FREE NEWSLETTER

There are those who seize control of their financial life—and then there are those who wake up to find a variable annuity in their IRA.

Latest PostsAll Discussions »

The condo, HOA, senior citizen conundrum

"We also owned a condo in an association that owned the streets and all of the infrastructure. They were built in the 70s. I didn’t feel that our contingency funds were sufficient to cover potential upgrades such as roads, water lines, and sewers. That was one of the reasons we decided to move. "
- DAN SMITH
Read more »

Penny Wise, Pound Foolish

"You are a perfect candidate for home roasting coffee. I've been doing it for over 30 years. Fresh single origin coffee from anywhere in the world every day currently at about $8/lb. It's a simple process. If you can make popcorn, it's easy. Google Sweet Marias for beans and roasting info.(you don't need an expensive roaster)"
- Bob Steele
Read more »

Staying Rational

IT'S BEEN MORE than six years since Covid first entered our vocabulary. It goes without saying that investors have experienced a lot, and for better or worse, recent market events provide some useful lessons. The first has to do with the nature of the stock market. What drives stock prices? Open a finance textbook, and the answer will be clear: The value of a stock should equal the sum of the company’s future profits. This idea is known as intrinsic value, and it’s the textbook explanation of how stock prices work. But there’s clearly a disconnect, since stock prices bounce around far more than the math suggests they should.  How can we square this circle? Over the long term, the data tell us that intrinsic value is a valid idea. Chart the price of any given stock, then overlay the company’s profits, and there will often be a reasonably close relationship. But only if you’re Rip Van Winkle. Over shorter periods of time, anything can happen. Stocks often move far above or far below their intrinsic values in response to the news of the day.  Especially during times of economic uncertainty, intrinsic value analysis is typically cast aside and replaced by some combination of emotion, conjecture, speculation and storytelling. That’s what we saw in the early months of 2020. Stores were closed, employees had been sent home and the economy went into recession. And since no one had a crystal ball, that’s when storytellers were able to step in with their extreme predictions, causing the stock market to drop more than 30% in the space of six weeks. The lesson for investors: No one can predict when the next crisis will roll around or what form it will take. But there is one very reasonable way to be able to keep it in perspective: by remembering that, at the end of the day, intrinsic value is what matters, and ultimately that’s what drives stock prices. Basic arithmetic illustrates how this can help us manage through the next crisis. Consider that the price-to-earnings ratio of the U.S. stock market has historically averaged around 16. The average company’s total stock market value, in other words, has been equal to about 16 times its annual profits.  Now let’s imagine that the next crisis results in every company in America losing an entire year of earnings. That’s extreme and hasn’t happened since the Depression, but it’s useful as a thought experiment. In that scenario, what would be the impact to those companies’ intrinsic value? In simple terms, it would be just one-sixteenth, or a modest 6%. What if a crisis were so severe that a company lost two years of earnings? Using this simple model, the impact would be about 12%. This is meaningful, I believe, because crises typically result in stock price declines that are far more severe than just 6% or 12%. In 2000 and in 2008, the market dropped more than 50%. While every crisis is different, I think it’s useful to keep these numbers in mind whenever the next geopolitical event causes stocks to drop. When that occurs, storytellers will inevitably take over, and the news will be downbeat. But if stocks drop to an extreme degree, as they have in the past, we can probably view it as an overreaction. That won’t help anyone’s portfolio recover any faster, but it should help us tune out the worst of the forecasters and maintain our equanimity. How else can you maintain an even keel during a market crisis? It’s important to understand the impact of recency bias. This bias is the tendency to extrapolate from current conditions, to assume that the future will look like the present, and to downplay the possibility that things might change. That tendency is what contributed to the cycle of negative news during the depths of 2020, and this is why I think it’s so important for investors to be aware of market history.  Again, extensive analysis isn’t required. We need only look back across some of the crises the country has weathered, from the Civil War to the Depression to World War II. In each case, the economy recovered and went on to become larger and stronger than before. The lesson for investors: In the depths of a crisis, it’s very difficult to know when or how it will end. But a sense of history can help carry us through. Those are ways to manage through a crisis. Covid also provided a lesson on how to prepare—specifically, how to prepare our portfolios—for a future downturn. In 2022, investors were caught flat-footed when popular total-bond market funds delivered surprising losses. These funds are one pillar of the well-known three-fund portfolio and have traditionally been viewed as the default choice for a set-it-and-forget-it bond allocation. But in 2022, when the Federal Reserve hiked interest rates, these funds dropped a surprising 13%. That was during the same year that the U.S. stock market dropped nearly 20%, creating a very difficult situation for those in retirement and needing to withdraw from their portfolios. The lesson for investors: Total-bond market funds may be well diversified, but they carry risk along another very important dimension known as duration. This is a bond metric that measures, in simple terms, how long it will take for bondholders to be repaid, and it’s a key determinant of risk. The longer the duration, the greater the risk of loss when rates rise. While total-bond market funds have holdings across a broad range of durations, they average out to nearly six years. That’s why they lost so much value in 2022. What’s the alternative? Short-term bond funds tend to have a duration in the neighborhood of just two years. As a result, in 2022, short-term government bond funds like Vanguard’s Short-Term Treasury ETF (ticker: VGSH) lost a far more manageable 4% of their value. To be sure, every crisis is different, and it’s easy to rationalize about the past once it’s in the past. But these lessons, I think, can help us better prepare both our emotions and our portfolios for whatever comes next.   Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
Read more »

