I've started playing this tonight and it is quite nice. I'm trying to resist the temptation to metagame myself and not check. But sometimes the story that's appearing doesn't demand a check. When I draw hazards, even if my first check was successful (i.e. a 4) is that still meant to create a challenging environment for my wanderer? Otherwise I'm having a lot of fun with it!
Glad to hear you’re enjoying the game so far! Essentially, every check represents some moment when there is a hazard with a potential risk of failure. It doesn’t have to be strictly one per day. If the story that’s unfolding for you doesn’t feel like there’s room for immediate dangers that day, keep writing until you do come across a potential challenge! I hope that helps - let me know if I misunderstood your question.