Heidi! Very timely post. Missus and me are in the same boat. We work for large companies with great health plans. We are 10 years out from qualifying for Medicare, but here we are contemplating early retirement. One of the things I have tossed around is this and it maybe something else you might keep in your tool box. We plan to retire at aged 57 and take COBRA because even with us paying full rates, it's gold standard health insurance and the full premiums would be comparable to a market place plan. At aged 57, we do get a small subsidy of about $4k per year towards health costs. Once COBRA at the current employer runs out, I might just take a role for 6-12 mos somewhere else, hop on their insurance, then do COBRA again for another 18 months. Then the missus can take a turn. This is hoping we can get hired, she's an RN, so that's in our favor. I could potentially take a job working retail at Home Depot or one of the chains and play the COBRA carousel. Just another path to consider. Of course it makes sense to compare ACA vs COBRA to see what make the most sense, but that's another option that most do not consider. Good luck and let us know how things go.
That strategy of tax loss harvesting and locking in losses intentionally can seem counter intuitive, but you are basically having the government subsidize your move from one equity which is under water or no longer suitable to a different one and using those losses to offset gains or even up to $3000 of ordinary income each year. I sued to think , I will just wait for it to come back... that is no longer my stance, if it is under water and there are better options, I sell at a loss, book the offset and move on. Waiting for the investment to even get back to par is a losing proposition in most cases.
Long time Employee Relations leader's (fortune 100 company) point of view. Take the comp. If you find another job don't tell them, they don't really want to know anyways. The language you described is standard in every severance agreement, in 25 plus years, I have yet to see it enforced. This isn't morally wrong or anything like that, it's how some attorney decided to write the agreement up because it sounds good on paper but they can't enforce it and don't care too. Enjoy the next stage in life.
I recognize that financial planning isn't a one size fits all strategy. I assume we all accept that reality. I'm no fan of annuities and my calculations say they are a bad deal for most. However, the peace of mind that it gives some cannot be underestimated. I'd never buy one because as Roth states, I can create my own income streams at a much lower cost while retainingcontrolof my money. Some people may think an annuity is beneficial to them and it's the job of the advisor to point out all the options available and help them chart the best course. All that said, I understand the point made by Roth but I have no issues if folks want annuities if it makes them sleep better at night.
One can only be miserable for so long until that becomes who you are
..Just a miserable curmudgeon. You will be miserable even when it recovers claiming it didn't do sa fast enough blah, blah. The more normal folks may even panic at first but will adjust as they realize the worse case scenario is still manageable. I'd like to think I'm not a perpetual curmudgeon and after some hand ringing I'd go on with life.
My parents are in their late 70s and we are in our mid fifties. I made our parents prepare wills and POAs. I told them I don't need to be guessing about their wishes and my job was to execute exactly as they wanted. My sister lives in England and she told them she trusts me to handle things. We both are ok financially and anything we inherit from our parents is gravy in the biscuit. I was clear with my parents that if they left me a mess to figure out, I'd let it all go the state, so have a freaking plan! Got the estate planning done post haste. Now, its a non issue.
Companies thrive and some fail, but for the most part, we know they sell a product. Based on their ability to sell this product for less than it costs, they earn profits that the investors hope will trickle down to them. Precious metals has some value and you can actually hold measure the item. For these coins, we know the story and it is likely one that doesn't end very well. Blockchain may very well have some type of value in transaction verifications and so forth, but the blind faith put into these coins make little sense to me. It is clearly hype, yet some have made millions!
Great insights for discussion. I'll attempt to answer both questions from the lens of simplicity with no AI input. What should the goal for financial planning be: insee this as three fold, and the order of importance not meaningful but can be tailored depending on the individual. A) Education and informing , B) Protection of assets and C) Optimizing. I can go on and on about how each three fits in, but this community is savvy enough to get my point. Success is measured by the sense of peace that the individual receiving the guidance feels. Its not the size of the portfolio, or the amount of taxes saved...its simply the peace of mind that comes from knowing you have the bases covered for what matters most. After all, it is still just personal finance.
While some say this is abad idea for various reasons, mostly related to the budget deficit, I think it's more nuanced than that. If people pull money out and spend it, it could create increased economic activity which could create an economic boom and in turn raise more revenue. I'm not saying it's a slam dunk, it's just that when you pull one lever, there are intended and unintended impacts. No one answer is correct.
