Pruning the Family Tree: Taking the Wheel of Your Journey

Pruning a tree involves selectively removing branches or parts of the tree for various purposes, such as improving the tree's health. Sometimes, we need to prune our family tree for the same reason. No, I am not saying you need to cut off a family branch because of interpersonal conflicts that may arise. That is a topic for another time. It might be time to prune even if your tree has flourished for multiple generations. The question to ask yourself is, are you only a passenger on the family’s journey or the driver? Are you letting the rising generation take their wheel?

Growing up in a small town outside of Chicago, we had a close family, all within walking distance of our home. Sundays were spent with cousins, aunts, uncles and grandparents. Every holiday, such as Easter, Thanksgiving, and Christmas, was a huge event. However, with a family business, we also spent our days working together. The next generation was fulfilling the vision of our great-grandparents.

But I had a different vision for my life outside of this family business and our small town. Fortunately, my parents encouraged me to fulfill my own passions and interests. They would proclaim, “The World is Yours.” At seventeen, I embarked on this journey when I went away for college, something my parents insisted we all do. Although I wasn’t even close to figuring my life out at that young age, my parents let me forge into the world, trusting that if I failed, I would also learn.

How we raise our children has changed with the rise of overprotective parenting, also known as helicopter parenting. These parents have an excessive desire to shield their children from any perceived harm or discomfort, often at the expense of allowing them to explore and learn independently. They may closely monitor their child's every move, from planning their activities to constantly hovering over them. While their intentions may come from a place of love and concern, this hyper-vigilance can hinder a child's development and ability to navigate the world independently. Striking a balance between ensuring safety and fostering independence is crucial for nurturing a child's growth and self-reliance in today's complex world.

If this is the case for you, consider pruning the tree to strengthen the family. Failure early in life can help develop perseverance. When I struggled with Electrical Engineering back in college, my parents' support was invaluable. They didn’t “save” me but let me figure out the direction I was to pivot next. So, when our son had the same issue at college, I let him decide whether to continue with engineering or not. Unlike me, he chose to stay the course, but it was his steering wheel.

So often, well-intentioned parents and grandparents try to make life easier. This is especially true for those with wealth. Family offices may manage a youngster's finances by monitoring their checking to ensure nothing bounces and even paying their regular bills so they don’t have the burden of “adulting.” Instead of helping, they are hurting their children by not having enough confidence in them to manage their money. Self-esteem gets eaten away.

I think of my friend, an artist struggling to make ends meet, who had her entire exhibit purchased by an unknown buyer. She later found out that her grandparents had bought her artwork. They intended to give her some early success so she would no longer have to struggle. Unfortunately, when she found out that it was her family who bought the artwork, her ego was deflated, and she became depressed. It made her feel like her family didn't have enough confidence in her to make it on her own.

Another challenge that arises for young people is the issue of family vacations. Often, these trips are fully funded by parents or grandparents, which can be tempting for the younger generation. However, such vacations can detract from the momentum they may have gained in their work or studies. Additionally, family obligations can be overwhelming, and they may not be satisfied with planning their trip.

To illustrate this point, consider our son's situation. He had always wanted to travel, but due to his friends' schedules, he never had anyone to go with. Eventually, he traveled to Australia, Africa, and South America. Although it required budgeting, planning, and saving, the sense of accomplishment was much more significant than if we had planned a big family trip where he would have to show up.

This is not to say that we should stop taking family trips altogether. However, it's essential to consider the consequences and message we send to the younger generation. What are they giving up in exchange for these trips? Work? Time with their in-laws? The opportunity to create their memories separate from the family? Perhaps the younger generation can plan the trip with a budget in mind. Or maybe they can opt out of the trip instead of feeling obligated to attend.

Our son had more fun on his solo trip to Africa than he would have had on a trip we financed and planned for him. Therefore, it's worth considering whether family trips are always the best option for the younger generation.

There is a common practice of treating adults as if they were children. I am aware of a grandmother who made all the decisions for her entire family until she passed away. However, instead of keeping the family together, her actions caused the family to fall apart. As a result, the family members in their 40s lacked direction and purpose. Is that the legacy you want to leave?

Trim the tree in such a way that the Next Generation isn't stifled. Instead, let them grow and flourish by recognizing them as the 'Rising Generation.' Use the cuttings from the tree to plant new ones, allowing the younger members to establish their own legacy. Encourage them to pursue their unique goals and ambitions without being confined by the family's vision. This will strengthen the family tree, making it more resilient for future generations. When every family member is independent yet supported by the family's profound history and legacy, the family tree will thrive for years to come.

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