The dilemma My ex-husband and I have always encouraged our children to pursue their talents and dreams. We supported their learning throughout school and university; we have never pressured them towards any particular career and have always encouraged extracurricular activities.

Following in their father’s footsteps, they have now acquired two buy-to-let properties. The rental yield has been disappointing, with most of the money consumed by upkeep on the property, or petrol money back and forth to the Midlands, where their investments are located. They speak about building multi-million pound property portfolios and devote time to social enterprises in Cambodia and the developing world. Any scepticism on my part is inevitably met with anger and accusations that I am jeopardising the venture by affecting their “mindset”.

It is now over two years since either of my children undertook salaried work. Neither keeps a regular schedule, and I worry they are losing the skills to market themselves. I need a way to broach the subject, which won’t drive a wedge between us or cause my lovely children to lose heart.

Mariella replies I’m flummoxed! Your letter made me chuckle, and for that I apologise. Although you’re not in Harry Enfield’s catchment of the west London elite, there are definitely similarities to his skewering sketches on the trials and tribulations of over-privileged teenagers.

“Seriously, Tris, Mum said if I don’t start tidying my room, she won’t pay for my Glastonbury tickets this year!” I love the marriage of your kids’ real estate ambitions with long distance, hands-off social projects in the developing world, while, I presume, living off the fruits of their parents’ hard labour. It reminds me of the tussles I witnessed in my early youth when angry, pimply teenagers would justify living off the ideologically unsound salaries of their capitalist pig parents, and bang on about equality, while battling for the Communist revolution to spread across the globe before their mums rustled up tea.

Back then, in the dark days before your parents let you drink their Chablis and smoke their grass, there was every reason to get the hell out as soon as possible. The soft cushioning of a comfy home was no competition for the hedonistic adventures on offer once you’d found a squat or bedsit to call your own.

Abandoning the roof over your head is always an option in efforts to remove lingering offspring

Your children certainly sound like a product of their times – sitting back and chilling while the troubadour of their generation, Ed Sheeran, examines his navel in pop pastiches. As the Bible said: “There is nothing new under the sun,” and predictably that seems to be increasingly the case. They seem perfectly unremarkable, and that’s the problem. They’re doing their bit by lending their skills to the less fortunate, but only so long as it causes no discomfort to their material needs and avoids any real risk for them.

What they would describe as a career plan the more experienced might dismiss as a wish list. As long as they are living under your roof and you are paying their bills, there is little or no impetus for them to change. I’ve no doubt that being a divorcee makes it harder to create a united parenting front, which is exactly what’s called for here.

Abandoning the roof over your head is always an option in efforts to remove lingering offspring, but will they simply slump on to your ex’s sofa instead? I used to covet the luxury of making my children’s road through life smoother than my own, but looking around I wonder if a safety net is actually a hurdle to success, and even the enemy of ambition. Why don’t kids move away any more?

Developing better relationships with our offspring was a noble post-Freudian pastime, but surely not to the extent that they never feel compelled to make their own lives. I laughed initially, but there’s nothing funny about your dilemma. The widening chasm between kids of different social strata is becoming an unbridgeable divide.

Instead of budging up ever closer to each other until we achieve the halcyon dream of a classless society, we seem to be shifting further apart. The gap between schooling and diet and health gets ever wider as those on the breadline struggle, and those above it Instagram beautifully crafted portraits of their indolence, and campaign for causes in 140-character opinions.

I’m painting it black because it really feels like we need a revolution; where’s the music of protest, the art of dissent, the new religion? The real world, with all its injustice, inequality and absence of opportunity, is still flourishing, but just out of range of our smartphones. Questioning your children’s lifestyle choices and disrupting their “mindsets” would seem to be doing them a favour. If you can get your ex on board, that’s definitely the boat I’d float.

If you have a dilemma, send a brief email to mariella.frostrup@observer.co.uk. Follow her on Twitter @mariellaf1