How do you know when it's time to go? A business owner's guide to retiring

Ostensibly, people dream about the day they can retire. They dream about days on the golf course or in the garden, time with the grandkids, traveling the world — all the rewards for the years of hard work and sacrifice. 

In reality, it’s not that easy for everyone — especially business owners. For the business owner, there’s more at stake. There’s legacy and a responsibility to the family’s future to consider. These variables can ratchet up the emotion in an already emotional decision. In my work as a family business consultant, I have witnessed family and closely held business leaders struggle to retire. 

The truth is it takes courage to retire. Many leaders get cold feet when it’s time to go, even if they’ve been planning for the succession for years. But knowing when to go is key. Everyone wants to go out on top (like Tom Brokaw) but many stay too long (ahem, Dan Rather). The key to getting it right is opening your mind to a wider view of the micro-considerations that will ultimately drive your decisions and timing around retirement. Start by asking yourself the following questions: