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Millennials nearing 40 are sharing their biggest mistakes so everyone can learn from them

Here are 21 of the most powerful responses.

millennials, regrets, millennial life lessons
via Pexels

Millennials are now old enough to seriously reflect on life.

It seems like only yesterday a millennial was a college kid that baby boomers chided for being entitled and Gen Xers thought were way too sincere and needed to learn how to take a joke. Today, the oldest millennials, those born around 1980, have hit their 40s and have lived long enough to have some serious regrets.

They also have enough experience to take some pride in decisions that, in hindsight, were the right moves. The good news is that at 40 there is still plenty of time to learn from our successes and failures to set ourselves up for a great second half of life. These lessons are also valuable to the Gen Zers coming up who can avoid the pitfalls of the older generation.

A Reddit user who has since deleted their profile asked millennials nearing 40 “what were your biggest mistakes at this point in life?” and they received more than 2,200 responses. The biggest regrets these millennials have are being flippant about their health and not saving enough money when they were younger.

They also realized that the carefree days of youth are fleeting and impossible to get back. So they should have spent less time working and more time enjoying themselves. Many also lamented that they should have taken their education more seriously in their 20s so they have more opportunities now.

The responses to this thread are bittersweet. It's tough hearing people come to grips with their regrets but the realizations are also opportunities to grow. Hopefully, some younger people will read this thread and take the advice to heart.

Here are 21 of the most powerful responses to the question: “Millennials of Reddit now nearing your 40s, what were your biggest mistakes at this point in life?”

1.

"Not taking care of my hearing, not even 35 and going deaf." — Kusanagi8811

2.

"Not getting healthy earlier." — zombiearchivist

3.

"Staying too long at a job in my 20s, just because it was safe and easy. When I finally got the motivation to leave, ended up with an almost 50% pay boost." — Hrekires

4. 

"Thinking that I could and should put myself on the back burner for anything and anyone else." — lenalilly227

5.

"Smoking and not dealing with my shit the right way." — Allenrw3

6.

"Pining after the wrong person." — runikepisteme

7.

"I turned 40 this year and just started liking who I am. Why the fuck did it take 40 years for self acceptance?" — guscallee

8.


"Take care of your fucking back. Lift with your knees. Sure it's rad when you grab a fridge by yourself and lift it in the back of a moving truck unaided, but one day that shit is going to have consequences that won't just magically go away by resting and "taking it easy" for a week." — GuyTallman

9.

"I wish I spent more time with my dad while I had the chance." — CharlieChooper

10.

"I'm 37. I absolutely could have taken better care of my body, but I'm in relatively good health. I'm starting to realize how important it is to maintain my health. I do also think I drank far too much in my 20 and early 30's. I'm trying to rectify that now, but it's hard. So that I guess." — dartastic

11.


"I'm not sure if people have experienced the same but when I entered my 30s I became convinced I was rapidly running out of time. Rather than using that as motivation I let it paralyze me with indecision because I "couldn't afford to make the wrong choice." Consequently, I'm now 39 and, though I've had great things happen in my 30s, I regret spending so much time worrying and so little time committing to a course of action." — tomwaste

12.

"Work to live, don’t live to work. You have half your working life after you turn 40 but only 20-25 years to really live it up before the responsibilities become heavy and your joints start to ache. Live life. Really LIVE it. Experience as much you can. Every sensation, sight, sound, touch. Be open. Be brave. Live your first few decades in the fast lane. You have the rest of your life to take it easy, when you have no choice." — MrDundee666

13.

"I should have paid more attention to my parents telling me to save money and less attention when they were teaching me about purity culture." — Arkie_MTB

14.

"If I could tell my 18 year old self one thing, it would be to save 10% of every paycheck I ever got." — PutAForkInHim

15.

"Thinking that I have time to do everything I want only to find myself loosing time, and the endless energy I used to have in order to purse them." — ezZiioFTW

16.

"Not wearing sunscreen." — blueboxreddress

17.

"Not recognizing the importance of work/life balance earlier in life. My late teens, all 20's, and early 30's were spent pulling 60-100+hr weeks because I thought it was what was required to succeed. How wrong I was. Others stabbed me in the back and reaped the reward.

