Randy, yes as you can reimburse from years ago - you just have to have clear receipts and documentation that reimbursements didn't occur with another account. I'm scanning receipts now and also keeping hard copies (ha). It will be a long term process that I'm curious to manage :) , but I'll keep an eye on the account and sell on occasion. "You can reimburse yourself from your HSA for qualified medical expenses incurred in the past, even years ago, as long as the expenses were incurred after the HSA was established. There's no time limit for requesting these reimbursements. However, you must have documentation (like receipts) to prove the expenses were qualified medical expenses and that they were not reimbursed from another source".
David, I have an HSA than I am currently using sparingly. My daughter will inherit in the future. I am keeping a detailed list of all health care expenses/receipts that I have accumulated and not tapped the HSA for. My goal is to see the account grow - hoping for at least another 10 years or so. The list is accessible, and my instructions are that she could reimburse the estate immediately for all the built-up expenses. So the funds would effectively 'used up.' I will keep an eye on it, though, in case I need to take this step in advance.
Thank you, Jonathan, for continuing to share your journey. I wish you well that the effects of chemo and radiation can dissipate so you can feel like your old self again soon.
Adam, as always thank you for your thoughtful perspective. So helpful to be able to step back amid the onslaught of hype about AI.
It doesn't help when bosses seem to be exerting a power dynamic to employees: AI is coming for all jobs; 'everyone' is at risk. It also doesn't help when each week we learn more about implications for AI deliverables (this link describes how well AI tools are advancing to synthesize data about oneself based on searches- talk about surveillance or use for profiles for credit or jobs or ...whatever): What LLMs Know About Their Users - Schneier on Security The swirl of uncertainty around AI adds to generalized anxiety about job security and hence financial security/planning. Fixed costs - rents, mortgages, homeowners insurance, car prices/insurance, day care - have escalated for many, including my three children in their 20s/30s. Emergency funds will be more critical than ever along with investing in low-cost index funds. And perhaps more support at critical moments from retired parents, if/when they can provide help.
My husband was pretty frugal in general from the earliest days of our marriage, setting the stage for long term financial returns. He was also particular about laundry, telling me once that I would be getting a 'D' after not taking the care of shirts to his standard. I asked, how to I get an F? He took care of his own laundry after that, economizing perhaps not in laundry detergent but gaining bountiful returns in marital peace.
Rick, thank you for thinking of quiet and substantive ways to assist your friend and his wife. My husband passed away exactly 10 months from his diagnosis of lung cancer. In the flurry of those months, we completed his estate planning. Alas, even with my experience managing finances, some details were overlooked, causing delays afterward. Checking beneficiaries and proper titling on accounts is critical - I missed one, having assumed everything was in place for that account (check the forms!). And when setting up a modest trust for our kids where I would be the trustee, our attorney suggested a successor trustee. Excellent planning; my brother was named as successor trustee to me. Alas, the language also included a trust firm just in case my brother couldn't do it. The language, though, was written as "my brother AND the firm" but could have been 'my brother and/or the firm.' So if I pass away my brother has to reach out to a firm for sign-offs, which will charge a fee for very little work.
Fifteen months ago I bought a new Subaru Forester after keeping my trusty Toyota Sienna minivan for literally a generation: 24 years, 442,444 miles (same engine! everything else changed out - a lot). Bought that oh-so-reliable van when pregnant with my third child and drove it beyond her college graduation. Kept it simply to see how far it would go (and yep how much I saved on new car payments). What a friendly and safe vehicle- no accidents, countless road trips from the Midwest to all points in the US in the days before DVDs, let alone Ipads. Books on tape! I had high hopes that my kids would listen as avidly as I did to The Black Swan by Nassim Nicholas Taleb but my son shrieked "I HATE the word random!' Fast forward, I really appreciate all the superb safety features but they are complex - and the manual is perplexing too. My cousin, a long-time service rep, suggested buying the extended warranty given all the new embedded electronics. Ouch- even a new windshield from highway gravel costs much more thanks to the 'eye' sensors in the glass.
Hi Rick, very timely. I've struggled with this issue too, especially on communicating finances with young adult children. For several years after my husband died, as I prepared my solo estate documents, they didn't want to 'hear' anything about my planning. It was too hard for them to contemplate another parent's death. As they've gotten older, it is bit easier, but I find that each one has different interests in learning about finances. My letter of instructions gets longer with explanations (plus a callout that they review Humble Dollar articles!).
I am also encouraging siblings to share information. Five of my six brothers are single, in their 60s, and scattered across the country. Nudging them to acknowledge the basics of estate plans and at least inform one other sibling of location of documents is taking a while (we get along too!). Keeping in touch over the decades will be important to help future discussions about independence.
Hi Sundar, this is a thoughtful post, not only for oneself, but also for siblings and close friends.I have several siblings who never married; other friends/relatives are divorced or widowed like myself.Financial pressures in retirement plus lack of immediate family will loom large for many. So much uncertainty - really tough choices are ahead for those who aren't willing to start planning well ahead... or who simply can't plan ahead emotionally. The decisions will cast ripple effects among extended families and friends.
Comments
Randy, yes as you can reimburse from years ago - you just have to have clear receipts and documentation that reimbursements didn't occur with another account. I'm scanning receipts now and also keeping hard copies (ha). It will be a long term process that I'm curious to manage :) , but I'll keep an eye on the account and sell on occasion. "You can reimburse yourself from your HSA for qualified medical expenses incurred in the past, even years ago, as long as the expenses were incurred after the HSA was established. There's no time limit for requesting these reimbursements. However, you must have documentation (like receipts) to prove the expenses were qualified medical expenses and that they were not reimbursed from another source".
