stop selling assets, or we might still want to sometimes. For example, we might want a large sum, beyond monthly cash flow, or we might want to exit a taxable position. And regardless, we’d still want to be doing Roth conversions. If we did buy an annuity it wouldn’t necessarily be with after tax dollars. I Having that taxable account gives immediately accessible money without the same tax bite as we’d create taking a large sum from a Traditional IRA or 401(k).
Post: Automatic Income stream? How important to you?
Link to comment from June 28, 2026