We all know that doing new things is scary. Whether it’s applying for a job you’re unqualified for or confessing your love for someone, these moments can make or break us. But, you know what? Sometimes you just have to go for it, and that’s exactly what these people did.
#1 Disney World
I once decided that I was going to skip a few days during a work conference and go to Disney World and Universal. Sorry, but there was no way I was getting a free pass to Florida and not going to the Wizarding World of Harry Potter. Looking back on it now, I don’t regret anything because it was worth every second.
#2 Hard Phone Call
I called my wife and told her I had a problem with partying. It was a really hard phone call to make, I’ll tell you that. Of course, she already knew, most did. But, getting it out there verbally was hard. I’d also like to thank Topo Chico bubbly water for satisfying my “need to drink cold bubbly drinks” and my “need to be holding a beverage” urges. I’ve been sober and hydrated for one and a half years.
#3 Greyhound Ticket
I was going through some domestic stuff and wasn't allowed to leave the home for months at a time. Can't remember all of what they did to me. My grandmother had passed away and I'm pretty sure it was the intent to get me out of the way for my inheritance. The inheritance money finally came in after about six months of this treatment. While the other person took his half and went on vacation, I took my half, bought a Greyhound ticket and got out of there. Best decision I ever made.
#4 Trauma Hospital
I was a flight nurse at a company who liked firing people. We were transporting a patient from a car accident who became pulseless. Per policy, we were meant to go to the closest hospital. Our closest hospital was nine minutes away, however this hospital was tiny and couldn’t care for our patient. 13 minutes away there was a trauma hospital. Our patient was gone and statistically speaking was going to stay that way. But, his only hope was the trauma hospital. I told the pilot to go there, knowing full well this would be reviewed and I would be fired for violating policy. Fortunately, the trauma hospital did a fabulous job and he survived. I was reviewed but not fired.
#5 I Want it All
About ten years ago now, I followed my now-husband all the way to Canada. We were together for less than a year, so I know how it seemed to a lot of people. That said, I have absolutely zero regrets. From the outside, it sounded really silly, but we knew it was an all-or-nothing moment. We both wanted it all.
#6 World Traveler
I bought a sailboat and quit a decent paying job that I hated. I sailed from New York to the Caribbean where I hung out for a year. Then, I sold the boat back in Florida and then spent the next five months hiking the Appalachian Trail. I went back to work for a year and now I’m backpacking through South East Asia for the next six months.
#7 Can I Call You Back?
Asking my now-wife if I could call her back. She initially called me, looking for a roommate who had moved out. We talked for a couple of hours that night. I didn’t want it to end, and neither did she, apparently. So, I called her back the next night. We've been together now 17 years and got married two months ago.
#8 Asking Her Out
I once decided that it was time to ask my crush out to a dance in middle school. But, what made it even scarier was that I asked her out in front of all her friends and a lot of other kids. She politely declined, but I’ll be honest. The simple act of asking her was a victory for a shy kid like me to even do it.
#9 Backpacking at 18
I once decided to go on a solo backpacking trip when I was 18 years old. I'm a worrier and not very good at handling stressful situations. Not to mention, at the time I decided to go, I was also super introverted. The good news is that my trip really helped me realize that I’m capable of a lot more than I thought.
#10 Follow Your Dreams
I once told this woman how I felt about her, even though I was 100% confident that she didn’t feel the same way about me. Well, we’ve now been married for two and a half years with a beautiful baby girl. Follow your dreams, gentlemen. Take it from me and similar stories. You never know what could happen, apparently.
#11 Going Skydiving
For me, skydiving was one of those moments where I decided to just go for it. The plane they take you up in is such a pile of trash, so I actually felt safer jumping out of it than landing in it. The way the door shudders as you get to jump altitude really didn't help either. Honestly, I just wanted out of there.
