I'm almost 30, but I was doing better financially at age 21. I made the best career move for my health, and I'm not ashamed.

• I'm 28 and my dad asks me regularly if I'm all right with money.
• He asks because he knows I'm not fine after quitting my job to become a freelancer.

It has become a bleak ritual. I speak, first, to my mother, who tells me about her week and the deteriorating state of our aging relatives. She passes the phone to my father, and we, too, catch up and maybe chat about football. Then, inevitably, comes the lull in the conversation, the dead air on the line, the intake of breath before the question is posed.

"You all right for money?"

The slight awkwardness of his tone — he would prefer not to ask, but he's a loving, supportive father who's worried about his only child. It's an embarrassing subject, but he is duty-bound to ensure that the boy — aged 28, soon to turn 29 — is doing OK.

My reply is the same as always: "Yeah. Doing grand."

He knows I'm lying. Why else would the question arise so persistently, week after week?

I quit my job for my mental health

There was a time, long ago now, when I worked a steady office job with a fixed, albeit modest, salary and even four weeks of paid time off. He didn't ask how I was doing for money back then.

I made my decisions, though. The bank balance was relatively healthy during that period, but the headspace was not. Afflicted by a terrible longing to see the world, not to mention a youthful naivety that blindly presumed things would work out fine, I quit the job and moved away. I was going to make it as a freelance writer.

Viewed financially, this was a terrible mistake. We're six years into this freelancing experiment now, and I'm less financially stable, as 30 creeps into view, than I was as a fresh-faced graduate of 21.

But — and it's a big but — viewed in terms of my mental health, the decision to go it alone was an inspired one. Freed from the confines of a job that made me miserable, I have seen the world and generally managed to scrape by. I'm a happier person for it.

I can't get a mortgage

My dad, though, has done the math. He understands that I can't be earning enough to amass much in the way of savings. He knows I won't ever secure a mortgage. He knows that even a modest rise in living costs affects me greatly and that the future of my industry isn't looking especially rosy.

If he wasn't worrying, I'd question his love for me. But that doesn't mean it's not humiliating. It's demeaning to be infantilized and to depend on your parents at my age.

I don't live at home, and I don't rely on my parents to pay my rent or fund my follies and travels. But I'm on their Spotify plan. Whenever I go home to visit them, my dad allows me to use his car and often fills up the tank before I can. If ever we go for a meal, they won't for a moment entertain the idea that I might pay for it.

My parents are kind people, and I do not take that for granted. But at this stage in my life, it would be nice if I could comfortably pay for their meals or simply maintain my own Spotify account. It would be nice to feel secure.

My parents had a house and a car at my age

A reasonable retort to my whining could be to point out that nobody forced me to quit my old job. Besides my own vague sense that I should be living life as a bohemian, there was no reason to leave. But I did.

A fair point.

Except, it misses the fact that I'm not alone. While my stupidity may largely be to blame for my specific circumstances, it doesn't quite explain why so many of my peers are in a similar position. Despite working "proper" jobs, they don't own homes, can't afford to start families, and hold no hope that things will improve.

As a 20- or 30-something-year-old today, it is painful to take stock of your worth and discover it amounts to nothing. When I compare what my parents had at my age — a decent house, a car, and the most wonderful baby — to my collection of secondhand books and a small wardrobe of shabby clothing, I fear I've probably messed up somewhere along the way.

It's hardly surprising that I'm defensive when my dad asks how I'm doing for money.

But the world has changed. For millennials to compare themselves to preceding generations that generally had things a bit easier is misguided. While acknowledging that fact won't pay the bills, it might help us to feel less ashamed.