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Relative Affluence

WHEN RESTRICTIONS ON travel eased this year, I visited Kolkata, India, where I grew up and my mother still lives. The airline ticket and other travel costs were almost 75% higher than my last visit four years ago.

This year, I’ve grown used to price shocks at every turn, from groceries to gas, so the steep ticket price didn’t shock me. What did surprise me was my feeling of affluence once I arrived.

Traveling to a low-cost country as a tourist doesn’t necessarily feel like a bargain because most items still have an international price tag. But living like a local is another matter. Everything seems dirt cheap to folks from high-income countries. Curious to know how far my U.S.-earned dollars went during my stay in India? Consider:

A dime would get me a freshly made hot tea from a roadside tea stall, served in a disposable earthen cup. For a nickel more, most sellers would upgrade it to a masala chai—milk tea flavored with ginger, cardamon and other aromatic spices.

A quarter paid for the return bus ticket to my aunt’s place four miles away. What else could I buy for a quarter? How about a recently picked large guava to savor with rock salt, or a bag of fresh flowers that my mother needed for her morning offerings to the gods?

A half-dollar would buy a hearty Bengali breakfast dish from an outdoor eatery, if you didn’t mind waiting while the cook prepares it right in front of you. The food would typically be served on a Sal leaf plate, to be trashed afterward in a designated bin.

A dollar for a man’s haircut might sound like a promotional offer, but that’s the regular price in the neighborhood salon—and it wasn’t due to the thinning hair of its regular customers. The small shop not only had the needed hygiene standards, leather seats and air-conditioning, but also offered nice add-ons, like a 30-minute head and shoulder massage for one dollar more.

Two dollars was the cost of my cab ride from the Kolkata airport to our house five miles away. As soon as I walked out of the arrival gate, a few touts approached me to offer a no-wait, luxurious ride. I declined and waited in the queue for pre-paid cabs. Fifteen minutes later, I got a cab assigned to me, helped the driver to load my bags and was on my way.

Five dollars covered the electrician’s labor for two visits to our house to take care of a few things for my mother. The work didn’t take long but, as a courtesy to my mother, he also bought the necessary fixtures from our neighborhood electrical store.

Ten dollars may not seem like a lot, but it was enough for a trained masseuse to come over and help me with my sore calf muscles and feet. The massage lasted about an hour, not including a brief break for tea and light snacks that my mother made for him.

[xyz-ihs snippet="Holiday-Donate"]

Fifteen dollars was the cost to take my mother for a sumptuous lunch at a trendy restaurant on Park Street, the Fifth Avenue of Kolkata. The fresh green coconut water added another dollar to the restaurant bill. The experience and service were well worth the hefty tip we left.

Twenty dollars got me an all-day ride in a private, chauffeur-driven compact car. We started in the morning to visit a few places within a 25-mile radius and returned in the evening. I could’ve used a ride-hailing service instead, but the neighborhood operator seemed more friendly and convenient.

Twenty-five dollars covered both the labor and materials for a long-overdue plumbing overhaul of the main bathroom. The plumber replaced the leaking pipes, ran a new water connection to improve the flow and installed a new showerhead. He took two days to complete the work, and it was immaculate.

One hundred dollars connected our home with high-speed broadband internet for a year. I tested to check if the connection lived up to the advertised speed of 100 Mbps. It outperformed.

One thousand dollars covered the cost of new Bosch appliances I bought for my mother and sister-in-law. These included an energy-efficient refrigerator, an automatic front-loading washing machine and a high-powered kitchen chimney. The cost, which included delivery and installation, was lower than I expected thanks to the seasonal discount for the Diwali festivals.

My feeling of affluence was shattered as soon as I was on my way back to the U.S. A cup of tea purchased past the security checkpoints at Kolkata airport cost $3. Thirty hours and 9,000 miles later, I was home, catching up with my wife after being away for a month. That was a moment worth $1 million.

Sanjib Saha is a software engineer by profession, but he's now transitioning to early retirement. Self-taught in investments, he passed the Series 65 licensing exam as a non-industry candidate. Sanjib is passionate about raising financial literacy and enjoys helping others with their finances. Check out his earlier articles. [xyz-ihs snippet="Donate"]
Read more »

Retirement Accounts

I WAS SCROLLING through social media recently and saw somebody dismiss retirement accounts as “paper wealth.” The argument was familiar: Your money is locked away and you’re waiting for permission to access it.

Post Example

There’s a grain of truth here. Retirement accounts do come with rules. But much of the discussion online ignores how flexible these accounts actually are. More important, it ignores the enormous tax advantages.

Most people today will likely live well beyond age 59½. Many will spend two or three decades in retirement. Even if somebody retires early, they’ll still need assets later in life.

That’s why ignoring retirement accounts at age 30 often isn’t wise. You could end up giving away 30 or 40 years of tax-advantaged compounding.

It also isn’t an all-or-nothing decision. We can use taxable brokerage accounts, Roth IRAs and 401(k)s together. Each account serves a different purpose.

Retirement accounts also provide rebalancing flexibility that taxable accounts don’t.

Inside a Traditional or Roth IRA, investors can rebalance portfolios without triggering capital gains taxes. Somebody who wants less stock market exposure can freely sell shares and buy bonds, Treasurys or other funds without generating an immediate tax bill. That matters over long periods of time.

The other misconception is that retirement accounts are completely inaccessible until age 59½. 

Let's talk about Rule 72(t), also called Substantially Equal Periodic Payments, or SEPP. This IRS rule allows penalty-free withdrawals before age 59½ if specific requirements are followed.

Using online 72(t) calculators, a $500,000 retirement account could potentially generate annual withdrawals of roughly $30,000 while avoiding the normal 10% early-withdrawal penalty:

72(t) calculator

The payments must continue for a required period and the IRS rules are strict. Still, the broader point remains: There are legal ways to access retirement funds earlier than many people realize.

The Rule of 55 is another example.