1.) Putting work first for too long. Work is my #1 priority during work hours now. After quitting time, I don't think about it (much) anymore. I don't vent to my wife or friends about it anymore either.

2.) Investing more into fast cars than solid long-term investments. Sure, it was fun, but I could have made bookoos more had I put that towards less-fun investments.

3.) Not using PTO and just waiting for the payout. All those years, missed. I'm in my mid 30's and I didn't actually have a real vacation until 3 years ago.

4.) Not realizing that "the good guy" often loses. Just because you're morally justified doesn't mean you're going to win. Just because there's a number to call doesn't mean anyone will actually help you. Just because "law" exists, doesn't mean people follow it, enforce it, or create justice. The world is dog eat dog and cynicism can be healthy in moderate doses." — [Deleted]

18.

"When you get out of college, keep your friends. No matter how hard it is. Hold on to them." — mpssss22

19.

"I imagine these are kinda universal:

  • Not getting fit and healthy
  • Assuming I'd be offered proper guidance on how to achieve my goals
  • Assuming higher education would help me achieve my goals
  • Spending far too long caring what people think
  • Not taking risks that might better my life when I was younger and had nothing to lose
  • Staying in relationships too long after they were clearly done." — katapultperson

20.

"Always ask for more pay. Starting, yearly, before leaving, whatever. Get that money." — SensibleReply

21.

"Spending too much time in front of a screen and not enough enjoying life." — BellaPadella


This article originally appeared two years ago.

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Parenting

Millennial dad of 3 unloads on boomer parents over their unreasonable holiday plans

"Yeah, not this time," he said. "I think for the holidays I'm just gonna stay in and relax."

via Canva/Photos
A Millennial dad has had it with his boomer dad's expectations.

The holidays are supposed to be a time for enjoying special moments with family, but often they become a source of stress. Traveling, navigating familial relationships and tensions, talking politics at the dinner table, and handling the all-encompassing issue of "presents" can wear down even the most patient and even-keeled person. It can be especially challenging for parents with young kids who are expected to travel long distances in the name of "family togetherness."

A TikTok video posted by @carrerasfam is going viral, with over 300,000 views, because so many millennial parents can relate to the frustration of grandparents having unrealistic expectations related to visiting with the kids.

In the satirical video, a husband stages a conversation with his "practically retired" baby boomer dad, in which he explains politely but firmly that he’s not taking his 3 young kids on a 400-mile drive to their house for the holidays.

Carerras Fam is a popular TikTok page about “all things postpartum and mamahood.” Together, the mom and dad share funny skits and slices of their life with three little ones.

The husband opens the conversation with his dad by explaining all the inconveniences of taking 3 young kids on a long road trip. “I know you want us to drive down for the holidays, but it's kinda ridiculous that you want me to pack my 3 kids with their portable beds with my clothes, their clothes, the formula, everything that goes on with raising 3 kids and having them feel comfortable. Drive down for over four hours just so that we could spend some time in your house?” the husband says while absurdist music plays in the background.


@carrerasfam

Sorry it’s just so much work. But you’re welcome to visit us #millennial #millennials #parents #parenting #parentsontiktok #boomers #millennials

It’s obviously inconvenient for the couple to pack up their kids and drive 4 hours, but it’s also unsafe because the house is not baby-proof. "I'm gonna have to run around, make sure that they don't break any of your stuff, and which you will 'take care of them,'” the husband continues using sarcastic air quotes. Most parents eventually realize that visiting with the kids does not equate to getting help with them — no, it means chasing them around frantically yourself until it's time to leave.

The dad brings up another great point: His parents are in good health, so why don’t they drive to their house? “You could visit. You don't have little kids,” the dad continues. “You don't have anything going on.

"Why is it that every time I have to make the effort for you, yet you can't do the most basic thing for me?”

millennials, baby boomers, parenting, dads, moms, babysitting, grandparents, parenting tips, family, love, kidsAll parents feel like this when it comes to spending time with the grands.Giphy

It’s clear from the phone call the dad understands that traveling with the kids and staying in a house that isn’t correctly set up for young kids will make the holiday a struggle. Instead of making memories, they’ll most likely be running around bent over trying to save their kids from breaking something or hanging out at Target buying electrical socket plugs and a bottle brush because they left theirs at home. What's especially frustrating is the pressure and expectations. Parents are often guilted for not wanting to pack up the the kids and travel, even though it's not hard to see why they hate it so much.

