Mistakes happen—but they're not always a disaster. In fact, sometimes they end up seeming pretty, pretty lucky.
1. The Wrong (Right) Woman
I asked the wrong woman on a date. I have a problem remembering names and faces. There was a girl at school I had been chatting with during lunch breaks, Vicki. There was another that I had met and spoken to exactly once during an outdoor cookout at our college, Marie.
I had an occasion where I was performing. The event included dinner and dancing and I could bring a date. I planned to ask Vicki as I had spent more time with her and felt I knew her better. I was rushing between classes and I was stopped by a girl who said hello. Vicki.
I surprised her by asking her to accompany me to my event. She said yes and I got out my notepad to write down her number (prehistoric days before cell phones) and wrote the name Vicki. She said, “That's not my name”. I apologized for my memory glitch and asked what her name is. Marie. Then it dawned on me.
I had just asked out the wrong girl. But she had said yes and I was a gentleman so I would not back out. We went on our date. We both fell in love that night. We were engaged three weeks later. That was 38 years and one son ago. We are still together. And yes, she knows the story.
2. He Was Very Determined
I drove through a mountain pass in a blinding snowstorm to make an interview. I was moving about 10 mph and wasn’t sure I was still on the road. It became too late to turn around, and I white-knuckled the steering wheel for about four treacherous hours until I met up with two snow plows outside El Paso.
They couldn’t believe I’d tried to come through the pass with its 65 mph winds. I eventually arrived at my destination: Carlsbad, NM. I met the publisher, the editor, the beat reporter…and got the job.
Years later, the publisher told me, “I hired you because you were the only one stupid enough to drive through a two-foot snowstorm to the interview. You were the only candidate who made it. So I hired you”.
3. The Coffee Shop
The best mistake I have ever made would be leaving my art on a coffee shop table in New York, along with an open tablet with the current book I was writing on it. I had only gone to get a coffee and came back to see this really hot guy in a three-piece business suit reading and looking at my stuff.
I didn’t know what to do, so I approached him and sat down before pulling my small sketchbook from my purse. I started to draw him while he looked at my artwork and book. When he realized I was there he flinched slightly, but I only smiled at him. He looked confused before I turned my sketch for him to see and his jaw dropped.
I had drawn him holding my tablet with one hand, his knees crossed, my art propped on those knees and his coffee in his free hand. He was in utter shock. He asked me my name and who I worked for. I told him that I was only there for a few days on a class trip for my college and that I would leave in the morning.
He told me my writing was great and my art was inspirational. He made me smile. As I was leaving I tore the drawing of him out of my sketchbook after signing it and gave it to him. We haven’t seen each other since and the reason it was the best mistake was because it was the boost in confidence I needed at that time.
I was in a depression, hating my art, and just couldn’t finish my book. His words and drawing that sketch made me so happy. He said he was going to hang my drawing in his office. I’m glad I decided to go get that coffee.
4. Sometimes Oversleeping Is A Good Thing
The best mistake I ever made was waking up late. My friends and I had scheduled to pick me up at 9 am for a picnic that day, but I slept in and missed their pick-up time. I woke up half an hour later. I was truly fortunate that I did, because my friends got into a car crash that day.
The side driver seat, where I was meant to be sitting, was completely crushed. Not going that day saved my life.
5. The Unexpected Baby
LET'S HAVE A BABY WITH A WOMAN I DON’T KNOW! Said no one ever. It was a mistake not using protection—but the best one I ever made.
I had been angry, depressed, self-absorbed, and lazy in most respects. I had talent, but always just “mailed it in”. This little kid changed all that for me. I started working to afford a place for him, his mother, and I to live. It’d be hard to be a good dad from behind bars.
I didn't really care about myself, but now I was responsible for him—and he didn't ask to be born to two teenage parents. I have failed a lot, I will fail again, but I will not fail at this. The journey this started is impossible to put into words.
The questions I was now asking myself were more important in my development than anything I had thought heretofore. How do I teach him to be strong and kind? How do I teach him to respectfully pursue his passions and push through adversity? How do I teach him to manage his fears and anxieties in a healthy way?
How do I teach him…well how could I teach him anything if I didn't first learn and practice it myself? I meditate. I’m strong and kind. I can manage my emotions. All of it was made possible because of this “mistake”.
6. Right Number
My mother asked me to dial Grandma's number for her, but I accidentally dialed my grandaunt (my mom's aunt) instead.
Mom: How are you, Ma? How is your health?
Grandaunt: I am fine, dear. It's been a very long since I heard from you. Thanks for remembering this old soul.
My mom was surprised to hear this as she spoke to my grandma the day before yesterday. She checked the dialed number on her phone and realized it was her aunt. Her aunt doesn't have any children and rarely receives calls from anyone, except on holidays. My grandaunt was very happy to hear from my mom.
They continued their conversation for more than an hour. After she ended the call, my mom was very happy and emotional. Now mom calls her frequently. This best mistake of mine made them much closer.
7. Good Riddance
My so-called friend borrowed something from me and was constantly asking me to take it back from her instead of her coming to my place and returning it. We were friends for 18 months and she has this habit of complaining.
She texted again yesterday evening, saying, “Come and take your stuff; it'll hardly take you two minutes”. I was near her building so I thought I would go and get my things. But instead of replying, I mistakenly sent her a text meant for someone else, which was “Hmm” to which she must have decided that I was not going to come. Now the best part.
I did go to her place. The door to her room was open and she was complaining happily about me with her roomies. She made up things, cooked up stories, and showed how talented she was in putting people down. I stood there in the hall listening to everything, every single word she spoke, loud and clear.
