People Reveal When They Realized They Were Rich, Stories Are Internet Gold

What's it like to realize you're rich?

As OutKick readers know, I'm a regular blue-collar working class man from rural Wisconsin. I might be rich in friendship, spirit and love, but that's about where the gravy train ends for me and my kind.

We grew up having to fight for everything we had, and I wouldn't have it any other way. That's how you develop grit and put hair on your chest.

Reddit users reveal when they realized they were rich.

While the good people of rural Wisconsin might have come from humble beginnings, this is America and there are plenty of rich people.

That leads me to the following Reddit thread I discovered while sipping on my black coffee:

"People who grew up with wealth, what was your 'I'm privileged' wake up call?"

I couldn't click fast enough. My curiosity got the better of me, and it didn't disappoint. The answers were really fascinating.

Take a look at some below, and make sure to hit me with your thoughts at David.Hookstead@outkick.com:

• Realizing how having my college tuition covered by parents put me so much farther ahead than everyone else in the long term
• When i was a kid my best friend came to our house for the first time he kept saying "wow". He was really impressed that we had 2 TV's, it embarrassed me enough that I didn't tell him we had 4.
• I took my friend to my parent’s cabin and he said "wow this is nicer than my house"
• My parents are wealthy, but I grew up in a place where many of my peers parents were super duper crazy wealthy, so I had a really skewed understanding of wealth. It was really eye opening for me when I went to college. I didn’t have to take out student loans, my parents were able to just pay for it, but I had friends who even with financial aid had to work their butts off year round to cover the cost of school. I realized pretty quickly just how privileged I was and that I did in fact grow up with wealth.
• When I was confused about people on Maury complaining their spouse was at "the club," and I couldn't figure out what type of country club would let people like that through the front security gate.
• Every summer, I went to 8 weeks of overnight camp, or some other cool summer program (30 day bus tour across western U.S., 3 weeks in Australia). I had no idea what those cost at the time!
• At this point I already knew I was very well-off, but after I had gotten laid off for the first time a few years ago I took a break for about a month before diving into a job search. I was at the self-checkout at the grocery store next to a woman paying with food stamps. I had recently gotten $100,000 from my grandmother's inheritance and it hit me "I'm unemployed, not even trying to find a job, and I just got a boatload of money because somebody else died. And she's the one people think is the freeloader".
• I don’t really come from wealth, just solidly upper middle class, but as part of my job I do home visits, and have many clients who are poor. When I first started my career in my 20s, I was shocked to discover there were people in the US who lived in homes with no indoor plumbing or electricity, with dirt floors, or had outdoor kitchens (not like a BBQ setup, like there was no kitchen inside where they lived, so they had to cook on an oil drum outside). I had no idea.
• My parents loved to travel. By the time I was 16 I had been to every continent aside from Antarctica. I didn’t realize that this was privileged behavior until I went to uni and most of the guys I met had never left the country. In fact, I grew up thinking I was less privileged because everyone at my school was just obscenely rich. Like all their stuff was high end designer stuff while I was in converse.
• In 9th grade I (unhappily) attended a fancy private school. When we'd go on a field trip through the most expensive old money neighborhood in town, everyone on the fancy school branded busses would point out at every 3rd house - "Oh there's my house, and there's yours, that one's John's" etc. At the time, I lived in another plenty nice--if less expensive & exclusive--neighborhood and found the whole thing eyeroll worthy. In 10th grade my parents let me transfer to a local public arts school where overall I was much happier. One day we were riding a rusty yellow city school bus on a field trip through that very same fancy old money neighborhood and 90% of the kids on that bus rushed to the windows, gasping and pointing at the houses - "OH MY GOD guys look at that house! And that one! Whoa these are HOUSES?!" etc. The difference 6 months and a new school make. It was wild. Really stuck with me/in my brain.
• We wanted to try the new rail transit system. Our friend’s driver dropped us off at one station, so we could get tickets and ride the train. When we got to the next station, we got off and proceeded to find our friend’s driver, who was waiting there to pick us up and take us home.
• When I went to my husband’s parents’ house for the first time, after dinner the mom wheeled in a dishwasher and hooked it up to the kitchen faucet. I’d never seen nor heard of this type of dishwasher.
• Dad was an engineer, so professional wealth, but not like dgaf wealth. Probably hearing about a kid whose family had to give his dog away due to the cost in elementary school. Giving away our dog wasn't on the radar or even on the table. But it was only out of the question because my parents had the money for it to be out of the question.
• When I learned that not everyone has a summer cottage or trust fund, and not all grandparents have weekend and summer homes.
• Blows my mind that people can ever be so disconnected from reality that they actually think everyone has those things
• When I realized that some of my friends only had part-time maids not full-time live-in maids
• Probably told this story here before: Grew up in the San Francisco Bay Area. During summer break when I was maybe 10-11? I was watching Fresh Prince of Bel Air. Episode finished and I ran downstairs to my dad, who was on his knees pulling weeds out of the garden and said "Dad, you should become a millionaire so we can have a butler like in Fresh Prince!" He just looked at me and said "Goosfrabbah, I AM a millionaire…" and went back to weeding…
• Realizing how lucky I was for my parents to pay for my car to get me a good reliable car that I will have for years to come and taking care of the maintenance for it
• My oldest brother was raised by grandparents in another country. I remember when he moved to the states after turning 18, he was in awe of seeing a garage door automatically open. That’s when I realized we grew up way different than him. Sad really. But man he sure did rise and become the most successful of all us siblings.
• We did a exchange program to Berlin, I had to share my room with 2 of my classmates, it was totally normal to them. That really Opened my eyes that even if you’re not America type of rich your still rich on a global level
• In college, I went on a road trip with friends and one asked how much money he should put in the gas tank. I told him to fill it up…he kept asking "ok but how much should I pay?" And I kept saying "fill it up!" Turns out he had only ever put $10-15 at a time and it had never occurred to me that some people never filled their gas tanks to the top.
• A friend in college told me they had never flown on an airplane before, I straight up did not believe her. Another person had to break it to me.
• My father cut me off his AMEX and I honestly never knew only filling up my car on a monthly base is already cutting a big share out of my net income, you only realize what you have when you lose it.
• I went to Africa to do volunteer work for a summer long and seeing how kids lived there made me realize where you get born makes a huge difference and all Americans already are wealthy at that point
• Living as an American kid in Kyrgyzstan, my family wouldn't have been wealthy to any other American, but I grew up feeling very, very rich. At recess my school had a soccer ball to play with. Through the chicken-wire fence, I could see all the other kids kicking a clump of leaves tied with string.
• I was in 8th grade and my mom flew on a PJ to get a purse for a wedding accessory.

Lots of wild and interesting stories in there. It certainly makes you feel grateful for what you do have. The only story I'll tell on this topic (I could go on for days, but that's not what we're about here) is the time I was forced to fly Frontier.

My fiancée booked tickets to a wedding, and I didn't do any due diligence on the airline selection. I will never make that mistake again.

I can't believe people fly that way. It's like being herded in a cattle car. My hand was bigger than the entire food tray.

I'm not kidding at all. Look at the tweet below from 2022 where I can legit grip the entire food tray, and it's like I'm a 6'8" NBA player.

I'll spend a fortune before I ever fly like that again. Spending time in GITMO would have been more humanizing and enjoyable. I might not have much in life, but at least I'll always have enough to never step foot on that airline ever again. Do you have a fun story about money? Let me know at David.Hookstead@outkick.com.