A crash pad is a must, but not always your own
The most important thing in outdoor bouldering is a good crash pad under the problem. In the gym nobody gives it a second thought. Outdoors it's your responsibility.
When you're out with me, I bring the crash pads. If you go on your own or with your own group: you can rent crash pads (many climbing shops in larger cities offer this), or you split the weight with friends.
One pad usually isn't enough. Two is ideal. One directly under the boulder, one as an extension for the top-out.