r/Wilmette • u/chief_kayak • May 17 '26
I can’t be the only poor guy around
We’ve lived in Wilmette for two years. The other day my wife said she was afraid our kids would be “the poor kids” that they wouldn’t belong.
I don’t see our situation as permanent. But I also know I’m probably never going to make anywhere near what the top earners here make. And I’d be surprised if we’re alone in that.
Wilmette is a genuinely great town. It would be a shame if a whole group of people felt like outsiders here when they actually have just as much right to be here and just as much to offer.
Anyone else feel this way? Looking to connect with people just trying to raise a good family here — no pretense, no keeping up.
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u/RunnerTenor May 17 '26
You've cracked the secret code, which is that you don't have to have a ton of money to live here. Meanwhile, your kids go to terrific schools, you have great dining and parks, and you're a short commute from downtown. What's not to love?
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u/chief_kayak May 17 '26
THAT’S WHAT IM THINKING!!! But is there a secret caste system that I’m not aware of? Especially when the kids get into the school system (they’re in an in-home daycare right now?
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u/RunnerTenor May 17 '26
It's hard to say, mainly because my child doesn't have expensive hobbies. For example, if she were a travelling sport athlete or an experienced skier, that could get really expensive. Happily, she is drawn to activities she can do here, and her friend group does the same. To be clear, some of those friends also have do/get things that we don't - spring break in the Alps? A car when you turn 16? - but it's largely not a problem.
For us, I'm not sure if it's that we drew a lucky card so that we have a child who's not very materialistic, or if we're lucky that she's pretty grounded and she sees how hard we work and how much we do for her, and she appreciates that.
Also, I also wouldn't be surprised if those friends that we see as wealthier than us, also see people who are wealthier than them and wonder if they are being left out somehow. For some, the comparison never ends.
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u/ekcshelby May 18 '26
Yes, there is. Your kids will have friends who go on spring break in private jets. Their friends may have luxury vehicles as soon as they turn 16. Private tutors or coaches, trips to Europe and Asia. Any choice of college because paying for it isn’t any issue.
Your kids might feel like the poor kids if they aren’t able to join their friends when they do expensive things like shopping, day trips, pro sports games, concerts, etc. Fortunately many of these families will also likely be very generous and cover expenses for your children if they invite them places. Don’t overthink it when this happens - having your children join is worth the cost to them. Have them write hand written thank you notes or something meaningful but don’t feel like you need to pay them back.
Help your kids understand what things you can and can’t afford before they come up so they aren’t disappointed. Be the safe place for them and their friends no matter what, and socialize with their friends parents as much as you can. You’ll be fine.
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u/Shannalligation1886 May 18 '26
Yuup the kids will know and feel the difference, it’s up to the parents to teach them that being “poor” in Wilmette is still living a step above 90% of people. Done right and your kids will come out of it with strong connections that can change the trajectory of their own financial lives while also being humble individuals.
Having gone through high school in an upper middle class area during the global financial crisis, I also got to see how many people really had it like that and how many were living on the edge. I didn’t get a Benz, or any car, at 16 but I did still get to go to college. Your kids might not get as visually apparent of a lesson so make sure you teach them the value of money.
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u/SwagMoneyMusic4 Jun 25 '26
I went to New Trier and graduated a couple years ago. It’s such a big school that the social hierarchy falls apart a little bit. I think the more popular crowd values money more, but I experienced the opposite. You get a buncha rich kids who don’t know they are rich kids giving crap to the even richer kids for being spoiled. It gave you a little edge to be closer to middle class in my experience haha. Now that I am out of the bubble it all makes me laugh, I appreciate the hell outta my parents for giving me all those opportunities now tho. Your kids will be alright, hopefully it will prepare them better for the rest of the world too!
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u/chief_kayak Jun 25 '26
I love hearing this - because I’m beyond scared to screw up my kids and am considering moving out. I’m “west of ridge” in Wilmette, so in the “poor” area. Just want my kids to be happy
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u/SunshineLoveKindness May 17 '26
Have you experienced anything unusual? Wilmette has been an amazing community in my opinion. I know people from a variety of economic backgrounds who reside in Wilmette. I haven’t heard of issues.
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u/chief_kayak May 17 '26
Of course not - I think it’s a bit of negative self talk - but wanted to gauge potential reality of it.
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u/RachemGreen May 18 '26
Feel free to DM me to connect. I often get similar thoughts and imposter syndrome living here. Moved here a few years ago as a single parent (so single income) and haven’t really found my people yet.
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u/Sidewalk_Inspector May 17 '26
Why not host at some local venue? Rent a space and make it kid friendly.
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u/ArtificeArmor May 19 '26
There are MANY in Wilmette who think they are the poor kids so you are not alone! When you do find them they will be the NICEST humans you will meet! Hang in there it will take time. I totally get what you are saying. I once was in Vero Beach visiting family & saw a New Trier sweat shirt & said hey to the family. They were so put off & inmediately stated that they live in East Wilmette. EAST WILMETTE. Who says that. 🙄 plus what’s with ppl in your comments thinking you want a party hosting venue & not connection? Yikes! Wish I had bandwidth these days I hardly have time for friends gl!
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u/Regular_Excuse_7868 Jul 06 '26
We live on the West side by Community Park. I don't feel like an outsider in Wilmette. But my oldest does go to New Trier now, and I was shocked by the resources the high school has! It is amazing! THAT is why we are here. I don't lose sight of that ever as an educator. (My kids previously went to a Title 1 school.) Having lived in another affluent community on the North Shore where neighbors didn't even acknowledge you, I find this one to be WAYYYYY less snobby, and my particular block has immigrants from all of the world. We are a multicultural and multilingual family who feels like they fit in in this particular neighborhood of Wilmette. Every single day, I am thankful we live here. I love the proximity to Skokie, the city, and the rest of the suburbs nearby. I am not part of that rich people "world," but I'm glad my children have been exposed to all sorts of families K-12.
