Some adjustments to humn's story, which with one major exception produce a very good fit:
The higher-ups (my peers) in our company drop f-bombs all the time, so I'd had enough of them and decided to go on an journey, escaping the current situation.
Depart from Escape key, on same row as F (function) keys.
First, I headed south-east, and the first place I stopped at was full of surprises.
I continued on south-east, then decided to go east several miles during which time I experienced thefts on multiple separate occasions. As it turned out later, what I was wearing then was attracting thieves.
In view of the next stop, this must be QWERTY (or maybe ASDFG or ZXCV). I don't yet understand why. Here's one possibility I don't like much: QWERTY is a famously bad password so if "wearing" can mean "using as password for protection" and "theft" can mean "compromise of computer account" -- and if we don't distinguish between "what I was wearing" and "what route I was travelling" -- then that kinda-sorta fits, but it seems an awful stretch. (It fits questioner's hints better than it does the original clue.)
Trying to change my luck, I changed direction and headed north-east. I played some one-armed bandits there, and hit the jackpot.
I think this must be 7 because lots of slot machines have a ("lucky", I guess) 7 as one of the symbols they use. And perhaps "and hit the jackpot" is pointing at the & on the same key. (At humn's request in comments, I note that I wondered briefly whether it might be 6/^ because the caret is sometimes used as an insertion mark, and one inserts things into a slot machine when playing it.)
After leaving the casino, I headed east and decided to bet on horse racing, where my money multiplied.
* (shift-8). There might possibly be an allusion to % (shift-5) here -- probabilities! -- but I don't think that's intended.
Then I continued east, and for some reason, I got this sudden feeling that something new might start up, and it did! But they say that everything that has a beginning has an ending, and what promised to be a new beginning for me came to an abrupt end in just a mile.
() (shift-9 and shift-0)
After pulling myself together, I drove southeastward and parked my car for a while.
After a bit of a rest, I headed north-east, and then got on the eastbound highway. To stave off sleepiness, my wife riding shotgun started asking me simple math questions.
+ and = (on same key). Possibly - as well, which is where the NE and E roads met.
Continuing eastbound, we suddenly began to lose consciousness, not from drowsiness but rather due to some external force that we had no control over. Our memory of the entire journey up to that point was completely erased. Today I can share this story with you thanks to the diary I kept during the trip. Keeping records has saved the day.
Backspace key deletes things.
(Although I think it likely that this is basically The Correct Answer, I hope humn ends up getting most of the rep for this question because I don't think I would ever in a million years have figured out what this was about. Also, his answer is much funnier than mine. So if you're reading this and inclined to accept or upvote it, go give humn's answer an upvote first.)