FREE NEWSLETTER

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

Latest PostsAll Discussions »

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

"Why do you say the accounts would slowly die? That implies that they would not be used to save for retirement. They would be used at least as much as all retirement accounts today I would think. Social Security will be fixed, just not likely before 2029 because are operating on a warped agenda."
- 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.  
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.

Read more »

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"]
Read more »

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 »

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

"It is still available for purchase through various suppliers including the University of Illinois Press, titled Traveling with Service Animals."
- Chris G
Read more »

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

"Why do you say the accounts would slowly die? That implies that they would not be used to save for retirement. They would be used at least as much as all retirement accounts today I would think. Social Security will be fixed, just not likely before 2029 because are operating on a warped agenda."
- 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.  
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.

Read more »

Free Newsletter

Get Educated

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.

Daily alert signup

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: College

On the House

WANT A CONSERVATIVE strategy that can help you prepare for college costs? Consider prepaying your mortgage.
In 1992, when my oldest was 10 years old, we moved to a new home. We opted for a 15-year mortgage at 7.625% with 33% down. With our son’s graduation set for 2000, we began to prepay the mortgage so the last payment would coincide with the month before he began his freshman year. Thereafter, the payments previously sent to the mortgage company were instead directed to the college.

Read more »

Playing Defense

TRUTH HAS A FUNNY way of punching you in the gut. I received my punch thanks to the 2022 decline in the stock market, which put a dent in the “funded” status of the 529 college-savings plans for my two sons, ages 16 and 14.
Buy and hold is all well and good if you have an infinite investment time horizon. Strict adherents will argue that mark-to-market gains and losses are just noise. Time will smooth out the ripples.

Read more »

Finding Merit

THERE’S NO SINGLE, right way to legally crack the college admissions and financial aid systems. It’s up to teenagers and their parents to do the necessary work.

Still, it helps to have a tour guide—which is what you get with The Price You Pay for College, the new book from New York Times financial journalist Ron Lieber. Lieber’s book discusses why college costs so much, digs into the allure of elite schools,

Read more »

Saved by Borrowing

IN HIGH SCHOOL, I worked at a local roller-skating rink to save money for college. I calculated that, if I kept working at the same rate once I was in college, I could make it through my four-year degree without taking on any student loans.
I was determined to make it work.
In my freshman year, my plan started with a budget—and that budget included this simple edict: Spend the least amount possible on everything.

Read more »

Goodbye Assets

MY TWINS ARE SENIORS in high school. That means, pandemic or no pandemic, we spent the fall applying to colleges.
Here in California, the pandemic closed public schools in March and most did not reopen for in-person teaching with the start of the current academic year. That forced parents to stand in for college counselors. The preparations high school juniors usually engage in, such as visiting colleges and taking standardized tests, didn’t occur this past spring or summer.

Read more »

Beyond Saving

I’M CONSERVATIVE, but sometimes even I see the need to change. For instance, I belonged to a high-profile service organization for many years. They’re very proud of their tradition of raising money to give a Webster’s dictionary to each fifth grader in our city.
Let’s face it: These days, no self-respecting fifth grader is going to be caught dead with a hardcopy dictionary. Doesn’t everyone know that kids look up everything online? Traditions die hard—even when they no longer make sense.

Read more »

Spotlight: Gartland

One Man’s Junk

IN MY NEIGHBORHOOD, there are signs saying “we buy junk houses” and “we buy ugly houses.” These businesses target undesirable homes—those that have fallen on hard times and can’t be easily sold. Maybe the homeowners couldn’t afford the upkeep or got tired of caring for the place. Whatever the reason, the result is houses that look sad and have lost market value. Contrarian buyers see the houses not for what they are, but for what they could be. They need to have a vision, plus the money and skills to turn a beast into a beauty. You’ve probably seen these buyers profiled on TV shows about house flippers. They tear out the ugly and replace it with stylish features that appeal to today’s buyers. Sleek kitchens. Remodeled bathrooms. Updated entertainment areas. Potential buyers flock to these formerly unloved houses. I’m witnessing a similar trend among old cars. Auctioneers routinely sell cars from the 1950s and 1960s that have gone through a makeover. The cars are either returned to their original showroom sparkle or they’ve been customized. The customized cars, like the remodeled houses, are transformed according to the designer’s wishes. Years ago, these transformed cars didn’t find a strong market. Buyers preferred cars that had been restored to their original condition. Then the market turned. Customized cars had better brakes, power steering, more reliable engines, and creature comforts like air-conditioning and a booming stereo. What buyers got was a car that appeared vintage but worked like a new model. That combination—a car that looked like you might have driven it in high school, but now with up-to-date features—has proved irresistible. In my neighborhood, when people no longer want something, they leave it at the curb. If the neighbors want it, they’ll grab it. Otherwise, it will get scooped up by…
Read more »

Cool Has a Cost

I'M SITTING ON MY patio drinking coffee, as I do every morning before my wife and son wake up. I go to bed early and wake up before sunrise, so when I’m drinking my coffee, it’s still dark. This is a great time for me to think. This morning, I’ve been thinking about Jordache jeans. For those of you too young to remember, Jordache jeans were the thing to own in the late 1970s and early 1980s if you were a teenager or in your 20s. They were tight fitting and expensive compared to other jeans, and they had Jordache printed in large letters on the back pocket, so you couldn’t help but know what jeans somebody was wearing. There have been other jeans since, but I don’t believe the impact of owning these particular jeans has ever been duplicated. It was magical. All you had to do was own these jeans and you were one of the cool kids. I was introduced to the phrase “cool kids” by a woman I worked with. I think it describes perfectly those people in our lives we either wanted to hang out with or wanted to be. I’d venture to say everybody in the world has known or currently knows their own version of cool kids. These folks are all different, but in our eyes they’re cool. I don’t think it matters how much money they have or how good looking they are, they just have that thing we want. It could be the popular jeans, the car we’ve always wanted, that house we admired growing up or the number of goats they own, assuming that’s the measure of wealth where you come from. There will always be something we desire. We might buy it, it might remain on our “must have”…
Read more »

