Let’s just say that when big storm rumbles through, my can husband knows where he can find both myself, and my dog - it’s just a matter of who is in which bathroom, shaking like an idiot. 
Baghdad in 2006.
A few:
In my late 20s, just after getting married and moving into a new house with my bride, I climbed up on our steeply sloped roof (without even tying a safety rope attaching me to the chimney) to remove an old TV antenna. I still can’t believe I did that.
Earlier, when my GF and I were boating out on Lake Mendota (a fairly large lake in Madison, Wisc.), I dropped both sails on the Lightning sailboat I was piloting. It was calm. My GF and I jumped out for a swim. (I’ll bet you all know where this is leading to …)
Yep, a big wind suddenly came up and the sailboat’s sails, even though I had lowered them to deck level, caught enough wind and the boat started to sail away from us quite quickly. I started to swim madly after it, and after what seemed like an eternity – but was probably only 2-3 minutes – was just barely able to reach out and grab a short line that was dangling off of the stern. I was totally exhausted from my mad swimming, but I was eventually able to pull myself onto the boat.
When I sailed back to where my GF was treading water to scoop her out of the water, she told me that I got there in the nick of time, and that she was on the verge of going under. She still married me a couple of years later, and I’ve done progressively fewer stupid/dangerous things since.
But I didn’t quit cold turkey, though…
Two years ago on the island of Hawai’i, I was snorkeling with our teenage son, when we separated, mainly because I got caught in a rip tide and was heading out to sea. Luckily, we were at a beach with lifeguards (which was not always the case with our snorkeling ventures), and one of them dashed out to me on her rescue surfboard and brought me safely back to shore.
And just this last December, I was back on Hawai’i, snorkeling at Two Step (unofficial beach, no lifeguard), and went far out from the shore where people had spotted a pod or two of dolphins.
I found the dolphins, and swam with them up close (got some great videos with my mask-mounted camera) for a long, long, time. (Hey, it was mesmerizing … what can I say).
Well, I spent way too much time out in the bay, because I was totally exhausted by the time I finally swam the 100-150 yards back to shore. I had to be pulled out of the water by bystanders.
Oh, and that same trip, a few days later, I was riding my rented motorcycle on the no-services-for-50-miles Saddle Road that goes across the center of the island between the two major volcanoes, hurrying to get to a rendezvous with my family when I got caught in a terrible thunderstorm. Practically no visibility, with lightning strikes nearby. No place to pull off, so I slogged through it, albeit at a slow pace to keep myself from wiping out.
When the storm broke, I was way behind schedule, so I sped up to make up time. This was when I learned that the Yamaha FZ6 tops out at 119 mph. 
Oh, and I’ve been riding motorcycles since I was a teenager. Sometimes very fast. So there’s that, too.
I guess my wife knew what she was getting into…
ETA:
P.S. Oh, on that same trip last December, I also jumped off the cliffs at South Point (Ka Lae)!
Young and stupid in college, ~1989. I decided at 3am, since I was the only car on the road, that I was going to run every blinking red light to get to this house I was staying at in the rural outskirts of Dallas. I couldn’t see very well because I needed glasses but didn’t know it yet, and because I was drunk, so I interpreted one blinking red light as being farther away since it was lower on the horizon.
Turns out it was lower because it was a railroad crossing arm, which I drove through, shattering my windshield. Confused, I looked in my rearview to see a train was speeding by, which I would not have heard since I was blaring my stereo. I shrugged off that close call and continued to drive another five miles to the house with a shattered windshield and my head out the window, with tiny pieces occasionally breaking off and stabbing me.
Thankfully that was enough of a wake up call to make me stop being reckless and stupid with the drunk driving, a lesson way too many people I know still haven’t learned, 24 years later.
Firefighter stuff… some nontraditional:
- Being on a roof seconds before it collapsed. (have a picture above my monitor to remind me)
- Diving on a 5" hose that had the coupling fail to protect a new guy
- Diving on a bottle whose coupling failed and was bouncing on the ground to save the above new guy and 3 others. Mind you, SCBA bottle failures can be bad
The last two incidents happened 2 weeks apart from each other.
Sounds like you’ve gone from abject fear to employing appropriate avoidance techniques. I’m declaring the therapy a success. 
A colonoscopy.
I was 150ft underwater and swimming down fast as I was chasing another diver who had totally lost buoyancy control. The bottom was several hundred feet below us. Only had a single 72cuft tank which I had to share on the way up after I caught said diver.
Yes, but I’m only 3 inches tall! 
