My sister’s friend comes from a very different family than ours. We had a fun, easy childhood where we could enjoy the innocence and freedom of being children. Sure, we had chores around the house, such as, taking out the garbage, helping sweep up all the leaves, or walking the dog, which we were always happy to do because we then got an allowance. It wasn’t even enough to get a Starbucks.

The friend, on the other hand, had to start paying rent in her home at the age of 12, which meant she had to find a real paying job when she was in seventh grade. Her parents were less than warm and fuzzy, often forgot to make her a lunch for school, and rarely remembered to pick her up after school.

There would be days on end when she would sleep over and her parents never reached out to thank my parents or wonder where she was. I always felt so sad for her, but she was a happy person, and we all loved having her around. She was like another big sister for me.

She’s now decided what type of career she wants to go for and is heading back to school. Again, no one is helping her with tuition, rent, food, etc. She’ll have to work during these years which will set her back.

Our family wants to help but she’s too proud to simply accept a cheque. How can we help?

Financing

One thing I would NOT do is pay for anything behind her back. She is not going to appreciate anything that resembles charity or a handout. As you mentioned she is too proud and has managed to take care of herself for a dozen years.

But she never minded eating dinner at your house, or having your mom pack her a lunch for school on the days she slept over. So, here are some ideas that may be acceptable to her: when you bake, double up, freeze it and send it over; order a week’s worth of meals from a meal delivery service; shop at Costco and buy bulk that you can share (“I bought a whole salmon but I can’t eat it all”); when appropriate give her gift cards for “luxuries,” such as a mani/pedi or a haircut, places to grab a quick bite, such as Subway, or Amazon where you can get almost anything you need and/or want.

But, of course, inviting her over for the strength of family will replenish her and give her the energy to carry on.

My son has started a new school for the two years of middle school. He went knowing a handful of other kids, but the school is quite large, considering it’s only two years of grades. This is the first year that he has to move from class to class. Last year, he was still in a small school where the teachers moved around.

He came home from school every day last week completely mentally exhausted and overwhelmed. He doesn’t have a single class with any of the friends he switched with and doesn’t know more than one or two in each class.

How can I help him navigate this huge change?

Stressed student

This is completely normal – at any age – when a child switches schools. There’s a learning curve of how the school runs, where classes are located, meeting new teachers, etc. He’s lucky to be going through this now because it will make his transition to high school that much easier.

Support him emotionally, let him talk it out, offer helpful suggestions, be there for him how and when he needs you, catch him when he falls…. But let him fall.

FEEDBACK Regarding the woman ready to retire (July 31):

Reader - “Love your column but your suggestion that a 75-year-old woman continue to work to appease her boss is off the mark. Her boss is being incredibly selfish, and she owes him nothing. She could easily train someone in three months.

“She should sell her house with a caveat that the tenant stays until they find a new place to live - with a two-year limit, unless both the tenant and new owner agree otherwise. If her kids support her decision to move, then she already has all the approval she needs. They’ll be there for her and the so-called friends will do what suits them.

“A pre-existing tenant is a great mortgage helper and attractive to many potential buyers, while making the home more affordable to purchase. Life is short and every day is a gift. She deserves to enjoy the time she has left.”