Navigating a Turbulent Career

A RECENT article by Adam Grossman relayed an interesting story of the 2015 merger of Kraft and Heinz.  One of the aspects that made this merger unique was the involvement of Warren Buffet. Adam’s story is a cautionary tale for investors – research shows that, more often than not, the hoped-for corporate synergies and growth are elusive. The story provides more evidence for the benefits of indexing to investors. There is, however, another side to this story that is very important to an individual’s personal financial life. In addition to being investors, most of us are, or were, employees of a corporation.  What if you are an employee of a company that is acquiring another company, being acquired by another company, or part of a merger?  How do you navigate the challenges of this significant career event? In late November 1985, I interviewed with RCA’s Astro Space division in East Windsor, NJ.  Several weeks later I interviewed with GE Aerospace in King of Prussia, PA.  In between those 2 interviews it was announced that GE was acquiring RCA. I received an offer for a position in the thermal engineering group of both companies. The GE offer was for $32,000, $4,000 more than the RCA offer.  The GE plant was about 8 miles from our home; the RCA plant was 62 miles from our home.   I accepted the GE offer.  When I called the RCA manager to tell him my decision, he was professional and understanding.  He remarked that “who knows, we may end up working together and you got a better deal out of it”. Four months later that RCA manager became the senior manager of the merged thermal engineering organization – my new boss’s boss. Seven years later my division was sold to Martin Marietta, whose space operations were based in Denver, CO. Two years later Martin Marietta merged with Lockheed, in Sunnyvale, CA, to form Lockheed Martin.  Later that year it was announced that the company was closing its 2 east coast plants and moving the work to Sunnyvale and Denver.   Over the 31 years starting in 1986, I was part of numerous acquisitions, mergers, two plant shut-downs, and being sold to a private equity company. Somehow, I managed to stay employed, and grow my career. I wasn’t special – hundreds of colleagues trod the same path. When I look back I can identify some of the attributes that helped me navigate a turbulent career. Build your Reputation: Be someone that people want to hire. If you move up, be someone that people want to work for. My first senior manager position came about because the hiring team remembered me from 4 years previous  Maintain Flexibility: Are you willing to travel or relocate? Would you take a lateral position, or even a step down, if it meant keeping a job?  During my career I traveled extensively, commuted 62 miles for four years, and took new positions that challenged me and my family.  Focus on your Skills: What are the skills and behaviors that are valued by your company, and differentiate successful employees? These include technical, leadership, managerial, and interpersonal skills. My first GE manager provided a sound technical base, but also taught me just as much about work ethic, and professionalism. Focus on the Culture:  Combing organizations means combining cultures, just as much as products or processes.  This may require you to be open to a different way of doing things. It requires a willingness to learn and grow.  It will also likely require some diplomacy skills.  Change is hard for employees, and nobody enjoys being told their processes or products are inferior.  When we merged with RCA, we found there was a significant difference in the way that managers and senior technical leaders challenged their employees in public forums, in front of customers.  GE preferred to work out technical differences and approaches in-house, and present a united front to customers. This took some time to resolve into a shared approach. Focus on the People:  When my first GE manager retired, we held a group luncheon. He was universally liked and respected.  Someone described him as the best “BTU chaser” he’d ever seen, which was high praise. He gave a short speech at his retirement, where he discussed the exciting space programs he had supported. He ended that the thing that made his career special wasn’t the projects and technology, it was the people.   I was also fortunate to work on some exciting, ground-breaking projects.  It wasn’t always easy, and the path certainly wasn’t straight.  Looking back, it is the people I think of most, and I miss the most.    Richard Connor is a semi-retired aerospace engineer with a keen interest in finance. He enjoys a wide variety of other interests, including chasing grandkids, space, sports, travel, winemaking and reading. Follow Rick on Twitter @RConnor609 and check out his earlier articles.
Read more »

A Life You Build

"Mark, I was thinking the same thing about my life. Looking back I took the correct path when I met numerous forks in the road and was "lucky" to choose the correct path most times. Getting across the finish line is the important thing. How you get there can be an infinite number of paths as I've read over the years here on Humble Dollar."
- Tom Brady
Read more »

Something to Think About

"This is an issue for an optimizer but not a satisficer. I'm more concerned with the total amount I convert each year than the timing. But I do have optimizer tendencies: I tend to leave maybe half or more of my Roth conversions for December so I can guess better and make my income near the top of the tax bracket and keep my capital gains in the 0% bracket."
- Randy Dobkin
Read more »

One Good Call?

