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 😕
 
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