I will speak up as someone who has spent a thousand or so hours driving under-equipped light aircraft around in crappy weather amongst tall rocks. The first rule I learned was to expect that the weather forecast was just a guess and the winds and ceiling will, not may, be different. And expect Mother Nature to throw you a curve ball on a regular basis. Where you really need to know the weather, there will not be a reporting station. So always launch with a backup plan and a hard limit of what weather will trigger going to plan B.
The second rule I learned was that when it was time to go to plan B, do it. You never every "gotta" get home today. The folks at a thousand small airports offer great sympathy and hospitality to wayward aviators. You meet wonderful people at unscheduled stops.
Then I learned that I do not have to fly a straight line to get to my destination. Some days, running 100 miles in a different direction from my desired course line will allow me to get where I want to go rather than flying up to some bad weather and sitting stuck while a big glob of low ceilings takes its time moving overhead.
Finally, the best decision making is done before you crank up and start taxiing. Know before your wheels leave the ground that it is OK to launch to look at the weather but decide before the throttle goes forward how just far you will go to look at the weather. Plan where you will go as soon as the weather gets worse than a limit you have set for yourself.
If you can make yourself think about the enroute weather, make a plan, make a backup plan, and then make yourself follow the plans, you can work your way home through surprisingly challenging weather. But only if you understand that its a step-by-step process and that process does not guarantee that at the end of that day you will be at your destination airport. If you are flying an VFR airplane and absolutely have to get somewhere, drive or buy an airline ticket.
In my small airplane travels, I have managed to cajole Mother Nature into letting me fly small airplanes with no equipment from Boston to San Francisco and from Montreal to Galveston. But Mother Nature is ruthless, gives the test before the lesson about it, and should always be viewed with a little paranoia as you study at her College of Aeronautical Knowledge.
The only way to build experience is to fly. Don't fly the same one flight 1000 times. Fly 1000 different flights and build your knowledge one bit at a time.
Merry Christmas,
Wes
N78PS