The Best Mistakes You Could Ever Make

October 27, 2023 | Scott Mazza

The Best Mistakes You Could Ever Make


Everyone makes mistakes.  Some are small, like a typo on an important document, and some are so large they change lives.  The people below share their best mistake—the one that altered the course of their lives, taught them something important or brought unexpected joy to a loved one.


1. The Wrong (Right) Woman

There once was a time when I mixed up the identities of two girls I knew at school. Remembering names and faces has always been a struggle for me. One of the girls, Vicki, I became friends with because kept running into her during lunch breaks. The other, Marie, I had met only once at a college cookout.

An interesting event was around the corner where I was going to perform. It was quite an affair with dinner and dancing, and I had the chance to bring a date. I decided to ask Vicki since we had shared many conversations and I felt more comfortable with her. As I was hustling from one class to another, a girl greeted me. My mind registered Vicki.

Without wasting time, I asked her to be my date at the event. To my delight, she said yes. Taking out my notepad (since this was way before the era of cell phones), I started to write down her number under the name Vicki. 

She then corrected me, "That's not my name". Feeling embarrassed, I apologized for my mix-up and asked for her real name. It was Marie. The reality hit me like a ton of bricks.

I'd invited the wrong girl to be my date. However, as a polite young man, it was unthinkable for me to retract the invitation. So, we went on our date. Little did I know it at the time, but that one mistake set the course of the rest of my life. 

We both fell head over heels that evening and within just three weeks we were engaged. Fast forward 38 years and one son later, and we're still happily together. And of course, she knows the whole story about my original blunder.

Best Mistake

2. He Was Very Determined

I braved a terrifying snowstorm while driving up a mountain pass to get to an interview. I was barely going 10 mph, uncertain if I was still on track. Turning back was no longer an option, so fearfully gripping the steering wheel, I trudged on for a grueling four hours until I met two snow plows near El Paso.

They were shocked that I had taken on the pass, battling its fierce 65 mph winds. Nevertheless, I made it to my final stop: Carlsbad, NM. I met with the publisher, the editor, the beat reporter…and secured the job.

Several years on, the publisher revealed to me, “I gave you the job because you were the only one audacious enough to tackle a hefty two-foot snowstorm for the interview. Since you were the only applicant who made it, I decided to hire you".

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3. The Coffee Shop

The finest error I ever made was accidentally leaving my artwork and a novel I was penning on a cafe table in New York. I'd only stepped away for a quick coffee refill and returned to find a strikingly handsome man in a tailored suit engrossed in my pieces.

Puzzled over how to react, I decided to sit down and fetched my sketchbook from my bag. As he delved into my art and book, I began to sketch him. When he noticed me, he jumped a bit, to which I responded with a smile. His confusion faded when I showed him the sketch I'd made—his stunned expression said it all.

The sketch was of him, holding my tablet in one hand, sitting cross-legged with my artwork on his lap, and his coffee in his other hand. His shock led him to ask about me and my employer. I clarified that my visit to the city was short—a college field trip, and I'd be heading home the next day.

He complimented my writing and praised my art as moving. His appreciation warmed my heart. As I left the cafe, I signed and tore the sketch of him from my book, offering it as a keepsake. We haven't crossed paths since. But the encounter reinforced my self-assurance when I needed it most.

I'd been grappling with a depressive period, disliked my artwork, and my book seemed far from completion. But his kind words and the joy his sketch brought me provided a much-needed uplift. He promised to display my sketch in his office. I regret nothing about that unplanned coffee run.

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4. Sometimes Oversleeping Is A Good Thing

The most fortunate blunder I ever made was oversleeping one day. My buddies and I had planned for a 9 am rendezvous for that day's picnic, but I failed to wake on time and missed our pre-arranged meet-up hour. I arose 30 minutes tardy. But that ended up being a blessing in disguise—as that day my pals ended up in a car wreck.

The passenger side of the car, which was supposed to be my seat, was utterly smashed. My absence that day might've well saved my life.

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5. The Unexpected Baby

"I'm going to have a child with a woman I don't know!" Nobody says that, but that's what happened to me due to a lack of precaution. However, it was the best mistake I've ever made.

I used to be angry, sad, self-centered, and largely unmotivated. I had potential but I wasn't putting in the effort needed. Then, along came this little one, and my life took an unexpected turn. I hustled, worked hard to provide a home for my child, his mother, and me–because being a good father wasn't possible from lockup.

Before, I only thought of myself. Suddenly, I had someone dependent on me–a child who didn't ask to be born to young parents like us. I've made many mistakes and I know there will be more, but I am determined not to fail him. It's been a life-altering journey, one that's hard to describe in words.

The questions I was faced with propelled my personal growth unlike any other time. How do I teach this little guy to be resilient yet tender? How can I help him to passionately chase his dreams and overcome struggles? How can I guide him to better handle his fears and anxious moments?

And how can I teach him any of this unless I learn and exemplify these things myself? So, I make a conscious effort. I meditate. I'm gentle yet strong, and I can regulate my own emotions now. All these changes in me are due to what seemed like a "mistake" in the beginning.

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6. Right Number

My mom asked me to call Grandma, but I mistakenly phoned my great-aunt (my mom's sister) instead.

Mom: How's it going, Mom? How are you feeling?

Great-aunt: Oh, I'm doing well, sweetheart. It's been quite a while since we last spoke. I appreciate you thinking of me, it means a lot.

My mom was puzzled by this response since she just chatted with my grandma two days ago. Checking her phone, she saw she'd indeed dialed her aunt. Since her aunt doesn't have any children and mostly gets calls on holidays, this was a pleasant surprise. My great-aunt was thrilled to hear from my mom.

They kept chatting for over an hour. After hanging up, my mom was touched and quite cheerful. Now, mom rings her up regularly. This little mix-up of mine ended up bringing them closer.

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7. Good Riddance

My so-called buddy borrowed an item from mine, but then repeatedly insisted that I pick it up, rather than returning it herself. Despite our friendship of a year and a half, she endlessly griped.

