I am so sorry to hear this news. Jonathan's wisdom and insights have been a tremendous blessing to so many people over the years. He will be deeply missed by this wonderful community he founded. His wisdom will live on in our minds through the words he wrote. His strength of character and purpose will endure in our hearts because of the unselfishness and courage he showed after he was diagnosed with cancer. And his voice will continue to be heard through the legacy of straightforward advice he gave to all of us, which he would want us to freely share with other individuals who need and can benefit from what he taught his readers throughout his life. I pray he will experience little pain in his last days, and for a peaceful passing.
Some people impact others by either their work, their personal story, or the strength and kindness embodied in their character. But it is a rare, good, and very gifted individual who makes an impression on and changes the lives of others through all of these means. Jonathan, you are someone who has done that for many years. And, perhaps even more importantly, when faced with what could certainly be described as a discouraging and impossible "no-win" medical condition, the depth and steadfastness of your life's light has shown brighter and with even greater intensity as you have continued to counsel and encourage others after your life altering and likely life ending cancer diagnosis. Like so many other members of the Humble Dollar community you established, I'm saddened by your situation, and I will grieve your loss if the treatments, medications, or divine intervention do not reverse your precipitious health decline. Please know that there are many folks who are thinking of you now and who will be praying for you in the coming days. We deeply appreciate and are so grateful for the tremendous testimony of your life. And we are amazed at and will always remember how you unselfishly continued to teach us throughout your personal medical adversity. Thank you for what you have done and for what you are still doing.
This was an interesting article – both thoughtful and thought provoking, as is evidenced by the number and quality of many of the comments it’s received. I appreciate that you not only said what you didn’t like about our present system for retirement saving but you also gave some ideas about how you think it can be improved. While I agree with some of your observations, I disagree with your conclusions. I think the present system is both powerful and workable for folks who are willing to take the time and make the effort to understand what they need to know to be successful at building a separate “Nest Egg” that can be used to supplement the income they hopefully will get from Social Security – which is a fantastic retirement “Safety Net” that provides an “earned benefit” – not a check from an “entitlement program.” IMO, Social Security should be strengthened and preserved as it is, without any benefit reductions for people age 45 and older. The thought of making people even MORE dependent on Social Security by doing away with our current individual and employer based retirement plans, and at the same time giving more power and responsibility for our retirement welfare to folks who think “long-term” is their next Election Cycle and who can’t see beyond a “Ten Year Federal Government Budget Window” seems like an obvious disaster to me. Somewhat akin to giving the keys to your favorite vehicle to an irresponsible driver with poor vision and lousy decision making skills, who also suffers from drug and alcohol abuse. Who would do that? It’s a total non-starter for me.
I believe, and have seen up close and personal, that knowledge is power when it comes to managing and achieving financial success. Granted, nothing is guaranteed but death and taxes, but at my church I’ve helped teach both Ron Blue’s “Master Your Money” program and Dave Ramsey’s “Financial Peace University” curriculum. The students often had little financial acumen before enrolling, but after completing the classes they knew enough about the basics of personal finances to take control of, and in many cases, dramatically change, the course of their financial future. They were also equipped to understand and take advantage of the plethora of free financial information that is available these days to anyone with a computer or Smartphone.
In today’s world it’s not that hard to be able to learn about how to manage your money, plan for your financial future, and invest for retirement, including some of the examples you gave – like how to understand the difference between Target Date Retirement Funds and Index Funds, or how to choose appropriate investments within a 401(k) plan. This learning does require time and effort, but the potential benefits are well worth it.
Considering how much money our country spends on education, we should be able to create an empowered nation of citizens who are highly financially literate almost without exception. Doing that would allow people to be more responsible and successful when it comes to earning and managing their money. It would lead to better individual outcomes, with less reliance on the government for help. I believe it would also result in more personal charitable generosity.
Our existing system IS quite complex when it comes to retirement planning, tax planning and preparation, and investing. I argue not in favor of the complexity for its own sake, some of which I personally abhor as a professional Tax Practitioner, but rather for the opportunities and benefits the current system offers to those who learn how to apply it to improve their present financial well being and their future financial independence.
I’m working on a “real life” hypothetical example which I may post separately to this comment. Or I may reach out to Jonathan about the possibility of submitting it as an article, given that I think it could possibly be an interesting and insightful read. Dick, thanks again for passionately expressing your views in this article.