I considered her a friend but she obviously didn't. I left and never spoke to her again.
8. Meeting Matt
I kissed someone who wasn’t my boyfriend. My relationship with Taylor was a fairly good one by all general definitions, and it didn’t seem like there were any problems with it. I logically just told myself that this would be my last relationship, knowing that this boy had every intention of marrying me.
But deep down I knew that his feelings were much deeper than my own. And I think I always knew that it just wasn’t right for me, but I prayed that I was wrong. I convinced myself that I was simply reading into things too much. Because Taylor had to be the one for me. He had to be…
During spring break, my brother and I went up to Canada to visit an old friend, Lauren. It had been ages since we’d been north of the border and it was great to finally get a chance to visit again. While we were there, we ran into our old neighbor, Matt, who’s a couple years older than me.
Now, while we were living in Canada (10 years ago now) Matt and I weren’t exactly close, but our families were good family friends and he and I would interact a lot. A decade makes for a lot of changes…I was no longer the awkward and scrawny 13-year-old he remembered.
I was a confident 23-year-old graduating with an engineering degree. And he had grown too. He seemed almost more full now, for lack of a better description. He was genuine and charismatic and full of life. He swept me off my feet…and that was a problem.
For a good while I completely denied to myself that I had any sort of attraction to him, convincing myself that it was just simple intrigue. I couldn’t be attracted to him. Because I never felt anything towards anyone who wasn’t my boyfriend. But Matt seemed to break that trend.
I admired how comfortable he was in his own skin. He was unbelievably genuine and it made me realize how uncommon a trait that really is. Matt went out with us one night.
My brother went off to try out some new pickup line on some unfortunate girls at the next table, and Lauren was off flirting with some guy trying to get free drinks. This left Matt and I alone at the table. Even though it can be difficult to have a conversation in a loud and crowded bar, we managed.
We spent the entire night talking and laughing and just having a good time. At the end of the night, we all headed back to Lauren’s apartment. It was agreed that Matt would sleep there for the night, since it wasn’t safe to drive. The sleeping arrangements were tight.
After a lot of playful banter, everyone sort of just fell into where they were going to sleep. Matt had somehow found a comfortable place right next to me. And after the light was out he quietly, but not so subtly, wrapped his arm around me and pulled me closer.
I laid there on his chest for a while, until everyone else had fallen asleep. And it felt perfect. At one point, I shifted my head a bit so that my neck was in a more comfortable position. As I did so my nose brushed his cheek. And before I knew it his lips were on mine.
And I can honestly say, there wasn’t one part of me that wanted to pull away. When I got back home, I broke up with Taylor. The intensity of the feelings I’d felt towards Matt had shown me that the relationship I was in was not meant to be. I had only been comfortable and content, not truly in love.
Matt and I have been together for five months now, and even though our relationship is still young I know beyond a shadow of a doubt that he is the man that I’m going to marry. I love him so much that sometimes I’m almost startled by how much emotion I can feel towards one human being. And I know with just as much certainty that he feels the same about me.
Even though our relationship started with me being unfaithful to a previous boyfriend, I can easily say that it’s the best mistake I have ever made.
9. Right Place, Right Time
I’m definitely not alone when it comes to finding it hard to wake up in the winter months. It’s dark and miserable until about 10 am on a good day. On this particular day, I accidentally hit the snooze button and woke up when I was supposed to be arriving at work.
I knew my boss would be irritated so I got ready in record time and ran out the door. My office was a 15-minute walk from my flat and I always went the same way. I was nearly there when I saw a very elderly lady, unresponsive and facedown on the floor.
Two other people were standing over her but not doing anything. Having had first aid training many years before, I asked one person to call an ambulance while I looked after the lady. She came round and said that she had tripped and hit her head.
Her ankle was very badly swollen and her nose was bleeding, but I kept her calm, reassured her, and checked her over to make sure she wasn’t seriously hurt. She couldn’t stand and the ground was cold so I gently lifted her over to a nearby bench.
A paramedic arrived about 15 minutes later, but said she would have to wait about an hour for an ambulance because he couldn’t help her get in the car. Being considerably bigger than the paramedic, I picked the lady up and put her in the passenger seat of the paramedic’s car, and off they went to the hospital.
She was a lovely woman in her late 80s, more apologetic and embarrassed than anything else. Ultimately my hitting the snooze button put me in the right place at the right time to help her. Life has a funny way of doing that.
10. Homemade Chocolate Bars
My family and I went biking the other day, and before we left, I convinced my mom to take some chocolate-covered almonds along as a snack. During the bike ride, my mom unzipped her backpack to find that our treat had melted in the scorching heat, the almonds swimming in the thick, liquid pool of dark chocolate.
We ate granola bars instead. When we went home, I put the mess in the refrigerator, not entirely sure of what would happen. Tonight for dessert, I had a cold chocolate bar with almonds. It was delicious.
11. Some Much-Needed Motivation
I failed out of college. I ended the 2nd semester of my freshman year with a GPA that was close to zero. When the school year ended, my parents drove four hours to campus to help clean out my dorm room and take me home. During the ride home, I remember staring out the car window in complete silence for the entire four hours.
I was devastated. I had no idea what I was going to do. My parents were upset and disappointed. They didn’t have anything to say. Neither did I. Their disappointment was nothing compared to the numbness I felt. I was far more disappointed in myself than they ever could be. It was completely my fault and I knew it.
I was accepted to attend the only college I applied to. And now I failed out of the only college I applied to. I struggled all through Freshman year of college until it got to a point where I felt I had no chance of success. My grades were terrible. So, I didn’t show up for any of my final exams.
