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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.

Modern Families

Retired couple lives on a cruise ship because it's cheaper than a mortgage

"We have been frugal all our lives to save and invest in order to achieve our goal."

cruise ship, angelyn burk, living on a cruise
via Pexels

The Emperor of the Seas.

Imagine retiring early and spending the rest of your life on a cruise ship visiting exotic locations, meeting interesting people, and eating delectable food. It sounds fantastic, but surely it’s a billionaire’s fantasy, right?

Not according to Angelyn Burk and her husband Richard. They’re living their best life hopping from ship to ship for around $100 a night, depending on the cruise.


"Cruise costs vary quite a bit, our goal is to average about $100 per night, for the couple, or less across an entire calendar year," Richard told Upworthy.

The Burks have called cruise ships their home since May 2021 and have no plans to go back to their lives as landlubbers. Angelyn took her first cruise in 1992 and it changed her life goals forever.

- YouTube www.youtube.com

“Our original plan was to stay in different countries for a month at a time and eventually retire to cruise ships as we got older,” Angelyn told 7 News. But a few years back, Angelyn crunched the numbers and realized they could start much sooner than expected.

“We love to travel and we were searching for a way to continuously travel in our retirement that made financial sense,” she said.

They looked into deals they could find through loyalty memberships and then factored in the potential sale price of their home and realized their dream was totally affordable.

The rough math makes sense. If the couple hits their goal of spending $100 per night to live on a cruise ship, that’s $36,500 a year. Currently, the average price of a home in Tukwila, Washington—where the couple has a house—is about $561,359.

Plus, on a cruise ship, the couple doesn’t have to pay for groceries.

cruise ship, angelyn burk, living on a cruise A cruise ship. Photo credit: Maurício Mascaro/Pexels

The Burks are able to live their retirement dream because they’ve spent a lifetime being responsible.

“We have been frugal all our lives to save and invest in order to achieve our goal,” she said. “We are not into materialistic things but experiences.”

Angelyn said that cruising takes the stress out of travel. “It is leisurely travel without the complications of booking hotels, restaurants, and transportation while staying within our budget,” she told 7 News.

The couple travels lightly with just two suitcases between them and if they need anything, they just buy it on the ship or in the next port.

The one thing to consider before embarking on a never-ending cruise is COVID-19. The coronavirus is easily spread in close quarters. Before 2025, the CDC recommended that people get vaccinated before going on a cruise and that immunocompromised people should consult with their physicians before traveling.

Richard told Upworthy that he believes COVID-19 safety is still very important and has had both his shots and a booster. "I would suggest wearing a mask at all times when out in public no matter whether on a ship, in a movie theater, at a restaurant or even meeting with friends inside or outside," he said.

The Burks' favorite destinations, no matter how they get there, are Italy, Canada, Iceland, and the Bahamas. Their ultimate favorite place to stop? Singapore.

cruise ship, angelyn burk, living on a cruise Singapore. Photo credit: Timo Volz/Pexels

Looking to give it all up and go on a permanent vacation just like the Burks? Angelyn has some advice for those wanting to get started.

"First and most importantly, make sure you enjoy being at sea," she said. "Cruising is not for everyone. Try different cruise lines to see what appeals to you."

This article originally appeared on 05.11.22

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.

Snoopy, peanuts, woodstock, puppy, snoopy lookalike, pets

Stop what you're doing. There's a dog that looks just like Snoopy.

So, there's this dog that I'm pretty sure is the actual Snoopy come to life. Seriously, all the dog needs is a red dog house out back and a little yellow bird best friend. If you think it can't be true, then you're going to have to argue with the entire Internet about it because nobody can get enough of how much this sweet dog looks like the iconic cartoon character.

Snoopy is Charlie Brown's pet from the beloved comic strip Peanuts created by the iconic Charles Schultz. It began publication on October 2, 1950, and eventually spawned several cartoons, movies, merchandise, and even theme park rides. Amazingly enough, one dog, a precious good girl named Bayley, is a dead ringer for the black and white animated pup. Since we live in a digital age, people across the country have been falling all over themselves to get to the pooch's Instagram account and admire her cartoonish mug.


Bayley is a four-year-old mini sheepadoodle, which is a cross between a miniature poodle and an Old English Sheepdog. Her sweet face is something you have to see to believe—and even then you may question if she's real.

The dog's perfectly groomed curly fur makes her face look fluffy and cartoon-like. Once you add in her black ears and black button nose, you have the perfect Snoopy doppelgänger. Bayley came into her viral fame in 2023 after Doodle Dogs Club shared her photo on their Instagram account that has over 230,000 followers. Just like that, she was "famous."

The introductory post of the live version of Charlie Brown's best friend racked up over 1.4 million likes and 10.3K comments (Update: the post now has 1.7 million likes and over 12k comments). The comments ranged from people reminding others that Snoopy is, in fact, a Beagle to people demanding Bayley star in a live action version of Charlie Brown.