Do Who You Are

THE ONLY DREAM I HAD for my son was that he’d get a job. To most parents, this probably seems like small thinking. Why wasn’t I dreaming of him walking across the stage after earning his medical degree, or walking down the aisle with his new bride, or the joy of him holding his first child? Because that would not be his reality. It took me a while to accept this. Based on my life, I always felt folks could overcome most obstacles if only they tried harder. I thought my son was no exception. All his mother and I had to do was guide him through his public education and it would all work out. Well, that was not meant to be. My wife and I are totally different people. To those readers whose spouse is always on the same page, God bless ya. My wife and I disagree more than we agree. Our saving grace is that we can make each other laugh. This is a blessing, especially when you’re raising a special needs child. Every time I’d talk about his future career success in a 40-hour-a-week job, my wife would say, “You’re nuts.” She would tell me she sees him working maybe one or two days a week, with the balance of his time in adult daycare centers or volunteering in our town. This was unacceptable to me. I wanted him to carry his weight in society. I wanted him to contribute to our community. To Republican readers out there, I’m sure this is how you’d like all citizens to live. I can’t disagree. But matters didn’t turn out as I wished for my son. When he was in our public school system, he was exposed to many facets of education, as all students are. To the…
Read more »

Got Enough?

I LIVE IN CENTRAL New Jersey. Within walking distance of my house are some McMansions—huge homes clustered together in new developments. I look at them and think, “Who cleans these things?” I live in a three-bedroom ranch-style house with an unfinished basement and a two-car garage. My garage is filled with two cars and my tools. The basement is filled with my wife’s stuff. We bought the house when my wife was pregnant. Thirty-three years later, there are three people living in the house. It was big enough 33 years ago and it’s still big enough today. Why would I want more? My neighborhood gets noisy during the week, especially in the summer months, because all my neighbors have a landscaping service to mow their lawns. Now, if they all hired the same service, the noise would be limited to a single day. But because all use different lawn services, the landscapers come on different days of the week. The result is that the roar of these high-powered grass-cutting hot rods fills my world five days a week. Meanwhile, I mow my lawn with my self-propelled Honda lawn mower. Every morning, I begin my day with a coffee mug filled with black coffee and no sugar, which I raise up and say, “This is the day the Lord has made, let us rejoice and be glad in it. Help me to be glad.” Then I list those things that occurred the day before that I’m grateful for. Basically, I count my blessings. This practice should not be new to anyone. “Count your blessings” is something we’ve all been told over the years. But how many of us do it? Money has always been important to me, and I saved diligently throughout my life. As a result, I have money “in…
Read more »

Don’t Build Without It

YEARS AGO, I SAW a Looney Tunes cartoon starring Daffy Duck and Elmer Fudd. As always, good old Elmer was trying to kill a duck for dinner, only to be outsmarted by the much cleverer Daffy. In this particular episode, Daffy is playing a game of catch with his duck friends outside Elmer’s house. An overthrown ball crashes through a window. Elmer comes out and says, “Who broke that glass? Someone is going to pay for that.” The ducks all bump into each other in their efforts to run away. Elmer gets outfoxed, of course, but you don’t have to be a patsy like him when it comes to home repairs or remodeling. Imagine you’ve hired a contractor to work on your house. What happens if the contractor breaks a window or, worse still, drops a load of roofing shingles onto your new car? You may have done your due diligence in selecting a contractor by getting a recommendation from your neighbor, obtaining numerous quotes and reviewing the contractor’s Better Business Bureau ratings, so you might assume that your contractor will replace the broken glass or pay for your car’s bodywork. But instead, you may get the runaround. Maybe the contractor is broke. He may keep making promises without undertaking the repairs. He might even abandon your job without warning. To keep from getting fleeced, request a certificate of insurance from the contractor before he steps foot on your property. This one-page document typically tells you if the contractor or his subcontractor has three insurance policies in force: a general liability policy, a worker’s compensation policy and a commercial auto policy. What do these three policies cover? First, the general liability policy will cover any damage the contractor does to your property, such as a broken window or dented car.…
Read more »

Feeling Rich

ON ONE OF OUR TRIPS to visit my in-laws in South Carolina, my mother-in-law asked me what I thought of her home in a 55-plus retirement community. “It looks like a house,” I said sarcastically. Her response gave me food for thought. She said, “I feel rich living here.” My mother-in-law’s home was far from being a McMansion. It was a single-story two-bedroom house, but it had cathedral ceilings. I think it was the high ceilings that, in the eyes of my mother-in-law, made the house more majestic than it really was. I’m sure most HumbleDollar readers want to be wealthy, or well-off, or financially comfortable, or some similar goal. But what would make you feel rich? There are plenty of people who are rich but don’t feel that way because they compare themselves to “the Joneses,” who appear to have even more. Knowing others have more can make us feel poor. That’s a shame. What good is being rich if you don’t feel rich? I don’t have a degree in psychology, so I’m not qualified to say why some folks feel rich and others don’t. But I would venture to suggest that, if you have money and you’re content with what you have, you probably feel rich. Now, if you took a survey of HumbleDollar readers, I bet we’d all have different notions of what makes us feel rich. The behavior that makes me feel rich is buying everything with a credit card. Thanks to that magical piece of plastic, I never feel like there’s something I can’t have. Don’t get me wrong: I never carry a balance on my card from one month to the next and, in fact, I never buy anything unless I have the money in the bank to pay for it. Still, having this…
Read more »