"Jeremy. A very sharp observation, and it brings to mind that old saying: invert, always invert. To answer your question directly: no, I haven't analysed my wife's portfolio to that extent — and if I'm honest, I probably won't. She's determined to stay with the adviser, and I'm content with what we've achieved: a fee reduction and a new commitment to advise based on our total combined holdings rather than hers in isolation. Sometimes you have to know which hill to die on — and when to retreat with a partial victory."
- Mark Crothers
Read more »

What happens to Medicare Supplement coverage when moving to a different state?

"Triple check but I believe that the Medigap insurer you originally picked stays with you if you move to another county or state (and don't change plans or companies). A few states even allow you to change companies and/or plans without underwriting or higher premiums (community pricing). Each state has an 800 SHIP (State Health Insurance. Assistance Program)  hotline to connect you with knowledgeable folks."
- R Mancuso
Read more »

A Bit More Humble

I LOVE TO PLAN. My wife, Sharon, often catches me nestled in my chair, gazing out a window at a distant object as my mind wanders even farther afield. My musings become scribbles on a scrap of paper, destined for discussion with Sharon at length over coffee and long walks. Eventually, we hammer out the settled strategies we think will best bring us happiness in adventures ranging from our next hike to the next few decades of life. Of course, I know our intended track, or even the final destination, may change over time. I'm just a little boat on a big sea, blown about by winds and carried along by deep currents that may push me far off my charted course. Still, though it may be somewhat of an illusion, I cling to the comfort of control. Smooth sailing. And for most of 2025, life was comfortable. In April, I shifted to part-time work as a physical therapist. I termed my new lifestyle “semi-retirement”. My reduced salary, added to Sharon’s contribution from a few hours’ work each month, still gave us enough income from our jobs to cover expenses, with leftovers for a little investing and so forth. Along with that, we gained enough new-found, free time to pursue a bit more fun while catching up on projects around the house. As an added bonus, I expected delaying full retirement a couple of years might lead to more happiness in the decades ahead. How so? Because my post-retirement plan was still a work-in-progress. “I studied and planned for two years before I retired,” Mike told me at a large family gathering. In his mid-70s, his excitement was evident as he recounted his active lifestyle. At home, his schedule includes participation in our state’s Master Gardener program and regular trips to the gym. Abroad, he organizes groups to walk the Camino de Santiago in Spain.  I had a yen for a fulfilling retirement like Mike’s. My roster of reasons to jump out of bed each morning might have a different twist or two, but I wanted the same zest for living. My unique recipe for retirement happiness still needed time to cook, however. Oh, I knew I had plenty to keep my hands active. Even so, I wasn’t yet convinced I could substitute the mental stimulation provided by my patients and colleagues. According to a decades-long study from Harvard University, some folks discover that work supplies satisfaction not found elsewhere. I have a nagging suspicion I’m one of those restless souls, and I dreaded the thought of finding myself adrift, with little sense of purpose beyond indulging my own selfish needs. And let’s face it: I still get a thrill from watching my money grow. Earning an income delays the need to plunge my fingers into my pile of savings to pay the grocery bill. All told, I figured my best move was to stay put until a clear exit appeared. Unexpected storm. Meanwhile, my employer was moving in its own interest. In December, I learned that with the new year came new management for our outpatient physical therapy clinics. Our hospital system opted to outsource operations with the hope of securing guaranteed revenue. After the revamping, my boss would keep some new iteration of her job, but the outpatient clinics would report to the new administration, rather than her. The news was a blow to my ordered life. No longer was I sailing through calm waters toward the sunset of my choosing. Instead, I faced the probability of turbulence as our clinic transitioned to the new system. And we were already struggling to implement a comprehensive computer software replacement that would take many more months to fashion into a serviceable tool. I sensed danger ahead. Or, at the very least, a year or two of starts, sputters and stops before the clinic machine was humming again. I decided to bail, and on February 18th clocked my last day with my former employer, four days after Sharon. It turns out my radar was right. The details are dirty, but the gist is the transition is stalled and leadership of the affected clinics in limbo. New direction. On the face of the situation, it seems my “clear exit” did indeed appear, and that I acted with autonomy to choose the course of my life. After all, I had exercised the option of jumping out of a job headed south and into the retirement I had dreamed of for decades. On top of that, I landed in a new, part-time job with Miranda, an old friend. Back in December, Miranda called to ask if I could help cover patients in her clinic while she was out on extended leave. I wasn’t seeking more work, but she needed help. I couldn’t refuse. So, starting with one half-day per week in January, I’m now up to two or three half-days. Miranda’s made it clear I’m welcome to work more, but I’m satisfied for now. And the atmosphere in the clinic is great. It’s staffed by easy-going folks who are serious about patient care. Still, it’s hard to shake the sense I’ve been scrambling to right myself after getting shoved off balance. During the last few weeks with my former employer, I had the feeling I was getting pushed out of a satisfying job before I was ready to leave. My usual optimism suffered, as did my sleep habits and typical interests, like gardening and writing. Why? Perhaps the answer is the sudden, unplanned departure from my job. Research indicates forced retirement can lead to negative feelings about health and to depression. I have to admit I found my new temperament described in the pages of a research paper.  Other studies on job loss, found here, here and here, examine and compare the emotions experienced by losing a job to that of other types of loss, such as grief after the death of a loved one. Considered in this light, the Kubler-Ross model of the five stages of grief might help someone--like me–understand and deal with the psychological aftermath of job loss. Peering ahead. Back to my reality, I know I’m painting a grim picture of a life that’s actually very blessed. Others have experienced far worse with fewer complaints. My perceived suffering pales beside that of a person who’s lost a loved one, or an income needed for survival. Also, as I get used to the shift in my lifestyle, I’m beginning to find my groove again. Last spring, I started the season thinking I was at life’s helm, confident I could steer in any direction and choose my pace. I was thankful, but a little smug as I laid plans for my vision of retirement. One year later, I’m still planning and still thankful–but a bit more humble.   Ed is a semi-retired physical therapist who lives and works in a small community near Atlanta. When he's not spending time with his church, family or friends, you may find him tending his garden and wondering if he will ever fully retire. Check out Ed’s earlier articles.
Read more »