Yesterday, she sent another message which read, "Come pick up your things, it will only take you a moment". I was near her place, so I figured I'd retrieve my stuff. However, instead of a proper response, I accidentally texted "Hmm", which she must have interpreted as me not coming. Now, here's the juicy part.

I actually went to her apartment. Her room door was ajar, and she was freely ranting about me to her roommates. Untruths rolled off her tongue, she fabricated tales, and demonstrated her knack for belittling others. I just stood in the hallway, absorbing every single word, loud and clear.

I thought of her as a friend, but she obviously didn't feel the same way. I walked away and haven't spoken to her since.

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8. Meeting Matt

I once did something I thought I'd never do—I kissed someone who wasn't my boyfriend, Taylor. I mean, Taylor was a genuinely nice guy and our relationship was good by most standards, so I was pretty sure we'd end up together. He was so deeply in love with me, I convinced myself I felt the same.

But really, deep inside, I knew our feelings weren't equal and something didn't sit right with me. I'd dismissed those feelings, telling myself I was over-thinking. I wanted Taylor to be 'the one'.

Then, during a spring break trip to Canada with my brother, we bumped into our old neighbor, Matt, who was a little older than me. Although we were never really close back then, our families had been friendly.

A decade had passed since we last met, and we'd both changed. I was now a confident 23-year-old about to graduate with an engineering degree and he'd grown into this incredibly real and charismatic man who took my breath away.

For a while, I denied any attraction towards him, telling myself it was just curiosity. After all, I'd never been interested in anyone aside from my boyfriend. But Matt was different.

I admired his self-assurance, and his authenticity made me realize how rare it was to find someone genuine. One night, while out together, we ended up talking and joking all night, despite the noise in the bar.

We all headed back to a friend's apartment, buzzing with laughter, and somehow, Matt ended up sleeping next to me. Then, in the dark, he held me close and before I knew it, he was kissing me.

Honestly, part of me didn't want to stop. This kiss made me realize that my relationship with Taylor wasn't meant to be because I wasn't really in love, just comfortable. I ended things with Taylor when I got back from the trip.

Fast forward to today, Matt and I have been dating for five months. Even though it's still pretty new, it feels perfect. There's no doubt that I'll end up marrying him. My feelings for him are so strong that it surprises me sometimes.

Even though our relationship started by me cheating on my former boyfriend, it turned out to be the best mistake I've ever made.

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9. Right Place, Right Time

I'm certainly not alone in struggling to peel myself out of bed during the dreary winter months. You're lucky if the sun graces you with its presence before 10 in the morning. One day, I botched my alarm duties and only stirred awake when I should have been clocking in at work.

Fully expecting my boss's annoyance, I prepped myself in record speed and bolted for the door. My office was a brisk 15-minute walk from my flat, a route I knew like the back of my hand. As I neared my destination, I noticed an elder woman, unconscious, lying face-first on the ground.

Two bystanders stood over her but seemed unsure of what to do. Leveraging the first aid training I'd received years earlier, I requested one of them to dial for an ambulance, while I attended to the lady. She regained consciousness quickly enough to tell me she'd taken a nasty fall and banged her head.

Her ankle was noticeably swollen, and she had a bleeding nose, but I kept things under control, offered her solace, and checked her for major injuries. Unable to stand and languishing on the cold pavement, I gently helped her onto a nearby bench.

A paramedic showed up approximately 15 minutes later. However, he announced it'd take an ambulance another hour to arrive and that he was unable to assist the woman into his car. Given my size advantage, I hoisted the lady carefully and seated her in the paramedic's passenger seat, and they left for the hospital.

She was a charming woman, well into her 80s, and felt more embarrassed and apologetic about the situation than anything else. In the end, my failed encounter with the snooze button put me right where I needed to be to help her. Isn't it funny how life has its way of doing that?

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10. Homemade Chocolate Bars

The other day, my relatives and I thought it'd be fun to go on a little bike ride. I managed to persuade my mom to bring along some chocolate-covered almonds to serve as our treat. But to our surprise, as we were riding, mom discovered that in the blistering heat, our intended snack had transformed into a soup of molten chocolate, with the almonds bobbing around.

Switching gears, we opted for granola bars instead. Back at the house, I decided to pop the sticky mess into the fridge, admittedly unsure of the outcome. But to my delight, I ended up enjoying a delightful almond-laden chocolate bar for dessert tonight.

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11. Some Much-Needed Motivation

College didn't exactly start on a high note for me—I flunked big time. After barely surviving my first year with a GPA hovering close to zero, my parents drove from home to help me pack up my dorm room. The four-hour ride back was eerily quiet, with everyone lost in their thoughts.

I'd hit rock bottom—gloomy, lost and hollow. The disappointment in my parents' eyes was a mirror reflecting my own self-disgust. But it was less about their disappointment and more of my self-realisation—I had screwed up, and it was entirely my fault.

It was ironic. The only college I applied to had accepted me, and here I was, flunking out of the very same institution. Freshman year had been a total disaster, deteriorating to a point where I saw nothing but failure looming ahead. My horrendous academic records made me give up—I didn't bother showing up for the final exams.

With no way to pull through my finals, I admitted defeat. But as the car sped home, it hit me— I could have worked harder, done better. Looking for an excuse for my situation seemed futile; instead, I was on the hunt for Plan B.

Fast forward a week. I found myself back at home, living with my folks, slowly devising a comeback strategy. The university may have kicked me out, but I didn't see myself as a failure. I was stuck in a massive rut, but I knew it was up to me to get out of it.

It was time for a fresh outlook on life. Something had to change—I couldn't wallow in self-pity anymore. In spite of my lowly GPA leading to suspension, I mustered up the courage to call the admissions office, eager to find a way back.

The folks there suggested I take courses at a community college for a year and maintain a 3.0 GPA, post which I could reapply. That day marked the dawn of a transformation—I was a different Molly from then on.

