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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.

34 broken bones, a mural, and Buddy the Elf—what these three things have in common
True

The Bank of America Chicago Marathon took place on Sunday, October 12th. Every runner who took on the enormous feat of 26.2 miles is truly an inspiration. We’re proud to share three outstanding stories about the power of community, giving back and crossing the finish line. Not only did they run an outstanding distance, but they each also gave back by fundraising for an organization that changes lives for the better.

Running a marathon is so much more than race day. It’s sticking to a schedule, getting enough rest, learning how to fuel your body for long distances, and—perhaps the most challenging of all—building mental resilience.



Meet Leanne: Running after 34 Bone Fractures

Leanne was only 12 years old when during her middle school cross country practice, she fractured her right tibia, the shin bone in her leg. This wasn’t Leanne’s first time breaking a bone—it was actually her 34th fracture. After many years of being overlooked as "clumsy," Leanne felt immense relief and recognition when a doctor diagnosed her with brittle bone disease, an incredibly rare condition.

Lurie Children’s provided a care plan for Leanne to build strength and start running again. And as of October 12th, Leanne ran her second Bank of America Chicago Marathon. She said in an interview, “I never thought I’d run again. But against the odds, here I am, training for my second Bank of America Chicago Marathon... all because of Lurie Children’s.”

Leanne’s impressive journey is a testament to the incredible research of Lurie Children’s, where she gives back by volunteering at the hospital and running on its behalf. Talk about being a true inspiration.


Meet Everett: Running to Inspire Through Art

Everett is an artist who creates beautiful murals around the city of Chicago. He uses his art as a tool for storytelling for community and connection.

In addition to being an artist, Everett is a runner. He ran the 2025 Bank of America Chicago Marathon on behalf of Peace Runners 773, a non-profit organization that strengthens the community of Chicago. In this video, we follow Everett on a run to visit some of his favorite murals. The run ends at Garfield Park, where Everett just finished a mural that he dedicated to the organization—symbolizing growth, strength and togetherness. Everett didn’t stop there.

While building his strength as a runner, Everett is strengthening his city of Chicago. Through his running and artwork, Everett has brought more awareness and resources to his community.

Meet Joseph: Running on Behalf of Special Olympics


Joseph ran the Chicago Marathon on behalf of Special Olympics, dedicating each mile to one of 26 friends with a developmental disability. The last 1.2 miles were extra special. It was for one of his closest friends, Matt.

In this video, Joseph runs to Matt’s house. For every mile of this training run, he tells us a heartwarming anecdote about Matt. They met at camp and soon, Matt will be a groomsman in Joseph’s wedding. The duo even sends a Christmas card every year—most notably dressing up as Buddy the Elf and sharing a bowl of spaghetti with maple syrup (spoiler: it doesn’t taste good).

As Joseph runs, he says, “Before we get to Matt, a quick note about why I’m running on behalf of Special Olympics. Matt and I love sports. And so do many of my other friends. Donations help provide year-round sports training and competition for more than 20,000 people with intellectual disabilities across Illinois.”

Joseph is the perfect example of inspiration. Not only did he run an entire marathon, but he also found inspiration in his friends who love sports as much as he does.


Leanne, Everett and Joseph are three incredible people who have shown how much strength and perseverance it takes to run a marathon. Each runner is both empowering themselves and their community. Their dedication to the Bank of America Chicago Marathon shows that the people of Chicago have a passion for the city, their neighbors and their personal achievements.

Education

Social skills expert shares 3 'magic phrases' that make you more likable

Sometimes, we need to overcommunicate how we feel about others.

vanessa van edwards, likability, communications skills, people skills, people laughing, good advice

Vanessa Van Edwards and people at a party.

A familiar misstep people make when trying to be likable is trying to impress others. They want to show they are funny, intelligent, and a great storyteller. They think being the life of the party is the road to likability. However, study after study shows that it’s a lot easier to be likable. All you have to do is show interest in others. To put it simply: If you like people, you will become more likable.

There’s a slight wrinkle in the notion that liking more people makes you more likable. Many people you like aren’t sure that you like them. The psychological phenomenon known as signal amplification bias says it best. We tend to overestimate how clearly we broadcast our feelings and intentions towards others. So, the person we like and who likes us may not know the feeling is mutual.