"The question is, why has one Congress after another ignored the Trustee warnings for decades to fix the finances of the program." Politics. "in the worse case incoming taxes will fund most of promised benefits. It cannot go bankrupt as sometimes claimed." While it's true that Social Security isn't at risk of going bankrupt any time soon, if our dysfunctional elected representatives of both parties don't set aside their partisan differences and come together to "fix" the Program's finances within the next few years, the projected benefit cut could be between 18% and 25%. I don't believe that SSA Beneficiaries who might have to live on only 75% to 82% of their previously promised payments would call that 'fund(ing) most of promised benefits'. Such an unfortunate circumstance would likely pose a serious financial obstacle for many of them. What's especially frustrating is that, as you correctly noted, a combination of relatively modest changes would shore up Social Security's finances and stabilize the system for several decades. I used to be much more optimistic that the folks we send to Washington DC would come together to avert what would truly be a "fiscal cliff" for retirees. Now I'm much less certain that will happen. I'm not a betting person, but if I was, I'd say the current odds are about 50-50 that a viable solution is implemented before time runs out. I really hope I'm being too pessimistic and end up being wrong about that. I sincerely hope the current conventional wisdom that says "Congress would never let Social Security funding deteriorate to where the Program isn't able to pay promised benefits" ultimately prevails.
Good article Michael, but there's one item I'm unclear about after reading your post. You don't say in the article whether you concluded that your Nephew and his parents will have to deal with "Kiddie Tax" ramifications as a result of selling the shares that were gifted to him. At first glance it seems that Andy and his parents WILL likely be subject to the Kiddie Tax Rules when these gifted shares are sold. Is that what you're thinking? And if so, how/why did you decide to gift him shares of a mutual fund that had/has "significant capital gains" embedded in the income tax calculation for settling up with the IRS and State Tax folks? I'd be interested in hearing your thoughts on the tax consequences of this gifting decision if you're willing to share them. I expect the tax implications of this gifting transaction would both inform and interest others who read the article. Thanks again for sharing with your readers what you went through to make this idea a reality. It's certainly an innovative way to further reward your Nephew for the diligence and hard work that led to his high school academic success and subsequent college scholarship.
Comments
I am so sorry to hear this news. Jonathan's wisdom and insights have been a tremendous blessing to so many people over the years. He will be deeply missed by this wonderful community he founded. His wisdom will live on in our minds through the words he wrote. His strength of character and purpose will endure in our hearts because of the unselfishness and courage he showed after he was diagnosed with cancer. And his voice will continue to be heard through the legacy of straightforward advice he gave to all of us, which he would want us to freely share with other individuals who need and can benefit from what he taught his readers throughout his life. I pray he will experience little pain in his last days, and for a peaceful passing.
Post: Jonathan and website update
Link to comment from September 20, 2025
Some people impact others by either their work, their personal story, or the strength and kindness embodied in their character. But it is a rare, good, and very gifted individual who makes an impression on and changes the lives of others through all of these means. Jonathan, you are someone who has done that for many years. And, perhaps even more importantly, when faced with what could certainly be described as a discouraging and impossible "no-win" medical condition, the depth and steadfastness of your life's light has shown brighter and with even greater intensity as you have continued to counsel and encourage others after your life altering and likely life ending cancer diagnosis. Like so many other members of the Humble Dollar community you established, I'm saddened by your situation, and I will grieve your loss if the treatments, medications, or divine intervention do not reverse your precipitious health decline. Please know that there are many folks who are thinking of you now and who will be praying for you in the coming days. We deeply appreciate and are so grateful for the tremendous testimony of your life. And we are amazed at and will always remember how you unselfishly continued to teach us throughout your personal medical adversity. Thank you for what you have done and for what you are still doing.
