I was meeting with someone recently who told me of their adult child who was making the latest of a long list of bad decisions. The child had had numerous relationships, one of which bore a child of their own.

Meanwhile, the parent was funding their own child’s spendthrift ways; they paid every bill and had never given their child an annual stipend. As a result, their child has no idea of the value of money. They’d blow through the money and keep asking for more, with no realisation of their annual spend.

The parent was at their wit’s end.

I suggested that the parent make a gift to their child, call it a lump-sum stipend, with the warning that there would be nothing more for the next three years. What if they spent it early? “Let’s call it a lesson in budgeting.”

Parents want to protect their kids, often no matter how little they work to protect themselves. The hard call is to let self-destructive kids fail. No parent wants to see harm come to their children, especially when the parent can prevent it.

But at what point does not imparting tough love become even more harmful? When does mollycoddling – doting too much attention or kindness to the point of spoiling or overindulging the child – do more harm than good?

Countless parents have been there. Faced with a child seemingly spiralling out of control, they’re hard-pressed to impart those hard lessons.

The hard questions really fall to the parents. If tough lessons must be taught, will the kids learn them on their own?

Maybe not. In cases with those suffering personal issues, such as addiction to drugs, alcohol or wanton spending, or harmful habits, they must hit rock bottom before they have any chance of recovery. If the habits are recurring, in life, in business, even in school – it might be best to let them fail.

Admittedly, the real fear often is damaged self-esteem, not of the wayward child, but that of the parent. We often see our own success reflected in that of our kids. As we’ve written before, my son once was challenged in school. It wasn’t until we visited a shanty town in South Africa, where he met children trapped in a life of abject poverty, that his eyes were opened and his commitment to his own education changed.

We’ve read much about entitlement, kids getting bailed out – figuratively and literally – by their parents. They’re given third, fourth, fifth chances, to turn themselves around – to no avail. To be clear, we’re not talking about criminal actions, but habits and behaviour that could become lessons learned, if only the parents took the chance to teach them.

Life is full of “participation trophies.” It’s society’s way of teaching kids coming in second, third, or fourth, has merit. It’s time to pull the trophies and tell kids it’s OK to fail. Mollycoddling doesn’t thicken skin or build character. It softens the soul and leaves our kids ill-prepared for the realities of life down the road.

Everyone has instances of failure in their lives. Learning to deal with them and move forward is a critical part of life.

Any successful executive will tell you their most lasting lessons were more often from failure. One client failed in business numerous times before making his millions in business. Bernie Marcus was unsuccessful in business before co-founding The Home Depot in his 50s.

Somewhere along life’s journey of successful people, someone said no. Whether it was about school, a business idea, or largesse in their personal life, somewhere a parent was at wit’s end. And they said no more.

If you are having trouble with your minor or adult child and don’t know how to address their behaviour or reel in their wanton ways, let’s talk. Sometimes, a sounding board is all you may need to find the right approach to correct their self-destructive ways.