How the hell are we supposed to retire?

three of us - we were out-of-pocket $50k last year for health costs.
Cobra, Medicare, Medigap, Individual, deductible.
Knee replacement, hernia, complications, dental work - banner year.

Good news - Sue Medicare eligible, with $50 advantage plan
Kid is now employer qualified at $400/mo
i'm the anchor around $800/mo (UHC Advantage(?))
I'll blow through the 3k deductible with the surgery - then smooth sailing.
 
three of us - we were out-of-pocket $50k last year for health costs.
Cobra, Medicare, Medigap, Individual, deductible.
Knee replacement, hernia, complications, dental work - banner year.

Good news - Sue Medicare eligible, with $50 advantage plan
Kid is now employer qualified at $400/mo
i'm the anchor around $800/mo (UHC Advantage(?))
I'll blow through the 3k deductible with the surgery - then smooth sailing.
Wish you well for 2026......
 
I just found out that my friend (who I just finished riding across Florida with) wrote his own retirement planning software. Since I'm still in Florida, I haven't had a chance to try it out, but he gave me a quick tutorial and it looks pretty powerful. This is completely free and open-source code, and it looks like he did a very nice job with the documentation of the features and the math he used.

Give it try and let me know what you think.

Owl Retirement Planner
 
I just found out that my friend (who I just finished riding across Florida with) wrote his own retirement planning software. Since I'm still in Florida, I haven't had a chance to try it out, but he gave me a quick tutorial and it looks pretty powerful. This is completely free and open-source code, and it looks like he did a very nice job with the documentation of the features and the math he used.

Give it try and let me know what you think.

Owl Retirement Planner

thanks for ruining my productivity (at least from my employers persepective) for the reast of the day.
 
I just found out that my friend (who I just finished riding across Florida with) wrote his own retirement planning software. Since I'm still in Florida, I haven't had a chance to try it out, but he gave me a quick tutorial and it looks pretty powerful. This is completely free and open-source code, and it looks like he did a very nice job with the documentation of the features and the math he used.

Give it try and let me know what you think.

Owl Retirement Planner
He needs to write something to keep my wife from panicking. That’s what’s costing us 1%.
 
Question for the group. How are you paying for taxes when you withdraw. I am using the Fidelity retirement planner and it says move all dollar for conversion from IRA/401K to Roth, pay taxes and expenses from brokerage until empty. Once its empty do the conversion but pay taxes and expenses from Roth. I am confused about that. I would have thought letting the money that is already in Roth grow would be the better option.

We plan to talk to come CFP/CPA folks, to help us understand better and if anyone has any recommendation on professional help please send them my way so I can at least have a initial chat with them to see if they can help.
 
Question for the group. How are you paying for taxes when you withdraw. I am using the Fidelity retirement planner and it says move all dollar for conversion from IRA/401K to Roth, pay taxes and expenses from brokerage until empty. Once its empty do the conversion but pay taxes and expenses from Roth. I am confused about that. I would have thought letting the money that is already in Roth grow would be the better option.

We plan to talk to come CFP/CPA folks, to help us understand better and if anyone has any recommendation on professional help please send them my way so I can at least have a initial chat with them to see if they can help.
Are you talking about just taxes or living expenses? CFA has us withdrawing a bit out of each account depending on what the market is doing. We have too many accounts as far as I'm concerned but my wife likes the CFA so it's more on them for now. We are using the Roth less than the taxable accounts but will need to have some tax free income to hopefully get some ACA subsidies for a few years. Using COBRA now, so not an issue.
 
Are you talking about just taxes or living expenses? CFA has us withdrawing a bit out of each account depending on what the market is doing. We have too many accounts as far as I'm concerned but my wife likes the CFA so it's more on them for now. We are using the Roth less than the taxable accounts but will need to have some tax free income to hopefully get some ACA subsidies for a few years. Using COBRA now, so not an issue.
I was think more in terms of taxes for conversion and using Roth for living expenses. We have some appointment setup to talk with couple of firms that provide holistic view over the coming week.

I am so over my head with withdrawal strategy 😕
 
I was think more in terms of taxes for conversion and using Roth for living expenses. We have some appointment setup to talk with couple of firms that provide holistic view over the coming week.

I am so over my head with withdrawal strategy 😕

By paying the taxes with money from brokerage rather than a deduction from the IRA withdrawal, it moves money from a taxed account (brokerage) to a non-taxed account (Roth)

for example -
Moving $50,000 from IRA to Roth, taxed at 20% so $10,000
if deducted from the transfer, it would leave $40k in Roth growing tax free
and $10,000 growing at 15% when taken in brokerage.

if you paid it from your brokerage, you'd have $50,000 growing tax free and pay 15% on the brokerage gains now.
So going forward, you are saving 15% on brokerage gains forever. by moving principal and current gains into the Roth.

This will do a few things farther down the line. Distributions from an IRA count towards how much is owed for Medicare premiums (IIRMA - look it up.)
Roth does not - this is a $1 more scenario - make $1 more than the limit, and it costs $5k/yr in additional premiums.
You can control it until the required minimum distribution of a traditional IRA blows this up.
 
