Eve is a game about risk, of course. Every time you undock, you risk the destruction of your ship. For that reason, any good mentor will suggest that you shouldn't get too attached to your ships. Save your fits so you can recreate them when they die. Don't covet them. View them as the tools they are, not good friends.
And, try not to think about how many innocent crewmen die when your ship goes boom.
For that reason, everything we do goes into a cost/value analysis. Everyone does this, from the freshest newbro to the most grizzled, cutthroat veteran. Sure, the former may not have as much information feeding into that analysis and the veteran will tell you he flies recklessly even as he very carefully and automatically selects his fights, but they're asking themselves essentially the same question.
What are my chances?
In poker, they say that the thing that differentiates a winning player from a losing player isn't how big they win, but how small they lose: in other words, don't throw your money away on hands you have a low probability of winning, and make cheap mistakes instead of expensive ones.
In Eve, it's very difficult to differentiate a good risk from a bad risk sometimes. Sure, folks will point to lossmails and point out all the bad decisions that led up to them, but the simple truth is that 9 times out of 10, even that very combination of mistakes won't result in a loss. The trolls will do exactly the same things and make the same mistakes, but they will get lucky and survive.
We're constantly trying to push the envelope, sneak in one more cycle of ore, wait one more second before warping off, saving a few more seconds by risking a gate-to-gate jump in a pipe system with neutrals. Efficiency is the name of the game, and often, it works out okay.
Sometimes, it doesn't. And those times nag at us. They tug at our awareness, telling us something isn't a good idea even when we've done it countless times in complete safety. Recent experience can make us more blind or more aware of it, of course.
When I'm roaming in FW space in a frigate, It's quick align time means only squishy ships can catch it on gates, the kind of ships that usually can't tank gate guns. And that feeling persists, right up until I'm two-shotted by a gank Coercer.
But sometimes, we become gunshy because of a bad experience, an experience that tips the paranoia up a bit and makes us question all those little risks we take on a daily basis.
For me, it was when I lost my ratting alt's Tengu in Thera. I was nullifed, but I warped to 0 on a WH signature in Thera with about 500 mil worth of loot. I landed about 6 km from the wormhole... right on top of one of the ships that was camping it. I was decloaked by proximety and was bumped out of range of the hole before I could move that extra kilometer. It was about a 1.5 bil loss.
It was a ridiculously bad combination of factors. I happened to land on a hole being camped (in my experience, Thera holes really aren't camped that often), far enough away that I couldn't immediately jump, within 2,500 m of another ship, and on grid with bumping ships that were close enough to immediately push me away.
Sure, I could have avoided that loss by warping to the hole at 100 km to take a first look and bookmark the hold itself for a more accurate warp-in. But who really does that? I scan down hundreds of wormholes a week, and in 99% of them, I'd have no problems warping to 0 on the sig so I could quickly jump through and see where the other side leads. It's a fringe case, and the means of avoiding that loss really weren't practical on a regular basis. Loss is inherent to the game.
I was traveling a few days later in a Proteus when I came across a gang trying to catch me. I was nullified and cloaky, but they were faster and were setting up on each of my gates. I waited in system for about twenty minutes, and fifteen or so after they all cleared out of local. I hoped they had cleared out and moved on. When I jumped the next gate, I spawned in system exactly 250 m from one of the ships in their fleet... and it wasn't moving or orbiting. I tried to overload my AB and burn out of range to re-cloak, but I was predictably caught and killed. There was really nothing I could do in that situation, other than log off for the night or use a second scout account (both of which hack the conditions of the scenario).
Yet both were fresh in my mind last night when I was bringing some fresh ships in through the Nourvukaiken/Tama gate with a Viator. My old friends in Rapid Withdrawal were camping the gate with about ten or so ships, all were flashy, and they seemed to be pretty dedicated to it.
Now, normally, I'd do the quick calculation, figure outhe volume of space on the surface of a sphere with a 12km radius (really, more likely about 18-20 km, when you factor in the width of the stargate itself), and decide that I had more than enough empty space in which I could spawn safely.
But then that Proteus loss popped into my head. sure, I only had a couple hundred million in the cargohold, but I was counting on those ships for some fun, and re-buying and resupplying is still a pain, even with whole-fit buying. I had eight different ships, each of which would require a bunch of clicks. I couldn't be bothered to do that again!
So, I decided not to risk it. I docked up on that character and waited. And waited. And waited. Apparently, it was a slow day, as RDRAW stayed on that gate for the rest of the night. In the end, I never got the ships in through Tama. I ended up playing Deus Ex: Mankind Divided (no-kill path ftw) instead.
As I sit here, I'm wondering whether it was a smart move. On the one hand, I lost a day of roaming, but in reality it was only about an hour. Yet I also avoided having to absorb about a 400-mil loss. My balance is only now recovering to where it was back in May following a mass-plexing of my accounts and about 14-bil in Eve-Bet losses on the Penguins' playoff run. I really don't want to take stupid losses. Well, at least not any more of them.
Was it the right move? I'm still not sure. I could have gone around the other way, but that seemed like a lot of work.
In any case, it was just one of the kinds of decisions we face on a daily basis, upon which our killboard turns. Every day, we face risk of loss. Most days, we come through it unscathed. Sometimes, though, we take a bloody nose. The seeds of those losses tend to be a lot more mundane and omni-present than we think.