In my case, I admit to not paying much attention to the consequences. I bought a few tech stocks in a taxable account with a few thousand dollars in the mid-1990s and the valuations subsequently ballooned. At the time it seemed more like gambling than investing. Back then I just liked how the equities were making the account grow. Plus I was busy with a career and not thinking at all about my tax future. Looking back, of course the purchases should have been in an IRA, and maybe I shouldn't have let the shares languish after the dot com bust of the early 2000s or reach concentrated positions. Now I give some shares each year as highly appreciated donations to charity; otherwise, I still hold a large amount and think that they have room to grow. Not needing the cash now, and I hope, not in the future, I do like that they might all go eventually to charity with the stepped up basis.
Like some other posters, RDQ, I would increase the international exposure. Worrisome to me, though, is the single stock risk, whether the position is 20% of the total account, or 20% of the equities (not clear). From previous posts, I believe your single holding is a utility. No matter how well managed, utilities carry risks from gas pipeline explosions, wildfires, ice storms, nuclear mishaps, etc. One major event could result in years of litigation, dragging down the stock price and potentially suspending the dividend. While selling some stock would be desirable, I say this gently as I too have concentrated (tech) positions in a taxable account. To me, the tax consequences of selling and/or the intricacies of equity exchange funds (partnerships, holding periods, fees) have kept me from doing anything. As you note, heirs will have the stepped up basis. Also like you, I have a large muni position. Investing in munis, besides the tax benefit, in my opinion equates to support of one's community.
I agree, the story carries useful lessons for us all. When I attended the U of C (late 1970s), the cost of attendance including room and board was just under $5000. Adjusted for inflation and not considering tuition discounts or financial aid, that cost now exceeds three times as much. The unofficial description of the college then, "where fun goes to die", resonated with me and others, somewhat like a badge of honor. Endowment growth subsequently provided for many more student amenities, in turn enabling more selective admisssions. I wonder, could a university still be viable without those amenities? Would today's students apply?
For taxable accounts, consider also FDLXX or similar "Treasury Only" money market funds. A high proportion of income is exempt from state tax, yet the yield is virtually identical to SPAXX.
Of course, the return on gold is all about the time window of investment -- and just like any other asset, has no guarantee of an upward trajectory. Having been gifted around $3K of gold double eagles in 1992, I held on to them both out of sentimentality and also because of the small amount and the hassle to sell. Ditto for another like amount inherited in 2008. Has holding been worthwhile? In my case, yes: a 38% annual return for the gifted amount, and a 26% annual return for the inherited gold, albeit not compounded. Not bad for dragging my feet about selling, and for waiting out flat or falling prices.
I made my own end-of-life document. It is three single-spaced pages with annually-reviewed sections on: general info (former and current address, date of birth, ssn); employer info and supervisor contact (I am retired with a part-time job); health/insurance policies; financial accounts; donor advised fund account and successor trustee; credit accounts; memberships; hardware ids and passwords; software accounts; location of important documents; safe deposit box contents; and notifiy upon death (friends and family). Most sections contain contact information, for individuals and/or customer service. As for books on investing, I confess to reading only one, and that was decades after beginning my investing journey: The Prudent Professor, planning and saving for a worry-free retirement from academe, by Bridges and Bridges. I took away from it that keeping retirement funds in fixed income at TIAA is a reasonable proposition and that TIAA annuities are well structured and can be tailored to fit one's needs.
The act of building a budget, as I see it, is important in reinforcing and/or revising one's life goals. When I worked, I loved that I had to demonstrably link line items to institutional goals. It was a great planning tool. Now I like to see similar budget mapping by the non-profit for which I am treasurer. Do I do the same in my own life? To some extent, yes. My personal goals fit into the categories of "healthy, happy, responsible, prudent" and my budgets are guides to achieve the goals. The budgets themselves are less important for their dollar amounts than for how they fit the bigger -- and longer term -- picture.
With each IRMAA premium, I remind myself of the bargain that Medicare is compared to individual health insurance. I pay less now, despite being in a high IRMAA tier, than I did for private insurance in the first two years of retirement without Medicare. Even adding in premiums for supplemental, Medicare Part D, dental, and long term care insurance, my annual costs are still less than I would have had for individual health insurance alone.
Thanks for asking, Jeff. The one decision I would change was signing a phased, three-year retirement contract. Half time work in phased retirement was essentially full time work at half salary, amplified in part due to the pandemic and having to find new ways to do existing tasks. Had I been at full salary, I could also have delayed withdrawing from savings for at least one year longer.
Comments
In my case, I admit to not paying much attention to the consequences. I bought a few tech stocks in a taxable account with a few thousand dollars in the mid-1990s and the valuations subsequently ballooned. At the time it seemed more like gambling than investing. Back then I just liked how the equities were making the account grow. Plus I was busy with a career and not thinking at all about my tax future. Looking back, of course the purchases should have been in an IRA, and maybe I shouldn't have let the shares languish after the dot com bust of the early 2000s or reach concentrated positions. Now I give some shares each year as highly appreciated donations to charity; otherwise, I still hold a large amount and think that they have room to grow. Not needing the cash now, and I hope, not in the future, I do like that they might all go eventually to charity with the stepped up basis.