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Although a Roth account is called an individual retirement account, that's not quite true. It is more a legacy investment account. Congress is lazy and borrowed language from another part of the tax code, but the outcome is that the Roth is not just tax free for the rest of your life, it is tax free for the next ten years after you pass! On average price levels double every ten years, so your Roth can be worth twice as much to a beneficiary.

In an ideal plan, you pass down, not spend down your Roth.
In an ideal plan, you sell asset with low capital gains freeing up the capital. You pass down the highly appreciated assets for the basis step up at death.
In an ideal plan, you live off of Social Security, RMDs and capital gain sales.
 
Although a Roth account is called an individual retirement account, that's not quite true. It is more a legacy investment account. Congress is lazy and borrowed language from another part of the tax code, but the outcome is that the Roth is not just tax free for the rest of your life, it is tax free for the next ten years after you pass! On average price levels double every ten years, so your Roth can be worth twice as much to a beneficiary.

In an ideal plan, you pass down, not spend down your Roth.
In an ideal plan, you sell asset with low capital gains freeing up the capital. You pass down the highly appreciated assets for the basis step up at death.
In an ideal plan, you live off of Social Security, RMDs and capital gain sales.


and how often does 'ideal' happen, i get having a plan, but flexibility is also a must bc life doesnt give a fuck about your plan.
 
and how often does 'ideal' happen, i get having a plan, but flexibility is also a must bc life doesnt give a fuck about your plan.

yeah, don't under-live.
don't be worth more dead than alive.
those medical Dr University bills gotta get paid by someone!

Jim's plan does account for having money in an emergency, and I can vouch that he is not underliving.....
 
Just because life can throw curve balls to derail plans, that doesn't mean it's better to have no plan at all. The idea is to build in enough flexibility in the plan to adjust when necessary.

For example, I have no heirs and now in my mid-50s, I doubt I ever will. So, passing down assets is of secondary importance to me in a way that may not apply to most. Depending on how life works out, I stand to inherit some amount of "family money" from my mother. Since I have no heirs of my own and do have some interest in "keeping it in the family", my current plan is to will that money to one or more of my ten cousins' children, since I am likely to be in a position to do so more than most of my cousins.
 
Although a Roth account is called an individual retirement account, that's not quite true. It is more a legacy investment account. Congress is lazy and borrowed language from another part of the tax code, but the outcome is that the Roth is not just tax free for the rest of your life, it is tax free for the next ten years after you pass! On average price levels double every ten years, so your Roth can be worth twice as much to a beneficiary.

In an ideal plan, you pass down, not spend down your Roth.
In an ideal plan, you sell asset with low capital gains freeing up the capital. You pass down the highly appreciated assets for the basis step up at death.
In an ideal plan, you live off of Social Security, RMDs and capital gain sales.
What about those of us who want to spend our Roth and don't want someone else getting their grubby hands on it?
 
Just because life can throw curve balls to derail plans, that doesn't mean it's better to have no plan at all. The idea is to build in enough flexibility in the plan to adjust when necessary.

For example, I have no heirs and now in my mid-50s, I doubt I ever will. So, passing down assets is of secondary importance to me in a way that may not apply to most. Depending on how life works out, I stand to inherit some amount of "family money" from my mother. Since I have no heirs of my own and do have some interest in "keeping it in the family", my current plan is to will that money to one or more of my ten cousins' children, since I am likely to be in a position to do so more than most of my cousins.

not sure if you took my post to be 'YOLO' but i definitely advocate for having a plan, just pointing out the necessisity of having flexibility, be it plans b-c or b-z, and either way something is bound to happen outside of your plans so dont be surprised by it and maintain room for surprises.
 
Although a Roth account is called an individual retirement account, that's not quite true. It is more a legacy investment account. Congress is lazy and borrowed language from another part of the tax code, but the outcome is that the Roth is not just tax free for the rest of your life, it is tax free for the next ten years after you pass! On average price levels double every ten years, so your Roth can be worth twice as much to a beneficiary.

In an ideal plan, you pass down, not spend down your Roth.
In an ideal plan, you sell asset with low capital gains freeing up the capital. You pass down the highly appreciated assets for the basis step up at death.
In an ideal plan, you live off of Social Security, RMDs and capital gain sales.

Yeah, that was the reason why some of the recommendation does not make sense to me. The scenario that I am struggling with:

Convert set amount from IRA/401K --> Roth
Pay for conversion taxes, LTCG and living expenses from brokerage account. With the first likely to come from cash saving if that makes sense.
Brokerage account likely to run dry after 5/6 years (very rough estimate)
I am going back and forth on where the taxes and living expenses are coming from after brokerage runs dry. Right now I am leaning towards letting Roth continue to grow tax free and live off SS and conversion/withdrawal which pays for taxes and expenses.

I am hoping whichever advisor that we pick will help provide clarity.
 
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