The video struck a chord with many millennial parents. Nearly 500,000 people watched the clip with hundreds and hundreds pouring in to vent their own similar frustrations.


@carrerasfam

Something needs to change #parenting #parents

“First holiday with a kid… parents are confused why I won’t drive 9 hours with a 3mnth old for Christmas,” too_many_catz writes.

“The ‘not baby proofed’ part hit my soullllllll. It’s so stressful having to chase your kids around and ask to close doors, move pictures, block stairs, etc. And nobody takes you seriously!" OhHeyItsIndy added.

It’s also expensive for young families to travel. “Add to it they want us to spend money on gas, airfare, etc. when we live paycheck to paycheck and rent while they own homes and live comfortably off a pension,” another user wrote.

"My mom asked me to drive 13 hours with our 2 month old…she doesn’t work and has flight points," one mom added.

This one hit hard: “They always act like you're asking the world of them, yet they will willingly go on any other vacation that they choose,” Mackenzie Byrne wrote.

"They can never make the trip for us but they can make them trips to Europe and cruises to the Caribbean," another user noted.

TX Travel Chick may have hit the nail on the head with her explanation for why boomer parents expect their children to road trip it to their house for the holidays. “Because we are used to following their orders!!! REVOLT,” she wrote.

millennials, baby boomers, parenting, dads, moms, babysitting, grandparents, parenting tips, family, love, kidsSee ya next year, grandpaGiphy

Ultimately, it would be interesting to learn why boomer parents want to inconvenience their kids when it would be much easier for them to take a trip to see them, especially if they can afford a hotel. One wonders if they are being entitled or if they’ve forgotten how hard it is to travel with young kids. In some cases, it's a little more complicated — many baby boomer grandparents are still working and have less time and resources than previous generations did to help with the kids.

"Yeah, not this time," the dad sums up in the video. "I think for the holidays I'm just gonna stay in and relax."

It's a hilarious and relatable video, but ultimately, it's a skit. The power of boomer-grandparent guilt remains undefeated in many households, so the smart money says the Carreras family sucked it up and traveled for the holidays despite their annoyance. Here's hoping that together, we can eventually break the generational curse when our kids become parents one day.

This article originally appeared last year. It has been updated.

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Democracy

Philosophy expert answers the question: Why does it seem like dumb people are always in power?

"Why can't we get a better class of leaders?"

via Canva/Photos

A candidate running for office.

As the old song by The Who goes, “Meet the new boss, same as the old boss.” It’s a sentiment many of us feel every time a new mayor, governor, or president takes office, and we can’t help but feel that we deserve someone better. In a country with so many brilliant scientists, business people, educators, and public policy experts, why do the least impressive of us seem to rise to power?

Philosophy expert Julian de Medeiros, a popular TikToker and Substack blogger, recently wrestled with this question, and it must have been on a lot of people’s minds because the video received over 4.2 million views. “Why does it seem like so many people in power are so dumb? It's like, why can't we get a better class of leaders?” he asked.

@julianphilosophy

Why do stupid people have so much power? #chomsky #philosophy #psychology #power

Why is it that dumb people are always in power?

Ultimately, de Medeiros believes that power and intellect are often at odds. “I've thought about it a bit more, and I think this is my thesis: that power is inherently anti-intellectual. Because what does intellect do? Intellect questions power. It speaks truth to power. It critiques power. And power doesn't like that,” he says. “And so power has to speak to the lowest common denominator. It dumbs everything down."

"It's an anti-intellectual force. And that's why it seems like those in power are also the dumbest,” he concludes his video. The commenters further expanded on de Medeiros' thesis. “Also, intellectual people question and analyse everything. A leader needs to be invested in their opinion and abide by it,” one wrote. “Because those in power or seek power cares about the power only, so they make the decisions that keep them in power no matter what is the output,” another offered.

politicians, idiots, dumb people, anti-intellectualism, candidate, A candidate who wants your vote.via Canva/Photos

What is anti-intellectualism?