“We think our signals are obvious,” Vanessa Van Edwards told Steve Bartlett on the Diary of a CEO podcast. “If we like someone or if we’re having a good time, we think, ‘Oh, they for sure know it.’ They don’t.” Van Edwards is a communications expert and the author of Captivate: The Science of Succeeding with People.

To help people clearly communicate their feelings, Van Edwards suggests three “magic phrases” to show you care. Check out the video below.


Phrase 1: ‘I was just thinking of you’

“You think of a lot of people in your life all the time,” she said. “If you are thinking of someone and you can text them: ‘I was just thinking of you, how are you?’ I was just thinking of you, how’d that project go?’ was just thinking of you. It has been a while since we talked.’ You see a movie, you see a documentary, you see a matcha latte, you see a mug, you see a ceramic candle, and you’re like, ‘Ah, this made me think of you,’” Van Edwards said. “My text messages, my conversations, are full of actual moments where I was triggered to think of that person, actually,” she said, noting the importance of being genuine. “If you don’t think of someone, they’re not a person you need to have in your life.”


Phrase 2: ‘You’re always so …’

"So if you're with someone and you're impressed by them or they're interesting or they're funny, say, 'You always make me laugh. You’re always so interesting,’ or ‘You’re always so great in interviews.' Giving them a label that is a positive label is the best gift you can give someone, because it's fighting that signal amplification bias,” she continued.


Phrase 3: ‘Last time we talked, you mentioned …’

“We are so honored when we get brain space—that you remembered and you’re going to bring it up,” she said. “And you specifically bring up something that they lit up with, something they were like, ‘Ah, it was great, it was exciting, it was wonderful.’”


If studies show the more you like other people, the more likable you become, Van Edwards has the next logical step in becoming more likable. She makes it clear that, due to signal amplification bias, many people you like may not even know it. When we employ her three ways to be more likeable, though, we can let people know we like them without making them feel uncomfortable, thus establishing bond to build on.

teacher, teachers, hair, student, caring
Elementary school teacher Alice Yates does hair for student who lost a parent.

Teachers play a much larger role than simply being educators — in fact, teaching basic reading and writing pales in comparison to the nurturing and lessons on being human that they provide for kids. And elementary school teacher Alice Yates (@missaliceinteacherland) understands what it means to go above and beyond for her students, especially those in need.

In a video shared on Instagram in early 2025, Yates shared an emotional video about a student who recently lost a parent. After noticing she was coming to school with her hair unbrushed most days, she decided to step in with kindness and help take care of her by doing her hair everyday.


At the start of the video, Yates shows herself brushing out a little girl's hair as she tells her story in the captions. "A few months ago one of my student's parent died pretty suddenly...she was coming to school with her hair not even brushed most days," she writes. "I just wanted to help where I could. So I bought a cheap comb and hair ties so that I could at least do a basic pony for her to get her hair out of her face."

The small act of love did not go unnoticed. Her other students noticed Yates doing the student's hair, and wanted to get their hair done, too. "Then the other girls in the class started asking if I'd do their hair too. Now during breakfast, we have chitchats while we do hair! I wouldn't trade this time for anything. It has helped us all become so much closer.❤️"

She goes on to explain that she wasn't sure if parents would be okay with it, but was put at ease after getting a thankful message from one.

"I was a little nervous some parents might take it the wrong way that I'm doing their kids hair, but then I got this message: 'I just FaceTimed with [student's name] and saw her hair. It was adorable. Thank you for being extra sweet to my girl while I'm away. I don't even know what her hair looked like when she came in lol."

Yates offered more details as to why she treasures the personal interactions with her students. "I love being the teacher that I needed growing up...when I was a kid many of my teachers didn’t take the time to get to know us. They didn’t really show us love, tell us about their family, or even ask about ours," she writes. "They showed up, taught from a McGraw Hill Teacher Guide and went home. I think back on school and I hated it most years. I can count on one hand the teachers that I felt safe and happy with."

It was that experience that made her want to be a different teacher. "School filled me with so much anxiety and I think it’s a huge reason why I pour my heart and soul into teaching now," she writes. "I find so much comfort in looking into a parents eyes and telling them that I will take care of their baby, and they look back and me and know I mean it. ❤️"

Yates' emotional video got an incredibly supportive response from viewers. "

And that’s a vocation right there & exactly the teacher our children need 💕," one wrote.

