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Harriette Cole: I can no longer pretend my son’s path doesn’t worry me

August 27, 2025
Harriette Cole: I can no longer pretend my son’s path doesn’t worry me

DEAR HARRIETTE: I need help encouraging my son to pursue his education.

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He has started a bachelor’s program at least twice now and has taken a variety of classes, but he has never completed a program.

For some time, I let go of my own desires for him and tried to make peace with the idea that maybe school just isn’t for him, but the way the job market is looking these days, it’s less about my personal wishes and feels a lot more like a necessity.

He feels stuck in his career. He’s worked at a few different places but always seems to be in entry- or junior-level positions despite his growing experience.

Many companies list a bachelor’s degree as part of their requirements or preferences. I try to explain this to my son, but he’s still reluctant.

Is there something more I can do to help him if he does decide to try school again?

— Higher Education

DEAR HIGHER EDUCATION: Your son has to live his life. You cannot do it for him, no matter how difficult it may be to cheer from the sidelines.

Yes, for many types of employment, a bachelor’s degree is a bottom-line requirement, but there are plenty of jobs that do not have that rule.

What you can talk to your son about is what he wants for his life. Suggest that he assess how much it will cost to enjoy what he wants. Help him do the math so he can see how much money he should try to make in order to be in a position to support his desired lifestyle. That may motivate him to strive harder.

DEAR HARRIETTE: I grew up in New York and have been here my entire life. I decided about a year ago that I wanted to move to a new city.

I only flirted with the idea at first, but recently, my boss told me that if I’m serious, they could transfer me to the Chicago office. I’ve taken them up on their offer and will be moving within a few months.

I’m currently searching for the perfect place to stay, but I’ve never lived on my own, so this is all new to me.

Where I find a perfect balance of reasonable commute, safe neighborhood and proximity to necessities, I also find really high rental prices. I have seen some condos for sale, which would actually have more ideal monthly rates, but purchasing can be a big commitment.

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I have people around me advocating for both options, and I still feel torn between renting and owning. What do you think?

— New City

DEAR NEW CITY: Often when people move to new cities, they start by renting in order to check out the neighborhood to make sure it is a good fit. Once they get to know the city, they have better awareness of where they would want to live.

That said, buying property is often a good investment. Do your due diligence to see how the neighborhood is growing or changing, if property values have increased over time and what prices are like in the surrounding community. This will give you a sense of the potential resale value if you decide not to stay in Chicago.

Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to [email protected] or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.

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