There was no way I could study well enough to get passing grades on my finals. I gave up. During the drive home, I became painfully aware that I could have done better. I didn’t bother searching for an excuse to justify the horrible mistake I made. I had to figure out a Plan B.
Not even a week passed after moving back home with my parents before I started piecing together a plan. Even though I "failed" as far as the university was concerned, I knew I was not a failure. I certainly did not feel like one. I had dug myself into a very deep hole and I knew it was up to me to pull myself out.
I had to figure out how to approach life differently. I wasn’t doing it right. And it felt horrible. I knew I had to try again. The problem was, since my GPA was so poor, I got suspended from attending that college. I called the admissions office and asked how I could come back to earn my degree.
They told me I needed to go to a community college for a year and earn a 3.0 GPA, then I could reapply to be accepted back. My entire experience of life changed from that point on. I was never the same again.
Suddenly I had a goal to accomplish. I had never set ambitious goals for myself prior to that moment. I was social and active and participated in sports, but I was mostly just showing up. I never associated much of a purpose or goal with anything I was doing.
I did what the admissions office told me to do. I got a job. I took courses at the community college. I accomplished the GPA they required. A year after failing, I reapplied and was admitted back into the same college so I could finish my degree.
By the time I graduated with a Bachelor’s degree, I was getting grades that earned me a spot on the Dean’s List several semesters in a row.
12. This Is Adorable
I ordered Hush Puppies shoes on Amazon. I made the payment and checked out. After a couple of days, I received a call from my mother, “Son, did you order some shoes?"
I asked her to hold on for a minute, checked my Amazon, and realized that I forgot to change the address as I’ve shifted to this new place for a job around 1,000 km away from home.
“Yes, Ma! I ordered those shoes for Father. He’s going to attend a wedding next month, isn't he? That's why!" I lied a bit but their happiness was more important.
A month later, my mother was calling to tell me about how much my father liked those shoes and with how much excitement he told my grandparents and my aunts about me sending the shoes with my first salary. My father is a simple man and he has never worn branded shoes so that his family could get Pumas and Nikes.
I felt bliss.
13. A Happy Coincidence
I was recently divorced and working for a company that had just opened a branch in Germany. My boss told me four interns were coming from Germany. “You’re a supervisor," he said, “This is a very big deal, so make sure they are comfortable and happy here”. But there was a problem.
We had three shifts, and I was on the second shift—by which time my boss was long gone for the day, so he couldn’t introduce me in person. When I got to work I found only a list of four first names and the desks they were sitting at. And then when I got to that part of the office, there were only three guys.
I went over and talked to them for a bit, tried to make them feel welcome, made sure they had everything they needed. I was hoping one of them would mention the fourth fellow, but nobody did. I figured he’d be sitting somewhere else, so I excused myself and went to look around.
Then I heard a guy speaking German. I snuck a look at the name on his desk: Arnold, same first name as the missing fourth fellow, and a German last name. This was him! He turned out to be much nicer than the other three and we had quite a good talk. His English was excellent.
In the following weeks, I saw Arnold often and talked to him for a little while each time. The other three were polite, but distant. So when a fax came in written in German, I knew which one to take it to for translation. When I handed him the fax, he looked at it for a long time.
“I’m sorry," he said, “My German isn’t really good enough to read this”. And so it turned out that this Arnold wasn’t the fourth German at all—that particular Arnold, the intern my boss was so concerned about, had been out getting a sandwich the afternoon I came to meet them. Then he’d gone home to Germany a week or two later for some unrelated reason.
The Arnold I’d made friends with was an American with a German father—who had taught him just enough to get by in conversation. They’d spent plenty of time in Germany, so when I’d asked him questions about what it was like there, he knew all the answers. And living with his dad had given Arnold just a trace of a German accent in his English.
That was 20 years ago. Arnold and I are still having good talks daily—we’re married.
14. Get Outta Here
I needed a C to pass my college communications course. If I didn’t get a C, I would fail to meet my college major requirements, setting me back an entire semester. Here’s the problem: The semester was over, and I had a D+. My only hope was to email the teacher asking for a bump in my grade.
I wrote an email to her explaining how my past school performance warranted a higher grade and that not passing me would only hurt an ambitious student. When I hit send, I realized I made a HUGE mistake. I addressed her using another teacher’s name.
I tried to calm down, but then I remembered we’d spent half the semester covering email etiquette. Shoot! What did I do? Two days later, she emailed back. First, she addressed the glaring mistake then said she bumped my grade up to a C to never have me as a student again.
This is by far the best mistake I’ve ever made.
15. Thanks, Al
I had a terrible job. I stayed for too long. The pay was horrible. The customers were rude. My boss—whom we’ll call Al—was the worst boss on the face of the earth. For months and months, he spoke down to me. He was cold, ruthless, and bitter because his store made no money.
Many nights, I went home and was angry for hours. I wished bad things upon Al—very bad things. But there's a silver lining here. Now, any time I’m having a bad day, I just think of Al. And how he can’t tell me what to do anymore. It makes my day better. It reminds me of how much I should appreciate every job/boss I’ve had since.
You don’t know how good you’ve had it until you’ve worked for Al.
16. A New Type Of Photo Album
I had an iPhone two years ago but had to change to Android, so I bought Motorola and my mom took my iPhone. She isn't a tech person at all. She hardly knows anything other than basic cellular phone functions. I forgot to clear my data. I used to be a cute fat kid back then, so I used to take selfies, cute ones.
I saw my mom scrolling through the gallery of her iPhone a few days ago. She was like, “You look so good in this one! Wow, see this one! Hey! This was when you came back from coaching and we gave you a surprise. We bought parrots for you”.