Another shared, "This is beautiful bc when I was in 3rd grade my dad almost died in a motorcycle accident. Needless to say with no family nearby, most days I was barely dressed much less brushed. My teacher would bring barrettes to put up my hair and ill never forget the difference it made in my life ♡."

And another viewer added, "They will never forget you and the time you took for them ❤️."

If you would like to contribute to Miss Alice's classroom, you can shop her Amazon Classroom Wishlist here.

This article originally appeared in March. It has been updated.

hotels, women, safety, trafficking, safety tips, traveling, crime, culture, viral tiktok
Canva

Woman's frightening experience reminds everyone to lock hotel door.

Staying in a hotel feels safe. The doors are heavy and solid, the key cards don't have any identifying information on it (should you drop it), and most hotels will have security or at least front desk staff on site 24/7. However, it's still important for anyone traveling alone — especially women — to stay vigilant.

If you've ever stayed in a hotel, you know there's an additional lock you can latch as an added layer of protection. But sometimes weird things happen that make us rethink the comfort and security many of us take for granted.


TikTok user TayBeepBoop had a disturbing experience when a hotel front desk person attempted to enter her room while she was inside.

Some readers may find the story to be unsettling but it's a powerful reminder of exactly why situational awareness and caution are so important in today's world.

Tay, obviously frightened, uploaded clips from the event on her TikTok page, which has since garnered 6 million views. In the video, which is mostly the floor, door and bed, you can hear the man outside of her room knocking loudly asking to be let inside.

Tay asks the man repeatedly why he attempted to walk into her room using the hotel master key to which the man explains there's a problem with the woman's car. There's only one problem. Tay doesn't own a car and is only in town on business where she did not rent a car to get around town, relying only on other modes of transportation.

So, what the heck was the man doing at her door?

@taybeepboop

Replying to @dani klarić this was a really long and hard video to make, it was sort of traumatizing and I’m kind of freaked out about staying anywhere now and I dont leave my house much anymore tbh because I already was dealing with PTSD about my safety. I’m OKAY which is why im able to go through this footage now. I genuinely don’t want anything to do with this hotel, this is a PSA to stay safe and cautious. I don’t want people to go after this worker because I still don’t know what his intentions were and he could have just been trying to do his job

Tay was staying at the hotel alone and made sure to latch the additional lock on her hotel room door, which is the only thing that prevented this hotel staff member from getting into her room. Since the situation was so scary and went on for quite some time according to her video, she called friends on FaceTime to be a witness and help comfort her. Eventually the man leaves after repeated attempts to get the scared woman to open the door and Tay was able to get a male business partner to escort her safely to another hotel.

But the comments were filled with stories from women who have had similar experiences, and a few who had good safety tips.


hotels, women, safety, trafficking, safety tips, traveling, crime, culture, viral tiktok Take care to practice extra safety when traveling alone. Photo by Mario Heller on Unsplash

"Please never say you’re alone in the hotel. I know you were shaken but please please don’t rely on front desk call the police. I’m so glad you’re safe"

"A car smoking in a garage and he takes 30 minutes to go upstairs, harass you, and speak to you in the phone BUT NOT CALL THE FIRE DEPARTMENT?!"

"As a former front desk agent. I’m almost 100% sure it’s illegal for hotel staff to go into a room knowing someone in the room. Please contact hotel"

Many people explained the danger of admitting you're alone upon check-in, while other commenters sympathized with the woman not thinking to call the police right away. With people traveling more as COVID-19 restrictions subside, there could be a greater chance for things like this happening so it's best to be prepared and err on the side of caution when traveling alone.

Women on the Road has several tips for hotel safety including making sure your door lock works, putting a chair under the handle of the door or buying a rubber door stop. The site also highlights the importance of locking your windows if they open and not opening the door for people you don't know.

- YouTube www.youtube.com

Another site geared towards safety is Solo Female Traveler and it recommends getting a floor higher in the hotel to make it more of a hassle for someone from outside to break in. It, too, reiterates the importance of locking the additional lock in the hotel room while you're inside.