#12 On a Whim
Proposing to my wife. I was showering and started thinking about how much I loved her. I decided, “to heck with it, I'm marrying this woman.” I got dressed and drove directly to her place to propose. No ring, no fancy speech or atmosphere planned. Thank goodness she said yes. Six years later, we’re happily married with two kids.
#13 New House
I was sitting in a terrible apartment, listening to the upstairs neighbor play fetch with his dog in the house. They woke me up at 4:30 a.m. I’d been searching for a new apartment, but all I could see was my next bad rental. So, I ended up browsing Zillow and stumbled upon a townhouse in one of my favorite neighborhoods, in my price range, with all the features I wanted.
I stared at it for a week, then said “Alright, enough. I was going to end up buying a house in a few years, might as well just do it now!” Things got kind of chaotic for a few months getting funds sorted, getting inspections and packing and moving. But, I moved in over a year ago and absolutely love the house.
#14 Music Store
I had been playing guitar for approximately six months before leaving for college. I would walk by this music store every day. After half a semester of walking by the store, without thinking about it or planning for it, I actually went in. I then walked out with a Gibson SG and I've been playing it ever since.
#15 Grownup Decisions
I went to PetSmart and they had a rescue there trying to gain visibility for their adoptable puppies. I was there to get fish food for the class pet at school. However, I went over just to look at the puppies because… well, they’re puppies. Holding one, I thought, I wish I could have this puppy. Then I remembered, “I’m an adult in my own house. I can get a puppy if I want!” Then I got her, on the spot.
#16 Just Do It
Two years ago, I spent less time worrying about consequences and people’s opinions and just did stuff I wanted to do. I bought my first house and I have flatmates who pay off most of the mortgage. I also met some really cool people. I got my first tattoo and I’m still getting compliments on it. I also tried stand-up comedy for the first time. I'm still doing it regularly, made some great friends, and it's been amazing for my depression and social anxiety.
#17 Wrong Place, Wrong Time
I got into some bad stuff, even though I didn’t actively seek it out. I was in the wrong place at the wrong time with the wrong people. What I tried was incredibly euphoric — too euphoric. I started doing it more and that led me to a ten-year spiral into a debilitating addiction. I’ve been clean for three years now, though.
#18 Hand Holding
Holding my boyfriend’s hand. I know it’s super lame-sounding, but it was pretty big for me. He had his hand right over mine and I know he wanted me to hold it. So, I did and it was huge for me because I was so anxious about it. I decided I would go for it and hold his hand even though we had only been talking for a few days. We’ve been together for five years now.
#19 Across the World
For me, it was deciding I was going to move across the world for a job. It started out just as me being curious about it and asking questions. Next thing I know, I was being offered an interview and then the job. I decided to throw caution to the wind and just do it. It turned out to be a wild experience, but one that I'm so glad I had.
#20 Against Better Judgement
A few years ago I met a guy on a dating site and we spoke for about a month before he asked me out. We went on the date, had a great time, and afterwards he asked me if I wanted to go back to his place. Mind you, I was raised very conservatively and also to be essentially scared of guys. Against all of my better judgment, I agreed and we walked back to his place. We had a good time and watched a little bit of TV. After a couple of hours, he walked me back to the diner, gave me a kiss on the cheek, and we parted ways. We were just married on August 31st of this year.
#21 Best Friend
I once called my best friend during a night when I had partied way too much and wasn’t exactly in a sound state of mind. I told her that I was in love with her and then proceeded to say much more about us. The follow-up conversation was basically finding out everything I said to her and seeing how she responded.
#22 Planned Parenthood
I was sitting in Planned Parenthood parking lot, debating whether I was ready to be a parent at 19. I don't particularly like kids, I’m selfish and just couldn't imagine myself having children. But, I couldn't bring myself to go in or put my child up for adoption. So, I said, "I’m doing this." It was the best decision I have ever made because my kid is great.
