This won’t take too long, but it’s of paramount importance to most of us.
Ask yourself why the concept of the Trojan Horse has lasted so long?

It works nearly every time, that’s why. When two sides are in direct conflict, using a proven winning strategy is, if applicable to the circumstances, very attractive. (Captain Obvious lurking in the shadows.)
One side thinks it has the ultimate advantage — only to find out, always way too late — their advantage was a mirage, and they’d been fooled badly. Usually it ends up being an almost total victory for the horse’s designers.
Take the relatively new (late ’70′s) qualified plans, known as 401(k)’s. A genius plan applying the Trojan Horse strategy.
Where’s the war or at least the two opposing sides?
Baby Boomers vs. Government.
Sure, it involves the younger generations too, but not nearly to the extent it does Boomers. We (I’m a proud card carrying Boomer myself.) have been shaping the country’s economy and culture since the very first Baby Boomer was born in the first second of 1946.
And there’s the rub.
It’s nearly been all good too. We drove the economy in so many ways. First as toddlers, then as young students, then college students. Of course that’s when we started to make ourselves heard — the ’60′s.

You see, we’re about to retire and the government can hear us coming.
We grew out of that to marry and raise families. We listened to our parents and/or grandparents, the Greatest Generation, and took their living example of courage and wisdom to heart, mostly. Life went on.
However, things changed radically right before our eyes. The problem was, we didn’t know what we were seeing.
It was the installation of the government’s own version of the Trojan Horse. Only they called it the 401(k), and later the IRA.
It was brilliant in its conception, and elegantly simple in its execution. Boomers never had a chance. We were like the Trojans, drunk from celebrating our non-existent victory.
Here’s how it works from their viewpoint.
First, you must accept the premise that Social Security has been robbed, plundered, and generally bent over the bar by politicians of every persuasion.
Few have offered a better imitation of Bonnie and Clyde than they have. Next, you must be able to discern how badly it’s been managed, and the embarrassingly low return on investment the government has produced on our behalf. A drunken high school sophomore could do better. Slowly but surely over time, we’ve arrive at the current dilemma — there are only three workers per Social Security recipient. In the next decade or two, it’s predicted that could easily have dropped to — just two workers.
In other words, 2/3 of the country is working so the other 1/3 can collect. How d’ya think that’s gonna play in Peoria?
A small detour here to explain how it began as at least a little bit of a sham in the first place.
FDR was nobody’s fool. He made a huge deal out this new program. He also did one thing to make it, at least for the first few decades, worthless to the average American. He set the age of retirement at 65. Sounds reasonable, right? Sure it does — until you know one itsy-bitsy little fact: Life expectancy back then hadn’t reached 65. Oops.
Oh. Oh indeed. It was a sham, meant, in my opinion, to appear to be solving a problem, while doing nothing but handing a placebo to the country’s aging population.
Some might call that cynical.
End of detour.
So back at Baby Boomer Ranch, it’s become evident to congress and various occupants of the White House, that we be gettin’ older — and all at once, kinda like a conspiracy.
Something had to be done. What was the big problem scaring the spirit right out of them?
Social Security was about to be exposed as a farce — a building constructed upon a foundation of sand. Their secret (well they think it’s a secret) funding source was about to explode in their faces. Tick tock.

Enter 401(k)’s.
It killed two birds with one very stealthy stone.
It took the responsibility of retirement planning from employers, and switched it to employees. The brilliance of it all, was how they so smoothly and elegantly made it appear to be for our own good.
The Greeks would’ve been proud.
They (gov’t) said — we’re gonna allow you to save a limited amount of money each year, and we’ll give you a tax break for doing it.
That was the bait, just like the Greeks pretending to surrender to the Trojans. Troy took the bait of a Greek surrender, then invited the Greeks to bring their symbolic gesture — the wooden horse full of soldiers, inside their city walls.
So now everyone’s deliriously happy about being allowed to keep more of their own hard earned money each year, (via tax savings) if they just put it into this new qualified plan — to save for their retirement. This was too good to be true! For once, we said, the government is getting something right.
Not so fast Boomer-Breath.
Let’s construct a married couple, who, beginning at the age of 25, both working, combine to contribute $10,000 yearly for 40 years. If they average about 8.5% annual return, they’d end up with roughly $3 Million. Pretty cool, right?
Maybe — maybe not.
Each year they happily fork over their 10 grand, and smile, happy in the knowledge this contribution has saved them around $3,000 or so. Why, that means over the 40 years they will have saved around $120,000!! A gift nobody would turn away.
Now let’s fast forward to their retirement. They’re 65 with about $3 Million in their bulging 401(k). If we continue to use the 8.5% annual yield, here’s what happens.
Their annual retirement income is roughly $255,000.

