Thanks for the timeless advice; your brother would be so pleased you are expressing the emotional underpinnings to all our measured planning: ‘’Today, retirement discussions often focus on numbers: savings targets, withdrawal rates, pensions, and Social Security strategies. Those things matter. But emotional health matters, too.
A successful retirement depends not only on what we retire with financially, but also on what we bring with us emotionally.”
i think you shouldn’t ignore that many well intentioned tax loopholes are abused. An example, is a politician who buried an ex-wife on his golf course and received a special cemetery tax reduction on the property. Here is the Chat-GBT summary on these: The most frequently cited and widely debated US tax loopholes primarily benefit high-net-worth individuals and large corporations, often by reclassifying regular income or avoiding capital gains taxes. [1, 2, 3] Prominent Individual Loopholes
Carried Interest: This allows hedge fund and private equity managers to have their performance-based compensation taxed at the lower long-term capital gains rate (up to 20%) rather than the standard income tax rate (up to 37%).
"Buy, Borrow, Die" Strategy: Billionaires avoid selling assets to prevent triggering capital gains taxes. Instead, they borrow money against their assets at low interest rates to fund their lifestyles. Upon their death, heirs receive a stepped-up basis, resetting the asset's taxable value to its current market price and effectively erasing decades of gains from taxation.
Backdoor Roth IRA: High earners who exceed the income limits for direct Roth contributions use a two-step process: contributing to a traditional IRA and then immediately converting it to a Roth account to secure tax-free growth and withdrawals.
Real Estate Depreciation & Losses: Real estate investors can use "paper losses" from accelerated depreciation to offset actual cash-flow profits or even other forms of income, sometimes reducing their tax liability to zero despite owning profitable properties. [1, 2, 3, 4, 5, 6, 7, 8]
https://advisors.vanguard.com/investments/personalized-indexing/what-is-direct-indexing#overview Here is a good description of these separately managed accounts (SMA). A financial advisor recommended one of these for my taxable account, however, after several years it lagged 2% a year behind my index funds and had higher fees. I found the tax loss harvesting sometimes couldn’t compensate for spiking prices in a few stocks that were dominating the fund, eg Tesla tripled, which was good, but it is hard to balance the fund without suffering high taxes. Tax loss harvesting is also available with index funds, though, I realize there are fewer levers. The total US fund can easily be taxed harvested, for example, with a S@P500 fund. I simplified and used tax efficient total market index funds rather than SMA and changed advisors.
I switched from a wealth advisor to a Vanguard personal advisor and he is excellent. I split my funds across the two for 3 years and the Vanguard index portfolio beat the active funds from the wealth manager by 2% a year and had 1/3 the fees. Vanguard has disciplined guardrails on retirement strategies and keeps the client’s interest foremost. The wealth advisor recommended a high risk hedge fund that I turned down and later lost money and pushed leveraged investments that I didn’t need.
Thanks for the nicely written, insightful article. You elicited a lot of responses on the joys embedded in contributing to nurturing family—your definition of family is just spread wider than most. Sacrifices for school expenses and trying to be a good example helps a lot of us.
Comments
Thanks for the timeless advice; your brother would be so pleased you are expressing the emotional underpinnings to all our measured planning: ‘’Today, retirement discussions often focus on numbers: savings targets, withdrawal rates, pensions, and Social Security strategies. Those things matter. But emotional health matters, too. A successful retirement depends not only on what we retire with financially, but also on what we bring with us emotionally.”
Post: My Father: The Peace He Never Found
Link to comment from May 20, 2026
i think you shouldn’t ignore that many well intentioned tax loopholes are abused. An example, is a politician who buried an ex-wife on his golf course and received a special cemetery tax reduction on the property. Here is the Chat-GBT summary on these: The most frequently cited and widely debated US tax loopholes primarily benefit high-net-worth individuals and large corporations, often by reclassifying regular income or avoiding capital gains taxes. [1, 2, 3] Prominent Individual Loopholes
Post: There is no such thing as a tax loophole, but here they are anyway
Link to comment from May 17, 2026
https://advisors.vanguard.com/investments/personalized-indexing/what-is-direct-indexing#overview Here is a good description of these separately managed accounts (SMA). A financial advisor recommended one of these for my taxable account, however, after several years it lagged 2% a year behind my index funds and had higher fees. I found the tax loss harvesting sometimes couldn’t compensate for spiking prices in a few stocks that were dominating the fund, eg Tesla tripled, which was good, but it is hard to balance the fund without suffering high taxes. Tax loss harvesting is also available with index funds, though, I realize there are fewer levers. The total US fund can easily be taxed harvested, for example, with a S@P500 fund. I simplified and used tax efficient total market index funds rather than SMA and changed advisors.
Post: Direct Indexing Anyone?
Link to comment from May 11, 2026
I switched from a wealth advisor to a Vanguard personal advisor and he is excellent. I split my funds across the two for 3 years and the Vanguard index portfolio beat the active funds from the wealth manager by 2% a year and had 1/3 the fees. Vanguard has disciplined guardrails on retirement strategies and keeps the client’s interest foremost. The wealth advisor recommended a high risk hedge fund that I turned down and later lost money and pushed leveraged investments that I didn’t need.
Post: Financial Planning
Link to comment from April 11, 2026
Thanks for the nicely written, insightful article. You elicited a lot of responses on the joys embedded in contributing to nurturing family—your definition of family is just spread wider than most. Sacrifices for school expenses and trying to be a good example helps a lot of us.
Post: Financial regrets about parenthood?
Link to comment from April 6, 2026