Comments
Heidi! Very timely post. Missus and me are in the same boat. We work for large companies with great health plans. We are 10 years out from qualifying for Medicare, but here we are contemplating early retirement. One of the things I have tossed around is this and it maybe something else you might keep in your tool box. We plan to retire at aged 57 and take COBRA because even with us paying full rates, it's gold standard health insurance and the full premiums would be comparable to a market place plan. At aged 57, we do get a small subsidy of about $4k per year towards health costs. Once COBRA at the current employer runs out, I might just take a role for 6-12 mos somewhere else, hop on their insurance, then do COBRA again for another 18 months. Then the missus can take a turn. This is hoping we can get hired, she's an RN, so that's in our favor. I could potentially take a job working retail at Home Depot or one of the chains and play the COBRA carousel. Just another path to consider. Of course it makes sense to compare ACA vs COBRA to see what make the most sense, but that's another option that most do not consider. Good luck and let us know how things go.
Post: COBRA insurance: No need to fear the bite
Link to comment from August 18, 2026
That strategy of tax loss harvesting and locking in losses intentionally can seem counter intuitive, but you are basically having the government subsidize your move from one equity which is under water or no longer suitable to a different one and using those losses to offset gains or even up to $3000 of ordinary income each year. I sued to think , I will just wait for it to come back... that is no longer my stance, if it is under water and there are better options, I sell at a loss, book the offset and move on. Waiting for the investment to even get back to par is a losing proposition in most cases.
Post: Taking a Loss?
Link to comment from July 29, 2026
Long time Employee Relations leader's (fortune 100 company) point of view. Take the comp. If you find another job don't tell them, they don't really want to know anyways. The language you described is standard in every severance agreement, in 25 plus years, I have yet to see it enforced. This isn't morally wrong or anything like that, it's how some attorney decided to write the agreement up because it sounds good on paper but they can't enforce it and don't care too. Enjoy the next stage in life.
Post: Fear of the Unknown…
Link to comment from July 23, 2026
I recognize that financial planning isn't a one size fits all strategy. I assume we all accept that reality. I'm no fan of annuities and my calculations say they are a bad deal for most. However, the peace of mind that it gives some cannot be underestimated. I'd never buy one because as Roth states, I can create my own income streams at a much lower cost while retainingcontrolof my money. Some people may think an annuity is beneficial to them and it's the job of the advisor to point out all the options available and help them chart the best course. All that said, I understand the point made by Roth but I have no issues if folks want annuities if it makes them sleep better at night.
Post: Better Alternatives to Buying an Annuity
Link to comment from June 11, 2026
One can only be miserable for so long until that becomes who you are ..Just a miserable curmudgeon. You will be miserable even when it recovers claiming it didn't do sa fast enough blah, blah. The more normal folks may even panic at first but will adjust as they realize the worse case scenario is still manageable. I'd like to think I'm not a perpetual curmudgeon and after some hand ringing I'd go on with life.
Post: Would You Be Miserable?
Link to comment from June 9, 2026
My parents are in their late 70s and we are in our mid fifties. I made our parents prepare wills and POAs. I told them I don't need to be guessing about their wishes and my job was to execute exactly as they wanted. My sister lives in England and she told them she trusts me to handle things. We both are ok financially and anything we inherit from our parents is gravy in the biscuit. I was clear with my parents that if they left me a mess to figure out, I'd let it all go the state, so have a freaking plan! Got the estate planning done post haste. Now, its a non issue.
Post: Time to share our financial info with children?
Link to comment from June 8, 2026
Companies thrive and some fail, but for the most part, we know they sell a product. Based on their ability to sell this product for less than it costs, they earn profits that the investors hope will trickle down to them. Precious metals has some value and you can actually hold measure the item. For these coins, we know the story and it is likely one that doesn't end very well. Blockchain may very well have some type of value in transaction verifications and so forth, but the blind faith put into these coins make little sense to me. It is clearly hype, yet some have made millions!
Post: A $1,000 Conversation With My Daughter
Link to comment from June 8, 2026
Great insights for discussion. I'll attempt to answer both questions from the lens of simplicity with no AI input. What should the goal for financial planning be: insee this as three fold, and the order of importance not meaningful but can be tailored depending on the individual. A) Education and informing , B) Protection of assets and C) Optimizing. I can go on and on about how each three fits in, but this community is savvy enough to get my point. Success is measured by the sense of peace that the individual receiving the guidance feels. Its not the size of the portfolio, or the amount of taxes saved...its simply the peace of mind that comes from knowing you have the bases covered for what matters most. After all, it is still just personal finance.
Post: Reflections on a Quiet Failure
Link to comment from June 8, 2026
Seminar boy! A new financial designation Dan?
Post: Setting the Hook, Reeling In the Fish
Link to comment from June 3, 2026
While some say this is abad idea for various reasons, mostly related to the budget deficit, I think it's more nuanced than that. If people pull money out and spend it, it could create increased economic activity which could create an economic boom and in turn raise more revenue. I'm not saying it's a slam dunk, it's just that when you pull one lever, there are intended and unintended impacts. No one answer is correct.
Post: Should Retirees Get a Temporary Flat Tax Window on IRA and 401(k) Withdrawals?
Link to comment from May 19, 2026