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:

Keep it simple. Show him how much he will have to save by a given retirement age. Even with your best investment advice, a combination of more savings and/or less spending will be need. Set a short-term goal of netting an extra $100 or $200 per month to get started.

Put his life on auto-pilot. Next month he'll start investing $200 in his IRA or 401(k). Many of his bills, such as cable and insurance, can be paid automatically through his checking account. He must pay for his groceries, entertainment, etc., out of what's left.

Don't try to nickel and dime every purchase. Your client may go crazy and feel deprived. Rather, try to get one or two bad spending habits under control. For example, for years I spent freely at Barnes and Noble whenever a new book caught my attention (which was every time I entered the store). I realized that I was spending around $150 a month-and running out of room in my house to shelve my books. I made one behavior change: I would check out books from the library, and limit my purchases to $200 a year.

Once he has started on the short-term plan, and he has some success under his belt for a month or two, sit down and explore the feasibility of either making an additional $500 a month, or saving an additional $500 a month. Of course, even this may not be enough, but every change brings Harry closer to his goal, as well as generating the momentum and confidence to keep going.

Does he have skills that he could use a consultant or as a tutor? Can he tutor ten kids a month in math or computers at $50 a session? Is he qualified to teach Sunday school? Alternatively, can he sell his house and move into an apartment? Of course this will be extremely difficult, either because the housing market is bad or because of the sense of shame and  embarrassment associated with middle-class expectations, family expectations and the logistical challenge of cleaning out and fixing up the house for sale. But the motivation of investing the equity built up in the house (if any) and adding to it monthly must be tangible. You may gently remind him of the danger of procrastination. If he hasn't fired you by now, he wants you to give him the strength and conviction to move forward. Obviously, you must do the calculation to see if this makes sense on paper. Harry may be waiting to be bailed out by the next housing boom. It will surely come, but it may come too late for Harry.

Remember that the main obstacle to salvaging Harry's retirement will not be the lack of financial genius. The main obstacle is fear of change and fear of the unknown. We've all had our ups and downs with going to the gym and losing weight. Who wants to risk another failure? You must bring to the table all of your financial expertise, as well as providing accountability to your "Come from Behind" client. We all need support groups to succeed.

Have your client write down the following and read it twice a day:
1.Fear is normal.
2.The fear of my current situation is more than making a change.
3.What's the worst that can happen.

One last word of advice. Don't be afraid to charge Harry a fair price for your services. You are earning it. And if you don't, well, you know how much people value free advice. It may be the best investment that Harry ever makes.

Frank Jaffe is a financial planner with Access Wealth Planning in Roseland, N.J. He can be reached at [email protected].