If you leave your employer during or after the year you turn 55, you can often withdraw money from that employer’s 401(k) without the normal 10% penalty. Again, the money is not completely locked away until 60.

Roth IRAs may also be flexible. Contributions can be withdrawn anytime tax- and penalty-free because taxes were already paid before the money went into the account.

That doesn’t mean people should tap retirement accounts early. But accessibility is very different from impossibility.

Roth IRAs also happen to be among the most powerful wealth building tools available.

Qualified withdrawals are tax-free. Dividends compound without yearly tax bills. Investors can buy and sell investments inside the account without triggering taxable events.

You may remember a famous example about Peter Thiel. According to reporting by ProPublica, Thiel reportedly grew a Roth IRA from $2,000 to more than $5 billion between 1999 and now. He turns 59½ in 2027, meaning those withdrawals could potentially be tax-free. Imagine if he had decided to skip retirement accounts because he wanted to “live now.”

Employer matches are another point often ignored online. Skipping a 401(k) match can be one of the costliest financial mistakes people make.

Suppose an employer offers a dollar-for-dollar match on the first 3% of salary contributed to a 401(k). Before the investments even grow, that’s effectively an immediate 100% return.

Very few opportunities offer that kind of risk-adjusted benefit.

In fact, somebody could theoretically contribute, collect the employer match, later withdraw the money, pay ordinary income taxes plus the 10% penalty, and still potentially come out ahead versus investing only through a taxable brokerage account with no match.

The tax advantages extend beyond employer matches.

Inside retirement accounts:

  • Dividends can compound without annual tax drag
  • Investors can rebalance without triggering taxable events
  • Capital gains taxes are deferred or eliminated, depending on the account type

Compare that with a taxable brokerage account, where dividends may create yearly tax bills and selling appreciated shares can trigger capital gains taxes.

Retirement accounts can also create opportunities for tax arbitrage.

Somebody contributing while in the 22% or 24% marginal federal tax bracket today might eventually withdraw money while in the 10% or 12% bracket during retirement.

State taxes can widen the advantage even more. Some states provide tax deductions on retirement contributions while later taxing retirement withdrawals lightly or not at all.

Early retirees often use Roth conversion ladders as well.

The process generally works like this:

  • Move money from a Traditional IRA or 401(k) into a Roth IRA
  • Pay taxes on the converted amount
  • Wait five years
  • Withdraw the converted funds penalty-free

Like Rule 72(t), there are strict rules involved. But these strategies exist because retirement accounts were never designed to be prison cells.

The larger point is that retirement planning should involve multiple tools working together. Taxable brokerage accounts provide flexibility. Roth IRAs provide tax-free growth. Traditional retirement accounts can reduce taxes during high-earning years.

None of these accounts are perfect by themselves. Together, however, they can create an extremely efficient system for building long-term wealth.

That’s why describing retirement accounts as “paper wealth” misses the bigger picture.

 

Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.  
Read more »

My Father: The Peace He Never Found

"Thank you for this, Andrew. You shed light on the other side of retirement that, as you say, is less discussed but even more important than all the financial maneuvering. I'm sure Jonathan is indeed looking over your shoulder when you write, and I know he's smiling."
- Andrew Forsythe
Read more »

A Time to Save

"Dan, things just seemed to align in those early years. One reason I was able to contribute 15% so early was the drugstore job. I was still working weekends there while I was at the magazine during the week. Another reason: my parents allowed me to live at home while in grad school at the time. It was an intense, busy, period and I was very fortunate for their generosity with the offer of shelter."
- D.J.
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Lifetime Supply

"I can’t think of a better way  to spend the summer than being on the beach and having the kids stay over most every weekend. "
- Dan Smith
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Should Retirees Get a Temporary Flat Tax Window on IRA and 401(k) Withdrawals?

"Bach said that if they do this he would withdraw his entire IRA immediately and pay the 12% rate. Intriguing idea."
- Ben Rodriguez
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The Art of Spending Money

"We started out that way, as did many of our friends, but found we spent a lot on hotels and restaurants, and we both had grown up in frugal households. After buying the van, which doubled as our second household vehicle, we kept detailed records and realized we could travel that way for around $100 a day inclusive, which suited our budget. Of course, that was in 2011!"
- Chris G
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Keeping It Simple

"I NEVER MEMORIZE anything I can look up." Albert Einstein, it seems, said this or something similar. I first heard the quote in my freshman physics class. The teacher asked a student to recite a formula. The student’s response: “I never memorize anything I can look up.”

I’ve adopted the same philosophy. My wife loves to point out that I don’t remember the names of streets in our neighborhood. But I don’t need to know them. I don’t live on those streets. I never provide directions to anyone who wants to go down those streets. Why fill my brain with unnecessary facts?

We humans make decisions on a daily basis that require remembering certain facts: your name, address, Social Security number, mother’s maiden name. You could look these up, but it’s more efficient to memorize them since they’re required on a frequent basis.

But what about other facts? I have a terrible memory. I know this, and it doesn’t bother me. I write down the facts that I think I’ll need, and I know where to find them. Consider my cell phone, which I keep in my car. I don’t remember the number, but I can look it up when I need it.

While president, Barack Obama owned only blue and gray business suits, so he wouldn’t have to give much thought to what he’d wear on any given day and hence make yet another decision. I understand this logic.

Many people are familiar with KISS, short for keep it simple, stupid. Keeping things simple means my days are simpler—and there’s less chance that I or my wife will make mistakes.

For instance, I use the same mutual fund for my Roth account as my wife uses. My theory is that, when I die and my wife consolidates our accounts, she’ll consolidate my Roth with hers, and not make the mistake of mixing traditional IRA dollars with Roth dollars and thus pay unnecessary taxes. Let’s hope my plan works.

My wife and I have all our retirement monies with the same mutual fund company. As with my Roth, I have just one mutual fund in my traditional IRA. I like simple and, again, I believe it'll be easier for my wife after I die.

We also use just one brick-and-mortar bank and one online bank for our joint accounts. That’s it. We could have more, but why? If I thought I was brilliant in moving money around, I’d invest more time in making financial moves.