Post: Health Update
Link to comment from September 6, 2025
This was an interesting article – both thoughtful and thought provoking, as is evidenced by the number and quality of many of the comments it’s received. I appreciate that you not only said what you didn’t like about our present system for retirement saving but you also gave some ideas about how you think it can be improved. While I agree with some of your observations, I disagree with your conclusions. I think the present system is both powerful and workable for folks who are willing to take the time and make the effort to understand what they need to know to be successful at building a separate “Nest Egg” that can be used to supplement the income they hopefully will get from Social Security – which is a fantastic retirement “Safety Net” that provides an “earned benefit” – not a check from an “entitlement program.” IMO, Social Security should be strengthened and preserved as it is, without any benefit reductions for people age 45 and older. The thought of making people even MORE dependent on Social Security by doing away with our current individual and employer based retirement plans, and at the same time giving more power and responsibility for our retirement welfare to folks who think “long-term” is their next Election Cycle and who can’t see beyond a “Ten Year Federal Government Budget Window” seems like an obvious disaster to me. Somewhat akin to giving the keys to your favorite vehicle to an irresponsible driver with poor vision and lousy decision making skills, who also suffers from drug and alcohol abuse. Who would do that? It’s a total non-starter for me. I believe, and have seen up close and personal, that knowledge is power when it comes to managing and achieving financial success. Granted, nothing is guaranteed but death and taxes, but at my church I’ve helped teach both Ron Blue’s “Master Your Money” program and Dave Ramsey’s “Financial Peace University” curriculum. The students often had little financial acumen before enrolling, but after completing the classes they knew enough about the basics of personal finances to take control of, and in many cases, dramatically change, the course of their financial future. They were also equipped to understand and take advantage of the plethora of free financial information that is available these days to anyone with a computer or Smartphone. In today’s world it’s not that hard to be able to learn about how to manage your money, plan for your financial future, and invest for retirement, including some of the examples you gave – like how to understand the difference between Target Date Retirement Funds and Index Funds, or how to choose appropriate investments within a 401(k) plan. This learning does require time and effort, but the potential benefits are well worth it. Considering how much money our country spends on education, we should be able to create an empowered nation of citizens who are highly financially literate almost without exception. Doing that would allow people to be more responsible and successful when it comes to earning and managing their money. It would lead to better individual outcomes, with less reliance on the government for help. I believe it would also result in more personal charitable generosity. Our existing system IS quite complex when it comes to retirement planning, tax planning and preparation, and investing. I argue not in favor of the complexity for its own sake, some of which I personally abhor as a professional Tax Practitioner, but rather for the opportunities and benefits the current system offers to those who learn how to apply it to improve their present financial well being and their future financial independence. I’m working on a “real life” hypothetical example which I may post separately to this comment. Or I may reach out to Jonathan about the possibility of submitting it as an article, given that I think it could possibly be an interesting and insightful read. Dick, thanks again for passionately expressing your views in this article.
Post: Retirement Do-Over
Link to comment from October 16, 2023
"The question is, why has one Congress after another ignored the Trustee warnings for decades to fix the finances of the program." Politics. "in the worse case incoming taxes will fund most of promised benefits. It cannot go bankrupt as sometimes claimed." While it's true that Social Security isn't at risk of going bankrupt any time soon, if our dysfunctional elected representatives of both parties don't set aside their partisan differences and come together to "fix" the Program's finances within the next few years, the projected benefit cut could be between 18% and 25%. I don't believe that SSA Beneficiaries who might have to live on only 75% to 82% of their previously promised payments would call that 'fund(ing) most of promised benefits'. Such an unfortunate circumstance would likely pose a serious financial obstacle for many of them. What's especially frustrating is that, as you correctly noted, a combination of relatively modest changes would shore up Social Security's finances and stabilize the system for several decades. I used to be much more optimistic that the folks we send to Washington DC would come together to avert what would truly be a "fiscal cliff" for retirees. Now I'm much less certain that will happen. I'm not a betting person, but if I was, I'd say the current odds are about 50-50 that a viable solution is implemented before time runs out. I really hope I'm being too pessimistic and end up being wrong about that. I sincerely hope the current conventional wisdom that says "Congress would never let Social Security funding deteriorate to where the Program isn't able to pay promised benefits" ultimately prevails.
Post: Retirement Do-Over
Link to comment from October 14, 2023
Good article Michael, but there's one item I'm unclear about after reading your post. You don't say in the article whether you concluded that your Nephew and his parents will have to deal with "Kiddie Tax" ramifications as a result of selling the shares that were gifted to him. At first glance it seems that Andy and his parents WILL likely be subject to the Kiddie Tax Rules when these gifted shares are sold. Is that what you're thinking? And if so, how/why did you decide to gift him shares of a mutual fund that had/has "significant capital gains" embedded in the income tax calculation for settling up with the IRS and State Tax folks? I'd be interested in hearing your thoughts on the tax consequences of this gifting decision if you're willing to share them. I expect the tax implications of this gifting transaction would both inform and interest others who read the article. Thanks again for sharing with your readers what you went through to make this idea a reality. It's certainly an innovative way to further reward your Nephew for the diligence and hard work that led to his high school academic success and subsequent college scholarship.
Post: An Appreciated Gift
Link to comment from August 1, 2021