Suddenly, I had a purpose for myself. This was a new experience—I was never one to set lofty ambitions. Sure, I was social, participated in sports, but I never dug deeper for a true goal.

So, I complied with the admission's office advice—I started working, took community college courses, and made the required GPA. A year after my downfall, I reapplied, was accepted back, and got to resume my dream of graduating.

By the time I got my Bachelor's degree, not only was I a different person, but my grades too reflected the change. I made it to the Dean's list for several semesters running—a testament to my comeback.

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12. This Is Adorable

I bought a pair of Hush Puppies shoes on Amazon, paid for them, and completed my order. A few days later, I received a call from my mom asking, “Honey, did you have some shoes delivered here?”

I quickly pulled up my Amazon account and I had a gut-sinking realization—I had forgotten to update my shipping address since I moved for work, a job that took me about 1,000 km from my original home".

Oh yes, Mom! Those are for Dad. He's got that wedding next month, remember? That's why I had them sent!" I may have stretched the truth a bit, but their joy was my main concern.

A month later, my mom rang me to share how much my dad adored the shoes. A huge grin came onto his face—he told my grandparents and my aunts about getting the shoes from my first paycheck. My dad is a humble man, always choosing to skip out on brand-name shoes so that his family could enjoy Pumas and Nikes instead.

Hearing it filled me with pure happiness.

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13. A Happy Coincidence

Recently, I found myself newly single and employed by a company that had just set up a new branch in Germany. My boss informed me that four interns were coming over from Germany, and my role as supervisor was to ensure their comfort and satisfaction during their stay. However, there was a small hiccup.

Our day was divided into three shifts; my shift fell during the middle of the day, by which time my boss had left. Thus, he couldn't introduce me to the interns directly. I arrived at work to find a list of four names, paired with the desks they occupied. However, upon reaching the designated area, I found only three gentlemen.

I approached and chatted with them, taking measures to make them feel at home and ensuring they had everything they needed. I was anticipating that one of them would mention the fourth one, but nothing came up. Assuming he was located elsewhere, I excused myself to look for him.

Soon, I heard German being spoken. I sneakily glanced to see the name on the desk: Arnold, which coincidentally was the name of the missing intern, and it was paired with a German last name. This was him! We hit it off immediately and he was much friendlier than the rest, and his English was impeccable.

Over the next few weeks, I frequently interacted with Arnold, while the others remained polite but distant. So when a fax in German came in, I naturally took it to Arnold for translation. However, after a long pause, he admitted his German wasn't good enough to translate it.

As it turned out, the real German intern named Arnold had been out fetching a sandwich when I first visited. He had returned to Germany after a short while for unrelated reasons. The Arnold I had befriended was an American, with a German father who had taught him just enough German to hold a conversation. Arnold knew the details about Germany from frequent visits there and his slight German accent was a result of living with his father.

Fast forward 20 years, the daily conversations I have with Arnold are still as enjoyable. Why, you ask? Well, Arnold is now my husband.

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14. Get Outta Here

I was on the edge of passing my college communications class; I just needed a C. A C was crucial because if I didn't receive one, it could jeopardize me meeting my college major's standards and delay my studies by a semester. Here's the catch though: The semester had ended, and I only had a D+. My last resort was to shoot an email to my professor, pleading for a grade boost.

So, I drafted an email to her, justifying why my past academic performances merited a higher grade, and how not passing could setback a determined student like me. However, just as I hit send, I realized I had done something seriously wrong—I had addressed her by the name of a different teacher.

Panic set in. Especially when it dawned on me that we had dedicated half of the semester to learning how to write professional emails. Oops! So what now? After an agonizing two-day wait, I received her response. She pointed out my obvious blunder but to my surprise, she agreed to raise my grade to a C, with the understanding that I wouldn’t be her student again.

This unintended faux pas ended up being the best mistake I've ever made.

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15. Thanks, Al

In the past, I held a really dreadful job. I stuck around there more than I should have. My earnings were pitiful, coupled with continuous encounters of impolite customers. My superior, let's call him Al, was the most unbearable supervisor on the planet. His store wasn't making any profit, a fact that led him to be cruel, heartless, and full of resentment. Month after month, he belittled me in every possible way.

I would return home furious on several occasions, carrying anger that lasted for extensive hours. I often found myself wishing terrible occurrences for Al, hoping he wouldn't have it easy as well. But, there's a silver lining in this gloomy cloud. 

Now when a day happens to be unpleasant, all I have to do is recall Al and the fact that he is no longer capable of bossing me around. This thought prompts a grin, brightening my day instantly. It also serves as a reminder to value every boss and job I've had up to this point.

The true magnitude of how fortunate you've been is only realized when you've suffered under the tyranny of Al.

Angry man in suit pointing at the cameraCraig Adderley, Pexels

16. A New Type Of Photo Album

A couple of years back, I switched from an iPhone to a Motorola Android. My mom took my old iPhone, even though she's not tech-savvy and can only handle the basic phone functions. I didn't remember to erase my old data, including a bunch of selfies from when I was a chubby, cute kid.

It ended up being the best "mistake" ever—just a few days ago, I caught her flipping through all the photos on her iPhone. She was gleaming, pointing out pictures, saying things like, "You look great in this one! Look! Here's when we surprised you after coaching with those pet parrots".

It turns out, she likes to reminisce by scrolling through the photos on the phone when I'm not around. It really seems to brighten her day.

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17. Inappropriate Messages

About a year ago, I arrived at my job to quite a surprise. The night prior, a coworker who didn't particularly like me asked for my computer password to supposedly print some "stuff". She took advantage of that access to sift through my messages sent to another coworker.

Sadly, those conversations were not suitable for a professional environment. After being shown these messages, my manager confronted me. I found my stuff packed up and then received news that I was no longer required, effective immediately.

This error of mine ended up costing me not only my job but also a friendship. The coworker I was messaging chose to resign that same day. But it was the following introspection that held the real significance.