But instead, I invest my time in trying to understand where I might trip up. Buying or selling usually involves trading costs, so fewer trades mean fewer costs. Maybe I’m leaving money on the table, but at least I’m not losing money. That’s more important to me than trying to make more.

I have a degree in mathematics, but I’m lousy at arithmetic. If I want to be sure I’m correct when I add or subtract, I need to use a calculator. I know this. I have the tool to get the job done. It’s simple and cheap, I know where to find it—and, when I need math answers, it allows me to look them up. Simple.

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The Company You Keep

AFTER ENRON'S COLLAPSE in 2001, there were numerous articles about employees who had most of their money in the company’s stock and how they’d lost it all. Taking that message to heart, I’ve endeavored to keep our holdings of my company’s stock below 10% of our net worth. I must confess, however, that in good times it’s crept up to 15%—and in bad times it’s fallen to zero.

I can’t claim any particular insights or novel thoughts on how to manage company stock. I’m willing to share what I’ve done, however, and let you decide how to handle your situation.

My company stock came from three main sources: the employee stock purchase plan, the match on my 401(k) contributions, and the stock options or restricted stock awards received as part of my annual compensation. As you’ll see, these three stock programs represent the good, the bad and the ugly of my investing career.

The employee stock purchase plan was the good. In our plan, we were allowed to divert up to 10% of our salary to company stock. The best part was that we could buy the stock at a 15% discount to current market prices.

Early in my career, there was a machine operator who was retiring. The word in the factory was that he was wealthy. He had been stashing 10% of his pay in company stock for the past 45 years. He had never touched the shares. I’m sure his retirement was much more comfortable than that of most machine operators.

I also spent my first five years at the company not touching the stock. We then sold it to make the downpayment on our house. Shortly thereafter, I decided I needed to rethink how to handle the stock purchase plan so I wasn’t overly reliant on the company.

For about 20 years, I was able to sell the stock after holding it for only a month. I would purchase the stock one month at a 15% discount and sell it the next month. I always made money. Depending on the market, sometimes I made more than 15% and sometimes less.

Some coworkers would scold me, telling me that I should hold the stock for a year to qualify for the lower long-term capital gains rate on my profits. My reply was that—depending on how you do the math—I was making an annualized return of as much as 603%, so I was happy to pay the ordinary income-tax rate. (For math nerds, a 15% discount is equal to an immediate 17.6% monthly gain on the purchase price. Compounded over 12 months, that comes to 603%.)

Some would look at me blankly, saying that I was only making 15%. When I couldn’t convince them that I was making far, far more than that on an annualized basis, I’d offer to lend them all the money they wanted at 5% a month. None of them took me up on the offer.

Eventually, to encourage long-term investing, the company changed the rules and required a year-long holding period before selling. At the end of the year, rather than selling, we’d donate the shares we’d purchased to charity, thereby avoiding any taxes on the gains.

For a while, the company paid its 401(k) matching contribution in company stock, which meant we had an ever-increasing exposure to this single stock. Shortly after Enron blew up, my employer stopped paying the match in company stock, while also allowing us to sell whatever company stock we had in our 401(k) and invest the money in one of the plan’s mutual funds.

I promptly traded half my company stock for shares in a broad-based mutual fund. Why only half? I’d heard about the tax advantages of net unrealized appreciation of company stock held within a 401(k). Executed correctly, when you sell, you pay income taxes on the original cost basis of the stock but the lower long-term rate on any gains. I thought that in 20 years, when I retired, this would be a good deal.

Fast forward 20 years. I was planning on withdrawing my company stock from the 401(k). Remember the good, the bad and the ugly? This is where we get to the bad. First, the stock had fallen in price, dramatically reducing both its value and the strategy’s tax advantages.

[xyz-ihs snippet="Mobile-Subscribe"]

Second, I read research by financial planner Michael Kitces suggesting that if you plan to own company stock for the long term, you’d be better off buying it outside the 401(k) to obtain the more favorable long-term capital gain rate on the whole investment and not just on a portion of it. I decided to sell all my shares and diversify using mutual funds in my 401(k). In hindsight, I realize I should have done this much earlier.

What about the ugly? That’s been the performance of my company stock options. Part of my compensation was “at risk” compensation. We were able to take this as either restricted stock units, which is a grant of shares at some future time, or as stock options, which would have value only if the shares achieved a specified price in the future. According to my employer, the value of either award was calculated to be the same when they vested in three years.

Every year, when it came time to choose how to receive this compensation, there would be lots of discussion about which was the better choice. When asked my opinion, I always said that what I was planning to do wasn’t appropriate for all people, but I’d be taking all my shares in stock options.

I had 20 years of data going back to 1978 showing that, if you held the stock options until they expired in 10 years, they performed significantly better than the restricted stock units. I planned to use my stock options as income during the 10 years following my retirement at age 60, and then claim Social Security at age 70.

I’m retired now and my remaining stock options are worth exactly zero dollars. Some may be worth money in the future if the company’s shares rise, but the hoped-for income stream from the stock options has vanished. Fortunately, I saved and invested well enough so I won’t have to claim Social Security before 70.

Although my stock option decision didn’t play out as planned, the poker player Annie Duke cautions people to not confuse the results with the decision-making process. In other words, you can be right and still lose money. I believe that my process was sound. I knew there was a potential for the options to be worth nothing and so, while it’s disappointing, it’s a financial setback I was prepared for.

While there are lots of valid ways to treat company stock, my advice would be to limit the value of your company stock to 10% or less of your total portfolio. As I’ve learned, company stock is a concentrated investment—and you may not be rewarded for the extra risk you run.

Kenyon Sayler is a retired mechanical engineer. He and his wife Lisa are extraordinarily proud of their two adult sons. He enjoys walking his dog, traveling, reading and gardening. Kenyon's brother Larry also writes for HumbleDollar. Check our Kenyon's earlier articles. [xyz-ihs snippet="Donate"]
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Direct Indexing Anyone?