She actually scrolls her photo gallery now and then when I am not at home. It makes her so happy.
17. Inappropriate Messages
I turned up to work just over a year ago. The previous evening my colleague had asked me for my password to my computer so she could print some “things” from my computer. This colleague did not like me. She then went through my messages that I had sent to another colleague.
These messages would be deemed inappropriate in the workplace. She showed these messages to a manager. At work the next day, my belongings were packed in a box and I was told I would not be needed at work today or ever again.
My mistake was sending the inappropriate messages to my colleague who subsequently resigned the same day. I cost myself a job and a friend, but I also cost my colleague his job. What happened from here though was a moment of self-reflection.
Instead of blaming my employer and my sneaky colleague I turned around and asked myself: “Why did I write those messages in the first place?” My mistake led me to realize that I had been a bad human being for a number of years.
Since being fired, I’ve opened my own gym, written for The Huffington Post, and spoken about this same mistake for the last year and how I learned from it. Being a bad person and getting caught was the biggest mistake I’ve ever made but it also made me the best man I’ve ever been.
18. Monsters In Love
My wife approached me at a shady nightclub in Eastern Europe, while I was having a deep conversation with an American investment banker from Goldman who I just met a few days before. She walked over and asked, “Can I sit here?" I looked at her. “Sure”.
She expected a conversation, but that didn't happen, as I turned my face and kept talking to my banker colleague. She angrily walked away. “Haha, you made her mad, dude," the banker said.
We kept talking about our financial past and deals which went wrong, then he finished a beer, and went to the bathroom. The girl approached me again. “Can I sit here”? Sure…
“Where are you from”? I spoke till 7 am with this girl who approached me initially, until we got kicked out of the nightclub. She gave me her number. I called her around noon the next day and she wanted to go for lunch. We went for lunch. And dinner. And spent the night together.
Three months later, we started living together. Within a year, we were married. She told me that when I rejected her, she first thought, What a jerk, how dare he reject me like that, no one rejects me like that. That turned out to be my best mistake given how long we've been happily married. She's a bigger monster than me.
19. Good For You
When I was 21, I started dating a guy who was 33 years old. At first, I was smitten. He was a musician like me (I play the piano and he played the drums), we enjoyed rock and metal, and he was older than me—which I thought was really cool. Then, the arguments started.
He once started yelling at me early in the morning because I hadn’t washed the shirt he wanted to use that day for work. There was always tons of laundry because we were living with his sister and most of the time I was the only one who washed clothes and put them to dry outside.
He also had the habit of throwing out all the clothes on the ground when he was trying to find anything, leaving the mess for me or his sister to clean. I had no idea he wanted that specific T-shirt, as he hadn’t mentioned it at all. I was supposed to have guessed it or something.
At the time, I was already doing my Master's Degree, and working at a call center to make ends meet. My schedule was pretty full and still, when I got home by midnight I had to cook dinner because he was too lazy to do it.
I would also leave my papers from class on the table, all piled up and organized by lesson number, just to come home and find everything scattered on the floor. When asked, he would say that he had no idea why I had left it all scattered there, and that I was really lazy. I often questioned if I was going crazy.
A lot of other things happened, but I’ll go straight to the end of it. We were arguing again and he told me, “If you don’t like things in my home, then just leave”. I stayed silent and he left to meet his friends. When I was sure he was already a few blocks away, I started packing.
I took my guitar, all of my clothes I was able to find, my books, and everything else I had at his home. It still wasn’t much, I had like four suitcases and a few bags. I called a taxi and asked for a large car. Then, I called my sister and asked her to tell her landlord that I wanted to rent the last free room at her house.
She gave me her landlord's contact, I said I needed to move urgently, and the landlord said I could move in immediately if I wanted to. I left and didn’t leave a note. He didn’t deserve it. When he realized what had happened, he went ballistic.
He called me a few times saying that I should have understood him, that I had to come back so we could “fix things”. There was nothing to fix anymore because he had tried to break me too many times, and I was done. Something had changed in me. I changed my cell phone number.
However, I’m really happy I dated him and lived with him. I learned a lot about how people can harm others. He manipulated me constantly. I thought I was insane because of all the accusations he would throw at me. He would often blame me for arguing, even though he started the arguments—I was just not good enough for anyone, and I was lucky to have him because nobody else would have me.
Fortunately, he was wrong. In the meantime, I’ve dated a few people and found out how I wanted to be treated—with respect and empathy. In the end, the most important lesson I took from this relationship was that I should never put up with someone who makes me feel bad.
20. The D In English
I got a D in English during my junior year of high school. My teacher said I couldn’t write and that I would never be published. I never considered myself a writer, yet felt bad about the grade.
When I started my own company, I felt I had a story to share. I turned to writing. Before I knew it, I had the opportunity to write for an Entrepreneur. I became a published writer in college, only three years after getting that D in high school English. What changed?
My attitude towards writing. My biggest realization as a writer is that the words I put down aren't final. Good writers know they'll be editing. At the time, I thought my mistake wasn’t trying harder in school. No one in my class got a D besides me.
Looking back, that D inspired me to change my work ethic and made me a better writer.
21. The SoundCloud Inspiration
I was trying to download a song. I couldn't find it anywhere. I accidentally clicked on a website I had never heard of. It was SoundCloud, back in 2014. If I signed up and followed the artist, it would let me download the song.
I don't sign up for many things, but this felt crucial. It may not seem like a mistake but I could've been downloading a virus for all I knew. Anyway, I favorited the song and made playlists with other songs I knew. What changed my life? SoundCloud would automatically play recommended songs.
