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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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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"]

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.

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:

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.  

BACK IN 2010, at the Berkshire Hathaway annual meeting, a shareholder challenged Warren Buffett. Noting that shares of motorcycle maker Harley-Davidson had nearly tripled over the prior year, he asked Buffett why he had chosen to buy the company’s bonds rather than its stock. Buffett’s reply was a two-minute masterclass in how to think about investments. It’s worth walking through it point by point. To start, Buffett acknowledged that hindsight can be cruel. “I might have asked the same question,” he said. But then he reminded the investor that we should never judge an investment decision solely based on its result. Instead, he emphasized the importance of a sound decision-making process. He then detailed how he thought about the Harley decision at the time. Buffett started at a high level, with a discussion of asset allocation, and here he made a counterintuitive argument. Many of Berkshire Hathaway’s liabilities extended out more than 50 years, he said, and with such a long time horizon, it might seem like the company could afford to take an almost unlimited amount of risk in the stock market. Buffett acknowledged that was indeed the case. But, he said, “we would never have all our money in stocks,” even if, on paper, it seemed like the best choice. Buffett and his partner, Charlie Munger, still chose to hold substantial amounts in bonds, even if that meant giving up potential gains. Why? Buffett went on to explain why holding bonds made sense even in the absence of any clear need. For starters, bonds provide flexibility during stock market downturns. And since bear markets always arrive without notice, and can last multiple years, it makes sense to hold bonds, more or less, at all times. Perhaps not surprisingly, Buffett once mentioned that a trust he’d established for his family was similarly structured, with 10% in bonds, even though it had a long time horizon and could theoretically afford to be entirely in stocks. Coming back to the Harley-Davidson decision, Buffett referenced his mentor, Benjamin Graham. In his book Security Analysis, he had explained the relative benefits of “junior” and “senior” securities. “Junior securities,” Buffett said, “usually do better, but you’re going to sleep better with the senior securities.” What did he mean by junior and senior? In a typical corporate structure, where a company has issued both bonds and stocks, bondholders would have first claim on the company’s assets if it went into distress. Stockholders, on the other hand, would be further back in line. For that reason, bonds are said to be senior, while stocks are junior. It’s an important distinction. Because of this structure, bonds are inherently more secure than stocks. They are essentially IOUs. But also because of that structure, bonds will normally have lower returns than stocks. Companies know they don’t have to offer as much in the way of interest to bondholders because of their more senior position. This is the technical reason why, all things being equal, bonds offer both lower risk and lower returns than stocks. Buffett acknowledged that Harley-Davidson was a beloved company. “I kind of like a company where your customers tattoo your name on their chest.” Still, Buffett said, there were no guarantees. Even great companies can run into trouble. It was for this reason, Buffett said, that buying Harley-Davidson’s bonds was a relatively easy decision. “I knew enough to lend them money. I didn’t know enough to buy [the stock].” That’s because buying the stock would have required a much more detailed analysis of the motorcycle market, including an understanding of consumer trends and the effects of competition on Harley’s profit margins. Buying the company’s bonds, on the other hand, “was a very simple decision. It was just a question of, are they going to go broke or not?”  When we choose to buy bonds, in other words, we’re intentionally choosing the slow lane, but it’s for a reason: because bonds offer a level of certainty that stocks can never provide. And because of that certainty, we shouldn’t feel badly when bonds deliver meager returns. It’s by design. Buffett wrapped up the discussion acknowledging that if he’d opted for Harley’s stock, he would have made far more money for Berkshire shareholders. But that wasn’t the right yardstick, he argued. “We are running this place so that it can stand anything.” That, I think, is the most important thing we can take away from this story. The investment industry spends a lot of time talking about performance—and specifically, about outperformance. Of course, we all want to see our investments grow, but what’s most important, in my view, is that your portfolio be resilient enough to “stand anything.” One of the benefits of stock market downturns is that they give us an opportunity to stress test our emotional response to the market. After a roughly 10% downturn earlier this year, stocks are back at all-time highs, so this is a good time to take the temperature of your portfolio. If you lost some sleep during the downturn this spring, or the one we experienced last spring, this might be a good time to shift some of your portfolio to more senior, more secure, securities. If, on the other hand, you barely even noticed these downturns, that’s important information as well. Investing, in other words, isn’t just about numbers. Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.

I'M ALL IN FAVOR of striving. But I’ve also belatedly come to see the appeal of acceptance. Should we strive for more, or should we accept what we currently have and what’s currently on offer? As I’ve noted in earlier articles, there’s great pleasure in striving. We love the feeling of making progress, even if our achievements don’t make us happy for long. It’s an instinct we no doubt inherited from our hunter-gatherer ancestors. Their striving is the reason they were able to survive and reproduce, and hence the reason we’re here today. Despite my terminal cancer diagnosis, I continue to set goals and strive toward them. Each day, I put in hours keeping HumbleDollar chugging along, trying to stay in shape and working on various writing projects. Still, striving in some areas of our life doesn’t preclude acceptance in others. We should accept the limits of our talents. We’re told that if we work hard, we can achieve anything we set our sights on. Really? We all know that’s not true of athletic and artistic endeavors. No matter how hard I worked, I simply never had the talent to be, say, a pro athlete or a concert pianist. Sometimes, gauging our talent is trickier. It took a while, but eventually I discovered during my career that I wasn’t an especially good manager and that my efforts to write about topics other than personal finance never turned out quite as well as I’d hoped. To be sure, some folks are more successful than their talents would suggest. Hard work may have played a role. But there was likely also an element of luck. That’s great—but it hardly seems like something we should bank on. We should accept that we’ll never be fully satisfied. We imagine that our next accomplishment will leave us happy forever, but then we end up moving the goal posts and targeting some new achievement. That’s just the way we humans are: We love to strive. But we should also accept that this striving will never leave us with that ultimate sense of accomplishment that we crave. That doesn’t mean we should stop striving. But we should accept that it’s the journey we enjoy, and the destination won’t leave us permanently happier. We should accept that we’re unlikely to outpace the market averages. Want to outperform most other investors? The surest way is not to try—by simply buying index funds and collecting the performance of the market averages. Because of fund expenses and trading costs, index funds typically trail behind their benchmark index. But that’s better than most active investors, who lag by even more. We should accept that there are things we can’t control. We might be able to control our own behavior, though even that can be a struggle. What if we try to control the behavior of others? Life can get awfully frustrating awfully fast. This is crystal clear in the world of investing. We can control how much risk we take, the investment costs we incur, and our own buying and selling. But we can’t control the behavior of other investors, as reflected in ever-fluctuating stock and bond prices. Instead, we need an investment strategy that doesn’t depend on others behaving the way we want, at least in the short-term. Got just a few years to invest? Don’t count on other investors acting on your wishes and bidding up the price of the stocks you own. We should accept our own mortality. We may continue to strive every day. But this can’t go on forever and, in my case, probably not for much longer. When do I stop striving and accept the inevitable? I don’t have the answer, but I suspect the question will be answered for me. With each passing month, I move more slowly and I have less energy. I haven’t chosen to strive less, but it seems I am. As I observe what’s happening to me, I imagine that I’m aging, like so many before me, but for me it’s happening over months, rather than decades. I’m not saying this slowing down is enjoyable. But it also isn’t so terrible—because I feel like it’s helping me to accept what’s to come. Jonathan Clements is the founder and editor of HumbleDollar. Follow him on X @ClementsMoney and on Facebook, and check out his earlier posts. [xyz-ihs snippet="Donate"]