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Writing a Book in Retirement: The Good, the Hard, and the Surprisingly Meaningful

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Relative Affluence

WHEN RESTRICTIONS ON travel eased this year, I visited Kolkata, India, where I grew up and my mother still lives. The airline ticket and other travel costs were almost 75% higher than my last visit four years ago.

This year, I’ve grown used to price shocks at every turn, from groceries to gas, so the steep ticket price didn’t shock me. What did surprise me was my feeling of affluence once I arrived.

Traveling to a low-cost country as a tourist doesn’t necessarily feel like a bargain because most items still have an international price tag. But living like a local is another matter. Everything seems dirt cheap to folks from high-income countries. Curious to know how far my U.S.-earned dollars went during my stay in India? Consider:

A dime would get me a freshly made hot tea from a roadside tea stall, served in a disposable earthen cup. For a nickel more, most sellers would upgrade it to a masala chai—milk tea flavored with ginger, cardamon and other aromatic spices.

A quarter paid for the return bus ticket to my aunt’s place four miles away. What else could I buy for a quarter? How about a recently picked large guava to savor with rock salt, or a bag of fresh flowers that my mother needed for her morning offerings to the gods?

A half-dollar would buy a hearty Bengali breakfast dish from an outdoor eatery, if you didn’t mind waiting while the cook prepares it right in front of you. The food would typically be served on a Sal leaf plate, to be trashed afterward in a designated bin.

A dollar for a man’s haircut might sound like a promotional offer, but that’s the regular price in the neighborhood salon—and it wasn’t due to the thinning hair of its regular customers. The small shop not only had the needed hygiene standards, leather seats and air-conditioning, but also offered nice add-ons, like a 30-minute head and shoulder massage for one dollar more.

Two dollars was the cost of my cab ride from the Kolkata airport to our house five miles away. As soon as I walked out of the arrival gate, a few touts approached me to offer a no-wait, luxurious ride. I declined and waited in the queue for pre-paid cabs. Fifteen minutes later, I got a cab assigned to me, helped the driver to load my bags and was on my way.

Five dollars covered the electrician’s labor for two visits to our house to take care of a few things for my mother. The work didn’t take long but, as a courtesy to my mother, he also bought the necessary fixtures from our neighborhood electrical store.

Ten dollars may not seem like a lot, but it was enough for a trained masseuse to come over and help me with my sore calf muscles and feet. The massage lasted about an hour, not including a brief break for tea and light snacks that my mother made for him.

[xyz-ihs snippet="Holiday-Donate"]

Fifteen dollars was the cost to take my mother for a sumptuous lunch at a trendy restaurant on Park Street, the Fifth Avenue of Kolkata. The fresh green coconut water added another dollar to the restaurant bill. The experience and service were well worth the hefty tip we left.

Twenty dollars got me an all-day ride in a private, chauffeur-driven compact car. We started in the morning to visit a few places within a 25-mile radius and returned in the evening. I could’ve used a ride-hailing service instead, but the neighborhood operator seemed more friendly and convenient.

Twenty-five dollars covered both the labor and materials for a long-overdue plumbing overhaul of the main bathroom. The plumber replaced the leaking pipes, ran a new water connection to improve the flow and installed a new showerhead. He took two days to complete the work, and it was immaculate.

One hundred dollars connected our home with high-speed broadband internet for a year. I tested to check if the connection lived up to the advertised speed of 100 Mbps. It outperformed.

One thousand dollars covered the cost of new Bosch appliances I bought for my mother and sister-in-law. These included an energy-efficient refrigerator, an automatic front-loading washing machine and a high-powered kitchen chimney. The cost, which included delivery and installation, was lower than I expected thanks to the seasonal discount for the Diwali festivals.

My feeling of affluence was shattered as soon as I was on my way back to the U.S. A cup of tea purchased past the security checkpoints at Kolkata airport cost $3. Thirty hours and 9,000 miles later, I was home, catching up with my wife after being away for a month. That was a moment worth $1 million.

Sanjib Saha is a software engineer by profession, but he's now transitioning to early retirement. Self-taught in investments, he passed the Series 65 licensing exam as a non-industry candidate. Sanjib is passionate about raising financial literacy and enjoys helping others with their finances. Check out his earlier articles. [xyz-ihs snippet="Donate"]
Read more »

Retirement Accounts

I WAS SCROLLING through social media recently and saw somebody dismiss retirement accounts as “paper wealth.” The argument was familiar: Your money is locked away and you’re waiting for permission to access it.

Post Example

There’s a grain of truth here. Retirement accounts do come with rules. But much of the discussion online ignores how flexible these accounts actually are. More important, it ignores the enormous tax advantages.

Most people today will likely live well beyond age 59½. Many will spend two or three decades in retirement. Even if somebody retires early, they’ll still need assets later in life.

That’s why ignoring retirement accounts at age 30 often isn’t wise. You could end up giving away 30 or 40 years of tax-advantaged compounding.

It also isn’t an all-or-nothing decision. We can use taxable brokerage accounts, Roth IRAs and 401(k)s together. Each account serves a different purpose.

Retirement accounts also provide rebalancing flexibility that taxable accounts don’t.

Inside a Traditional or Roth IRA, investors can rebalance portfolios without triggering capital gains taxes. Somebody who wants less stock market exposure can freely sell shares and buy bonds, Treasurys or other funds without generating an immediate tax bill. That matters over long periods of time.

The other misconception is that retirement accounts are completely inaccessible until age 59½. 

Let's talk about Rule 72(t), also called Substantially Equal Periodic Payments, or SEPP. This IRS rule allows penalty-free withdrawals before age 59½ if specific requirements are followed.

Using online 72(t) calculators, a $500,000 retirement account could potentially generate annual withdrawals of roughly $30,000 while avoiding the normal 10% early-withdrawal penalty:

72(t) calculator

The payments must continue for a required period and the IRS rules are strict. Still, the broader point remains: There are legal ways to access retirement funds earlier than many people realize.

The Rule of 55 is another example.