What Bangladesh Taught Me About Enough

"Thank you Sundar for sharing your experiences and your encouragement to keep writing. I appreciate it."
- Andrew Clements
Read more »

The condo, HOA, senior citizen conundrum

"We also owned a condo in an association that owned the streets and all of the infrastructure. They were built in the 70s. I didn’t feel that our contingency funds were sufficient to cover potential upgrades such as roads, water lines, and sewers. That was one of the reasons we decided to move. "
- DAN SMITH
Read more »

Penny Wise, Pound Foolish

"You are a perfect candidate for home roasting coffee. I've been doing it for over 30 years. Fresh single origin coffee from anywhere in the world every day currently at about $8/lb. It's a simple process. If you can make popcorn, it's easy. Google Sweet Marias for beans and roasting info.(you don't need an expensive roaster)"
- Bob Steele
Read more »

Staying Rational

IT'S BEEN MORE than six years since Covid first entered our vocabulary. It goes without saying that investors have experienced a lot, and for better or worse, recent market events provide some useful lessons. The first has to do with the nature of the stock market. What drives stock prices? Open a finance textbook, and the answer will be clear: The value of a stock should equal the sum of the company’s future profits. This idea is known as intrinsic value, and it’s the textbook explanation of how stock prices work. But there’s clearly a disconnect, since stock prices bounce around far more than the math suggests they should.  How can we square this circle? Over the long term, the data tell us that intrinsic value is a valid idea. Chart the price of any given stock, then overlay the company’s profits, and there will often be a reasonably close relationship. But only if you’re Rip Van Winkle. Over shorter periods of time, anything can happen. Stocks often move far above or far below their intrinsic values in response to the news of the day.  Especially during times of economic uncertainty, intrinsic value analysis is typically cast aside and replaced by some combination of emotion, conjecture, speculation and storytelling. That’s what we saw in the early months of 2020. Stores were closed, employees had been sent home and the economy went into recession. And since no one had a crystal ball, that’s when storytellers were able to step in with their extreme predictions, causing the stock market to drop more than 30% in the space of six weeks. The lesson for investors: No one can predict when the next crisis will roll around or what form it will take. But there is one very reasonable way to be able to keep it in perspective: by remembering that, at the end of the day, intrinsic value is what matters, and ultimately that’s what drives stock prices. Basic arithmetic illustrates how this can help us manage through the next crisis. Consider that the price-to-earnings ratio of the U.S. stock market has historically averaged around 16. The average company’s total stock market value, in other words, has been equal to about 16 times its annual profits.  Now let’s imagine that the next crisis results in every company in America losing an entire year of earnings. That’s extreme and hasn’t happened since the Depression, but it’s useful as a thought experiment. In that scenario, what would be the impact to those companies’ intrinsic value? In simple terms, it would be just one-sixteenth, or a modest 6%. What if a crisis were so severe that a company lost two years of earnings? Using this simple model, the impact would be about 12%. This is meaningful, I believe, because crises typically result in stock price declines that are far more severe than just 6% or 12%. In 2000 and in 2008, the market dropped more than 50%. While every crisis is different, I think it’s useful to keep these numbers in mind whenever the next geopolitical event causes stocks to drop. When that occurs, storytellers will inevitably take over, and the news will be downbeat. But if stocks drop to an extreme degree, as they have in the past, we can probably view it as an overreaction. That won’t help anyone’s portfolio recover any faster, but it should help us tune out the worst of the forecasters and maintain our equanimity. How else can you maintain an even keel during a market crisis? It’s important to understand the impact of recency bias. This bias is the tendency to extrapolate from current conditions, to assume that the future will look like the present, and to downplay the possibility that things might change. That tendency is what contributed to the cycle of negative news during the depths of 2020, and this is why I think it’s so important for investors to be aware of market history.  Again, extensive analysis isn’t required. We need only look back across some of the crises the country has weathered, from the Civil War to the Depression to World War II. In each case, the economy recovered and went on to become larger and stronger than before. The lesson for investors: In the depths of a crisis, it’s very difficult to know when or how it will end. But a sense of history can help carry us through. Those are ways to manage through a crisis. Covid also provided a lesson on how to prepare—specifically, how to prepare our portfolios—for a future downturn. In 2022, investors were caught flat-footed when popular total-bond market funds delivered surprising losses. These funds are one pillar of the well-known three-fund portfolio and have traditionally been viewed as the default choice for a set-it-and-forget-it bond allocation. But in 2022, when the Federal Reserve hiked interest rates, these funds dropped a surprising 13%. That was during the same year that the U.S. stock market dropped nearly 20%, creating a very difficult situation for those in retirement and needing to withdraw from their portfolios. The lesson for investors: Total-bond market funds may be well diversified, but they carry risk along another very important dimension known as duration. This is a bond metric that measures, in simple terms, how long it will take for bondholders to be repaid, and it’s a key determinant of risk. The longer the duration, the greater the risk of loss when rates rise. While total-bond market funds have holdings across a broad range of durations, they average out to nearly six years. That’s why they lost so much value in 2022. What’s the alternative? Short-term bond funds tend to have a duration in the neighborhood of just two years. As a result, in 2022, short-term government bond funds like Vanguard’s Short-Term Treasury ETF (ticker: VGSH) lost a far more manageable 4% of their value. To be sure, every crisis is different, and it’s easy to rationalize about the past once it’s in the past. But these lessons, I think, can help us better prepare both our emotions and our portfolios for whatever comes next.   Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
Read more »