Post: Critique my investment strategy or lack thereof
Link to comment from February 26, 2026
Like some other posters, RDQ, I would increase the international exposure. Worrisome to me, though, is the single stock risk, whether the position is 20% of the total account, or 20% of the equities (not clear). From previous posts, I believe your single holding is a utility. No matter how well managed, utilities carry risks from gas pipeline explosions, wildfires, ice storms, nuclear mishaps, etc. One major event could result in years of litigation, dragging down the stock price and potentially suspending the dividend. While selling some stock would be desirable, I say this gently as I too have concentrated (tech) positions in a taxable account. To me, the tax consequences of selling and/or the intricacies of equity exchange funds (partnerships, holding periods, fees) have kept me from doing anything. As you note, heirs will have the stepped up basis. Also like you, I have a large muni position. Investing in munis, besides the tax benefit, in my opinion equates to support of one's community.
Post: Critique my investment strategy or lack thereof
Link to comment from February 26, 2026
I agree, the story carries useful lessons for us all. When I attended the U of C (late 1970s), the cost of attendance including room and board was just under $5000. Adjusted for inflation and not considering tuition discounts or financial aid, that cost now exceeds three times as much. The unofficial description of the college then, "where fun goes to die", resonated with me and others, somewhat like a badge of honor. Endowment growth subsequently provided for many more student amenities, in turn enabling more selective admisssions. I wonder, could a university still be viable without those amenities? Would today's students apply?
Post: Endowment Lessons
Link to comment from February 21, 2026
I'm curious if UK tax advantaged accounts are shielded from creditors and liability suits. In the US, protection varies by state.
Post: A Very Sensible Conclusion
Link to comment from February 19, 2026
For taxable accounts, consider also FDLXX or similar "Treasury Only" money market funds. A high proportion of income is exempt from state tax, yet the yield is virtually identical to SPAXX.
Post: High Interest Savings Accounts vs Bond funds
Link to comment from February 8, 2026
Of course, the return on gold is all about the time window of investment -- and just like any other asset, has no guarantee of an upward trajectory. Having been gifted around $3K of gold double eagles in 1992, I held on to them both out of sentimentality and also because of the small amount and the hassle to sell. Ditto for another like amount inherited in 2008. Has holding been worthwhile? In my case, yes: a 38% annual return for the gifted amount, and a 26% annual return for the inherited gold, albeit not compounded. Not bad for dragging my feet about selling, and for waiting out flat or falling prices.
Post: The Playground Indicator
Link to comment from February 1, 2026
I made my own end-of-life document. It is three single-spaced pages with annually-reviewed sections on: general info (former and current address, date of birth, ssn); employer info and supervisor contact (I am retired with a part-time job); health/insurance policies; financial accounts; donor advised fund account and successor trustee; credit accounts; memberships; hardware ids and passwords; software accounts; location of important documents; safe deposit box contents; and notifiy upon death (friends and family). Most sections contain contact information, for individuals and/or customer service. As for books on investing, I confess to reading only one, and that was decades after beginning my investing journey: The Prudent Professor, planning and saving for a worry-free retirement from academe, by Bridges and Bridges. I took away from it that keeping retirement funds in fixed income at TIAA is a reasonable proposition and that TIAA annuities are well structured and can be tailored to fit one's needs.
Post: Your two best investing books—and do you also keep an End-of-Life “family binder”?
Link to comment from January 5, 2026
The act of building a budget, as I see it, is important in reinforcing and/or revising one's life goals. When I worked, I loved that I had to demonstrably link line items to institutional goals. It was a great planning tool. Now I like to see similar budget mapping by the non-profit for which I am treasurer. Do I do the same in my own life? To some extent, yes. My personal goals fit into the categories of "healthy, happy, responsible, prudent" and my budgets are guides to achieve the goals. The budgets themselves are less important for their dollar amounts than for how they fit the bigger -- and longer term -- picture.
Post: Can a budget do all that?
Link to comment from January 2, 2026
With each IRMAA premium, I remind myself of the bargain that Medicare is compared to individual health insurance. I pay less now, despite being in a high IRMAA tier, than I did for private insurance in the first two years of retirement without Medicare. Even adding in premiums for supplemental, Medicare Part D, dental, and long term care insurance, my annual costs are still less than I would have had for individual health insurance alone.
Post: Enough with IRMAA complaining
Link to comment from December 30, 2025
Thanks for asking, Jeff. The one decision I would change was signing a phased, three-year retirement contract. Half time work in phased retirement was essentially full time work at half salary, amplified in part due to the pandemic and having to find new ways to do existing tasks. Had I been at full salary, I could also have delayed withdrawing from savings for at least one year longer.
Post: If You Could Rewind 5 Years Before Retirement… What Would You Change?
Link to comment from December 27, 2025