#23 Lemme Take a Selfie
It was graduation and I decided, “To heck with it. I’m taking a selfie in front of everybody.” They called my name to accept my diploma and shake hands with the principal and that’s when I whipped out my phone and snapped a selfie. I ended up on the front page of the news the next day and became a legend afterward.
#24 See You Around
I met my current girlfriend at a party and she handed me her phone as she went to the washroom. Turns out, she didn't have a password, so I put my number in her contacts. We chatted the whole night and after walking her home, she called after me, "I guess I'll see you around or something.” So, I hollered back, "My number’s already in your phone." It was one of the smoothest moments of my life.
#25 Seeing Iceland
My first solo trip was when I decided to do something for myself. I was tired of living a routine and I honestly felt so empty and isolated. I decided to fly to Iceland and it was the most magical place I’ve ever seen. I actually got to see glaciers for the first time in my life. I would definitely do it again.
#26 Dressing Up
I have really bad stage fright; I’ve had it since I was little. I can't get in front of any sort of group of people without having a mild panic attack with shaking, dizziness and hard breathing. But, I love to perform. Two days ago, I signed up for a cosplay contest at a convention. I’ll be on stage in front of many, many people. But, I’m not backing out.
#27 Teaching Job
So, my first teaching job was on the border of Wisconsin and Illinois in a small town. It’s cold in February. It’s so cold that I remember going home one weekend, renting a stack of videos from Blockbuster and realizing I wasn’t going to talk to another person until I went back to work on Monday. So, I went in and told them I was quitting at the end of the school year and moving to California. Which I did. I lived on the beach in Newport for a year, then moved up to SF. It was the best “I’m doing it” moment I ever did.
#28 The Composer
On the first day of my freshman year, I was put in band class at my high school. I didn’t originally want to be in that class and would’ve rather been in a mechanics class. But, after realizing how cool the director was and how much of a pain it would be to switch, I stayed. Now, I’ll be going to college, majoring in music, starting this fall. My main instrument is the trombone and I have a career goal of becoming a composer.
#29 Man-Made Reef
For me, it was snorkeling in a man-made reef! It was honestly one of the most exhilarating moments of my life. I got to see all kinds of colorful fish and other sea life, which was awesome. I did, however, cut my foot on the reef, but I still had fun. I felt so adventurous at that moment and I’m glad I did it.
#30 Mutual Friend
I met an Australian girl at a mutual friend’s wedding. This girl was also traveling around the States and I joined her for a bit of it. She went to London to work a contract gig for six months and I went back to my seasonal chef job. We stayed in contact and decided to do some more traveling when our jobs ended.
We met up in the Middle East and saw many countries over three months. We then went back to work apart again and the next year did a big trip through SE Asia. One thing is certain, if you want to really get to know a person, do some long-term, rough travel together in third world countries for a while. Eventually, we just got tired of only meeting up in strange corners of the world and exploring them together. This May, we’ll have been married for 20 years.
#31 Euro Trip
I was really shy and insecure in high school. Although I was deemed "gifted," I avoided any extracurricular activities I thought were too nerdy because I was desperate to be popular. Somehow, I got an opportunity to go to Europe with a student ambassador program. Instead of noping out at the idea of three weeks with 40 strangers, I went all in. I had the greatest experience of my life at 15.
#32 Doing What’s Best
To be honest? My “I’m doing this” moment is from nearly 20 years ago when I checked myself into a mental hospital. It was torture. But, I knew I was a threat to myself and would succeed at causing myself harm if I didn’t do something. I can’t say that my life has been a bed of roses, but I’m here. That’s enough.
#33 Round One, Fight
When I was in high school, our wrestling teams had an annual boxing match against our rival school. The rules were that you couldn't have prior boxing training, in the hopes that everyone would be the same skill level. The year I did it, there was no one at the rival school in my weight class willing to fight. I trained for three months with the rest of my teammates, thinking I wouldn't get a match.