I didn't point fingers at my boss or the coworker who revealed my misdoings. Instead, I placed the mirror in front of myself, pondering "Why on earth did I send those messages?" This pondering unveiled that I had been in the wrong for quite some time.

Since my dismissal, I've embarked on a new journey. I've established my own gym, become a contributor for The Huffington Post, and also borne my tales of mistakes as lessons for others. Engaging in inappropriate behavior and subsequently getting caught was undoubtedly the biggest mistake I've made. Yet, it also molded me into a much better person.

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18. Monsters In Love

My future wife first crossed paths with me in a questionable nightclub tucked away in Eastern Europe. At the time, I was engaged in a deep conversation with an investment banker from Goldman whom I'd only met a few days prior. She offered me a shy smile and asked, "Can I join you?" I gave a nonchalant nod, "Sure".

She assumed we'd chat, but I caught her off guard by promptly returning to my chat with the banker. Offended, she huffed away. The banker chuckled, "You really ruffled her feathers, man".

Lost in stories about our financial ventures and the mishaps we'd encountered, we continued our conversation. When he left for a restroom break, the lady reappeared. "Can I join you"? I once again responded, "Sure…"

"And where are you from?" Fast forward to 7 am and we were still in deep conversation when the bouncers finally escorted us out of the club. We exchanged numbers, and I hit her up for lunch the following day at noon. One meal turned into two, and we spent the whole night together.

Fast forward three months; we decided to move in together. Not long after, within a year, we tied the knot. She confessed that my initial rejection had antagonized her. She recalls thinking, How audacious of him to dismiss me like that, no one dismisses me like that. Funnily enough, what seemed like a blunder ended up being a lucky charm. We're still happily married, and to my surprise, she's a more formidable force than I am.

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19. Good For You

At 21, I began dating a man who was 33. As a fellow musician—he on drums, me on piano—we had much in common, including our love for rock and metal. His age, older than mine, was an alluring quality. Things went south, however, when the fights began.

One afternoon, he lost his temper because I hadn't washed his preferred work shirt. Living with his sister meant heaps of laundry, and most of the time, I was the one dealing with it.

He also had a maddening tendency to upset the wardrobe in his search for clothes, leaving their cleanup to me or his sister. It wasn't my fault I hadn't washed the shirt; he never articulated his needs—it was as if I was supposed to magically guess them.

I was juggling studies for my Master's Degree while working at a call center. Each night after a hectic schedule when I came home around midnight, he wouldn't lift a finger to prepare dinner due to his lethargy.

My classwork would be neatly stacked on the table, only to find everything scattered when I returned. He'd simply shrug off my questions and toss blame back at me. Instances like these left me questioning my sanity.

To keep it short, I'll jump to the end. During one of our squabbles, he suggested if I hated living with him, I should leave. After he stormed out, I took his words to heart: I began packing my things.

I gathered my guitar, my clothes, my books—anything else I owned—and crammed them into several suitcases and bags. I hailed a large taxi and rang up my sister, requesting to rent the vacant room in her house.

The landlord agreed to my immediate moving in. Without leaving a note, I left. He didn't deserve any closure. Upon discovery, he lost his cool.

He insisted on reconciling, pleading for a second chance. But the damage was beyond repair. He had crushed my spirit one too many times. It was time for me to rebuild. I began by changing my mobile number.

Despite it all, I don't regret the experience. I gained invaluable insights about venom relationships, manipulation, and emotional torment. He continually made me feel that I was the cause of all conflicts, making me question my adequacy and sanity. He convinced me that without him, I'd be alone.

But he was wrong. Since then, I've met others that showed me what true respect and empathy in a relationship should be. Ultimately, I learned that I should never tolerate anyone who makes me feel inferior or unworthy.

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20. The D In English

In 11th grade, I scraped by with a D in English. My teacher asserted I lacked writing skills and would never make it to being published. I didn't think of myself as a writer, and this grade stung even more.

However, when I established my own business, I realized I had narratives to share. This brought me back to writing. Before too long, I found myself composing material for an Entrepreneur. Remarkably, by the time I was in college and just three years after the English grade incident, I became a published author. What was the catalyst?

A shift in my mindset towards writing. As an author, I took on board that my initial drafts were not the final product. Skilled writers aren't afraid of the editing process. I used to believe my blunder was not striving enough during my high school years. It was a humbling experience to be the only one in my class who got a D.

In retrospect, that D was a stepping stone. It sparked a determination in me that transformed my writing approach and helped me become a proficient author.

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21. The SoundCloud Inspiration

I wanted to download a specific song, but it was nowhere to be found. Then, I unintentionally stumbled upon a website called SoundCloud back in 2014. They told me that if I joined and supported the artist, I could get the song I wanted.

As someone who seldom signs up for anything, I felt this was important. Even though it might look like an error and there was even a risk of downloading a virus, I still did it. 

After marking the song as my favorite, I started creating playlists of my favorite songs. Then something unexpected happened—SoundCloud started playing suggested songs.

Then, this one song blew me away—"Far From Home" by Gamper and Dadoni, a German duo featuring a singer named Cozy. It was such an unforgettable moment. I was simply frozen, completely lost in the music. This song sparked my imagination to the point where I was envisioning a whole music video to go along with it.

So what did I do next? I decided to bring my vision to reality. This was uncharted territory for me, but the motivation was strong. I even coordinated with Airbnb hosts to use their properties for scenes in the music video. This led me all the way from London to China to shoot most of the footage.

This whole journey, which I attribute to SoundCloud, didn’t make much sense, but the result was a YouTube video with 28k views, shot entirely on my iPhone. Yes, the production quality was far from perfect, but that didn't bother me. I just followed where the call led me.

Since then, I’ve collaborated with others on short films and even made another music video during a trip to America (still using an iPhone). The editing process was frustrating due to my laptop continually crashing. 

Despite this, I managed to put everything together on a substitute bus service an hour from my destination, using Splice to organize everything with simple transitions.

