While it’s generally a good idea to defer as much income as possible into your available IRAs, 401(k)s and Roth accounts, as with everything else in life, too much of a good thing can be a problem as well.
When you have the bulk of your financial assets in retirement plans, you might accidentally expose yourself to some risks that you haven’t thought about… since retirement plan assets are much more likely to be impacted by changes to legislation – as we have seen in the past.
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In these days when Congress is looking for money just about everywhere, it’s not a stretch to imagine new legislation coming down the pike to tax retirement plan assets (like the 15% “excess” plan accumulations that was enacted in 1986 and later repealed). Other possibilities include accelerating required minimum distributions to achieve a faster payout taxation of the plan; eliminate the “stretch” provisions; or even nationalization (yikes!) as suggested to Congress by experts as recently as 2008.
Assets held outside of retirement plans enjoy capital gains tax treatment (under current law) that is generally much more favorable than the ordinary income tax rate. Plus, these assets also can receive a step-up in basis when passed to your heirs, removing the capital gains on a lifetime’s appreciation in the account, whereas retirement plan assets do not receive this treatment.
This is not to say that you want to eliminate your retirement plans altogether, but rather to balance your assets by tax treatment. It makes good sense to diversify by tax treatment, as a hedge against the various things that could occur to the retirement accounts.
There is no perfect formula for determining what is the appropriate amount to maintain in tax-deferred retirement plan accounts versus taxable versus Roth accounts – this is determined by the individual, along with his or her trusted advisors.
Sometimes it makes sense for the individual to have the lion’s share of his or her savings in deferred accounts, such as when we’re very young. At other stages in life (early retirement before age 70½, for example) it could make a lot of sense to start eliminating the deferred accounts in favor of Roth or taxable accounts.
The idea is to weigh the tax impacts of moving money about against the potentialities that are out there for massive changes to the tax treatment rules on those accounts.
You may or may not be familiar with the concept of Net Unrealized Appreciation (NUA) as it relates to company stock owned in your 401(k) plan. Click the link to get a rundown on it if you’re not familiar with 
Among the many things that are important to deal with regarding your retirement accounts, you must consider the impact of your own disability and how your IRAs will be dealt with. A very good way to do this is to have a durable power of attorney (DPOA) document signed that gives someone you trust the authority to make investment decisions, take distributions, and create new IRAs from your current accounts.
There is a piece of legislation hanging around in the Senate that makes a good deal of sense, and really shouldn’t cause too much grief to implement in the long run.
If you happened to do a Roth Conversion during 2010, you’re likely aware that you can elect to spread the tax over 2011 and 2012, or pay all of the tax on the conversion during 2010.
I recently received the following question from a reader. It’s a unique situation that you may find interesting, so I thought I’d share the interaction with you:
So you have a substantial IRA (or several IRAs), and you’ve retired. For the first time since you started your career, you’re in a low tax bracket. You’re not age 70½ just yet, so you don’t need to concern yourself with Required Minimum Distributions (RMDs).
Once again in the category of terrible things you can attempt to do with your IRA, there is the concept of a “cross loan” from your IRA to another, unrelated party.
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And if you've come here to learn about queuing waterfowl, I apologize for the confusion. You may want to discuss your question with Lester, my loyal watchduck and self-proclaimed "advisor's advisor".