Generating retirement income would be laughably easy—if we had one piece of information: how long we’ll live.
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 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:
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:
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.
NO. 57: WE FAVOR possessions for their lasting value, but often we get greater happiness when we spend money on experiences. Forget the new car. Instead, take the family to Paris.
MARKET EFFICIENCY. As news breaks that effect the economy and individual companies, investors immediately buy and sell stocks in response, so share prices reflect all publicly available information. Because the market is so efficient, it’s all but impossible for investors to beat the market averages over the long haul, especially after figuring in their own investment costs.
SHARE YOUR PAYSTUB and financial statements with your kids. This show and tell will give you a chance to discuss the importance of saving, the power of compounding, and how much of your income goes toward taxes, housing and other items. Any one conversation might be brief and appear to have little impact. But over time, your children will learn a lot.
NO. 66: WE HUNGER for a sense of control, and a great place to start is our financial life. By taking charge of our finances early on, we can avoid a lifetime of money stress. Meanwhile, we’re often miserable when we’re dependent on others—something likely to occur as we age. As our physical and mental faculties fail us, we may feel we’re losing control of our life.
NO. 57: WE FAVOR possessions for their lasting value, but often we get greater happiness when we spend money on experiences. Forget the new car. Instead, take the family to Paris.
While there are thousands who have been following Jonathan’s columns and articles for decades, I started reading his articles only about a year and a half ago.
His articles influenced me to change my investing behavior. Now I am focused only on broad market ETFs and not reacting to frequent market gyrations. I am sure many of you have learned much from him and made changes to how you think about investing.
This goes beyond financial lessons.
I have no desire to oversee a website where folks work out their anger issues by posting snarky political comments. But lately, that anger has been on full display, and we all know why. Love him or hate him, Donald Trump clearly elicits strong emotions.
But here’s the thing: Those strong emotions may be justified—but they’re hard to justify on financial grounds, just as they were hard to justify during the Biden presidency. Consider:
The unemployment rate was 4.1% when Biden left office,
AT THE 2016 SUMMER Olympics in Rio de Janeiro, South Africa’s Chad Le Clos challenged Michael Phelps for the gold medal in the 200-meter butterfly. A famous image emerged from that event: Throughout the semifinal, Le Clos repeatedly looked over at Phelps as he struggled to keep up. Meanwhile, Phelps just kept looking forward. The result: Phelps ultimately won the gold, while Le Clos trailed in fourth place.
I believe there’s a parallel between what we saw in that race and what we see in the investment world.
An article in Employee Benefits News paints a dim picture of retirement. One that may reflect the real world beyond the HumbleDollar community.
Here again we are relying on a survey so who knows how accurate, but I bet worrying and anxiety over money in retirement is not uncommon. Can you imagine retiring with no clue about the viability of your finances?
It says retirees are struggling to make their savings stretch.
According to Schroder’s 2025 U.S.
I love going to bed. There’s something comforting about lying in the darkness, wrapped in the sheets and blankets, knowing the wider world is unlikely to intrude. What bad could possibly happen? To me, there’s no safer place.
No doubt others feel differently, finding a sense of security elsewhere—in their SUV safely separated from other drivers, in the hefty balance in their checking account, in their large house fenced off from their neighbors, in their modest monthly financial obligations,
Hi Jonathan,
I found you by reading an article you wrote for AARP, which led me to your HumbleDollar site and everyone’s articles. Very informative and useful!
I too got a surprise diagnosis of metasticized cancer a few years ago and fortunately have been successfully treated, so far. It has indeed illuminated my perspective on life. I expect to have more than a few months but am more cognizant of what is truly important in life.
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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:
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:
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.