If you leave your employer during or after the year you turn 55, you can often withdraw money from that employer’s 401(k) without the normal 10% penalty. Again, the money is not completely locked away until 60.

Roth IRAs may also be flexible. Contributions can be withdrawn anytime tax- and penalty-free because taxes were already paid before the money went into the account.

That doesn’t mean people should tap retirement accounts early. But accessibility is very different from impossibility.

Roth IRAs also happen to be among the most powerful wealth building tools available.

Qualified withdrawals are tax-free. Dividends compound without yearly tax bills. Investors can buy and sell investments inside the account without triggering taxable events.

You may remember a famous example about Peter Thiel. According to reporting by ProPublica, Thiel reportedly grew a Roth IRA from $2,000 to more than $5 billion between 1999 and now. He turns 59½ in 2027, meaning those withdrawals could potentially be tax-free. Imagine if he had decided to skip retirement accounts because he wanted to “live now.”

Employer matches are another point often ignored online. Skipping a 401(k) match can be one of the costliest financial mistakes people make.

Suppose an employer offers a dollar-for-dollar match on the first 3% of salary contributed to a 401(k). Before the investments even grow, that’s effectively an immediate 100% return.

Very few opportunities offer that kind of risk-adjusted benefit.

In fact, somebody could theoretically contribute, collect the employer match, later withdraw the money, pay ordinary income taxes plus the 10% penalty, and still potentially come out ahead versus investing only through a taxable brokerage account with no match.

The tax advantages extend beyond employer matches.

Inside retirement accounts:

  • Dividends can compound without annual tax drag
  • Investors can rebalance without triggering taxable events
  • Capital gains taxes are deferred or eliminated, depending on the account type

Compare that with a taxable brokerage account, where dividends may create yearly tax bills and selling appreciated shares can trigger capital gains taxes.

Retirement accounts can also create opportunities for tax arbitrage.

Somebody contributing while in the 22% or 24% marginal federal tax bracket today might eventually withdraw money while in the 10% or 12% bracket during retirement.

State taxes can widen the advantage even more. Some states provide tax deductions on retirement contributions while later taxing retirement withdrawals lightly or not at all.

Early retirees often use Roth conversion ladders as well.

The process generally works like this:

  • Move money from a Traditional IRA or 401(k) into a Roth IRA
  • Pay taxes on the converted amount
  • Wait five years
  • Withdraw the converted funds penalty-free

Like Rule 72(t), there are strict rules involved. But these strategies exist because retirement accounts were never designed to be prison cells.

The larger point is that retirement planning should involve multiple tools working together. Taxable brokerage accounts provide flexibility. Roth IRAs provide tax-free growth. Traditional retirement accounts can reduce taxes during high-earning years.

None of these accounts are perfect by themselves. Together, however, they can create an extremely efficient system for building long-term wealth.

That’s why describing retirement accounts as “paper wealth” misses the bigger picture.

 

Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.  
Read more »

My Father: The Peace He Never Found

"Thank you for this, Andrew. You shed light on the other side of retirement that, as you say, is less discussed but even more important than all the financial maneuvering. I'm sure Jonathan is indeed looking over your shoulder when you write, and I know he's smiling."
- Andrew Forsythe
Read more »

A Time to Save

"Dan, things just seemed to align in those early years. One reason I was able to contribute 15% so early was the drugstore job. I was still working weekends there while I was at the magazine during the week. Another reason: my parents allowed me to live at home while in grad school at the time. It was an intense, busy, period and I was very fortunate for their generosity with the offer of shelter."
- D.J.
Read more »

Lifetime Supply

"I can’t think of a better way  to spend the summer than being on the beach and having the kids stay over most every weekend. "
- Dan Smith
Read more »

Should Retirees Get a Temporary Flat Tax Window on IRA and 401(k) Withdrawals?

"Bach said that if they do this he would withdraw his entire IRA immediately and pay the 12% rate. Intriguing idea."
- Ben Rodriguez
Read more »

The Art of Spending Money

"We started out that way, as did many of our friends, but found we spent a lot on hotels and restaurants, and we both had grown up in frugal households. After buying the van, which doubled as our second household vehicle, we kept detailed records and realized we could travel that way for around $100 a day inclusive, which suited our budget. Of course, that was in 2011!"
- Chris G
Read more »

Keeping It Simple

"I NEVER MEMORIZE anything I can look up." Albert Einstein, it seems, said this or something similar. I first heard the quote in my freshman physics class. The teacher asked a student to recite a formula. The student’s response: “I never memorize anything I can look up.”

I’ve adopted the same philosophy. My wife loves to point out that I don’t remember the names of streets in our neighborhood. But I don’t need to know them. I don’t live on those streets. I never provide directions to anyone who wants to go down those streets. Why fill my brain with unnecessary facts?

We humans make decisions on a daily basis that require remembering certain facts: your name, address, Social Security number, mother’s maiden name. You could look these up, but it’s more efficient to memorize them since they’re required on a frequent basis.

But what about other facts? I have a terrible memory. I know this, and it doesn’t bother me. I write down the facts that I think I’ll need, and I know where to find them. Consider my cell phone, which I keep in my car. I don’t remember the number, but I can look it up when I need it.

While president, Barack Obama owned only blue and gray business suits, so he wouldn’t have to give much thought to what he’d wear on any given day and hence make yet another decision. I understand this logic.

Many people are familiar with KISS, short for keep it simple, stupid. Keeping things simple means my days are simpler—and there’s less chance that I or my wife will make mistakes.

For instance, I use the same mutual fund for my Roth account as my wife uses. My theory is that, when I die and my wife consolidates our accounts, she’ll consolidate my Roth with hers, and not make the mistake of mixing traditional IRA dollars with Roth dollars and thus pay unnecessary taxes. Let’s hope my plan works.

My wife and I have all our retirement monies with the same mutual fund company. As with my Roth, I have just one mutual fund in my traditional IRA. I like simple and, again, I believe it'll be easier for my wife after I die.