They paid off their mortgage (40 years, remember?). Their kids are of course, long gone. They are almost totally devoid of any tax write-offs. It’s called being Tax-Naked — a phrase I just made up.
Works though, doesn’t it?
If we combine their state and federal tax rates, conservatively speaking, they’d probably easily owe 30% a year. In this case, that means, in round numbers, about $75,000.
Let that sink in.
In just two short years of retirement, they will have paid more taxes than they saved in the 40 years.
As that realization hits you, go back to our Trojan Horse analogy. The population of Troy is celebrating wildly, drinking freely, only to be shocked as the soldiers crash through their homes’ doors to enslave them.
If you read this blog somewhat regularly, you’ll know what is meant by Purposeful Planning. If you don’t — click on the link and listen to the podcast.
It’s really not hard to figure out — but it’s a powerful concept.
Back to our now retired couple. We’ll grant them 20 blissful years in retirement before they pass away at 85.
Due to the Baby Boomers reaching retirement age, Uncle Sam’s Purposeful Planning is about to trade $120,000 in tax savings over 40 years for $1.5 MILLION over the 20 years our folks were retired. Pretty slick isn’t it?
Ask yourself — would you trade $120,000 for $1.5 Million — millions of times? Uh, duh, yeah.
So every time an unsuspecting taxpayer puffs up a little on April 15th because they saved a few grand in taxes, remember how much he’s gonna pay the government upon retirement. Then ask yourself one more question.
Given 40 years, or 30, or 20, or whenever you can start — whatever your 401(k) ends up with, will be peanuts compared to what you could’ve done through prudent, intelligent Purposefully Planned real estate investments.
After all, if you’re gonna get taxed into oblivion anyway, why not make the net a whole bunch more?
You might also wanna stop getting so excited about trading a dollar in tax savings each year for the privilege of paying 10-30 bucks a year –every year of your retirement — until your gone.
My generation, our generation, needs to wake up and see the Trojan Horse for what it is, before it’s too late.
The plain and simple truth is — your retirement can be so much more abundant.
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Jeff, this has got to be one of your finest articles ever. I can’t stop laughing…brilliant…comparing the Trojan Horse to the IRS. And when I got to the “tax naked” with the picture of the classic Venus, I was on the floor!
Here’s another part of the trick on all of us. Self directed IRA’s have administrators that love to plummet you with fees every time you move your money. Fees to transfer your cash (because the administrator doesn’t pay interest on your cash), fees for each new investment, and finally fees to get a distribution of YOUR OWN money. So add on to the 1.5 million in your example the fees to get your money OUT of the self directed IRA. What will be left then?
Fortuneately, with our on going purposeful plan, we will find a way to dig a tunnel under the trojan horse and escape.
Cher – FIUL – That is, when you’re comfortable enough to pull the trigger.
By the way, I’m curious to find out about your New England trip.
Starbucks!
And Cher? Thanks so much for your kind review! It means a lot coming from you.
Jeff,
I am now only venturing through your blog and I must say, right on!!! Americans just seem to miss reality, even when guys like us bring it to their attention.
I am curious about your views on the new Roth 401(k). I have not decided yet, but using your mortgage to fund a Roth IRA was one of the topics I have blogged about before, so this may be worthwhile also.
Using a mortgage as a financial tool is something everyone needs to get a better understanding of or the majority of Americans will continue to fall short of true financial freedom.
I agree with Robert( and Bawldguy also encourages people to use their equity for investments). The initial thought of a bigger mortgage was difficult as I was so driven to have a free and clear mortgage. The trick is to give up the “feel good” of the moment for much more security in the future. A tall order, and many Americans have trouble with letting go of instant gratification, but it can be done with courage and holding a vision of a properous future.
One of these days, Cher, I’m gonna offer you a job.
A nice article. I give it two thumbs up.
Hey, Jeff, Not a bad idea…hee hee. I’ve got time on my hands since those property managers of yours are not needing too much supervision lately.
Jeff this is an extremely well written article with a powerful truth. It is important to note however that the ROTH IRA gives the tax benefit on the earnings from investments and while the investor is taxed on the income they invest they are not taxed on it while drawing down during retirement . So the ROTH which allows investment now of up to $5,000 per individual or $10k per married couple is not a Trojan Horse but the real deal though admittedly insufficient.
Scott — You’re correct. One of it’s insufficiencies is the dollar limitation per year’s contribution.
So many taxpayers are able to put in up to 10 times as much, but are prohibited. Also, in some of the tax free insurance vehicles, the freedom is relatively unlimited when it comes to either need or planning.
Roth isn’t a Trojan Horse.
I’ve read a lot of investing articles and I was really caught off-guard by the “tax-naked” too.
Good writing.
Jon Boyd
Ann Arbor real estate buyer’s agent
The Home Buyer’s Agent of Ann Arbor
Thanks Jon — much appreciated.
I totally agree with the big picture here. But unless I’m missing something (totally possible!) it seems to me that the most accurate representation of this story would have mentioned the compounded gain on the deferred taxes. The $3,000 per year would also have been growing at 8.5% for 40 years. That comes out to about a million bucks gained on the deferred tax, and only 1/3 of that will be paid back as taxes.
-Dave in SF
]
[novice and budding real estate investor
Welcome Dave — In my 40+ years I’ve not met the couple who religiously separated the tax savings from anything giving them tax shelter, and invested it. Of course, if they did, they’d do demonstrably better. But here’s what makes the point moot.
The real gift I gave the couple in the post was not even one year of loss. 3-4 decades of stock market investing and not one down cycle? Really? Not gonna happen. The reality is that when we have a losing year, we’re transferred to the ‘investing for retirement’ treadmill. We ‘run’ on it ’till we’ve spent enough time, usually 1-3 years or so, just catching up to where we were. This couple was burdened with that reality.
How many people do we all know who’re now still working due to the last
Wall Street downturn? That’s a huge problem with 401Ks/IRAs. You simply CAN’T afford to have losing years. The folks still working instead of enjoying their retirement, never, for the most part, knew this could happen to them.
Am I makin’ sense?