I have a lawyer friend who specializes in collections. With a sad smile he said “It’s the way of the world. When the economy gets awful I get busier. I love the income and I hate the way I am earning it.”

We spent a long lunch looking at the patterns that lead people to behave badly around money. He was concerned about the torn relationships that come from unresolved money issues. He needed to talk, to sort out his own feelings. Yes, lawyers do have feelings! I watched as his mind went through the nooks and crannies of people and money.  “It is one thing if there is a real problem about having the funds to pay, that can get quick resolution. Yet, more often there are misunderstandings that are left to fester and never really get resolved. And then there are the power games that waste my time someone else’s money and seem to have a life of their own.”

So, why is it excruciatingly difficult to resolve so many issues that surround money? It is because money is so much more than a means to pay the mortgage or buy the vacation. It is about validation, it is about retribution, it is about winners and losers. It is about the unfulfilled pasts of ourselves and about how we look at what matters in life.

I shared with this good, big hearted man a situation that has been on my mind of late. It concerns a friend who I have known for years who I contracted to do some work for me. The quality of what came through was for me disappointing, I would give it a “c” rating. I decided to bring the work to an end and go with a more up-to-date company.  

Here is the dilemma. My friend and professional contact wants my business, needs the money. Yet, I am not getting the service I require.  How much do I say? Do I tell him my truth or do I smile, thank him for his participation in the project and move on? Do I offer to give him some of the advice I have recently received? Do I suggest to him that there are newer, more sophisticated ways to get the work done?  He is, as he has reminded me more than once, the expert in his field. He may have been; he is not now. If he were just a friend without a business relationship would I have felt free to share what I have learned?  Now, to complicate the issue, there is money involved, and disappointment about the ROI.

Rather than focus on him I am spending time looking at my own patterns around money and relationships. I am observing myself, wanting to understand the tender points that create tension and interfere with conflict resolution, even within myself. I may well lose a friend if I say what I really think. And I may well lose a friend if I keep quiet. What would you do?