Navigating a Turbulent Career

A RECENT article by Adam Grossman relayed an interesting story of the 2015 merger of Kraft and Heinz.  One of the aspects that made this merger unique was the involvement of Warren Buffet. Adam’s story is a cautionary tale for investors – research shows that, more often than not, the hoped-for corporate synergies and growth are elusive. The story provides more evidence for the benefits of indexing to investors. There is, however, another side to this story that is very important to an individual’s personal financial life. In addition to being investors, most of us are, or were, employees of a corporation.  What if you are an employee of a company that is acquiring another company, being acquired by another company, or part of a merger?  How do you navigate the challenges of this significant career event? In late November 1985, I interviewed with RCA’s Astro Space division in East Windsor, NJ.  Several weeks later I interviewed with GE Aerospace in King of Prussia, PA.  In between those 2 interviews it was announced that GE was acquiring RCA. I received an offer for a position in the thermal engineering group of both companies. The GE offer was for $32,000, $4,000 more than the RCA offer.  The GE plant was about 8 miles from our home; the RCA plant was 62 miles from our home.   I accepted the GE offer.  When I called the RCA manager to tell him my decision, he was professional and understanding.  He remarked that “who knows, we may end up working together and you got a better deal out of it”. Four months later that RCA manager became the senior manager of the merged thermal engineering organization – my new boss’s boss. Seven years later my division was sold to Martin Marietta, whose space operations were based in Denver, CO. Two years later Martin Marietta merged with Lockheed, in Sunnyvale, CA, to form Lockheed Martin.  Later that year it was announced that the company was closing its 2 east coast plants and moving the work to Sunnyvale and Denver.   Over the 31 years starting in 1986, I was part of numerous acquisitions, mergers, two plant shut-downs, and being sold to a private equity company. Somehow, I managed to stay employed, and grow my career. I wasn’t special – hundreds of colleagues trod the same path. When I look back I can identify some of the attributes that helped me navigate a turbulent career. Build your Reputation: Be someone that people want to hire. If you move up, be someone that people want to work for. My first senior manager position came about because the hiring team remembered me from 4 years previous  Maintain Flexibility: Are you willing to travel or relocate? Would you take a lateral position, or even a step down, if it meant keeping a job?  During my career I traveled extensively, commuted 62 miles for four years, and took new positions that challenged me and my family.  Focus on your Skills: What are the skills and behaviors that are valued by your company, and differentiate successful employees? These include technical, leadership, managerial, and interpersonal skills. My first GE manager provided a sound technical base, but also taught me just as much about work ethic, and professionalism. Focus on the Culture:  Combing organizations means combining cultures, just as much as products or processes.  This may require you to be open to a different way of doing things. It requires a willingness to learn and grow.  It will also likely require some diplomacy skills.  Change is hard for employees, and nobody enjoys being told their processes or products are inferior.  When we merged with RCA, we found there was a significant difference in the way that managers and senior technical leaders challenged their employees in public forums, in front of customers.  GE preferred to work out technical differences and approaches in-house, and present a united front to customers. This took some time to resolve into a shared approach. Focus on the People:  When my first GE manager retired, we held a group luncheon. He was universally liked and respected.  Someone described him as the best “BTU chaser” he’d ever seen, which was high praise. He gave a short speech at his retirement, where he discussed the exciting space programs he had supported. He ended that the thing that made his career special wasn’t the projects and technology, it was the people.   I was also fortunate to work on some exciting, ground-breaking projects.  It wasn’t always easy, and the path certainly wasn’t straight.  Looking back, it is the people I think of most, and I miss the most.    Richard Connor is a semi-retired aerospace engineer with a keen interest in finance. He enjoys a wide variety of other interests, including chasing grandkids, space, sports, travel, winemaking and reading. Follow Rick on Twitter @RConnor609 and check out his earlier articles.
Read more »

