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When you discover you have more money than time, you should stop pursuing money and focus on getting the most out of your time.

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Taste Bud Training

"I think your grocery experiment is a good one. We do the same. We found as you have, that some store brands things are good and some not. We try to have an open mind, but there are some things we have learned to stick with the name brand. Like Tide. Anything else makes Spouse break out. Chris."
- baldscreen
Read more »

Time to scrap IRAs, 401k, 403b and all the rest

"Yes they have. Plus the current (false) idea is we can economically grow our way to SS solvency which is absurd and why nothing is being done to make real changes. Several relatively minor changes would fix the problem."
- R Quinn
Read more »

Lifetime Supply

"Mike, congratulations — that's fantastic news! If you find yourself with some free time in Dublin, it might be worth checking out a Shamrock Rovers match. They play Friday nights in the League of Ireland Premier Division, it's a compact 10,000-capacity ground, so you're right on top of the action. Well worth a look!"
- Mark Crothers
Read more »

My Father: The Peace He Never Found

"Thank you Mike for sharing that. Your comment really stayed with me and yes I am very fortunate to have found my father’s handwritten reflections, difficult as they were to read at times. I’m sorry you never had that same opportunity with your own father. I think many men of that generation struggled to express what they were feeling beneath the surface. Your words mean a great deal to me. Thank you Mike."
- Andrew Clements
Read more »

A Time to Save

"Your story of slowly moving toward indexing is similar to mine, D.J. I started a little later in life, however, which necessitated a larger chunk of my pay going toward retirement, to wind up with enough. Thanks for posting your story."
- Edmund Marsh
Read more »

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.  
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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?

"Here’s a Gift Article for the May 16 Wall Street Journal piece Stock Gains Without All the Taxes? How the Hottest Trade on Wall Street Works."
- ostrichtacossaturn7593
Read more »

Taste Bud Training

"I think your grocery experiment is a good one. We do the same. We found as you have, that some store brands things are good and some not. We try to have an open mind, but there are some things we have learned to stick with the name brand. Like Tide. Anything else makes Spouse break out. Chris."
- baldscreen
Read more »

Time to scrap IRAs, 401k, 403b and all the rest

"Yes they have. Plus the current (false) idea is we can economically grow our way to SS solvency which is absurd and why nothing is being done to make real changes. Several relatively minor changes would fix the problem."
- R Quinn
Read more »

Lifetime Supply

"Mike, congratulations — that's fantastic news! If you find yourself with some free time in Dublin, it might be worth checking out a Shamrock Rovers match. They play Friday nights in the League of Ireland Premier Division, it's a compact 10,000-capacity ground, so you're right on top of the action. Well worth a look!"
- Mark Crothers
Read more »

My Father: The Peace He Never Found

"Thank you Mike for sharing that. Your comment really stayed with me and yes I am very fortunate to have found my father’s handwritten reflections, difficult as they were to read at times. I’m sorry you never had that same opportunity with your own father. I think many men of that generation struggled to express what they were feeling beneath the surface. Your words mean a great deal to me. Thank you Mike."
- Andrew Clements
Read more »

A Time to Save

"Your story of slowly moving toward indexing is similar to mine, D.J. I started a little later in life, however, which necessitated a larger chunk of my pay going toward retirement, to wind up with enough. Thanks for posting your story."
- Edmund Marsh
Read more »

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.  
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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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Manifesto

NO. 18: SUSTAINED happiness lies not in winning the approval of others—by collecting promotions and status symbols—but in devoting our days to activities we’re personally passionate about.

Truths

NO. 17: IT’S OBVIOUS—in retrospect. Looking back, we forget about all the financial uncertainty that existed at the time. Instead, what happened in the economy and the financial markets seems all too predictable. This so-called hindsight bias encourages us to act on today’s investment forecasts and it could lead us to make overly bold financial bets.

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.

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Manifesto

NO. 18: SUSTAINED happiness lies not in winning the approval of others—by collecting promotions and status symbols—but in devoting our days to activities we’re personally passionate about.

Spotlight: Insurance

Home, Auto & Umbrella Insurance—“Longevity Benefit”?

Recently, and spurred by the horrific fires in L.A., there’s been a lot of attention on home insurance, including skyrocketing premiums. Like many people, we have our home, auto, and umbrella policies with the same company, and have seen our premiums increase dramatically in the last few years.
I’ve occasionally heard mention, without much in the way of specifics, of a “longevity benefit” in staying with the same insurance company rather than constantly shopping around and switching.

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Choosing Life

NONE OF US WANTS to contemplate our own mortality. But we all need to think about it—including thinking about life insurance.
I was lucky enough to have a long tenure with a large company that provided term insurance at reasonable prices. My employer provided two times our salary in coverage and we had the option to purchase additional coverage equal to eight times salary. I was also able to buy insurance on my wife’s life equal to three times my salary.