We also use just one brick-and-mortar bank and one online bank for our joint accounts. That’s it. We could have more, but why? If I thought I was brilliant in moving money around, I’d invest more time in making financial moves.

But instead, I invest my time in trying to understand where I might trip up. Buying or selling usually involves trading costs, so fewer trades mean fewer costs. Maybe I’m leaving money on the table, but at least I’m not losing money. That’s more important to me than trying to make more.

I have a degree in mathematics, but I’m lousy at arithmetic. If I want to be sure I’m correct when I add or subtract, I need to use a calculator. I know this. I have the tool to get the job done. It’s simple and cheap, I know where to find it—and, when I need math answers, it allows me to look them up. Simple.

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The Company You Keep

AFTER ENRON'S COLLAPSE in 2001, there were numerous articles about employees who had most of their money in the company’s stock and how they’d lost it all. Taking that message to heart, I’ve endeavored to keep our holdings of my company’s stock below 10% of our net worth. I must confess, however, that in good times it’s crept up to 15%—and in bad times it’s fallen to zero.

I can’t claim any particular insights or novel thoughts on how to manage company stock. I’m willing to share what I’ve done, however, and let you decide how to handle your situation.

My company stock came from three main sources: the employee stock purchase plan, the match on my 401(k) contributions, and the stock options or restricted stock awards received as part of my annual compensation. As you’ll see, these three stock programs represent the good, the bad and the ugly of my investing career.

The employee stock purchase plan was the good. In our plan, we were allowed to divert up to 10% of our salary to company stock. The best part was that we could buy the stock at a 15% discount to current market prices.

Early in my career, there was a machine operator who was retiring. The word in the factory was that he was wealthy. He had been stashing 10% of his pay in company stock for the past 45 years. He had never touched the shares. I’m sure his retirement was much more comfortable than that of most machine operators.

I also spent my first five years at the company not touching the stock. We then sold it to make the downpayment on our house. Shortly thereafter, I decided I needed to rethink how to handle the stock purchase plan so I wasn’t overly reliant on the company.

For about 20 years, I was able to sell the stock after holding it for only a month. I would purchase the stock one month at a 15% discount and sell it the next month. I always made money. Depending on the market, sometimes I made more than 15% and sometimes less.

Some coworkers would scold me, telling me that I should hold the stock for a year to qualify for the lower long-term capital gains rate on my profits. My reply was that—depending on how you do the math—I was making an annualized return of as much as 603%, so I was happy to pay the ordinary income-tax rate. (For math nerds, a 15% discount is equal to an immediate 17.6% monthly gain on the purchase price. Compounded over 12 months, that comes to 603%.)

Some would look at me blankly, saying that I was only making 15%. When I couldn’t convince them that I was making far, far more than that on an annualized basis, I’d offer to lend them all the money they wanted at 5% a month. None of them took me up on the offer.

Eventually, to encourage long-term investing, the company changed the rules and required a year-long holding period before selling. At the end of the year, rather than selling, we’d donate the shares we’d purchased to charity, thereby avoiding any taxes on the gains.

For a while, the company paid its 401(k) matching contribution in company stock, which meant we had an ever-increasing exposure to this single stock. Shortly after Enron blew up, my employer stopped paying the match in company stock, while also allowing us to sell whatever company stock we had in our 401(k) and invest the money in one of the plan’s mutual funds.

I promptly traded half my company stock for shares in a broad-based mutual fund. Why only half? I’d heard about the tax advantages of net unrealized appreciation of company stock held within a 401(k). Executed correctly, when you sell, you pay income taxes on the original cost basis of the stock but the lower long-term rate on any gains. I thought that in 20 years, when I retired, this would be a good deal.

Fast forward 20 years. I was planning on withdrawing my company stock from the 401(k). Remember the good, the bad and the ugly? This is where we get to the bad. First, the stock had fallen in price, dramatically reducing both its value and the strategy’s tax advantages.

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Second, I read research by financial planner Michael Kitces suggesting that if you plan to own company stock for the long term, you’d be better off buying it outside the 401(k) to obtain the more favorable long-term capital gain rate on the whole investment and not just on a portion of it. I decided to sell all my shares and diversify using mutual funds in my 401(k). In hindsight, I realize I should have done this much earlier.

What about the ugly? That’s been the performance of my company stock options. Part of my compensation was “at risk” compensation. We were able to take this as either restricted stock units, which is a grant of shares at some future time, or as stock options, which would have value only if the shares achieved a specified price in the future. According to my employer, the value of either award was calculated to be the same when they vested in three years.

Every year, when it came time to choose how to receive this compensation, there would be lots of discussion about which was the better choice. When asked my opinion, I always said that what I was planning to do wasn’t appropriate for all people, but I’d be taking all my shares in stock options.

I had 20 years of data going back to 1978 showing that, if you held the stock options until they expired in 10 years, they performed significantly better than the restricted stock units. I planned to use my stock options as income during the 10 years following my retirement at age 60, and then claim Social Security at age 70.

I’m retired now and my remaining stock options are worth exactly zero dollars. Some may be worth money in the future if the company’s shares rise, but the hoped-for income stream from the stock options has vanished. Fortunately, I saved and invested well enough so I won’t have to claim Social Security before 70.

Although my stock option decision didn’t play out as planned, the poker player Annie Duke cautions people to not confuse the results with the decision-making process. In other words, you can be right and still lose money. I believe that my process was sound. I knew there was a potential for the options to be worth nothing and so, while it’s disappointing, it’s a financial setback I was prepared for.

While there are lots of valid ways to treat company stock, my advice would be to limit the value of your company stock to 10% or less of your total portfolio. As I’ve learned, company stock is a concentrated investment—and you may not be rewarded for the extra risk you run.

