Feeling Trapped in Family Business

We sat in awkward silence in his car outside the office. It was dark outside, but it somehow felt darker inside. Twenty-five years ago, the client’s company was basically printing money. A small operation had turned into multiple companies, a small staff had turned into a large group of employees, and a small income had turned into significant wealth. But now the president of the 100-year-old company we were hired to help was at wits’ end. He had just shared he was struggling with depression.

He didn’t want to be here. He was trained in another field and was getting established in his career when he got sucked back into the family business. He now yearned for the next chapter in his life. It had been easy to avoid the unrealized regrets when the money was flowing. But the industry had changed, and profit was dwindling. Worse, his sister was sabotaging the business and he didn’t have the power to stop her. Years of bad decisions and convoluted legal structures created an impossible web of mixed incentives and family-breaking arguments just waiting to happen. “What do I do?” he asked. “I just feel trapped.”