A Life You Build

"Mark, I was thinking the same thing about my life. Looking back I took the correct path when I met numerous forks in the road and was "lucky" to choose the correct path most times. Getting across the finish line is the important thing. How you get there can be an infinite number of paths as I've read over the years here on Humble Dollar."
- Tom Brady
Read more »

Something to Think About

"This is an issue for an optimizer but not a satisficer. I'm more concerned with the total amount I convert each year than the timing. But I do have optimizer tendencies: I tend to leave maybe half or more of my Roth conversions for December so I can guess better and make my income near the top of the tax bracket and keep my capital gains in the 0% bracket."
- Randy Dobkin
Read more »

One Good Call?

"Jeremy. A very sharp observation, and it brings to mind that old saying: invert, always invert. To answer your question directly: no, I haven't analysed my wife's portfolio to that extent — and if I'm honest, I probably won't. She's determined to stay with the adviser, and I'm content with what we've achieved: a fee reduction and a new commitment to advise based on our total combined holdings rather than hers in isolation. Sometimes you have to know which hill to die on — and when to retreat with a partial victory."
- Mark Crothers
Read more »

Free Newsletter

Get Educated

Manifesto

NO. 59: MOST FOLKS should avoid alternative investments. Yes, they promise returns uncorrelated with the stock market and gains when shares are tumbling. But isn’t that why we own bonds?

act

ALERT U.S. EMBASSIES to your travel plans. Before leaving on a foreign trip, sign up for the State Department's free Smart Traveler Enrollment Program and detail where you’re going. The local U.S. embassy or consulate will then contact you if, say, there’s a natural disaster or terrorist incident while you’re traveling abroad—and it may be able to offer advice or help.

think

INFLATION RISK. Suppose inflation runs at 2.5% a year. If you were living off a traditional employer pension or interest from long-term bonds, your income would lose more than half its spending power over a 30-year retirement. What to do? You might keep more in stocks, while also delaying Social Security so you have more inflation-indexed income.

humans

NO. 64: WE MAY feel stuck—but often others can point the way forward. We’ve all struggled with seemingly intractable problems, mulling them over and over, trying to figure out the answer. But sometimes, the solution isn’t to think harder. Instead, it’s to ask others, who will have a different perspective—and may suggest solutions that hadn’t occurred to us.

Final Book

Manifesto

NO. 59: MOST FOLKS should avoid alternative investments. Yes, they promise returns uncorrelated with the stock market and gains when shares are tumbling. But isn’t that why we own bonds?

Spotlight: Taxes

Some people are never satisfied

The Washington Post has an article on yet another effort to cut taxes for the wealthy. This time it is stepping up the cost basis for capital gains to account for inflation. You’d think they’d at least wait for the dust to settle from the recent give away.
I don’t know whether the article is behind the pay wall, it’s not giving me an option to share it so I did a straight copy.

Read more »

Capital Gains Planning

THE IRS RECENTLY announced inflation adjustments for the tax year 2026.
2 quick changes:

Standard deduction

For single taxpayers, the standard deduction rises to $16,100 for 2026, an increase of $350 from 2025.
For married couples filing jointly, the standard deduction rises to $32,200, an increase of $700 from tax year 2025.

Capital Gains Rates

For single taxpayers, long-term capital gains are taxed at 0% if the taxable income is up to $49,450 ($98,900 for married couples filing jointly).

Read more »

Tax Strategies for W-2 Employees

I get a lot of questions from W-2 employees asking, “How can I save money on taxes?”
Many people know that business owners have a lot of flexibility to lower their tax bill, but what about W-2 workers? I’ll skip some of the more “obvious” strategies, like:

401(k)
Backdoor Roth
HSA/FSA

Here are some other ones you might want to think about:
 
Commuter benefits
Some companies offer pre-tax commuter benefits that can be used for transportation expenses such as transit passes or parking.

