I have been coaching youth sports for many years and ice hockey is my favorite.  Currently I am working with eleven- and twelve-year-olds. During practice while teaching the players skating techniques, they inevitably make it a point to avoid falling. They try so hard to stay upright. This might seem logical and even desirable considering you can’t play hockey well if you’re always falling during a game.

This logic misses the point.

The only way to truly improve is to push yourself to the limit, understand and master that limit, then move beyond it. You will fall when you begin to approach your limit and you will grow if you learn from approaching the limit and falling. I frequently tell the players that if they are not falling, they are not trying. Failure (“falling”) is essential to growth as anyone who has ever learned to ride a bike will tell you. To be clear, falling isn’t really the same as failing unless you don’t learn from the experience and/or you use it as an excuse to give up trying.

For enterprising families it is essential when developing the next generation to allow for and even encourage failure. It is part of the kind of risk-taking that is necessary for entrepreneurialism and multi-generational stewardship. And just as my players are given proper instruction and good protective equipment to minimize the chance that falls lead to broken bones, next generation family members need support and mentoring but ultimately need the opportunity to stumble and fall, and occasionally, fail altogether.

Enterprising Families: Seek out opportunities to allow the next generation to take real, calculated risks that allow for failure and learning. Be sure to assess the worst case outcome and make sure that it is manageable but also that success is possible.

Advisors to Enterprising Families: You are trusted and in a highly valued role with your family clients. When you see the senior generation holding on (too) tightly, remind them that if their goal is to pass on the family enterprise, they must let the younger generation get its bumps and bruises. Facilitating discussions between both generations about ways to allow risk-taking in the next generation will help your current clients and gives you the chance to prove yourself to the sons and daughters of your clients – an important consideration since they are the ones who will decide which advisors to make their own.