Kenyon Sayler is a retired mechanical engineer. He and his wife Lisa are extraordinarily proud of their two adult sons. He enjoys walking his dog, traveling, reading and gardening. Kenyon's brother Larry also writes for HumbleDollar. Check our Kenyon's earlier articles. [xyz-ihs snippet="Donate"]
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Manifesto

NO. 61: WHEN in doubt, we should invest long-term investment money in a target-date index fund. Most of us will struggle to design and maintain a portfolio that performs any better.

think

INSTINCTS. Our brain’s instinctual side makes most decisions. That’s usually a plus: It tells us to jump out of the way, even before we’re fully aware of the speeding car. But our instincts can also lead us to overspend and to panic when markets tumble. Making money decisions? Try pausing, so your brain’s slower-moving, contemplative side can weigh in.

act

AUTOMATE YOUR bill paying. That way, you’ll avoid late payments—crucial to maintaining a good credit score. The downside: You need to be vigilant about keeping enough in your bank account, so you don’t trigger fees for overdrafts or insufficient funds. This is a particular concern with credit card bills, which can vary so much from one month to the next.

Truths

NO. 69: RECEIVING a pension or Social Security benefits is akin to owning bonds. Most pensions are like a fixed-interest bond, while Social Security is like an inflation-indexed bond. One implication: If you’ll receive a hefty portion of your retirement income from these two sources, you may have the leeway to invest more heavily in the stock market.

College-bound kids?

Manifesto

NO. 61: WHEN in doubt, we should invest long-term investment money in a target-date index fund. Most of us will struggle to design and maintain a portfolio that performs any better.

Spotlight: Advisors

Late to the Rescue

MY FATHER-IN-LAW William retired from Duke University after teaching there for more than 30 years. He had a good pension, which—along with Social Security—covered all his expenses at the continuing care retirement community (CCRC) where he spent most of his retirement. Almost to the end, he was mentally sharp. I saw no need to inquire about his finances. I was mistaken.
In summer 2014, my wife noticed that William, then age 96, had left a large check for a matured life insurance policy on his desk for a couple of months.

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Paying Them to Worry

EVERY SO OFTEN, I see comments on social media about Vanguard Group’s Personal Advisor Services (PAS). One person posted that he’d talked to a growing number of people who quit PAS. There was no particular reason given for why they left. But I don’t doubt it. I’m a PAS client. I’ve often thought about terminating my relationship.
I’ve been with PAS since 2018. When I first joined, the PAS advisors made a few changes to my investment portfolio.

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Financial Advisor – NEVER AGAIN

Last year I decided to try the advice of a “Financial Advisor”.  This trial was to be for a three month period at no cost to me.  What could go wrong.  The advisor is associated with a long running newsletter that deals primarily with Fidelity products, but they are as far as I know, NOT representatives nor endorsed by Fidelity.
My wife and I each have our separate Fidelity accounts, since she like her independence, but I have managed her investments since our marriage 37 years ago. 

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Your Results May Vary

“SELL THE SIZZLE, BOYS.” With those words from the sales manager at a big insurance company, the 2003 class of newly minted registered representatives were off to the races, extolling the virtues of the firm’s products to family, friends and anyone else who would listen.
I still vividly remember that moment. Yes, I was there.
To become registered reps, the 2003 class had to pass the necessary exams to get a Series 6 securities license and a license to sell life and health insurance.

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“A Complex Portfolio, a Modest Account”

Question: If someone has a relatively small IRA—say, around $54,000—do they need to be as diversified as someone managing a much larger retirement portfolio?
Here’s what prompted the question.
My neighbor recently lost his wife. She had taken the lead on their finances, working closely with an advisor at a national investment firm. Now he’s on his own, trying to navigate retirement decisions without much guidance.
I tried to help by simply asking questions—not giving advice.

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For Richer or Broker

I’VE SEEN FINANCIAL advisors do great work and I’ve seen them do poor work. Which brings me to my late father’s experience.
Dad was a heck of a small businessman. Starting in 1956, he and his partner sold and serviced radios, televisions, appliances and furniture. Forty years later, he sold the business to four of my brothers.
By the mid-1960s, Dad had accumulated what was for him a small fortune. This was the time of the stock market’s so-called go-go years.

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Spotlight: Friedman

Summer School

WHEN I WAS a teenager, I couldn’t wait to get a summer job. Just the thought of it would give me goose bumps. Why? I could earn my own money and buy the car I desperately wanted: a two-tone 1956 Chevrolet Bel Air with a big steering wheel that looked like it belonged on a bus. My dream was to gain some independence and drive myself wherever I needed to go. After working a number of summer jobs, I bought the car at the beginning of my senior year in high school. You want to know something about that new used car? At the time, it was the best car I’d ever been in. The reason: I bought it with my own money. I was so proud of myself. It was my first big purchase and I didn’t have any buyer’s remorse. Later in life, I realized the most important thing about my summer jobs wasn’t the money or the stuff I was able to buy. Instead, it was what I learned about life and how it prepared me for fulltime work. During those summer jobs, I met people from all walks of life. Some were kind and helpful, others not so much. It was a small glimpse into what working life was going to be like as an adult—something that can’t be taught in high school or college. Today, it isn’t as easy for teenagers to get a summer job. But if they’re fortunate enough to land one, there are six key benefits: Temperament. In the workplace, you deal with people who hold opposing political views and are from different cultural or religious backgrounds, and you have to learn to interact with them. You need to have the patience and personality to develop a working relationship with your coworkers.…
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Be Like Burt?