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Self Defense

ONE SPRING DAY IN 2022, an elderly woman entered Paris’s Picasso Museum to see a new exhibit. Among the items on display was a decorative blue jacket, which was positioned on a wall next to a portrait of Picasso.
The woman liked the look of the jacket, so she took it down from its hook, put it in her bag and quietly walked out the front door. Only later did the museum discover the theft,

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Life Sentence

WOULD YOU ADVISE someone—who doesn’t drive, doesn’t need a car and doesn’t plan to get one in the foreseeable future—to buy car insurance? I wouldn’t. But it seems some financial advisors think otherwise. That, at least, is the impression I got when an acquaintance, whom I’ll call Laura, mentioned her variable universal life insurance policy to me.
A single woman in her mid-40s, Laura has a decent income and lives on her own. She has no one other than herself to support financially.

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Vet These Policies

YOU LOVE THEM LIKE family. You want them to have the best care possible. You have insurance for yourself, your family, your home, your car and your upcoming vacation. Why not for your pet?
One of our friends recently opted for pet insurance—after multiple trips to the vet, with more than 20 medications prescribed. Intrigued by the idea of pet insurance? Here are eight choices and what they offer:

Pets Best covers everything, including medications,

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Works If You Can’t

BE HONEST: WHEN WAS the last time you thought about disability insurance? As co-founder of a website that sells insurance, it’s a topic I think about every day, but I realize most folks have other things on their mind. Yet becoming disabled is one of the biggest financial risks that working people face.
Disability can result from accidents or sickness and can impact people of all ages. According to the Social Security Administration, a 20-year-old entering the workforce has a one-in-four chance of becoming disabled for a year or more before retirement.

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Spotlight: Flack

Artfully Dodged

I HAD THE OPPORTUNITY to view Gustav Klimt’s most famous work of art, The Kiss, while visiting Vienna a few years back. It depicts a couple locked in an intimate embrace. It’s an oil painting with a significant amount of gold leaf—quite distinctive. A few weeks later, I had an opportunity to buy a Klimt. I was in a gallery in Salzburg and came across a drawing of his which was titled Stehender Rückenakt - 1913. I can’t remember the exact price. But since I didn’t buy it, it most likely cost a little more than I thought it was worth—or more than I currently had in my wallet. Still, I’ve always wondered what it would look like in both my living room and my portfolio. This pleasant memory all came back to me recently when a friend emailed me a link offering me a second chance to add artwork to my portfolio. I must admit I was a little leery when I first clicked on it and the newly opened web page allowed me “to skip the waitlist!” It announced that I was now “invited to join an exclusive community investing in blue-chip art.” The link also informed me that Masterworks is a company that buys multi-million dollar works of art, creates a Delaware limited liability company to own each one and sells shares in that company to the public. It resells the art a few years later, presumably at a higher price, and then disburses the proceeds to shareholders. Masterworks enables the fractional ownership of art—basically art for the little people. I accepted the offer and opened an account. Before I could start investing, I needed to make an appointment with Masterworks’ registered financial advisor so he could learn more about me and answer any questions I might have.…
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Lost Abroad

ONE OF THE GREATEST business books I’ve ever read is Antifragile by Nassim Nicholas Taleb. In it, he postulates the idea that, while things that become damaged by stress are considered fragile and things that resist stress are considered resilient, “there is no word for the exact opposite of fragile,” things that become stronger due to stress. So, he coined the word “antifragile” and then wrote an entire book about the subject. Well, we’re all familiar with a tax loophole, which has been defined as an “unintentional omission or obscurity in the law that allows the reduction of tax liability to a point below that intended by the framers of the law.” The backdoor Roth IRA is a good example. It allows those who wouldn’t ordinarily be able to make regular annual contributions to a Roth, because their income is too high, to instead contribute to a traditional IRA and then—voilà!—convert it to a Roth. What’s a word for an “unintentional omission or obscurity in the law that allows the increase of tax liability to a point above that intended by the framers of the law”? There is none, so I’ve coined the word “antiloophole,” though I won’t be writing an entire book about it. Like many of you, I own shares in publicly traded foreign stocks and have therefore had to pay foreign income taxes on my foreign dividends. Since I was filing a joint return with my wife and we paid less than $600 in foreign income taxes, we claimed the entire credit for these foreign taxes directly on our 1040. I like the diversification that foreign stocks afforded me, so I kept buying more and more, comforted by the innumerable articles and experts that stated that—if we lost more than $600 to foreign income taxes—all we need…
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Not Cool