This journey started with a random click, and it ended up taking me to places I never expected. I initially just wanted a song but found myself directing two music videos instead.

It's amazing how the smallest things can dramatically change the trajectory of our lives.

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22. The Daughter

Marriage. I tied the knot with someone who, it turned out, didn't really care, and we got divorced within half a decade. We initiated our romance when I was 17, and by 18, I was already signing the marriage paperwork. So, why do I see this as a positive error?

This marriage blessed me with my precious, loving, and nurturing daughter—a blessing I could only have dreamed of. She erases all regrets. Her value surpasses every piece of hardship and pain, every tear shed and moment of desperation. She is the most amazing thing that has ever unfolded in my life.

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23. The Obsession

A few years ago, I tanked my first year of university. I was shattered, immensely sad, and filled with negativity. But since this was the first major setback I'd ever encountered, I was determined to understand why I'd slipped up and how I could stop it happening again.

In the beginning, I was on a mission to discover certain ways to dodge this kind of failure again. However, I learned incredible things about myself along the way. This misstep became the best one I've ever made due to what I learned from it. I don't regret it all. Actually, I'd be ready to do it again if needed.

That's because this mistake was the key that unlocked my mind, filling it with insights that some people never discover in their whole lives.

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24. The Umbrella

While on a family trip to Mcleodganj, India, we planned to go see the Bhagsu Falls. Unfortunately, we found ourselves in the middle of a massive traffic jam during a torrential downpour. Without any umbrellas with us, we rushed to purchase a couple from a roadside shop.

As soon as we stepped out of the taxi, we noticed one of the umbrellas wasn't working right—it would only half-open. With traffic not moving and unable to fully cover ourselves from the rain, we decided to call off our visit to the falls. My father decided to just leave the faulty umbrella by the side of the road as it was of no use to us. Fate would give it a new important purpose, however.

In a matter of minutes, a traffic worker picked up our discarded umbrella. Despite the wet and chilly weather, the worker didn’t even have a raincoat. He was overjoyed to get the half-open umbrella as it helped shield him from the rain.

This worker, cheerful despite the faulty umbrella, continued directing traffic in the rain. And we couldn't help but smile, thinking how things truly have a way of working out for a reason.

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25. Light Of His Life

Every night after using the bathroom and preparing for bed, I make a point to turn off the outdoor stairway lights. But one night, I simply forgot and hopped into bed. Soon after, my friend rang me up.

Her: How's it going?

Me: Just the usual stress!

Her: Don't let life weigh you down.

Me: Light! Oops, I forgot. I'll call you back.

From inside the house, I attempted to turn off the outdoor lights but it was a no go. Reluctantly, I went outside and received quite the surprise.

There was a young man on his terrace near my house engrossed in a book and using my outdoor lights to read! Pretending not to notice, I just left the light on and went back to bed. The next day, my mom told me he was studying for his HSC board exams. And given his grandpa's ill health, he had to use the terrace to study!

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26. When Forgetting Is A Good Thing

Here's the most memorable blunder I've made, and it happened during my time in Vietnam. I was racing around an old Quonset hut, a leftover from the French era. Suddenly, I halted at a door, realizing I'd accidentally left something behind. About a minute and a half later, the area outside the door was rocked by an exploding B-40 rocket grenade.

Believe it or not, if I hadn't made that small oversight, I would've been caught up in the blast.

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27. All Worked Out In The End

So, I started an online relationship with a woman who lived in a different country. After some time, we committed to each other despite the distance. We spent about half a year in a long-distance situation, visiting each other for two-week intervals, which was challenging. We were both mature individuals craving stability and consistency.

She was reluctant to move to my country due to a potential income decrease, while for me, the move promised a pay upgrade. Hence, I decided to transition to her country and left behind a rewarding career I had built painstakingly for six years. I disregarded certain warning signs before moving, assuming our long-distance frustrations were to blame.

However, living together unveiled the truth. Our disagreements amplified, and our dynamic became a battleground with each fight outdoing the last. I experienced frequent emotional distress.

Simultaneously, job hunting in a costly country was causing my savings to dwindle rapidly. I fell into a depressive state. My only escape was submitting applications and hoping to find stable employment, as my finances were not sufficient to get my own place at that time.

After a grueling application process, a multinational company eventually hired me. Although it was a demotion in rankings, my work experience still ensured an attractive salary. Now affording my own place, I still chose to cohabitate with her. I thought job search stress and adjustment to living together had strained our relationship, so I decided to give it another chance. Sadly, I was mistaken yet again.

Our incompatible personalities and mismatched outlooks on life were irreconcilable, despite even seeking professional counseling. There was simply no solution, and three months later, the relationship ended, and I was abruptly shown the door.

But as they say, when one door closes, another opens. I found my own space after a brief hotel stint and established friendships with my colleagues. Things gradually started improving.

Thanks to the strong local currency, after two years of labor, I purchased a modest studio apartment in my homeland, outright. I could even afford a year-long break, and returned home for some well-earned relaxation. As for my colleagues at work, they became my closest comrades.

Best MistakeShutterstock

28. Will Take The Next Opportunity

Back in 2012, I was curious about the whole hype surrounding Bitcoin. I was just a college student, halfway through my degree, when I started to dig into this industry. At the time, the price was $20 per Bitcoin. But after studying the price history, I concluded it was too risky for my college budget.

As it turns out, if I had invested just a bit back then, I'd be pretty wealthy today. But in a twisted way, life taught me an invaluable lesson: "The best time to plant a tree was 20 years ago. The second best time is now". You can bet I won't let another opportunity slip by.

Dodged a bulletUnsplash

29. Don’t Listen To Dad

Under pressure from my father, I hastily wed in 2012, a time when I was just beginning to embark on my career journey and earning a fair, but not considerable, income. A few matches had come my way, however, the initial three didn't pan out.

My father began implying that my career uncertainties were to blame. He constantly highlighted my flaws and failures, comparing me unfavorably with my peers, making me feel that I was falling short in his eyes.

