A 62-year-old small business owner from suburban Denver came to me a few years before retirement. In addition to selling his manufacturing company, he owned a rental property in Colorado that had been in his family for decades. He planned to sell the property and use the proceeds to help fund retirement with his wife. The challenge was that he had become fixated on a valuation he heard during the peak of the real estate market. Every offer that came in was compared to that number. No matter how reasonable the offer was, it felt disappointing because it was not “the price.” Emotionally, every opportunity was being measured against what might have been rather than what the property was worth today.
During our conversations, I learned that the peak valuation represented more than money. To him, it validated years of hard work and smart decisions. Selling for less felt like admitting failure, even though he was still sitting on a substantial gain. Rather than debating market conditions, I asked him a simple question: “If you didn’t already own this property, would you buy it today at its current price and accept all the responsibilities that come with it?” The room went quiet. For the first time, he stopped thinking about what the property was once worth and started thinking about its role in his future.
Several months later, he accepted an offer and reinvested the proceeds into a diversified retirement portfolio. More importantly, he felt relieved. The constant frustration and anxiety of waiting for the market to return to an old valuation disappeared. The experience reminded me that investors often become anchored not just to prices but to hopes, expectations, and memories. Sometimes our job is helping clients let go of a number that no longer serves them.