While it's statistically unlikely you'll be a victim of a hotel robbery or whatever was happening with Tay, her experience is a reminder to research hotels and practice caution when traveling. In the end, Tay was safe, and has a thriving business sharing home tips and hacks for her audience of almost 2 million followers.

The rest of us should remember: always lock the deadbolt or chain.

This article originally appeared three years ago. It has been updated.


millennials, Gen Z, salon, hairstylist, TikTok, viral video, Alexis Rex, Rex Artistry, hair trends, Y2K fashion, confidence, generational humor, subtle color, bold contrast, Olaplex, client behavior, social media, Maryland salon, pop culture, self expression

A hair stylist trims a man's hair

While millennials and Gen Zer’s often get lumped together as the “young group,” they are certainly not the same. (Although it is kind of hard to tell with all the Y2K fashion floating around.)

But speaking as a millennial, we definitely have different approaches to life, many of which seem to come down to a sense of self-assurance. That goes for shopping, socializing, self-expression…and even going to the hair salon, apparently.


Alexis Rex (@rex.artistry), hairstylist and owner of Rex Artistry Salon in Maryland, gave a brilliant (and hilarious) demonstration of some key personality differences between her millennial clients and her Gen Z clients in a now-viral TikTok video.

subtle color, bold contrast, Olaplex, client behavior, social media, Maryland salon, pop culture, self expression Each generation has its own salon swag. Photo credit: Canva

First, Rex played her Millennial Customer.

Millennial Customer gently knocks on the door and immediately expresses her gratitude. “Hey girl! So good to see you! So excited!”

But at the same time, Millennial Customer wants in no way to be an inconvenience, so she immediately comes back with, “Where should I put my purse? It's okay, I'm just going to shove it in my own personal space so it's not in your way. At all."

Never one to demand attention, Millennial Customer wants a very subtle hair color change. Really, "it shouldn't even look like I got my hair done.” Not “super bold,” not “in your face.”

Then after flooding the hair stylist with compliments, Millennial Customer (ever wanting to be a good student) will ask a bunch of follow-up questions about how to maintain the style.

Then, Rex played her Gen Z Customer.

Gen Z Customer bolts through the door with a “Hey queen!” like a hurricane (who has time to knock?!) and is ready to plop her stuff down anywhere. Unlike her millennial counterpart, Gen Z Customer is perfectly fine to take up space unapologetically and even show up with hair that “hasn’t been brushed in a month.”

Gen Z Customer also knows exactly what she wants, and it’s anything but subtle. “I wanna do like in-your-face, bold contrast…I wanna look like a different f**king person. Let’s do it.”

The confidence…it’s…palpable.

Gen Z Customer has a different approach to complementing her hairstylist: “Oh my god! F**king Queen! You did that! God I love you.”

No further questions. Gen Z Customer already knows her brand of hair care products, and it’s “Olaplex. All Olaplex.”

hairstylist, TikTok, viral video, Alexis Rex, Rex Artistry, hair trends, Y2K fashion, confidence, generational humor It can be hard asking for what you want at the salon if you're from the generation that has a hard time even speaking on the phone. Photo credit: Canva

Rex’s post quickly racked up 8.6 million views, generating literally tens of thousands of comments about how spot-on her imitations were.

Millennials in particular chimed in, many of whom couldn’t help but applaud its accuracy of depicting how millennials seem to constantly be apologizing for simply existing.

“I’m a millennial and once I missed the armhole for a sec when putting the cape on. I was convinced I had ruined the appointment,” wrote one person.

Another added, ‘I’m sorry for my hair. I’m sorry my hair takes so long. I’m sorry I had to move my head, omg I’m sorry. You offered me a drink? I will say yes. And then sorry.”

Many were also quick to applaud how Gen-Zers seemed to have no issues in this arena.

“Gen Z just fully owning the ability to take up space,” one person commented.

"As a millennial I love Gen Z so much. They’re so free to be themselves and so open,” wrote another.

While there may be differences between generations, we can all learn something from one another. And we all enjoy getting our hair did.

By the way, Rex didn’t leave out her Gen X or Boomer clients. She has plenty videos of her imitating them, as well as some nifty style predictions on her TikTok, found here.

This article originally appeared last year.