This song came on. Gamper and Dadoni: Far From Home. A German duo. With vocals from a guy called Cozy. I can still remember how I felt. I was in absolute awe. My jaw dropped. Standing. Not moving. Immersed in the song. My imagination was putting scenes together synced to the music and creating a music video. How crazy does that sound?!
So, what did I do? I filmed exactly what I saw in my mind. I had never done anything like this before but I felt compelled. I talked to people on Airbnb to use their homes as part of scenes. That’s how far I took it. I then flew to China to film the bulk of it. China! From London!
I don't know why I did what I did, but this was definitely SoundCloud’s fault. The video I made amassed 28k views on YouTube. I filmed it with my iPhone. It’s a terrible production. I didn't care. It came calling. I answered.
Since then, I've worked with other people on short films. I made another music video of my recent adventure in America (still using an iPhone). This was a horrible editing experience because my laptop kept crashing. It's tough when the vision is more powerful than my laptop. I gave up. I was angry.
However, as I sat on a replacement bus service an hour from my destination, I downloaded Splice and organized the clips with basic transitions. I didn't mean to click on a random link, but this is where it has taken me. Wanting a song but ending up directing two music videos.
The most seemingly insignificant thing can ultimately alter the course of our lives.
22. The Daughter
Marriage. I married a person who proved not to care and it ended in divorce within five years. I was 17 when our relationship started, and signed the papers at 18. Why was it the best mistake?
That marriage gifted me with the most beautiful, loving, and caring daughter I could have ever wished for. I don't regret anything because of her. She's worth all the pain and struggle, all the tears and desperation. She's the most beautiful thing that ever happened to me.
23. The Obsession
I failed my first year of university a few years back. I was devastated, depressed, and pessimistic. However, since I had never experienced such failure in my life, I became obsessed with finding out why I had failed, as well as how I could prevent myself from failing in the future.
My initial quest was to find sure ways to go around this sort of failure, but I ended up learning amazing things about myself during the process. My failure has become the best mistake I’ve ever made because of the things it taught me. I do not regret it one bit—in fact, I’d be more than willing to repeat it.
Simply because it was a mistake that opened up my mind and filled it with ideas that some go entire lifetimes without knowing.
24. The Umbrella
During a family vacation to Mcleodganj in India, we were en route to visit the Bhagsu Falls in our taxi. It was raining extremely heavily and the road was jammed with cars. Since we had no umbrellas, we decided to buy some from a shop next to the road. Hurriedly, we bought two (overpriced) umbrellas without checking them.
When we got out of the car, we realized that one of the umbrellas was defective and was not opening completely. It was sort of semi-opening. Anyhow, since the jam was too much, we decided to return without seeing the falls. Since we didn't want to carry the defective umbrella as it was useless to us, my dad decided to leave it on the roadside.
Within minutes, a worker—one of many people trying to direct the cars—took the umbrella. He was completely drenched and cold and didn’t even have a raincoat. He was so happy to see the umbrella. Even though the umbrella was defective, it still sheltered him from the rain.
He took it and happily started re-routing the traffic. We couldn’t help but smile thinking how everything happens for a reason.
25. The Dating Site
I ended up signing up for a dating website. Having absolutely zero experience with online dating, I ended up having absolutely NO clue what was going on. I believed all profiles to be authentic and was shocked by the torrent of dirty/inappropriate messages that welcomed me.
It was quite an experience, and after having spent almost the entire day on the website, all I could figure out was how to surf a few profiles and drop them polite messages. Where I made the mistake: I didn’t read the fine print.
So, the website had a nifty little thing that told you how far someone is from you! I met a couple of nice people and exchanged messages, but this particular profile stuck out. I felt we had a spark, and the icing on the cake was that the website said she lived just 3/4th of a mile away from me! This could be something.
She was smart, funny, and could hold a conversation really well. She had this aura of putting you at ease, helping you unwind, and she was so aware and knowledgeable that she could talk about almost everything that walks the Earth. Saying that she was perfect is just an understatement.
She said all the right things at all the right instances, like a character from my dream that just stepped out to reality, just a whole lot better than I could have imagined. She was so good to be true, that I knew there had to be a catch.
Maybe she was a really old lady pretending to be 20, maybe I was being catfished because girls like her were not found on dating websites. Things got intense and the spark was now a full-blown fire, and quite taken by her, I ended up asking her to be my girlfriend.
Being the well-measured person she was, she asked me to take it slow, and I did—I waited four days and told her that I am in love with her and on the fifth day I started hinting that we should meet up. She politely laughed me off initially but of course, I knew she wanted to meet too, what we had was so real, and all we needed was to make it tangible.
One fine day, she finally gave in and suggested that if we were to meet up, I might as well book the tickets. RECORD SCRATCH. Wait, what? Book the tickets? But she only lived about a mile away! The long and short of it is, the site had said that she lived 1.2k km away, which basically is 1200 km (745 miles) and not, as I had assumed, 1.2 km!
This, by far, is still hands down the best mistake I have ever made, because quite honestly, had I known that she lived that far from me, I wouldn’t have given us a shot. Until then, I had never experienced the bittersweet emotions of a long-distance relationship, and hence was of the opinion that they never quite work out.
I would have lost out on an amazing partner. Yes, we are still together and plan on spending our lives that way. She still is witty, charming, and supportive, and does not fail to inspire or stun me every single day. I am glad being blind to the distance gave me a chance to actually put myself out there and take a leap of faith and it paid off gloriously.
The best thing in my life happened due to a silly mistake.