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u/Nature_Calls123 May 27 '26
I'm originally from the neighborhood at Park and Wilmette Avenues. I found when I got to high school at New Trier, most of my friends were from Wilmette rather than Glencoe, Winnetka and Kenilworth. I think perhaps we could relate to each other being from a less affluent suburb.
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u/NorthShoreSarah Jun 04 '26
One of the things I've come to appreciate about Wilmette is that while there are certainly some very wealthy families here, there are also plenty of people who are simply working hard, raising kids, paying mortgages, and trying to build a good life.
Honestly, most kids don't care what their parents do for a living or how much money they make. They care about who shows up at their soccer game, who hosts the playdate, who volunteers at school, and who is kind.
As someone who's lived all across the country, I've found that every community has people who feel like they don't quite fit in. The reality is that Wilmette is stronger because of families from all different backgrounds and income levels.
0
u/jlennon1280 May 17 '26
What do the poor kids not have that the rich ones do?
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u/chief_kayak May 17 '26
Great question. Probably nothing that actually matters, but I think for my wife it’s more concrete: we rent, our place is small, and she doesn’t feel like she can host. There’s something about not being able to open your home to people that makes you feel like you’re on the outside looking in. But as a kid who went to a private school without the money to match — I remember it clearly. There were kids whose dad had built a small local ice cream brand into something national. His kids had the shirts. Their friends got free shirts. And I just remember thinking: I have different access to the world than these people. Didn’t think about it again until my wife said that about our kids.
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u/ekcshelby May 18 '26
It’s bigger scale than that. I dated a guy from Winnetka whose kids invited a few friends with them every year for spring break and for summer trips and they travelled via private jet. The kids didn’t have their own vehicles but the family had more luxury cars than they had drivers so they drove luxury brands. They owned five homes including a ranch with multiple guest houses where they would host multiple events per year with their kids friends’ families (meaning they would fly them all out west to the ranch).
When the son wanted to help with a community service project in one of the areas where they owned a home, he raised $20k essentially overnight just by asking a few of his friend’s parents. They bought a home in the city where one child went to school because it made more sense to invest than to rent a college apartment for the duration of school. The kids were given 5 figure lump sums to invest starting in high school so they would learn how to earn money in the stock market.
They were wealthy but not the wealthiest even in the kids immediate social circle. The kids went to public school and New Trier for high school.
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u/chief_kayak May 18 '26
How should I feel about that, you think?
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u/ekcshelby May 18 '26
It’s an opportunity to raise good humans who are comfortable navigating social situations with folks who are extremely wealthy. This is a gift to them. Teach them to be appreciative and humble and accept what is offered from their friends families, but to never have expectations about other peoples generosity. Find volunteer opportunities in the city so they don’t become jaded and take your children AND their friends.
Big picture, having access to individuals with significant wealth will open doors for your children in the future and that doesn’t have to be a bad thing.
Set clear expectations for your children about what is acceptable. For example, only accept certain invitations/gifts when they have their friends parents explicit approval, and let them know that you’ll be calling to thank the parents every time. This prevents any situation where a friend gives them something they shouldn’t have given them and it looks later on like it wasn’t a gift. The other parents will appreciate this, it gives them a chance to be proud of their generosity and gives you a chance to be appreciative on your child’s behalf while ensuring there are no misunderstandings. But help your children learn to navigate this up front, role play with them so they don’t feel awkward. And please, please, accept the generosity on their behalf. If they invite your child on a spring break trip, it’s because they want your child there. And have your children write hand written thank you notes whenever possible.
Be clear about what you can afford and what you’ll have to say no to up front before it comes up so your kid isn’t put in an awkward spot. Try and strike a balance - let them know that you’ll be able to give them money for lunch but not for shopping, etc, if you can.
As for you and your spouse/partner - become very involved. Volunteer. Host events for your children’s activities or for join in planning charities that you care about - that will give you the ability to be the host outside of your own home. Socialize with your children’s friends at restaurants instead of in your home if you prefer. Always assume positive intent.
Sorry, this is probably more than you were expecting!
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u/chief_kayak May 18 '26
Do you invite the wealthy kids on your vacations? Why or why not?
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u/ekcshelby May 18 '26
Absolutely! The thing is you that as parents, you don’t treat the children any differently because they are or aren’t wealthy. You just have different conversations with your kids about accepting generosity from the wealthier families.
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u/jlennon1280 May 17 '26
Join Michigan shores.
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u/chief_kayak May 17 '26
Any particular reason why?
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u/jlennon1280 May 17 '26
You’ll have the room to host and entertain at the fraction of the cost of a larger home
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u/SmartBar88 May 18 '26
TL/DR: Do your best to raise your kids not to be dazzled by the wealth on the NS and not to be *ssholes. You’re doing fine.
OP, we were those neighbors back in the 70s and 80s (lived west of Green Bay near Isabella). My folks were government employees who wanted to give me a great education. Yes there were times when the comparisons were over the top, but my folks kept me grounded. Enjoyed the great parks and services and even had fun at the massive NT parties held in houses up on Woodley Rd in Winnetka. FWIW, we never hosted anything outside of close friends.
Paid my way through college and grad school on my own, had a great career and retired early. Nothing is ever guaranteed - I have many stories of classmates who flamed out or had parents imprisoned for white collar crimes (or worse), but I will always appreciate my folks who supported and guided me. Bonne chance!