Winter is approaching and snow will soon be upon us. Last winter my 15-year-old son Jeremy was feeling industrious and decided to make some money shoveling in the neighborhood.  We have him pay for his iPhone and the monthly data charges so cash is essential – a great way to combat entitlement and help him understand the value of a buck.

I watched out the window as he and his slight and not-so-athletic buddy headed out in over a foot of snow and knocked on the door of a corner house (read as: huge sidewalk wrapping around the corner, and the sidewalk must be clear of snow according to  local ordinance). Fifteen minutes in, his buddy vomited and went home. I kept checking out the window as Jeremy plugged away in the wet and heavy snow, alone, never giving up.

Many times I was tempted to throw on some boots and grab a shovel to help him out. I love him so much and it is a pleasure to be with him and work on a project together.

I did not give in to temptation.

Each time I felt the impulse to go out and help I kept reminding myself that he is old enough to struggle and live through it – and that it is very important for him to struggle and sometimes succeed and other times fail. This is where character and self-esteem come from. It can be tough as a parent to watch as a child teeters on the brink of failure and struggles to overcome it.

Ultimately, the owner felt so bad for him that he let Jeremy try to start his old snow blower to no avail. It took several hours but Jeremy ultimately accomplished the job with his shovel and I managed to remain in the house believing I had done the right thing despite my strong desire to help.

What is the Lesson?

Enterprising Families: In the age of helicopter parents, famously hovering over their Millennial kids, do your best to remember the importance of letting kids struggle and sometimes fail. If they fail too often they will give up. If they succeed without struggle (particularly with too much parental involvement) they can become spoiled, arrogant and lacking in perseverance. In developing the next generation, look for ways to challenge kids and young adults that balance gratification and frustration: this is the key to growth.

Advisors to Enterprising Families: Once again I will point out the tremendous opportunity for trusted advisors to go beyond the technical, beyond the business/financial to help their family clients succeed.  For example, develop programs to educate family clients about raising kids in the context of a family business or significant wealth. There is a trend occurring: these families are asking their advisors for direction on raising kids, communicating about wealth and other issues related to combining family and economic life. If they are not asking you, they are asking someone else and that is a lost opportunity for you. If you are unsure about how to provide this, reach out to me and I’ll be happy to provide direction.