His words had a deep impact on me. So, when the next potential partner showed interest, I agreed to tie the knot, and we got married in August 2013. Yet, only three months into our marriage, I began to see that I'd made a serious error. We faced severe compatibility problems, strained trust, and there was a slew of crucial facts about her family that had remained undisclosed until after the wedding.

She moved out in October 2013, and by the following year, we were officially divorced. Jumping headfirst into the marriage was a regrettable choice, one that I wish I could reverse. However, I've learned my lesson. I threw myself into my career, experienced a significant boost in my salary, and started taking my father's words with a grain of skepticism.

Need to Leave Now factsShutterstock

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30. Paying It Forward

I recently moved to a new job and, as per usual, it took me a bit to settle in. The work culture here was a little unfamiliar to me. I'd grown used to a collaborative environment where people stuck around after hours if someone needed a hand.

But here, as soon as people wrapped up their duties, they bolted for the door. I discussed this with my boss, who suggested I follow suit and stay professional. There were times when their indifference left me somewhat disheartened, struggling alone with a mountain of tasks.

This began to impact my mood and I grew grumpy, leading others to form incorrect impressions of me. One day, after finishing my work, I decided to lend a hand to a coworker swamped with a lot of work, despite knowing there was no monetary incentive.

But, when my manager found out, I got a lecture. They told me it wasn't worth my time since no one here helped each other and money was everyone's top priority.

Then, yesterday, I ended up with a tonne of unfinished work again. To my surprise, the coworker I'd helped that once jumped in to help! I certainly wasn't expecting that! Once everything was done, I thanked him for his kindness. He simply said that I'd helped when he'd needed it, without expecting anything in return.

That's a real team spirit for you. I don't think I've ever experienced such joy. Everything's starting to make sense now. I'm beginning to really like it here and enjoy my work.

Best MistakePexels

31. A Different Point Of View

My friends, family, and peers once advised me to complete my degree, warning me that I'd regret it if I didn't, especially since I was only a year away from graduation. However, there was an underlying conviction I held; I firmly believe that time is our most valuable asset.

I took a good look at the last year of my degree plan and noticed that the majority of it was centered on replicating real-life scenarios, much like an internship. It was hands-on training with no further skill development.

While others found this final year exhilarating, I found it illogical. I questioned, why simulate real-life experiences when I could venture into the real world and create my own? Consequently, I decided to leave my degree behind. Society may view this as a blunder, but I consider it one of my wisest decisions.

That’s How That Works factsShutterstock

32. Aditya The Hero

I was asked to jump on a project that was basically a disaster in the making. It already seemed to be spinning out of control before I even came onboard. "Surely, it can't be that messy?" I questioned myself. But as soon as I agreed to take on the task, I realized what I was dealing with.

Having spent years helping teams get derailed projects back on track, some really challenging ones I might add, this one took the cake. However, there was a silver lining.

Enter Aditya.

Part of the reason I was roped into this project was my previous experience in discovering and coordinating expert teams to handle tough issues. I had often faced scenarios where several uncertainties loomed large or other companies stepped back, as solutions seemed impossible to predict.

Regardless of whether the project required heavy-duty programming, design tasks, or some simple data entry, I had an excellent network and knew how to swiftly find the right person for each role.

Given the project's complexity, I anticipated doing a lot of the work myself. However, I extended my reach beyond my usual network and added some new members to the team, always on the lookout for potential talent. One of these newcomers blew my mindand I'll never forget it.

Despite the project's escalating pressures, he consistently displayed calm, self-assuredness, and receptiveness. He asked brilliant questions and paid attention to details that I overlooked. His communication was on point and his interaction was grounded—no confusing jargon or rigid ideologies.

Such traits are hard to come by in the software industry where developers often boast about their eloquent language skills. So, I began to provide him with more technical knowledge, and started reviewing his decisions rather than making them myself. He acclimated to changes with ease. Any modifications or revisions in his work were simple and smooth.

He would ask me thought-provoking questions and request test data from me. We both learned and grew from this experience. Agreeing to this project might have been a blunder, but recruiting Aditya turned out to be the best inadvertent decision of my life.

Best MistakePexels

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33. Burning That Bridge

I said goodbye to a high-paying salary and I dared to do it. Most folks might find that unwise, but my decision to leave stemmed from moral concerns, and I believe, rightfully so. That's a decision I made four years ago.

Fast-forward to the present, I've become my own boss and have a team of four. I make sure they're compensated well, and I am committed to never asking them to trade their values or honesty for a quick buck. My hope is that it stays this way. From the comfort of my home, I decide my working hours and live my life simply, without the need for extravagance.

Office Drama factsShutterstock

34. Breaking The Policy

Taking on a set project scope was always going to be a gamble—I knew that and had committed to avoiding these types of undertakings due to the inherent risk. If we incorrectly judged the workload, we could end up working for free and losing money in the process. 

But then this incredible opportunity walked through the door, attached to a high-profile client. It was just too promising to pass up for my business's reputation.

I found myself caught between a rock and a hard place: I could embrace the project potentially detrimental to my business or forfeit an invaluable growth opportunity. Choosing the former, it initially felt like a win. However, life quickly forced me to reckon with this grave mistake. We'd severely miscalculated the project density and couldn't rein in the client's ever-expanding feature requests.

In the blink of an eye, we were legally bound to complete a job that threatened our financial stability. I began soul-searching for optimism when I recalled the policy against set project scopes my partner and I agreed to just one month prior. We urgently shifted into crisis management mode and innovatively conceived a low-cost, low-hazard engagement called roadmapping.

This separate, exploratory phase served as a safety net against poor project assessments and the hazards attached to defined project scopes. We began offering roadmapping to our clientele and, within a year, had generated a staggering $1 million revenue solely from it.

Unexpectedly, we transformed our precarious developer agency into a flourishing company boasting millions in annual reoccurring revenue. My greatest mistake simultaneously became the best decision I've ever made.