Read more »

New 2025 Tax Deductions

THE IRS JUST released a new form called Schedule 1-A, which includes all the new tax bill deductions.
I wanted to quickly go through some of it, so that you are more aware of the new potential savings opportunities.
I’ve previously discussed some portions of the bill, but this is the first time we have a peek of the new lines.
All of these deductions are in addition to the standard deduction or itemized deduction.

Read more »

Roth Conversion Timing and Amounts to Maximize Benefits

I thank everyone in advance for any assistance and advice you can provide regarding my Roth conversion scenario. I am currently 56 with a potential retirement age of 58 (approx. 2 yrs). My wife is younger and will continue working for another 8 years following my retirement. I plan on deferring Social Security as long as possible, age 70.  I have $850,000 in a regular IRA and an additional $600,000 in a company sponsored 401K.  My wife and I file jointly and are currently in the 24% tax bracket ($206,700- $394,600).

Read more »

Effective vs. Marginal? Nah…..

Perhaps what we should be debating is which is the most important line on the tax return. I can tell you that most would say line 34, “this is the amount you overpaid, or line 37, “this is the amount you owe. I contend line 24 matters most, “this is your total tax”. Rarely, and I mean well under 1% of the time, did a client ask me how much tax they paid. As a matter of fact,

Read more »

Spotlight: Hayes

Introverted Me

NOW THAT I'M RETIRED—and living in a warm desert climate—walking has become one of my favorite activities. Most days, I log between six and eight miles trekking around our neighborhood. I usually listen to a podcast during my journey, but it just serves as background noise. My real focus is contemplating dog training strategies or the subject matter of my future HumbleDollar posts. Some days, I play the “what if” game. I contemplate how my life’s trajectory would have been altered if I’d made different choices at certain junctures. I also often reflect on how my personality has shaped nearly every aspect of my life. Ten years ago, I read the book Quiet. As I consumed each page, it became apparent I finally had a word—introvert—to describe my personality. Up until that point, I’d never fully understood why I enjoyed the activities I did. As a child, I preferred spending time alone. Given the choice between going outside to play or staying indoors and reading a book, I’d always choose the latter. I spent hours writing stories and poems, with plots that almost always revolved around animals. As a teenager, I spent more time with my livestock than I did with friends. I found animals easier to interact with than humans. In college, I spent my time studying. I always signed up to earn more credits than I needed to be considered a fulltime student. Unsure of my career path, I used the time to take classes in a variety of subjects. The social aspects of college held no interest for me. When I was in graduate school, I landed an unpaid internship at a clinical laboratory located within a large medical school. I quickly became a valued member of the lab and was offered a paid position a few…
Read more »

Priceless to Me

AT AGE 55, I'M PERHAPS a bit young to spend time reflecting on my life. My maternal grandmother died at 101, so I could have many more decades to go. Nevertheless, I find myself more nostalgic now than I was just a few years ago. I often think back to my childhood and how it shaped who I am today. In 1976, when I was in fourth grade, my parents purchased a two-and-a-half-acre property in a small town outside of Eugene, Oregon. Within a couple of years, our hobby farm was filled with a variety of animals. Twelve Siberian husky dogs, a handful of barn cats and a herd of dairy goats resided in the various outbuildings my father constructed. Rabbits, chickens, sheep and a couple of pigs eventually moved in as well. My love of animals grew out of my daily interactions with our menagerie. Helping to care for all those creatures fell squarely on my shoulders. Every day, there were goats to milk and stalls to clean. Doing daily chores was a given. In return for my efforts, no monetary compensation was provided. I suspect my work ethic was shaped, in part, by the hundreds of hours I spent performing manual labor on our farm. In sixth grade, I became a member of the local 4-H club. During summer 1978, I attended my first county fair. Staring at the trophy table—filled with an assortment of gaudy plastic figurines mounted atop faux marble bases—my competitive nature was ignited. I walked away from that first fair with just a handful of ribbons. But I vowed to return the following year and bring home some hardware. For the next 12 months, I dedicated myself to learning as much as I could about the various competitions. My work paid off. My bedroom…
Read more »