26. When Forgetting Is A Good Thing
The best mistake I have ever made was when I was in Vietnam. I was hurriedly going through an old Quonset hut that the French had left earlier. I suddenly stopped at a door because I had mistakenly left something behind. 90 seconds after this, a B-40 rocket grenade landed and exploded just outside the door.
If I had not stopped because of that little mistake, I would have been toast.
27. All Worked Out In The End
So, I met this woman online. We lived in different countries. After meeting a few times, we decided to be exclusive. We were long-distance for about six months, taking turns visiting each other every two weeks, but it was still hard. Neither of us was young, and we wanted something constant and stable.
She didn’t want to move to the country where I worked because the pay would be a downgrade for her. Whereas for me, it was the opposite. So we decided that I should be the one who moved to her country. And so I did. I took the plunge.
I left behind a good and stable career I’ve worked on from the ground up. I went from a nobody into a somebody after six years of working my butt off in that company. There were some red flags I chose to ignore prior to moving. I thought it was because we had a long-distance relationship and we were both just frustrated with the situation.
I thought things would be better once we lived together. Boy, was I wrong. All of the red flags became more and more apparent. We argued constantly, and the fights would get worse each time. I was emotionally mistreated all the time.
On top of that, I had to keep on looking for a job, and my savings were rapidly depleting because the cost of living in that country is so high. It was a terrible time. I sunk into severe depression. I kept on sending resumes. It was my way out. I didn’t have enough money to rent my own place so I had to suck it up.
Finally, a hundred resumes later, I landed myself a job in a good multinational company. I had a downgrade in terms of position, but I didn’t care. I was happy that I found a job. And the pay was good due to my work experience.
At that point, I could already afford my own place. Yet, I still lived with her. I thought maybe the stress of job hunting, and her having to adjust to living with someone, hurt the relationship. I gave us the benefit of the doubt. I was wrong, AGAIN.
We had a personality clash and very different points of view towards life. An extreme one. We even went to counseling. Nothing helped. There was nothing we could do about it. So, after an additional three months of staying together, it was really over. Oh, and she kicked me out too.
Anyway, I managed to find my own place—after a week of staying in a hotel. I made friends with my colleagues. I got myself together. Here’s where it got better.
Since the currency of that country is quite strong, after almost two years of working, I managed to buy a studio apartment in my home country. In cash. It was small, but it’s mine. I could also afford to give myself a year of sabbatical, and went back to my home country. As for my colleagues, they’re now my best friends.
28. Will Take The Next Opportunity
Back in 2012, I wanted to see what all the Bitcoin buzz was about. I remember I was halfway through college and decided to check the price after extensive research into the industry. $20 a coin. I looked at the price history and decided it wasn’t worth it—I was a poor college student.
If I would have thrown a little money in, I would be very rich right now. But, since life is funny, this taught me the most valuable lesson: “The best time to plant a tree was 20 years ago. The second best time is now”. You won’t see me missing an opportunity anymore.
29. Don’t Listen To Dad
I rushed into a marriage just to avoid pressure from my Dad. This was in 2012 when I was just getting started in my career and was making decent but not a lot of money. I had a couple of alliances come my way, but the first three matches didn’t go through.
My dad started saying that it was because I wasn’t settled in my career. He started pointing out all my mistakes and shortcomings and kept saying how I was not the ideal son and how others my age were doing really well.
This took a real toll on me and I said yes to the next match who was interested in my profile and our marriage happened in August 2013. However, three months later, I realized that it was a huge mistake as we had huge incompatibility and trust issues and there were a lot of things that the girl’s family had kept hidden from me before marriage.
The girl moved out in October 2013 and we got divorced in the next year. Rushing into the marriage was a mistake that I wish I could undo. But I have learned from it too. I focused on my career and did really well and my salary has quadrupled since then. I also started taking everything my dad says with a pinch of salt.
30. Paying It Forward
Recently, I had to change my workplace and as usual, it took some time to adjust. But in the new workplace, the environment was a bit different. I was accustomed to working in an environment where people helped each other after their work hours or after their work was finished.
At the new place, I came across people who just simply left once their work was done. I spoke about this with my manager, who told me to act professionally and do the same. Some instances made me a bit disappointed as many times I was left alone with a pile of work to do.
This had been affecting my nature and I started getting irritated. This also started giving other people the wrong perception of my personality. One day my work was over and I decided to help my fellow worker who was left with a huge task. Even though I knew I would not be getting paid for it.
The next day, when this was reported to the manager, I was advised not to do so as it would yield nothing to me because no one helped each other here and everyone was only concerned about money.
Yesterday, while I was again left with the same situation (a huge pile of work yet to be finished), the guy I had helped once started doing my work as well! I never expected this! After I was finished, I thanked him for his generosity and he told me that I was there when he needed help and I didn’t care about money.
This is how a team works. Trust me, I was never this happy. I can see things falling into place now. I like the workplace and enjoy working.
31. A Different Point Of View
Friends, family, and fellow students all told me to finish my degree—that I would be making a mistake if I didn’t. After all, there was only one year left. But deep down I had a belief I knew I had to uphold: Time is the most precious resource we have.
After examining the curriculum for the final year of my degree, I found the majority of the course was about simulating the real world. Similar to an internship. Very practical. On the surface, it looked great, but there was no more teaching of new skills.
To everyone else, it was the most exciting year. To me, it didn’t make sense at all. Why would I simulate the real world, when I could do it for real, in the real world? So I left. To society, it was a mistake. To me, it’s one of the best decisions I’ve made.
32. Aditya The Hero
I had been approached to help with the worst kind of project. It was well underway and nearly off the rails already. “How bad can it be?" I thought. Once I accepted the project, I started to learn the answer.