Two weeks before the event, the boxing coach told me there was a kid at the other school who said he would box. But, he had been boxing for six years and was actually the champion in our region. He was also undefeated so far. They weren't going to let him fight unless I agreed to it. So, I thought, “Alright. I’ll do it.”
Two weeks later, the match started and the whole first period I was getting completely destroyed. I was so tired by the end of the first round that I couldn't even hold my head up. I went three rounds and was a complete mess. After the fight, I don’t think I moved for a whole two days. It was horrible. But, at least I did it.
#34 On Second Thought...
I once asked a girl to prom who I was friends with. I also invited her to see this one show at the local performance theatre. She said yes to both. However, she later said to me that she’d made a huge mistake by agreeing to go with me and never spoke with me again. At least I got to see a good performance, though.
#35 Storyteller
I posted an original horror story on the r/NoSleep subreddit a few years ago. I debated with myself for days on whether it was any good. I posted it and didn't look at it for a day or so. It did pretty well, so I posted more stories, which did even better. Now I say, “Alright, I’ll do it” every few months when I publish another book on Amazon because I still worry if it's any good.
#36 Started From the Bottom
My friends and I talked of starting a company with no outside backing or salaries, just sweat equity… during the Great Recession. I had two toddlers at home then found out that our third was on the way. Some of my best friends tried to talk me out of it. My wife and I sat down and decided that no matter what, we'd get through it together and never looked back. Ten years later, we have 400 employees in 13 countries.
#37 Leap of Faith
I jumped off a 40-foot cliff after sitting at the top for at least 20 minutes. I wasn't going to let myself climb all the way back down and there was a big crowd of people counting me down. Fun fact: that was the moment I really committed to living honestly and bravely. I told a guy how I truly felt about him the next day, started standing up for myself on the spot, moved across the country... all sorts of things. Nothing was ever as scary as staring down into that water thinking I'd always regret not jumping.
#38 Off to School
Applying to and going to grad school. I got laid off from a retail position and was feeling really dissatisfied in life. I’d been contemplating going back to school for a bit. Getting laid off kind of flipped a switch in my head. I used half my final paycheck to pay fees on the applications and the GRE. I’m just about to finish up my first quarter.
#39 Moment of Revelation
I was out to eat with a bunch of guys from my fire department. I was a junior at the time, so under 18 and not a full member. I was a pretty shy, dorky kid. Two guys that I really looked up to were going back and forth about whether this one girl at the bar was someone one of them used to date. She was there with a friend and both were really attractive and totally out of my league, particularly for a shy kid.
But, after 10 minutes of them discussing it — and neither having the courage to go up to them — I had enough. I got up, walked over, and asked if she was who my friends thought. She laughed and said no. I thanked her and returned to my table. Nothing more happened with the two girls. I wish it ended with something juicier, but it didn’t.
What did come of it, however, was that I stopped idolizing those two guys I worked with. It was then and there that I realized they were just as afraid to talk to hot women as I was. I also realized life wasn’t going to end if I got out of my shell, so it ended up being a huge turning point in my personality.
#40 Valentine’s Day
My roommate from college worked with this beautiful woman. I mean, she was way out of my league. At the time, she was dating this good-looking idiot who cared more about his hair than her. I once went by the store where they worked on Valentine’s Day. She was upset because he didn’t even call her on, in her words, “the most romantic day of the year.” So I thought, “I’m doing this” and went down to the florist and bought her a bouquet of a dozen red roses. I then told her that she deserved better than what she had. Two weeks ago, we celebrated 28 years of marriage.
#41 Heading to Africa
Going to Zambia, Africa without my parents or anything. I was 16 and was with adults, but they mainly just let me do my own thing. It was well-organized and we were staying with people who we knew very well. We’d help them with this puppet show, so it was fun, but I was still 7000 miles away from my parents and all my family. Regardless, it was one of the best experiences I've ever had.