Strange And Puzzling EncountersShutterstock

35. Finding A Better Route

I once lived in a place where traveling by subway was typical. Funny enough, I accidentally hopped on the wrong train one day. I found myself wandering without a clear path and haphazardly picked another train. Shockingly, I arrived at my final stop quicker than I would have if I'd stuck with the right route from the start.

Guess what? I chose to replicate that "blunder" every time I needed to travel to that place.

Creepiest Experiences FactsShutterstock

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36. The Mistaken Mistake

My buddy seems to stumble into fortunate situations often. He aspired to be a reporter for a newspaper. During the application process, he had to send samples of his work. Without intending, he included a piece he had previously corrected with a retraction. Thinking he'd messed up, he decided to just let it go—and his risk paid off big time.

Surprisingly, he was invited for an interview with the newspaper. They told him they admired his bravery in submitting an error as part of his representative work to show how he addresses mistakes.

Big And Small TriumphsPexels

37. Stalling Out

One evening, I was on my way home from work on my motorbike when I found myself behind another vehicle at a left-turn lane. When the green arrow signaled our turn, I set off, but oddly enough, the other car didn't budge. Reacting quickly, I slammed the brakes and inadvertently let the clutch slip causing my bike to stall.

Feeling frustrated at both me and the driver upfront, I was startled by a loud crash sound. When I glanced to see the source of the noise, I recognized it was a truck that had ignored the red light, crashing into the rear of the car that was stationary ahead of me. 

It dawned on me that, if my ride hadn't come to an unexpected stop, I probably would have ended up as the new decoration on a Dodge Ram’s hood.

Best MistakePexels

38. Freelancing

I'd been doing some side jobs for a buddy when I was let go from my job for doing the freelance work during office hours. That very day, I went off and submitted my resume to a slew of other potential employers. The very next day, one of them got back to me, asked to have an interview, and before I knew it, I was hired on the spot.

I was really freaked out when I lost my job, but surprisingly, I ended up landing a gig that paid way better within just a day.

My Friends Are JerksPexels

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39. More Than Just A Pinch

As I was preparing a casserole for dinner, I decided to add a dash of cayenne pepper. We had just bought a new bottle that had a unique flip-top lid—it revealed a small sprinkler-like grill when opened. But I was more familiar with our old bottle where you had to take off the lid to access the grill.

Without noticing the change, I unscrewed the top and poured it in. Before I knew it, half the bottle had emptied into the dish. Stunned, I tried to remove some of the pepper with a spoon, but it was fruitless. Regardless, I mixed in the excess pepper and carried on—I didn't want to waste food even if I thought I had spoilt our meal.

Surprisingly, the casserole ended up tasting great.

Best MistakeShutterstock

40. The Right Email

So, I was stuck in a job that was going nowhere, right? I ended up emailing one of my coworkers, kvetching about how my attempt to finagle an interview with another department through HR had flatlined. Here's the twist—I accidentally sent it to a top executive instead! He spoke to HR, my much-wanted interview materialized, and voila! I aced it and bagged the new position in my desired field.

Now, fast forward a decade, and I'm the chief technology specialist for our crew. Heck, I've even started rejecting offers to move up into mid-level management positions.

Tech Support Horror StoriesShutterstock

41. Love On Omegle

Back when Omegle was just starting out, and didn't even have a webcam function, I was roaming around Yahoo when I unintentionally clicked on an ad for Omegle. Suddenly, I found myself chatting with a random person. We ended up conversing for an hour, and even swapped email addresses. Later on, we decided to meet up in person, and instantly clicked. That was three years ago.

As I'm writing this, he's right by my side. Ever since our first meeting, we've been inseparable.

Best MistakePexels

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42. What A Race

In a horse race, I was placing a trifecta bet and mistakenly chose the wrong horse for a place position. What I intended was to pick the horse that was the second popular choice with a 3-1 odds. However, I accidentally selected the horse that had the least favorable odds at 20-1. Unfortunately, the moment I discovered my mistake, it was past the point of correction.

Shockingly, the 20-1 horse secured a placement and my ticket won me a few hundred dollars. Ironically, my original choice of horse didn't even earn any win.

Best MistakePexels

43. The Lottery

My folks, who are quite the fanatics when it comes to playing the lottery, experienced something unusual. Each day, Mom heads over to the neighborhood shop to invest $5 in the daily four lottery game, sticking to the same combination of numbers. However, on one particular day, the shop assistant incorrectly inputs the number of tickets, selling her 13 instead of her usual five.

Unfazed, Mom decides to just go along with it. And you know what? That was the very day my parents lucked out and won the lottery. They ended up winning more than double the amount they usually would have gotten, all thanks to the cashier's seeming "blunder".

Cruel pranksShutterstock

44. A Typo That Paid Out

During one visit to a casino, I found myself engaged in a game of electronic roulette. I planned to stake £1 on 25—oh, that number is still fresh in my mind! Instead, I unintentionally put £11. But guess what? It hit, and I bagged a cool £385.

Best MistakeShutterstock

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45. The Wrong Room

I was aiming to land a job as a beginner coder. I took a trip to the job placement agency, and there's a funny story here—I misheard the room number from the front desk person and ended up in a totally different room. As luck would have it, that room was where they were interviewing for an advanced coder role, in the same team no less.

That's how my resume ended up in their system too. Nobody actually clarified which job I was there for. At one point, I started realizing the types of questions they were giving me were way beyond a beginner's level. But the twist? I actually knew the answers to most of them! Long story short, I bagged a senior-level job just because I walked into the wrong room.

Workers quittingPexels

46. The Best Dog

Here's the story: I ended up with a dog that I hadn't originally chosen. You see, I'd picked out another pooch at the shelter, filled out all the paperwork, and even paid the fees. But, when I came to collect her three days later, they handed me a different dog.

Apparently, the dog I'd initially chosen had already been adopted. There was some mix-up with the paperwork at the shelter when I was filling out mine. They mistakenly tried to give me the roomie of the dog I'd originally selected.