After decades of helping teams turn around projects—some real doozies—this was the worst situation I ever saw. But there was a huge upside.
The new guy, Aditya.
I had been brought in on the project partly because I had experience finding and organizing teams of experts to tackle tough problems. I’d often take on problems where many unknowns were involved or other firms preferred to stay away because a solution was impossible to estimate.
Whether the project needed “hardcore” programming, design, or some grunt work data entry, I had a great network and ways to quickly find people who fit the jobs needed.
In this case, it was a complex situation so I expected to do a lot of the work myself. Still, I reached outside my network and brought in some new team members hoping to find some good people. One of the new people crushed every assignment.
As the pressures in the project mounted, he always seemed to be relaxed, confident, and open. He asked great questions. He caught details I missed. He was proactive in his communication and down to earth—no jargon, no dogma.
That’s rare in the software world where programmers beat their chests and routinely show off their big diction. So I started sharing more technical background, and reviewing his decisions instead of making them ahead of time. He handled change gracefully. When we needed to refine or revise his work, it was low friction.
He’d ask great questions and get me to give him test data. He learned. I learned. We both improved. Taking the project was a mistake, but hiring Aditya made it the best mistake of my life.
33. Burning That Bridge
I walked out on a six-figure income. I burned my bridge and was happy to do it. Many would consider that a mistake but I left over ethics issues and felt fully justified. That was four years ago.
Today, I'm self-employed and have four employees of my own. I pay them well and I never ask them to compromise their values or integrity for the dollar bill. I hope I never do. I work from home, choose my hours, and live freely without needing excesses in my life.
34. Breaking The Policy
I knew I shouldn’t have taken the project. I had told myself to say no to fixed-scope projects because I knew they were risky. If we estimated too low, we could get locked into unpaid work and lose money. But this one just seemed too good to be true: a major-name client, a big opportunity, and a major boost to my company’s notoriety.
I had a choice: take a project that could potentially damage the company, or pass up on a huge opportunity to grow. I took the deal. And at first, it was great. But then I realized I’d made a HUGE mistake. We had vastly underestimated the work for the project. We couldn’t control the feature creep by the client.
Suddenly, we were contractually obligated to finish a job that could bankrupt us. I tried to stay positive. But then I remembered that my partner and I had decided on a no-fixed-scope policy just a month before. We went into survival mode. Then, we came up with an idea for a new type of engagement: roadmapping.
A low-cost, low-risk exploratory engagement, separate from the main project. An automatic bulwark against bad estimations and dangerous fixed-scope projects. We started selling roadmapping to our clients. Within a year, we were doing $1 million on roadmapping alone.
Suddenly, we went from a near-bankrupt dev agency to a thriving, growing company with millions in ARR. That was the best mistake I’ve made in my entire life.
35. Finding A Better Route
I used to live in an area where subway transportation is very common. Once, I took the wrong train, ended up walking in a random direction, took a random train, and actually ended up at my destination a few minutes faster than I would've if I had taken the correct route the whole way.
I decided to make that "mistake" every time I wanted to reach that destination.
36. The Mistaken Mistake
My friend falls backward into a lot of good things. He wanted to be a journalist at a newspaper. When he was applying, he sent examples of his work. He accidentally sent one story that he had to print a retraction for. He figured he screwed up, so just moved on.
He got an interview with the paper and they said they appreciated the fact that he had the courage to send a mistake as part of his writing samples to see how he dealt with mistakes.
37. Unexpected Presentation
I was working for a large consulting firm. For weeks, I was preparing a report about localizing a well-known International ERP (used by Enterprises to manage the business).
I was a junior at the time, a back-office guy working behind the scenes to deliver value. A value that my supervisors had to present and demonstrate. There were hundreds of thousands of dollars on the line.
After weeks of preparations, we were ready to present the results to the ERP Vendor and demonstrate how their Enterprise Software would support the Greek Legislation (aka Localization).
I was in the room to support my team in case they needed the one small detail that I knew, that would save the day. I repeat: I was never meant to present the report. Everything was going fine until my boss looked at me. "Theo will present the results of the analysis he performed in the past few weeks," he said.
I started to sweat bullets. My hands began to shake while I nervously looked around the room. I knew I should refuse politely and with diplomacy. I clenched my fists and decided to do it with zero preparation. And that was the "best" mistake I've ever made. "Best" because:
1) I didn't lose my job that day.
2) I learned something from it.
I stood up and I tried to pitch. It lasted around two minutes (that felt like a year) before they asked me to step down in order for someone else to take the lead in the presentation. I will remember that moment forever. I learned to always be prepared for the unexpected.
38. Freelancing
I was doing freelance work for a friend and got fired from my job because of using company time to do it. I ended up applying at a multitude of other jobs that same day, got a call back from a job the next day, scheduled an interview, and got the job immediately.
I was scared about getting fired, but after that, I ended up with a much higher-paying job within 24 hours.
39. More Than Just A Pinch
While I was making a casserole for supper, I wanted to throw in some cayenne pepper. We had just gotten a new bottle that had a different style to the lid. It was a flip-top, that exposed the little grill that a small amount can sprinkle through. But I was used to the last bottle that you had to unscrew and remove the top to expose that grill.
So I unscrewed it, didn't look, and just started dumping it. At least half the bottle went in immediately, and I stopped in shock. A pile stayed floating on the top, so I tried removing some with a spoon but it was no use. Oh well, I stirred it in and continued. I hate wasting food even though I was sure I had ruined dinner.
It turned out to be delicious.
40. Love On Omegle
When Omegle was fairly new (no webcam features), I was browsing Yahoo and there was an ad for it that I had accidentally clicked on. I was connected with a stranger. We ended up talking for an hour and exchanging emails. Then we met up and hit it off. This was three years ago.