Post: Beyond fees, is using a financial advisor, advisable? If you do or don’t why?
Link to comment from July 12, 2025
David, I have an HSA than I am currently using sparingly. My daughter will inherit in the future. I am keeping a detailed list of all health care expenses/receipts that I have accumulated and not tapped the HSA for. My goal is to see the account grow - hoping for at least another 10 years or so. The list is accessible, and my instructions are that she could reimburse the estate immediately for all the built-up expenses. So the funds would effectively 'used up.' I will keep an eye on it, though, in case I need to take this step in advance.
Post: Beyond fees, is using a financial advisor, advisable? If you do or don’t why?
Link to comment from July 12, 2025
Thank you, Jonathan, for continuing to share your journey. I wish you well that the effects of chemo and radiation can dissipate so you can feel like your old self again soon.
Post: Extra Innings
Link to comment from July 12, 2025
Adam, as always thank you for your thoughtful perspective. So helpful to be able to step back amid the onslaught of hype about AI. It doesn't help when bosses seem to be exerting a power dynamic to employees: AI is coming for all jobs; 'everyone' is at risk. It also doesn't help when each week we learn more about implications for AI deliverables (this link describes how well AI tools are advancing to synthesize data about oneself based on searches- talk about surveillance or use for profiles for credit or jobs or ...whatever): What LLMs Know About Their Users - Schneier on Security The swirl of uncertainty around AI adds to generalized anxiety about job security and hence financial security/planning. Fixed costs - rents, mortgages, homeowners insurance, car prices/insurance, day care - have escalated for many, including my three children in their 20s/30s. Emergency funds will be more critical than ever along with investing in low-cost index funds. And perhaps more support at critical moments from retired parents, if/when they can provide help.
Post: The Jevons Paradox
Link to comment from June 28, 2025
My husband was pretty frugal in general from the earliest days of our marriage, setting the stage for long term financial returns. He was also particular about laundry, telling me once that I would be getting a 'D' after not taking the care of shirts to his standard. I asked, how to I get an F? He took care of his own laundry after that, economizing perhaps not in laundry detergent but gaining bountiful returns in marital peace.
Post: Ninety Nine, I mean Eight Retirement Tips
Link to comment from June 27, 2025
Rick, thank you for thinking of quiet and substantive ways to assist your friend and his wife. My husband passed away exactly 10 months from his diagnosis of lung cancer. In the flurry of those months, we completed his estate planning. Alas, even with my experience managing finances, some details were overlooked, causing delays afterward. Checking beneficiaries and proper titling on accounts is critical - I missed one, having assumed everything was in place for that account (check the forms!). And when setting up a modest trust for our kids where I would be the trustee, our attorney suggested a successor trustee. Excellent planning; my brother was named as successor trustee to me. Alas, the language also included a trust firm just in case my brother couldn't do it. The language, though, was written as "my brother AND the firm" but could have been 'my brother and/or the firm.' So if I pass away my brother has to reach out to a firm for sign-offs, which will charge a fee for very little work.
Post: Tempus Fugit, Vol II
Link to comment from May 17, 2025
Always appreciate your perspective Rick.
Post: Let’s revisit an important retirement living topic. How’s it going? Great expectations
Link to comment from May 9, 2025
Fifteen months ago I bought a new Subaru Forester after keeping my trusty Toyota Sienna minivan for literally a generation: 24 years, 442,444 miles (same engine! everything else changed out - a lot). Bought that oh-so-reliable van when pregnant with my third child and drove it beyond her college graduation. Kept it simply to see how far it would go (and yep how much I saved on new car payments). What a friendly and safe vehicle- no accidents, countless road trips from the Midwest to all points in the US in the days before DVDs, let alone Ipads. Books on tape! I had high hopes that my kids would listen as avidly as I did to The Black Swan by Nassim Nicholas Taleb but my son shrieked "I HATE the word random!' Fast forward, I really appreciate all the superb safety features but they are complex - and the manual is perplexing too. My cousin, a long-time service rep, suggested buying the extended warranty given all the new embedded electronics. Ouch- even a new windshield from highway gravel costs much more thanks to the 'eye' sensors in the glass.
Post: Car talk- Quinn likes friendliness
Link to comment from April 15, 2025
Hi Rick, very timely. I've struggled with this issue too, especially on communicating finances with young adult children. For several years after my husband died, as I prepared my solo estate documents, they didn't want to 'hear' anything about my planning. It was too hard for them to contemplate another parent's death. As they've gotten older, it is bit easier, but I find that each one has different interests in learning about finances. My letter of instructions gets longer with explanations (plus a callout that they review Humble Dollar articles!). I am also encouraging siblings to share information. Five of my six brothers are single, in their 60s, and scattered across the country. Nudging them to acknowledge the basics of estate plans and at least inform one other sibling of location of documents is taking a while (we get along too!). Keeping in touch over the decades will be important to help future discussions about independence.
Post: How Will You Know When It’s Time?
Link to comment from April 13, 2025
Hi Sundar, this is a thoughtful post, not only for oneself, but also for siblings and close friends.I have several siblings who never married; other friends/relatives are divorced or widowed like myself.Financial pressures in retirement plus lack of immediate family will loom large for many. So much uncertainty - really tough choices are ahead for those who aren't willing to start planning well ahead... or who simply can't plan ahead emotionally. The decisions will cast ripple effects among extended families and friends.
Post: Senior Care Crisis – Are we prepared?
Link to comment from March 5, 2025