She sat back in the winged chair in my office. It always seemed too large for her and enveloped her small frame. She was always impeccably dressed, had earned all the correct credentials and drove a luxury car and lived in a large house in a fashionable area. She worked at all the most prestigious companies at one time or another and if you looked at her resume, you’d assume she was winning the game of capitalism.

“I’m broke!”. She exclaimed and shrank back into the safety of the oversized winged chair.

“At least we can agree on one thing…” I thought. I had worked with this client for three years. She never listened to any of my advice or followed up on action items I gave her. She was mortgaged to the hilt, an eye watering amount of student loan debt and was late on many bills. Property taxes were due on her properties and she was going to pay late. Again.

This client simultaneously fascinated, confounded and enraged me - I had given her the best information and advice and had she listened she’d be on her way to resolving many of these problems permanently and creating generational wealth for her young son. She had more than enough income to take this on. What was her problem?

She lifted her designer eyeglass to dab her eyes with the Kleenex I placed discreetly next to her. I had my assistant place Kleenex on my desk next to clients that I knew would dissolve to tears at some point during the meeting.

“ I don’t know what I’m doing wrong. I went to a good school, I have a great job and everything just never came together with the money. What is wrong with me?” She sobbed.

I leaned back in my chair. Everything I had tried with this woman had failed. If she was tired of her situation, I was too. Three years and more than enough resources to resolve any money problems she had. Yet there was never forward momentum.

I thought for a moment, took a deep breath and said….”tell me about your childhood family and money.”

That question changed everything…