I’ve spent a lot of time doing low-altitude surveys (sometimes less than 100 feet) from a small single engine plane over offshore islands and tropical forests. I’ve several times landed from a helicopter on a small pad chopped out of the cloud forest on top of a jungle peak. A plane crash into a jungle somewhere is probably the odds on favorite of how I’ll go if I cash out prematurely.
I’ve had a jaguar and a leopard walk within 30 feet of my tent at night, not to mention a battle royal between a pride of lions and a pack of hyenas within about 100 yards. I’ve inadvertently gotten within 30 feet of a forest elephant, and had my vehicle chased by them. I’ve had a bath in a river where only a few weeks later an acquaintance lost an arm to a Nile Crocodile.
I’ve climbed Long’s Peak and Mt. Shasta, but probably been in more dangerous situations scrambling up or down on any number of steep slopes in many other places.
I did a lot of hitchhiking in my younger days, including a coast to coast trip. Some of the rides were pretty dicey; not menacing but just bad drivers or crazy people.
A friend of mine and I once rollerbladed from his apartment in Queens, across the Queensboro bridge, and then all the way down to the battery.
At one point a cab tried to hit me and I had to jump onto the bumper of the car in front of me, which turned out to be a van full of cops. They laughed at me and told me “watch out for the yellow ones.”
I’ve gotten into some dangerous situations backpacking. Very steep and slippery slopes that I didn’t want to be on. I had a bad scare in 94 and scrapped myself up in a fall. I slid about 25 feet and then had to climb back up to the trail. That was the one time that I cut a trip short. I was banged up and sore for several weeks.
Still love backpacking but now I stick with known trails that I’m comfortable with.
Hmmm. At night in Tegucigalpa Honduras got seperated from my friends at a club. Let three strangers give me a ride back to the hotel. They turned out to be super awesome but still it was a potentially dangerous thing to do.
Same trip but in Guatamala let two locals talk me into going to a brothel with them. Again it could have been dangerous but they too turned out to be super cool.
I had open heart surgery last summer. They stopped my heart. That was probably the most dangerous moment I’ve ever experienced.
Retrieved a dropped umbrella from the subway tracks.
I thought this would end with the revelation that you are, in fact, Superman
A few incidents when was a teenager out hiking:
The only way to get to the other side of a small valley was to crawl through dense clumps of tea tree using tunnels made by feral pigs. We did that while pushing out backpacks ahead of us. We could hear pigs moving through other tunnels near by.
Hiking along the cleared area under high-tenson powerlines (again for speed) during a thunderstom.
A few years back I was running a camp and acting as a radio relay point between base and a group doing activities in a river valley. I was in a bus situated on a ridgeline in the saddle between two knolls (-35.72089,149.146142) if you want to see the exact spot. A big thunderstorm cam over and I had lightning strikes on the knolls in front & behind me. I relocated pretty quickly 
A couple of things while flying where, had I not taken the correct actions, could have ended badly. But I did, so it ended there. But the one time I felt I did something stupid that really put me at risk was very mundane.
I used to work at a rock climbing gym. If the guide lines with which we hung the climbing ropes fell out of the belay system while setting up or taking them down, we had to climb up the back of the wall to re-set them. It was rafters, about 40 feet high. One night this happened when I was closing up by myself. I should have waited, but instead I just did it solo. That is, I free climbed up, then braced myself at the top to work with both hands on the rope. When I briefly slipped I suddenly realized how foolish this was. If I fell, nobody would be there until the next morning. I finished and climbed down carefully.
On reflection, I think what tricked me into this was that it was climbing rafters, which look childishly easy compared to the business side of the wall. But it’s still way up there, and it was stupid to do it with no safety equipment or other people around.
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The flight deck of an aircraft carrier.
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The streets of the East Side of Cleveland after midnight.
I worked in a bank for a long time, so I’ve had guns pointed at my face, been assaulted by customers, fought fires (and pulled a child out of a burning car in the drive up), searched for and found bombs, and gone on countless currency runs where I carried tens of thousands of dollars in cash alone (as a small 20-something woman). Hell, even false alarms were fun: I would have to leave the bank building holding my hands up, my “official” ring of bank keys in one hand (this indicated I was a good guy). After the first time I always focused my eyes on the ground about 20 feet in front of me rather than the gathering of law enforcement folks with all sorts of guns trained on me.
Since then it’s mostly stupid stuff like riding my bike at 55mph down highway 9 from the summit and sailing San Francisco bay during the summer.