He's sitting next to me as I type this. We haven't left each other since the day we met.
41. What A Race
I was playing a trifecta wager on a horse race and accidentally keyed the wrong horse in a place spot. The one I wanted was the second favorite with 3-1 odds, whereas the one I picked had the worst odds on the board at 20-1. By the time I realized my mistake it was already too late.
The 20-1 ended up placing and the ticket paid a couple of hundred dollars. The horse I wanted wasn't even in the money.
42. The Lottery
This happened to my parents, who are pretty compulsive lottery players. Every day, my mom goes up to the corner store to buy $5 straight of the daily four. Same numbers every day. This one particular day, however, the cashier enters the wrong number of tickets—13 instead of five.
My mom decides to roll with it. And, wouldn't you know? That was the day my parents hit the lottery. They more than doubled what they ordinarily would have won, all because of a cashier's "mistake".
43. A Typo That Paid Out
In a casino once, I was playing electronic roulette and wanted to put £1 on 25 (I remember the number well). I accidentally put £11 on and it came in. I won £385.
44. The Wrong Room
I was looking for a position as a junior programmer. When I went to the recruitment company, I misheard the number of the room I was told at the reception and went to a different one. It turned out that by some magic coincidence, they were conducting an interview for the position of the senior programmer in the same group.
That's why my CV was in their database as well. They didn't ask me which position I was applying for. At some point, I just felt that the questions they were asking didn’t correspond to the level of a junior. Surprisingly, most of them were familiar to me. So, I got the job, all from going to the wrong room.
45. The Best Dog
I ended up adopting a dog that I did not pick out. Basically, the dog I chose, signed adoption papers for, and paid for at my local shelter was not the dog they presented to me three days after the adoption, when I went to pick her up.
It turned out that the dog that I had picked out initially had already been adopted by another person, but that paperwork had been misplaced when I was filling out my set of paperwork. So, the shelter instead was trying to give me the dog that had shared the living space with the dog I had initially picked out.
I ended up taking a "eh, what the heck" attitude towards the whole thing and left the shelter with the dog I did not initially intend to adopt. Five years, two hip surgeries (on the dog), and lots of love later, I can honestly say that that dog, Dallas, was the happiest mistake of my life.
46. The Right Email
Stuck in a dead-end position, I wrote an email to a work friend complaining about how my request to HR for an inter-department interview went nowhere. I accidentally sent it to a senior VP, who talked to HR, who finally got me the interview, which got me the job and moved me into my field.
10 years later, I'm now senior tech lead for the team and turning down middle-management promotions.
47. The Accident
I worked nights, but my mother needed a ride to make a payment. It was the last day and the company did not take credit cards but would take a check IN the office. So after a 12-hour shift, I picked up my mother, drove her to the office, and then was going to take her home.
I was too tired, I should not have been driving, but I was. I rear-ended a hatchback at moderate speed. The paramedics insisted on taking my mother to the hospital since the airbag had hit her, and her chest hurt. It was a crazy twist of fate.
They found Polycystic Kidney Disease on the X-Ray. My mother has since become her nephrologist’s star patient, even recovering some kidney function she had lost, all because of my accident.
48. Bet It Felt Good
I was 21 years old and worked at a fancy restaurant back in 1979. One day a couple came in with their parents and small child. They ran me ragged with special requests. I did my job honorably, but probably not with a huge smile on my face the whole time. When they left, I found a lonely penny on my tip tray.
That's not just a "stiff" as they say in the business. That's a profound insult to a waiter who managed to do his job despite the extra work and stress I had to go through for that family. I managed to hold in my anger at first. But then I saw the toddler playing around the balcony bar banister so I knew they were up there drinking.
I grabbed the kid and threw him across the room. Just kidding, I'm not an animal! But I went up to the bar and walked straight over to the adults sitting there, and I asked them why they left me a penny tip. They fumbled for words and then said I was arrogant toward them, or something like that.
My reply: "Sometimes people come here looking for excuses not to tip, and you are a perfect example of that". Then I just walked away. I tried to feel bad about lashing out like that but I couldn't. It was too satisfying. I've had no trouble telling my kids about this episode in my life, even the part about what happened next.
I got fired, of course! They happened to know one of my managers quite well. But losing that job started me on a path of entrepreneurship and self-employment that has been extremely satisfying and rewarding in many ways, and for the rest of my life.
49. Light Of His Life
I have a habit of switching off the staircase lights every night after using the washroom and getting ready to sleep. But one night I forgot completely and just got into bed. Soon my friend called me.
Her: How are you?
Me: As usual I am stressed!
Her: Try to take life lightly.
Me: Light! Oh, I will call you back.
I tried to switch the lights off from inside the house. But it didn't work. So I went outside—and made a surprising discovery.
There was a guy sitting close to my house on his terrace with a book, studying, using my lights to see. I pretended that I didn't notice anything and went to sleep without switching off the light. My mum told me the next day that he had his HSC board exams coming up. Since his grandfather was ill, the guy studied on the terrace!
50. Stalling Out
I was riding my motorcycle home from work one night and I came up to a left-hand turn lane behind another car. The light gave us the green left turn arrow and I started to move, but the car in front didn't. I hit the brakes and accidentally popped the clutch, stalling the bike.
I was cursing myself and the person in front of me when I heard a large bang and looked up. A truck coming from the other direction had blown through the red light and clipped the back end of the car that was just in front of me. If I hadn't stalled out, there is a good chance I would have become a new hood ornament for a Dodge Ram.
Sources: Reddit