Attitude Adjustment

MONEY HAS ALWAYS caused me stress. As a child, I worried my parents didn’t have enough, even though I had no idea what sum would have been considered enough for our family of six. In college, I worried about accumulating debt. I ended up living so frugally that I managed to save nearly all of the Pell grant that the government awarded me. I not only graduated debt-free, but also had a sizable emergency fund in place as I moved into adulthood. In my 20s and 30s, mortgages and car loans burdened me with anxiety. I fretted about not saving enough, while simultaneously worrying about how much I should spend to appear outwardly successful to friends and family. As a perfectionist, with a hint of OCD, I would sometimes spend hours combing over bank statements and checkbook registers, making sure my accounts balanced to the exact penny. Divorce plunged me into an entirely new relationship with money. Initially, I feared I wouldn’t be able to support myself. I reverted back to the extreme frugality of my college years. Once I realized my income was more than adequate for my lifestyle, I began saving nearly 50% of my paycheck. I believed if I ever wanted to retire, I needed to be in extreme savings mode. My anxiety shifted to the investment decisions I was making. Was I being too conservative? Was I being too risky? Every major stock market fluctuation, whether it was positive or negative, had me questioning my choices. These days, my personal net worth hovers close to $500,000. Just two years ago, I believed hitting that number would make me feel secure. Now I realize there’s likely no number that will make me feel completely comfortable. I’m capable of imagining numerous disasters that could wipe out the exact sum…
Read more »

Healthy Investment

DURING THE FIRST FEW months of the pandemic, my almost-daily trips to the gym ceased. I was home more of the time and snacking became a habit. I found myself five pounds heavier than I’d been a year earlier. Knowing that, at age 54, my metabolism isn’t quite as vigorous as it once was, I took action. I started a ketogenic diet and quickly dropped the extra weight. As we contemplate growing older, much of our time and energy is spent planning the financial aspects of our retirement years. But what about the health aspects of aging? Shouldn’t we be equally interested in investing in our physical well-being? A recent report found that more than 60% of U.S. adults over age 55 are overweight or obese. The health consequences are well documented. Besides an increased risk of dying younger, overweight and obese individuals suffer from more debilitating diseases than those who aren’t carrying extra weight. It’s difficult to deny the financial consequences of poor health, including the cost of multiple prescription drugs, insurance copays and health care deductibles. There’s recent evidence that 65-year-olds who describe their health as “good” or “excellent” are far less likely to require long-term-care services than those who say their health is “fair” or “poor.” What’s being done to combat elder obesity? Fitness programs like SilverSneakers are designed to target a 65-and-older population. Wearable fitness trackers, while not specifically marketed to older populations, provide an easy way to monitor how much exercise and sleep we’re getting, while also providing an estimate of how many calories we burn each day.
Read more »

From Half to Whole

FOUR YEARS AGO, at age 45, I got divorced. These days, divorces are equal-opportunity proceedings. Since our income streams had been roughly the same, and we didn’t have children, our assets were split 50-50. For me, that meant losing half my state pension. Along with that loss came the realization that my retirement dream was just that—a dream. Following the divorce, my lifestyle underwent a huge upheaval. Living on my own for the first time in my adult life, I realized I needed to educate myself on personal finance issues. I started reading books on how best to manage my money. I learned how to create—and stick to—a budget. I learned how to distinguish “needs” from “wants” and I began saving more of my paycheck. I met with a representative from the investment company that manages my current retirement fund and I learned about my investing options.  I educated myself on tax strategies, the differences between Roth and traditional IRAs, and I began to pay attention to the stock market for the first time. Studies show that women are 80% more likely than men to live in poverty during retirement, making it even more imperative they learn to manage their money after a divorce. I began my own education by reading a variety of books about personal finance, including the Jonathan Clements Money Guide (now available for free on this site) and The Simple Path to Wealth by J L Collins. I also started to follow financial websites, such as CNBC’s Personal Finance page. The investment firm that manages my retirement account created a website devoted solely to issues involving women and their finances—Woman2Woman—which contains a variety of useful information. Although my salary is quite modest—after 19 years of working for the same employer I now make $66,000 a year—I’ve…
Read more »

Heading Home (I)

JUST A FEW MONTHS ago, I wrote about my housing plans. Those plans included waiting until I was closer to retirement age before purchasing a home. Having spent the past five years as a renter, I assumed I’d keep renting until I was ready to leave fulltime work behind. Living in a relatively inexpensive apartment complex came with a few benefits. It allowed me to invest a large part of my income in various retirement accounts. I fully funded a Roth IRA three years in a row. I came close to investing the maximum allowed in my pretax retirement account at work. I lived way below my means and, as a result, built up a sizable retirement account balance before I turned 50. But living as a renter wasn’t always easy. I had to move, within my complex, three different times due to noise-related issues. I spent a substantial amount of money on various white-noise devices and sound-cancelling headsets, which I used—mostly unsuccessfully—to try to block the sounds of tenants in neighboring units. In the summer, the various apartments I rented were unbearably hot. In the winter, there were issues with snow and ice that made the outside staircases dangerous to descend. My dogs could never run loose and I longed to fall asleep to the sound of chirping crickets, rather than the noise of footsteps pacing back and forth above me. And so, a few months ago, I began to contemplate becoming a homeowner again. I assumed that on my $70,000 salary, I’d be lucky to qualify for a $200,000 mortgage. In the greater Portland, Oregon, area, that kind of money might allow me to buy a small fixer-upper in one of the city’s distant suburbs. I spent a couple of weeks checking out houses I thought I could…
Read more »