SHOULD A REASONABLE real estate buyer expect the multiple listing service (MLS) to provide a reasonable description of the property being purchased? What if it doesn’t? All the previous times I’ve purchased real estate, the MLS accurately described the property I was buying. I realized that disclosures were also provided by the seller, and those specified the finer points of what was being purchased. Still, I’d come to expect a certain amount of integrity from the MLS listing itself. That all changed during my most recent real estate adventure. I signed a contract on a condo that, according to the MLS, came with a “large wine fridge.” A few weeks after signing the contract, I was again reviewing the disclosures and noticed that the large wine fridge wasn’t mentioned. The listing agent subsequently confirmed it wasn’t part of the deal, saying the wine fridge would have been part of the deal if I’d agreed to pay the list price. Now, I realize that legally the disclosures are what determines what is and isn’t part of the transaction, but I was dismayed to learn that an item so prominently mentioned in the MLS did not actually “convey,” as they say in real estate lingo. I then became concerned about whether the third space of the three-car private garage and the third of the three outdoor spaces would convey. Thankfully, they did. It also burned me that the large wine fridge would have conveyed if I paid “a full offer.” I’d never heard of such a thing. I wondered how much over asking would have enabled the seller’s Peloton to convey? I pushed my agent to go over the listing agent’s head to attain satisfaction, but the listing agent’s boss was even more obstinate. For most of my working life, I was…
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Beyond the Obvious

I JUST FINISHED rereading a book every serious investor needs to reread: Moneyball: The Art of Winning an Unfair Game. It was written by Michael Lewis in 2003, but it’s still quite relevant to baseball—and to investing. It’s the story of the Oakland A’s general manager, Billy Beane, and his struggle to create a competitive baseball team on a limited budget. How does this relate to personal finance? Well, first let me explain my connection to Moneyball. It was a time long ago, meaning the 1970s. Due to then-limited technology, a baseball player’s batting average was displayed on television only during his first at-bat. I have a distinct memory of watching a New York Mets game and asking my father, “What’s a batting average?” He patiently explained that it was basically the number of hits divided by the number of at-bats, and that it didn't include walks. I remember thinking that math may be more useful than I thought and... why weren't walks included? When I watched subsequent games, read the newspaper and talked with fellow fans, a player’s batting average is what everyone wanted to talk about. After all, having the highest batting average enabled a player to claim the prestigious title of batting champion. I quickly realized that walks were incorporated into another number, the on-base percentage. This number is basically the number of times a batter safely reached first base divided by the number of plate appearances. As there were many players skilled at obtaining walks, a player’s on-base percentage could be significantly higher than his batting average. And because a walk was as good as a single, I realized that a player’s on-base percentage was a much better indicator of a player’s worth than his batting average. For instance, in the 1970s, there was a coach…
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House in Order

"I WOULD SAY TO the House, as I said to those who have joined this government: I have nothing to offer but blood, toil, tears and sweat. We have before us an ordeal of the most grievous kind. We have before us many, many long months of struggle and of suffering…. You ask, what is our aim? I can answer in one word: victory. Victory at all costs—victory in spite of all terror—victory, however long and hard the road may be, for without victory there is no survival." What Winston Churchill said to his House during Great Britain’s darkest hour, I would say about selling yours. Selling a house shouldn’t be easy. If you sold one and it was, you didn’t do it right. It’s likely the biggest financial transaction of your life, so I don’t think it’s too much to ask that you put in a little effort. The non-comprehensive checklist below is based on a lifetime of experience. I haven’t always followed it, though when I didn’t, I paid for it. Know your home’s value. When you meet with your agent, you need to have an idea of what your home is worth. If you don’t, how can you be sure the sales price your agent suggests is the correct one? Find the right agent. Using the agent that sold you your home may be the easiest route, but it may not be the most profitable one. It may take a while, but you need to spend the time to find the best agent to sell your home. Remember, they all cost the same, so you might as well hire the right one. News flash: You need to interview more than one agent. And maybe, just maybe the best agent may be… you, via a “for sale by…
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My Proxy Wars

I JUST RECEIVED an email from TD Ameritrade Clearing, Inc., imploring me to “Vote now! KYNDRYL HOLDINGS, INC. Annual Meeting.” For the few who haven’t read my fascinating earlier article, I will share my heuristic for voting proxies: “yes” to independent chairmen, “no” to classified boards, “no” to options, and then “yes” or “no” to whatever piques my interest. I’ll usually spend 10 minutes max thoroughly reviewing the issues for the first proxy I receive in the new year. I’ll spend about one minute for the last one I receive—with a logarithmic decrease in between. Well, after voting my Equity Residential (symbol: EQR) proxy back on May 3, I thought my yearly work was done. That meant I could begin a well-deserved rest until next year’s onslaught begins. I could use my newfound free time to work on a miniaturized model of the New York Stock Exchange trading floor. Unfortunately, the TD email interrupted my reverie. I was quite tempted to delete it. But then I just had to find the answer to the same three questions that you must be asking yourself right now: What the hell is Kyndryl (KD)? What the hell does it do? And what’s with the name? I also wanted to know how I came to own a stock with such a ridiculous-sounding name. Years ago, I bought shares in a company with an equally ridiculous-sounding name—Enron—and there’s no way I would make that mistake again. That said, Enron did sound better than its next name: Enron Creditors Recovery Corp. I was hoping that after clicking on the annual report and reading “A Message from Our Chairman and Chief Executive Officer”—so much for the independent chairman—I could quickly get answers to my questions. No such luck. All I learned was “Kyndryl has solidified its place in…
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