Another reason people who are a few fries short of a Happy Meal are often voted into office is that there is a deep vein of voters who are skeptical of intellectuals. These people tend to be populists who value “common sense” over intellectualism and may see experts or highly educated people as dangerous and out of touch with the common man. So, candidates position themselves against the “intellectuals” by either being their proud, dumb selves or by taking their IQ down a few notches while in public.

Theologian and philosopher Dietrich Bonhoeffer (1906—1945) believed that dumb people often ascend to power because evil people have difficulty getting elected. So, they champion someone who may be more charismatic or connected and ride their coattails into power.

Finally, much like de Medeiros, Bonhoeffer believes there is a big difference between intellectualism and power. Therefore, once one attains power they are highly lifely to look like a buffoon. It’s as if, “Slogans, catchwords and the like… have taken possession of him. He is under a spell, blinded, misused, and abused in his very being,” Bonhoeffer says.

It’s sad to realize that the very nature of power means that those who hold office, whether we voted for them or not, will probably disappoint us at some point. But the good news from this understanding is that we are freeing ourselves from the constant disappointment of having leaders appear rather dumb. Now, whenever we meet the new boss, we can assume he's just like the old boss and be positively delighted if they wind up slightly smarter.

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Pop Culture

The super interesting reason why people in the past looked so much older than people today

It isn't just the hairstyles.

via Nick Denner/Flickr and Canva/Photos

How are these both high schoolers?

Have you ever looked back at your parents’ high school yearbook and thought that all the 11th graders looked like they were in their early 30s? Whether they were in school in the ‘60s and the kids had horn-rimmed glasses or the ‘80s with feathered hair, they looked at least a decade older than today's high school kids. One wonders if in 30 years, kids look at a yearbook from 2025 and see boys with broccoli cuts and girls with nose rings and they think, “What are they, 35?”

The folks at Bright Side did a deep dive into the phenomenon and found a few reasons why people looked so much older in the past than they do now. It’s a mix of how our minds perceive older fashion and why people age more gracefully in modern times.

Why did people look older in the past?

“Specialists have looked into this phenomenon, and it does have some scientific facts to back it up,” the narrator states. “It's not necessarily that our ancestors looked older; it's more that we appear to look younger. And younger as generations go by, that's because over time humans have improved the way they live their lives in the us alone over the last 200 years.”

- YouTubewww.youtube.com

A big reason people looked a lot older when photography became common in the late 1800s is that it happened at a time when we were making tremendous advances in public health. The 1880s to the 1920s were a time of rapid advancement, when we began to understand infectious diseases and how they spread. “We gained access after safer types of foods, and we understand the importance of clean water. Our individual lifestyle choices can impact the way we look,” the video says.

The way we work has also drastically changed how people look. Working in an office for eight hours a day in air conditioning will keep you a lot younger-looking than working all day as a Victorian chimney sweep. Plus, for people who work outside, sunscreen has made it much easier to protect our skin and decrease wrinkles.

Let’s not forget the importance of a straight, white smile. Advances in dental care also help make people look younger.

1970s girls, high school girls, girls in uniforms, old high school photos, nostalgiaA "girl gang" in 1976. via Earthworm/Flickr

Why do people wearing styles from the past appear older?

Finally, there’s the clothes issue, and, yes, this does have a big impact on how we view the age of people from the past. “Our brains are wired to associate old trends with being old,” the video says. “For example, your grandpa might still have the shirt he wore in that 1970s picture, and it's because of that shirt that you retroactively associate that trend with being old, despite the fact that your granddad does look younger in the picture than he looks today. “

girls in school, '60s high school girls, class room, old-school cool,GIrls in class in the 1960s.via Phillips Academy/Flickr

In the end, the fact that people look a lot younger today than they did in the past is a testament to how the quality of life has drastically improved since cameras were first invented. However, that doesn’t mean that fashion has improved at all. You have to admit that your dad with that fly butterfly collar in his 1977 graduation photo looks better than that multi-colored, Machine Gun Kelly-style hoodie you see guys wearing in high schools today.

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Humor

A mom lost her son on a cruise ship. Turns out he was going viral from the karaoke room.

Tyler knew exactly where he was—rounding up aunties with his Keith Sweat performance.