#42 Take a Chance on Me
I decided to start a relationship with a guy who was overweight, unemployed, had really bad teeth and lived with his parents in his 30s. Also, he had a kid and wasn't allowed to visit her as per her mother. Sometimes, it is worth investing in a person. We’ve been happily married for over five years now and have our own kid. He just got promoted to a directorial position at his company. He’s in great shape and fixed his teeth. He’s an amazing person and the best husband I could have asked for.
#43 Switching Careers
I decided to stop studying pharmacy after four years (I only had a half a year before I graduated) and started dentistry from scratch. It would be another six years, but I was depressed about studying something I didn't like at all. I also only went because I didn’t get accepted into dentistry at first. Yes, my parents despise me.
#44 Chasing an Eclipse
I’m an astronomy nut. A buddy and I had planned on taking a trip to see the solar eclipse two years ago, but as the date got closer we never actually made arrangements. So, as I sat at a bar celebrating a buddy's birthday, the conversation steered to the eclipse. We talked and I explained some of the nuanced details of it. But, we were in Texas.
I already had that day off of work and out of curiosity started looking at the closest point from Austin where I could see 100%. I did some quick math and realized that I had 17 hours to make a 13-hour drive. So I got up, walked to my truck and drove overnight to Jefferson City, Missouri. I made it with enough time to enjoy a local celebration and see what I can only describe as the most incredible thing you will ever observe. I spent two nights in Missouri and drove home.
#45 Had Enough
I decided to escape my parents' house through a second-storey window. I had been living in that toxic situation and was finally fed up with how my parents treated me. I would've left through the front door, but I knew that they'd yell at me and get angry if they saw me leave. I retrieved my bike from the garage and biked eight miles through sleet and freezing rain to a friend's house, where I finished eighth grade.
I remember being insanely paranoid the whole time over my parents. But in the end, it helped me realize how messed up the situation I was in was. It also helped me realize how toxic a relationship I was in at the time. My ex-girlfriend was constantly trying to convince me to stay in this situation, even knowing how bad it was for me. I’m glad I got out.
#46 Runaway Bride
One rainy April day, I called my fiancé for almost two years and asked if he wanted to cancel the venue and reception for our wedding at home. I asked if he wanted to travel 1500 miles to Colorado to elope in the Rocky Mountains. He agreed and we saved a ton of money and a ton of stress. We’ve been married since July.
#47 Getting Closure
I once decided that it was time to write out the things my ex did in our relationship and how they affected me. I also acknowledged some not-so-awesome things that I did as well and apologized for them. I decided to do all of this two years after cutting ties, so I could finally get closure and speak my truth.
#48 Running Home
I once ran home at age 13 at 3:00 a.m. from a friend's house that was really far away. They were all being really, really rude and mean and at the time. I was contemplating just dealing with it and sucking it up for the weekend since I was supposed to stay over. But, I ran home. My parents were not exactly happy.
#49 End of the Line
Months ago, while I was a cashier, I had a really bad rush. About 10 to 13 people were waiting in line at this small, dollar-store like business. The procedure dictates that my manager on duty is supposed to help clear the line, so I called for her. She had a reputation for making excuses to avoid going to the register. Eventually, the customers got hostile and demanded that I go faster. I couldn't take it anymore.
I told everyone we were going to wait for my manager. It took 10 minutes and eight additional customers before she walked by asking why I wasn’t working. I showed her the employee handbook, stating that she has to be here in the event of this scenario, no exceptions. She got fussy, saying she knew the handbook.
So, I screamed, “Then if you know the rules, get off your hindquarters and apologize to these customers! Otherwise, I’m clocking out and our store manager can ask me why!” I felt bad because kids were there. So, I apologized to every customer who I rang up and wished them well. The next day, she got written up and I got a lecture. Totally worth it.
#50 Tiny Island
I decided that it was time to move thousands of miles away to a tiny speck of an island where I'd never been. I also didn't know one person there. Fast forward to 14 years later and I have a family. We built a house together. I also have an amazing career in a field I love. I really couldn’t imagine living anywhere else.