I RECENTLY HAD LUNCH with four friends I’ve known since the seventh grade. Because of the pandemic, this was the first time we’d all seen each other in more than a year. Every time we’re together, I’m reminded of how important my friends were in helping me start a new life when I left home for the first time. Our continuing support for each other is probably the reason we’ve stayed close for 57 years. At lunch, we spent a great deal of time talking about our health. It seems that's the way it goes when a bunch of 70-year-old retirees get together. Burt, who is overweight and loves his beer, might be the healthiest of the group. He doesn’t take any medication and jokes that his diet consists primarily of junk food. After a while, the conversation veered off into a discussion about money. Burt tells us that he doesn't think he’ll run out of money. I don’t doubt what he’s saying. Burt worked in the aerospace industry and earned an above-average wage with excellent benefits. You might assume he’s careless with money because of his undisciplined eating habits. But Burt was a good saver, which I’m sure was important in helping him achieve financial security. He and his wife still live in the same two bedroom, 840-square-foot house they bought in 1977. They raised two boys in that house, who shared the same small bedroom until the oldest left home. Listening to him, what I found so fascinating is the amount of money he has in annuities. He’s a multimillionaire who has about half his money in income annuities and the other half in stocks. He has no bonds in his investment portfolio. With this strategy, he’s confident he’ll never outlive his money, while leaving a legacy for…
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Journey’s End

A FEW MONTHS AGO, I received an early morning phone call from a nurse, notifying me that my mother had passed away. Even though she was age 96 and recovering from a mild heart attack, it was still a shock. Up to the time of her death, she was mentally alert and determined to show everyone that she belonged at home, not at a strange nursing and rehabilitation facility. She gave it her best, but she couldn’t overcome her weak heart. After spending seven years as my mother’s primary caregiver, I had become very close to her. When she passed away, I was overwhelmed by this strong sense of loneliness. Having family and friends to lean on provided me with much needed support at this difficult time—yet another reminder of how relationships are so valuable in our life’s journey. Ever since I retired, I’ve been my parents’ caregiver. I now have this big hole in my life I need to fill. I feel like I’m retiring again. Indeed, taking care of a loved one can, at times, seem like a job. It can be stressful, physically demanding and require long hours. Still, I wouldn’t hesitate to do it again. I’ll be moving next year and that will keep me busy. Rachel and I will be moving into my parents’ house. This move is something they would have wanted. I have some reservations about the move, because there are financial risks involved. The house needs a lot of work. It could be a money pit, where we blow through our budget if we aren’t careful. It’s the type of project you should undertake when you’re employed and have a steady paycheck—not when you’re retired and living on a fixed income. The house has an upstairs, which is not ideal for people our…
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Why I’m Sitting Tight

WHEN I WAS AGE 10, we moved from Ohio to California. My father got a job by answering a help wanted ad in a local newspaper. When we first arrived in 1961, we lived in a 36-unit apartment building in Inglewood. It’s located about two miles from the Forum, where the Los Angeles Lakers and Kings sports teams used to play their home games. One of our neighbors in the building was an older gentleman called Jack Tarentino. He loved to play chess. It seemed like Jack was always playing chess with someone. He would sit in the common area with his tiny chess set waiting for someone to challenge him to a game. One day, he asked me if I wanted to learn chess. I guess he was desperate for someone to play with. We played frequently until he moved away. After that, I didn’t play very often. But when I retired, I started playing more. One of the things I like about chess is that you have to think before you make a move. I like to believe the game has taught me to be more patient and to avoid too many emotional decisions. When I slow down and think about making a move during the current bear market, I can’t think why I should. Here are seven reasons I haven’t made any changes to my investment portfolio: 1. My financial goals haven’t changed. Since my goals and investment time horizon remain the same, there’s no reason to change my asset allocation in this bear market. More important, I sleep well at night because my current portfolio is appropriate for my risk tolerance. 2. It’s hard to time the stock market. If I sell stocks to protect myself from further losses, I’d have to be right at least…
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Flying Blind

IN THE EARLY 1990s, my employer—an aerospace manufacturer—sent a small group of employees to Winnipeg, Canada, to help set up a production line. We were chosen because of our familiarity with the product involved. The company provided us with a furnished apartment, a rental car and $40 a day for food. They flew us back home every two weeks, so we could take care of personal business. I’d fly to Los Angeles on Friday and return to Winnipeg on Monday. This went on for about one year. I’d take Northwest Airlines—now part of Delta—and the flight would always make a stopover in Minneapolis-St Paul. I never liked the flights between Minneapolis and Winnipeg, which were typically on smaller, older planes. One time, I noticed some of the overhead compartment doors were held shut with duct tape. I wondered what other parts of the plane were held together with tape. The plane seemed to rattle more than other planes. If you fly often, you’ll eventually encounter some problems. I’ve experienced my share of cancellations, delays and lost luggage. But my flight one morning from Winnipeg to Minneapolis was by far the most alarming. About halfway through our flight, the pilot told everyone to return to their seats and fasten their seatbelts immediately because of a severe storm in our path. The flight attendants, who were in the process of serving snacks, stopped what they were doing and hurried back to their seats. The flight got bumpy right away. You could see the lightning from the storm. Then the turbulence got intense. The plane was bouncing around like a rubber ball. There were loud noises as if the plane might fall apart in midair. I was wondering if they were still using tape to hold things together. I noticed a woman to…
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What Friends Do

I SENT HUMBLEDOLLAR'S editor an email saying I was taking some time off from writing for the site. I really didn’t think I was going to write again. It wasn’t because I didn’t enjoy it. Rather, I thought I didn’t have anything to say that I hadn’t already said. But when I read Jonathan’s June 15 article, I was inspired to write about friendship. Although I’ve never met Jonathan in person, he feels like a dear friend who I’ve known for many years. It’s because his writings aren’t just about money. They’re also about his life. He’s revealed so much about himself that you feel like you're a close friend. We know he’s a Cambridge graduate who moved from England to New York, and now lives in Philadelphia with Elaine. They recently remodeled their house. They don’t own a car like most families do. He has a daughter, son and two grandsons. He used to be a long distance runner, but because of an injury he now rides a bike. He’s also not afraid to talk about the difficulties in his life: he was bullied in school, experienced two divorces and now is in a fight with cancer. That personal touch is why I look forward to reading his Saturday articles. It isn’t easy finding a friend you can trust, which is what you feel when you read Jonathan’s writings. When I was 19 years old, a bunch of us guys got together to play a pickup football game. We decided to play tackle instead of touch football. I wasn’t thrilled about it because I was the smallest guy on the field. I was short and skinny, just like I am today, at age 73. We kicked off to the opposing team. My friend Mike caught the ball and avoided all the…
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