Photo credit: Canva

A mom lost her son on a cruise ship. Turns out he was going viral from the karaoke room.

Cruise ships are often the perfect family vacation. They allow you to go to multiple different locations on a tighter budget while also giving your family a resort experience with all the on ship entertainment and activities. But cruise ships are big. We're talking so large that they make the Titanic look like a tug boat, so, it's fairly easy to get lost on one. This is what one mom, Kim Heyworth, thought happened when her young adult son disappeared from the group for a while.

Thankfully, that wasn't the whole story. In turned out that the missing 20-year-old was going viral while his mom was actively looking for him. According to some comments, the missing kid, named Tyler, was supposed to be going to the pool but wasn't there when his family went looking for him. Instead of taking a dip, Tyler Heyworth went on a bit of a side quest after coming across a room full of people dressed up and singing karaoke.

Tyler on cruise; Tyler singing; kid singing on cruise; Tyler on Carnival; cruise ship; karaokeA large neon karaoke sign on the side of a building. Photo by Nikola Đuza on Unsplash

Clearly, Tyler was no longer interested in the pool. His calling suddenly became the stage, a microphone, and a room full of uncles and aunties waiting to be entertained—and entertain he did. Tyler grabbed the mic as a familiar tune filled the room: "Nobody" by R&B artist Keith Sweat. Was he actually going to sing Keith Sweat? He was. He did. And the 20-year-old knew every single word and tone without having to look at the screen. This kid was born an entertainer, clearly.

As soon as he starts singing the first few words, one of the women in the front of the room gets up and walks away before stopping to fan herself. It's clear that nobody in the room thought that song was going to come out of Tyler's mouth, probably because it's a pretty niche song that didn't seem to have much crossover when it was dominating the R&B airwaves.

@crazy_chickenlady03 full video of Tyler singing Keith Sweat Nobody.#carnival #karaoke #nobody #arethafranklin #carnivalcruise ♬ original sound - Kim Heyworth

Before long, Tyler's older brother comes looking for him, but fails to bring his brother back at all. The brother, Timmy, saw what Tyler was doing and decided to join in on the fun, both apparently forgetting they were supposed to be returning to their mother. Timmy dons a pair of sunglasses while rocking a messy bun and grabs the second mic. In time, the duo are grooving to the 2004 hit, "Let Me Love You" by Mario.

While the crowd was thoroughly entertained, their mother was confusedly still searching—now for both of her sons. In the meantime, Tyler was going viral on social media thanks to small snippets from cruise passengers that were quickly being reshared online. Soon, Carnival had reshared a clip and, serendipitously, John Legend did too. Funnily enough, Tyler didn't have his own TikTok at the time, which was a let down for fans looking to follow him. What fans did have, though was Tyler's first name and the name of his cruise ship.

@crazy_chickenlady03 Brothers Timmy and Tyler singing. #karaoke #carnival Paradise @TimmyHeyworth @tyler ♬ original sound - Kim Heyworth

Eventually, word got to Tyler's mom and she found her boys in the middle of their viral moment. Soon, she uploaded two full videos of the performances: one of Tyler singing alone and the other with his brother.

Carnival later reached out to Tyler, sending him a box full of goodies and inviting him back on one of their cruises with a guest. Tyler is good for business.

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I Googled to see if Maria Von Trapp remarried after Georg died. The result was horrifying.

Having blatantly false information as the top search result is actually a huge problem for us all.

Photo credit: Canva

Google's AI Overview sometimes gets basic facts wrong.

With AI being implemented seemingly everywhere for seemingly everything these days, it wasn't surprising when Google launched its "AI Overview" in the spring of 2024. With messaging like "Generative AI in Search: Let Google do the searching for you" and "Find what you're looking for faster and easier with AI overviews in search results," the expectation is that AI will parse through the search results for you and synopsize the answer.

That sounds great. The problem is, its synopsis is too often entirely wrong. We're not talking just a little misleading or incomplete, but blatantly, factually false. Let me show you an example.

