Bob and Susan are in their mid-50s.  They live what most people think of as The Good Life. Their income is solid, yet they are house poor.  They would like to retire in a couple of years but have locked themselves into having to work to support their real estate holdings: a large house with expensive maintenance costs, and a beach house on an exclusive island off the coast of Massachusetts.

 The mortgage payments for their two dream homes require that they both work at jobs that bring them little satisfaction. They yearn to live out their dreams, but can’t see how to break free of their current financial situation.

 So far Bob and Susan are not willing to sell either of their homes in exchange for a chance to experience what they said that they always wanted. Instead, they have locked themselves into working for the rest of their lives to pay for a lifestyle they seem to think they can't live without.  An interesting dilemma. And very confusing and frustrating for the people in it!

 I asked them to describe their ideal life after work. They both described very simple pleasures that were well within their means.  Bob wanted to plant some fruit trees on their land, and grow a vegetable garden. Susan wanted more time to work in her pottery studio.  These were not expensive hobbies.  They require more time than money.  Right now they have neither at their disposal.

 Bob and Susan came to me to help them get out of their maze, and to help them figure out how to retire while making the most of their money. Since I’m not an investment adviser or financial planner, my role was--in a very fundamental way--to help them use their money to attain a sense of contentment in life. Then they could use a financial adviser to help them work out their finances.  It is really emotional issues that have kept them from being free to follow their dreams.

 You see, the dilemma they are facing is not financial, but rather an emotional one.  They have to come to terms with what will truly make them happy, i.e. having their real estate, or playing in their creative interests and hobbies.  They have to resolve whatever feelings may be barriers to moving forward.  Those kind of feelings are usually complex and unconscious, and are therefore not easy to identify.

 With Bob and Susan, their sense of guilt in potentially living a life of leisure was a real issue, since their parents worked very hard through their middle 60s.  And here THEY wanted to retire at 55!  Their feelings of guilt were preventing them from taking the actions that can make their dreams come true.  In addition to feeling guilty, they were ambivalent. Part of them wanted to retire; part of them wanted to continue working.  If they continued to stay in their rut of “having to work” to pay for their high standard of living, they would never have to deal with the tough emotions that would come up if they could retire and live out their dreams.  Frustration was easier to tolerate than guilt.

 If you find yourself in a similar situation, think about the emotions that may be holding you back. What do you feel when you think of yourself as retired and playing at something creative, fun, athletic, adventuresome?  Financial freedom is certainly a possibility for everyone who makes smart choices today.  But that's the key: You will be better off if you begin making those choices sooner rather than later. And making those choices involves identifying your emotions with regard to the issue of retirement versus continuing to work.

 When you think about your life plan, design activities that will bring you a sense of fulfillment without necessarily making holes in your retirement nest egg. Think about trying activities that will satisfy your curiosity.  Pay attention to any feelings that come up.  They need to be dealt with, or they will act as roadblocks, preventing you from moving forward.  These feelings keep us in a maze, stuck in old habits and old belief systems.  Your task is to grapple with your money feelings today, so you can see a path to another, more fulfilling tomorrow.