My job was to help Mary bring the same guts and talent she shows professionally into her personal life. "I know you have it in you to do this," I told her. Here's the game plan:

Bring "Business Mary" Home

One of the best moments during our talk was when I asked Mary if she was good at her job. With a clear and confident voice, she quickly answered, "Very good." Oh, I loved that! Confidence! All too often women see their faults before their triumphs, or feel they shouldn't toot their own horn. That is so ridiculously wrong. I was happy that Mary is proud of her professional success. Now she needs to channel Business Mary's confidence when focusing on her personal life. No hesitation. No guilt. No worry. Focus on what needs to be done, and do it well—just like she does every day at the office.

Treat Grown Children Like Adults

While I wasn't thrilled that Mary's daughters were freeloading, we both knew that Mary helped create this dynamic—and let it go on far too long. Putting her financial foot down will not be easy, but it's not punishment, either. This is an important step that will help both daughters learn to respect their mother and to respect their word. They told Mary they would pay her for some of their expenses; it's in everyone's best interest if Mary holds them accountable.

Going over the daughters' finances, we determined that they could each afford to pay $400 a month. That $800 won't cover everything Mary provides for them, but it's a very good start. I also recommended that after talking to her daughters, Mary write out a financial agreement, spell out the penalty for not living up to the deal, and sign it with each daughter. I've found that bringing this level of formality to discussions can trigger a greater level of mutual respect.

Insure Only as Much as You Need

Mary was spending nearly $200 a month on three life insurance policies on herself. I understood her instinct to provide for her girls, but the truth is that they are adults. If Mary had the money to spare, I wouldn't mind so much. But she doesn't. She needs to focus on providing for herself in the here and now, not leaving her daughters something when she passes. I knew Mary wouldn't give up all three policies, but keeping just one that has a $50 premium frees up the other $150 a month.

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