I decided to go with the flow and took the unexpected pooch home. Fast-forward five years, two hip surgeries for the dog, and a whole lot of love, and I'm glad to say that Dallas—that's my surprise dog—was the best unintended choice I've ever made.

Unbelievable PetsShutterstock

47. The Accident

I had just completed a night shift when my mother needed a lift to pay a bill. It was the final day to pay, and the company only accepted checks in person, not credit cards. With a long work night behind me, I picked her up, drove her to the payment office, and planned to take her back home.

Despite feeling exhausted, I made the decision to drive. This led to an unexpected event—I ended up hitting the rear of a hatchback at a reasonable speed. The paramedics on the scene decided it was best to take my mother to the hospital as she was experiencing chest pain from the airbag deployment. It was remarkable how things turned out.

Remarkably, during her X-Ray, they discovered Polycystic Kidney Disease. Now, my mother is a shining star patient to her kidney specialist, even regaining some of the kidney functionality she had lost. And all this happened because of that unplanned accident.

The Customer Is Always WrongPexels

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48. Bet It Felt Good

Back in 1979, when I was 21, I was a waiter at a high-end restaurant. One day a family, including a young child and grandparents, came in. They made a lot of unique requests and definitely kept me on my toes. I did my best to meet their needs, though admittedly, I might not have been smiling the entire time. After they left, I discovered a single penny on my tip tray.

In the restaurant business, leaving no tip is called a "stiff". But this felt like much more than that—it felt like a pointed insult after all the extra effort I had put in for their family. I was livid but kept it to myself initially. Then I spotted the toddler dallying near the balcony bar railing. His parents were upstairs, presumably having drinks.

Of course, I didn't toss the kid across the room—I'm not a monster! Instead, I marched up to the bar and asked the adults point-blank why they'd left only a penny for a tip. They didn't have a good answer, murmuring something about me being arrogant.

My response? "Sometimes folks come here looking for an excuse to under-tip, and you're prime examples of that". Then I left them behind. I thought I'd regret the outburst, but it was too gratifying. I haven't hesitated to share this story with my children—what happened next was actually a blessing. 

Predictably, I lost my job—the family knew one of my managers quite well. But surprisingly, this loss paved the way to my journey as an entrepreneur. It's been highly satisfying and rewarding in countless ways.

Terrible Customer ServiceShutterstock

49. Unexpected Presentation

I was once an employee at a large consulting company, tasked with creating a report about adapting a famous international Enterprise Resource Planning (ERP) system for local business management.

As a junior staff member, I was the invisible guy, laboring behind the scenes to provide meaningful content. This content would then be presented by my bosses, with a considerable amount of money at stake.

After weeks of hard work, we were primed to showcase our findings to the ERP provider. We aimed to demonstrate how well their software system would conform to the Greek lawful requirements, which is what we mean by "localization".

I was there at the meeting, there to back up my team if they needed that crucial piece of information that I uniquely knew, which could potentially be a game-changer. Let me be clear: I had no intention of presenting the report. 

However, everything took a turn when my supervisor unexpectedly turned toward me, announcing, "Theo will present the results of the analysis he's conducted these past few weeks".

Suddenly, I was sweating profusely. My hands shook as I darted nervous glances around the room. I knew the polite and diplomatic thing to do was say no. However, I made a spur-of-the-moment decision to plow ahead regardless—a move I was entirely unprepared for. Looking back, it ended up being the "best" mistake of my life. Why "best"?

1) I still had my job at the end of the day.

2) I learned a valuable lesson.

I stood up and attempted to make my pitch. It lasted barely two minutes, (which seemed to stretch to eternity), before I was asked to step aside for someone else to finish the presentation. That experience is forever seared in my memory. It taught me the importance of always being ready for surprises.

Best MistakePexels

50. The Dating Site

So, I joined a dating website. I was entirely new to this online dating craziness and had no idea what was happening. I thought all the profiles were real and was immediately bombarded with some rather rude and unsolicited messages.

It was certainly an eye-opener. I spent nearly a full day on the site, managing to browse through a few profiles and sent out polite messages. Where did I go wrong? I didn't read the small details.

The website had this great feature that showed you how close someone was to your location! I encountered a handful of pleasant individuals and swapped messages, but one profile stood out. We seemed to click, and the cherry on top was the website showing she lived just three-quarters of a mile away from me! This could be interesting.

She was intelligent, witty, and conversed naturally. She had this vibe of being relaxing and comforting, and her knowledge about various topics was quite impressive. Calling her perfect doesn't quite cover it.

She always seemed to say the right things at just the right time, like a dream character sprung to life, but even better than my wildest imagination. She seemed too amazing to be real, and I sensed something was amiss.

Could she be an older lady pretending to be young? Or perhaps I was being catfished because women like her didn't pop up on dating sites. Despite my suspicions, things got serious, and I was so smitten that I asked her to be my girlfriend.

Being the level-headed person she was, she suggested taking things slow. And I did—I waited four days before declaring my love for her. By day five, I was suggesting we meet. Initially, she dismissed my idea with a laugh, but I was sure she wanted to meet as well. Our connection felt strong; we just needed to bring it into the real world.

Then one day, she finally agreed to meet, suggesting that I should book the tickets. Wait, book the tickets? But she was supposed to live nearby! The truth was, the site had displayed her location as 1.2k km away. Instead of reading it as 1200 km (745 miles), I had assumed it was 1.2 km!

To this day, this remains my all-time favorite mistake. Honestly, if I knew she lived that far, I doubt I would even have started this. I had no experience with long-distance relationships and didn't think they ever worked out.

I would have missed out on an incredible partner. Yes, we are still going strong and plan on doing so for the foreseeable future. She's still funny, delightful, and encouraging, and never ceases to awe me every single day. Sometimes, not seeing the bigger picture pays off, like it did in our case.

My life's best blessing occurred due to a silly blunder.

Best MistakeShutterstock

.Sources: 1, Reddit


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