Though they may be different breeds, there's no arguing that Bayley looks more like the Snoopy than real life Beagles. This probably has a lot to do with cartoons being...cartoons. Everything tends to be a bit bubbly and over exaggerated with cartoons.

Bayley's fluffy, curly fur gives her an advantage over actual Beagles when it comes to the ability to look like the famous cartoon character. It's something she probably couldn't care less about, unless every time she got compared to Snoopy equaled a dog treat. Otherwise, I'm sure the black and white sheepadoodle is perfectly happy just being a dog wondering why her mom keeps taking pictures of her.

Since Bayley's debut on Doodle Dogs Club, the animated dog come to life has climbed up to over 240k followers (Update: her account now sits at 438k followers!) and her fanbase (still) just can't get enough of her. To make people love her even more, the dog's mom uploads videos of Bayley using audio that makes it sound like the pup is a toddler trying to tell a story.

On August 10, 2023, Bayley got to meet the "real" Snoopy at California's Great America theme park in Santa Clara, California for what would have been the character's 73rd birthday. It was honestly a full circle moment and the photos are everything.

Check out some of the love Bayley gets on her Instagram account.

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

Love Stories

A guy may have met his 'dream girl' at a bar but she only gave him 80% of her phone number

It was a move straight out of a romantic comedy that had the entire internet rallying to solve the mystery.

phone number, napkin, viral, X, Twitter, HenpeckedHal, Jackie, Austin, dating, romantic comedy
via Tod Perry

An artist's recreation of Jackie's napkin note.

A woman named Jackie pulled a move straight out of a romantic comedy recently, and it has the internet rallying around her potential love interest. Jackie met a guy at a bar and liked him so much that she gave him her phone number. Well, 80% of her number, that is.

The world heard about it on January 17, 2023 when X (formerly Twitter) user @HenpeckedHal shared a picture of the napkin with her partial phone number written on it. "My 22-year-old cousin met his dream girl at a bar and it's going pretty well,” Hal wrote in the tweet.


“Call me! 512-3*1-2*04,” the message read, along with "I'm worth it." The 512 is an area code in Austin, Texas.

After congratulating his cousin on meeting his “dream girl,” he asked, "Did you get her number." The cousin replied, “Most of it.” The Tweet also attached a photo of a list of phone numbers the cousin called to try and get in touch with the elusive Jackie.

The tweet has gone insanely viral, racking up nearly 60,000 retweets, 85.6 million views, and 776,000 likes.

The next day, Hal revealed that the woman reached out to him. In the screenshot of her message, she wrote: “Heeeyyy, so you likely won’t see this but I’m Jackie from the tweet!”

"Tell your cousin that next time I see him I'm going to...” she continued, but Hal blurred out the rest of the message to conceal her identity.

“I just talked to him! WHAT’S YOUR NUMBER????” Hal replied. “He said he’s halfway through the list, which means he’s actually like 10 per cent of the way through it.”

“He may not be as clever as he thinks,” Jackie responded. “Give me HIS number, I’m taking over this operation.”

A lot of people in the comments said they thought Jackie was cold or arrogant for playing hard to get and making poor Hal’s cousin try 100 different numbers to find out which one was her. But Hal says that it’s all an extension of the conversation the two had at the bar.

"For the people saying she's arrogant, high maintenance or whatever: these kids talked for an hour about a shared interest in true crime, mysteries, etc,” Hal tweeted. “My cousin bragged that he always solves the case before the show ends (editor's note: not this time). I think she's awesome."

So, all Jackie did was give him another mystery to solve. If he’s such a great amateur detective then he should be able to reach her, right?

Some people in the comments have suggested that the story is fake. One person noted that the notebook page with the phone numbers on it had an indentation at the top which could be the “5” in Jackie’s phone number from the napkin. The implication is that Hal wrote on the napkin while it was on top of the notebook, leaving an indentation. But other people pointed out that the writing didn’t match.

Through everything, Hal has received a ton of support from people on X trying to help his cousin’s love life.

“The programmers who sent scripts and code, the excel junkies who sent me docs to share with my cousin, y’all are wild,” Hal tweeted. “I couldn’t come close to getting back to everyone, but I appreciate it.”

Nearly 90 million people have followed the story of Hal’s cousin and Jackie. Let’s hope there’s a happy ending or at least they get to meet up and see each other again to talk about the mystery that brought them both together.

Funnily enough, this isn't the first time Hal and his cousin have gone viral. In 2020, Hal shared a Tweet about how his then 20-year-old cousin had gotten his first place and...almost burned it down after an (avoidable) snafu with the oven.

Adulthood is hard, but entertaining. Thanks for keeping us all updated, Hal!

This article originally came out two years ago.