How to Avoid the Most Common Reason Retirement Plans Fail

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Let’s begin with some questions.

1. How much retirement income do YOU think it’s possible to create, given your current financial reality?

2. How many years are left ’til you retire?

3. Are you a fan of retiring on your savings — or on the yield from various investments?

4. Given your ability to save capital for investing and the time you have left to retirement, what annual return must you generate A) from now to retirement? and B) from retirement on?

5. Will your retirement be funded with one or multiple income sources? (SS doesn’t count.) 🙂

6. Are you a DIYer (do-it-yourself-er), or will you utilize an expert(s) to help enhance your results?

7. Given the nature of your retirement income sources, how much after-tax income will you actually enjoy?

Related: Why Your 401k Is A Retirement Income Loser!

In my opinion, there’s a single principle at the bottom of most retirement plan failures.

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The Most Common Reason Retirement Plans Fail

The reason for retirement plan failure lies in answers to questions folks never knew to ask.

Those answers are either eventually stumbled upon through blind luck — or are simply never discovered. We’re all pretty much able to find the answers to most questions via “the hookup to all mankind’s knowledge,” a.k.a. the internet.

But pretty please, tell me how long it takes us to find answers to unknown questions.

The answers to the next questions are guaranteed to make or break your retirement:

Have you considered how many answers out there are to questions you’ll likely never know to ask in a dozen lifetimes without reflection and research? Do you plan on seeking out not only new ANSWERS, but new QUESTIONS regarding your retirement?

You might ask, “But Jeff, what about all those DIYers who’re printing thousand dollar bills in retirement via real estate investing?” Frankly, I get asked that question a few times a month. It’s one of my favorites.

Here’s why.

I’ve been challenged dozens of times to take a “look back in time” at the portfolios of those already retired — and with impressive results. Still, in virtually every case, I’ve been able to empirically prove it would’ve been 50-300% higher if their strategies had been modified when it counted. Though it sounds difficult, it’s almost always like fallin’ off a log to see the proactive and passive mistakes that were made.

An analogy would be proving how and why today’s race cars would slaughter their ancestors from the 1940’s.

Or better yet, how much lower would Babe Ruth’s homer total and lifetime batting average be if in the last 2-3 innings of most games he played, he wasn’t facing has-beens and never-was/never-would-be pitchers? Or if on a daily basis he faced 84-90 mph sliders and split-fingered fastballs that disappeared as he started his swing?

In the same vein, how much better off would your retirement plan be if you could prepare some answers to future questions and build solutions for possible eventualities?

Related: The IRA Stretch—How Far Will Your Retirement Dollars Go?

Two Things to Ponder:

Old school thinking in general can be superb, just not all the time. Knowing what still works — and what’s been proven superior — is like having the key to the vault.

The answers to questions you’ll probably never know to ask don’t offer themselves up for your review.

You can find out those questions (and answers) now — or learn about ’em in retirement. Your choice. Take your time. No rush.

What answers regarding investments or real estate have you stumbled upon lately? What are the most important questions you’ve learned to ask?

Join our conversation below!

About Author

Jeff Brown

Licensed since 1969, broker/owner since 1977. Extensively trained and experienced in tax deferred exchanges, and long term retirement planning.


  1. Hey Jeff,
    You have a lot of questions here but no answers. It is hard for me to answer that question since I have never had to live off of retirement money. Right now other than social security I have some money saved in a self directed stock plan. I am contributing $1K per month but I only have 10 years until age 65. Of course I cannot collect full social security until age 67 and 9 months thanks to Jimmy Carter’s revamp of SS. My home and cars, office, and a small piece of farm ground are all paid off free and clear. It is my hope to have at least 10 high quality rentals fully paid off by time I retire to make the difference between an OK retirement and a great retirement. I am however starting to think I need to enjoy life more now. My wife and I have been frugal and never spent much on ourselves or taken much in the way of vacations. That may slow my retirement investing some.

    • Jeff Brown

      Hey Jerry — If you can’t answer those first 7 question about your situation, how on earth am I supposed to answer ’em for ya?

      I’d ask another question: How will you acquire and pay of 10 rentals in the next decade?

      Also, in your view, is there another way you might tweak that plan into producing far more retirement income, and in the same period?

  2. At what age do you start to pay down your rentals to have them free and clear in anticipation of retirement? Or do you simply continue to fund the 401K/Market or buy more properties?

    • Jeff Brown

      Hey Eric — That’s the bazillion dollar question. The equally valuable answer is that there is NO formula. That answer is all over the map, depending upon each investor’s various factors. It’s not even close to being a formula. Those who believe it is are destined for some nasty surprises and letdowns.

      • Thanks Jeff
        Here is more info. I am 54 and just jumped into the Boston market purchasing 4 properties total 1,9000,000 and inheriting 1 at 400,000, and after putting 30% down I am wondering whether given my age I should sell my $750,000 beach house and pay off 2 of the properties or if I should just take the cash and put it in the market. Total Cash flow is around 4 to 5K per month.

        • Jeff Brown

          Eric — We should do this in private. I don’t wanna go into detail with you on a public forum. Also, I’ll likely need a few more details. Please go to my site at and send me an inquiry, referencing this thread. We’ll get to the bottom of what’s really possible for ya.

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