Confidence will come with experience. The more you wear a diaper, you will build confidence, you will find your own preferences and problems. I personally wear a diaper 24/7, and have found that I use several different types. My usual got to diaper is a Leakmaster contour diaper, sometimes with an insert (at night) and without an insert at night. I gave birdseye cloth night diapers if I drink something late or I am not planning to get up early. I always wear plastic pants over my diapers. I also wear Leakmaster daytime diaper pull up (like now) if am doing out wearing a dress or tight fitting clothes I wear a depends, with a poise pad to catch leaks and plastic pants.
With experience you can find out what works for you, and unfortunately through mistakes, what may not be a good idea