I recently wrote an article about the real-life love story between Maria and Georg Von Trapp, and as part of my research, I found out Georg died 20 years after they married. I hadn't seen anything about Maria remarrying, so I Googled whether she had. Here's what the AI Overview said when I searched last week:

maria von trapp, ai overview results, false information, ai, InternetThis is what Google AI Overview said when I asked how many times Maria Von Trapp had been married. It's wrong.Screenshot via Google

"Maria Von Trapp married twice. First, she married Georg Von Trapp in 1927 and they had 10 children together. After Georg's death, she married Hugh David Campbell in 1954 and had 7 daughters with him. Later, she also married Lynne Peterson in 1969 and had one son and daughter with him."

Something about that didn't add up—and it wasn't just how it said she married twice but then listed three spouses. Maria Von Trapp was born in 1905, so according to the AI Overview, she remarried at 49 years old and had seven more children, and then married again at 64 years old and had another two children. That seems…unlikely.

old woman, elderly, golden girls, women, gifDid Maria Von Trapp have two children in her mid-60s? No. Giphy

So I clicked the link icon on the AI Overview, which took me to the Maria Von Trapp Wikipedia page. On that page, I found a chart where the extra two spouses were listed—but they very clearly weren't hers. Hugh David Campbell was the husband of one of her daughters. Lynn Peterson was the wife of one of her sons.

The fact is that Maria never remarried after Georg died. If I had just run with the AI Overview, I would have gotten it this very basic fact about her life completely wrong. And it's not like it pulled that information from a source that got it wrong. Wikipedia had it right. The AI Overview extrapolated the real information incorrectly.

Ironically, when I Googled "Did Maria Von Trapp remarry after Georg died?" in the middle of writing this article to see if the same result came back, the AI Overview got it right, citing the Upworthy article I wrote. (Yes, I laughed out loud.)

maria von trapp, ai overview results, false information, media, literacyAfter my article was published, the AI Overview cited it while giving the correct answer.Screenshot via Google

This may seem like a lot of fuss over something inconsequential in the big picture, but Maria Von Trapp's marital status is not the only wrong result I've seen in Google's AI Overview. I once searched for the cast of a specific movie and the AI Overview included a famous actor's name that I knew for 100% certain was not in the film. I've asked it for quotes about certain subjects and found quotes that were completely made up.

Are these world-changing questions? No. Does that matter? No.

facts matter, misinformation, disinformation, fact-checking, AIFacts should matter no matter what they are.Giphy GIF by Angie Tribeca

Objective facts are objective facts. If the AI Overview so egregiously messes up the facts about something that's easily verifiable, how can it be relied on for anything else? Since its launch, Google has had to fix major errors, like when it responded to the query "How many Muslim presidents has the U.S. had?" with the very wrong answer that Barack Obama had been our first Muslim president.

Some people have "tricked" Google's AI into giving ridiculous answers by simply asking it ridiculous questions, like "How many rocks should I eat?" but that's a much smaller part of the problem. Most of us have come to rely on basic, normal, run-of-the-mill searches on Google for all kinds of information. Google is, by far, the most used search engine, with 79% of the search engine market share worldwide as of March 2025. The most relied upon search tool should have reliable search results, don't you think?

Even the Google AI Overview itself says it's not reliable:

ai overview results, false information, google reliability, AI, misinformation Google's AI Overview doesn't even trust itself to be accurate.Screenshot via Google

As much as I appreciate how useful Google's search engine has been over the years, launching an AI feature that might just make things up and put them them at the top of the search results feels incredibly irresponsible. And the fact that it still spits out completely (yet unpredictably) false results about objectively factual information over a year later is unforgivable, in my opinion.

We're living in an era where people are divided not only by political ideologies but by our very perceptions of reality. Misinformation has been weaponized more and more over the past decade, and as a result, we often can't even agree on the basic facts much less complex ideas. As the public's trust in expertise, institutions, legacy media, and fact-checking has dwindled, people have turned to alternative sources to get information. Unfortunately, those sources come with varying levels of bias and reliability, and our society and democracy are suffering because of it. Having Google spitting out false search results at random is not helpful on that front.

AI has its place, but this isn't it. My fear is that far too many people assume the AI Overview is correct without double-checking its sources. And if people have to double-check it anyway, the thing is of no real use—just have Google give links to the sources like they used to and end this bizarre experiment with technology that simply isn't ready for its intended use.

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