I struck up a conversation at the gym recently with a fifty-something lawyer I'll call Harry. Harry has three kids attending college and grad school, a mortgage that that has been refinanced a few times and still has a hefty balance, and a desire to retire with enough resources while he still had the energy and health to explore a few projects he's never gotten around to doing.

How do we help baby boomer clients who don't have enough money to retire?The scary thing, he confided to me, was that he barely had a year's worth of living expenses in the bank. Retirement plan savings? He had a few scattered IRAs worth maybe $25,000. Harry always assumed that at this stage in the game he would at least see some light at the end of the tunnel. But recently he started to panic. Would he ever get out of debt and into retirement? How did this happen?

I understand Harry's predicament-and as an advisor, I'm sure you do, too. But how do we help our clients like Harry play catch up?

The first thing to realize is that Harry is not like our mainstream clients.

My typical client has the resources to more or less accomplish his goals. My retirement projection may show that he can't afford to retire at 62 or 65 as per his desire, but with some adjustments to his goals or to his strategies, he can still achieve his goals without the need to alter his lifestyle. The typical client needs tactical advice from us in order to know when and how he can realistically achieve his goals of retirement, educating his kids, and so forth.

However, Harry the "Comeback Kid" needs more than just an adjustment in his asset allocation model or an increase in his 401(k) contribution. Harry may need to consider more radical changes in order to dig out of the hole he's in: reducing spending, downsizing his living situation, and/or getting a part-time job (in addition to his full-time one) to make the numbers work. Harry needs more than strategic tactical advice; Harry needs to consider some behavioral modification in order to implement the difficult choices that we know are needed.

Clearly, behavioral changes are more difficult than tactical changes!

Many dieters, smokers and shoppers know what has recently been confirmed by a new study: Going against the grain in making difficult decisions requires extra motivation or confidence. In other words, Harry must fully understand and accept the urgency of making some hard choices if he really wants to retire. And we, as the advisor, need to try to deliver a clear message to both motivate and encourage him to do so.

To take the analogy one step further, we, as the advisor, may also need to step out of our comfort zone when advising the Harrys of the world. Haven't we become accustomed to telling our clients that we could help them to achieve their goals, based on their current lifestyle?

Here are some suggestions which may help us succeed with our clients along the comeback trail: