How to Unlock Tripped Achievement
Die outside of battle. The only way to do this is by using swamps. While in a swamp tile (both inside and outside a battle), any healing you get deals you damage, except for potions. Regeneration, vampirism and healing per day will hurt you instead.
You need to fill the road with swamps, put down a bunch of temporal beacons so time passes quicker and place a lot of Blooming Meadows to get a lot of healing per day. You just need to get a daily heal to kill you while in a swamp and outside battle. I don’t know how tricky this one is since I got it really fast, but I may have been just lucky.
There is a second way to do this, but it requires a specific trait called Blissful Ignorance. If you get this, your hand will be filled with oblivions, and using oblivion will heal you for a small amount. If you manage to get this trait during a run, stop the Hero on top of a Swamp and start deleting other tiles to reduce your health.