What is the first thing that comes into your mind when you find a great contest that you really feel you have the skills to win? Is it something like "I know I could be the one to win this one, BUT... I would be afraid to take the trip to get there", or "I have to lose some weight first... I wouldn't want my picture taken like this!" or maybe even "I'm too old".
It's ok to be a bit apprehensive, in fact, it's normal. However, when self-criticism keeps us from doing the things we love, it then becomes unhealthy and can keep us from living a full and happy life. The way we "talk" to ourselves can have a big impact on our actions, or lack thereof, so it is important to be just as kind with ourselves as we would be with anybody. You wouldn't tell your best friend that she was too "big" to have her picture taken as the "grand prize winner", in fact, it most likely wouldn't even come to mind. Instead, you would be supportive and encouraging. So why not be just as loving and caring with yourself?
Increasing self-confidence can start with agreeing to be your own best friend. Look at your strengths, compliment yourself for any job well-done, and replace self-critical comments with loving ones. When you have thoughts of passing on a particular contest that you would love to win, stop yourself and become the loving and encouraging friend that you need in order to get over that initial hurdle, and just enter! Taking that first step will increase your confidence level, and you may find it to be much easier than you had ever anticipated.
Being prepared increases confidence tremendously, as well. For example, if you have always dreamed of overseas travel, yet have been unwilling to enter sweepstakes with vacation prizes to overseas destinations because you may not be able to find anyone to watch the kids while you are away, set some time aside and look over the details of what is really needed to make a trip such as this happen. Ask Grandma or another available relative if she'd be a willing standby for when the win really does come, and then go ahead and get your passport now, along with making any other arrangements that can be done in advance (someone to feed the cat, etc.). This will also have an added benefit of stress relief in not having to do everything at the last minute, keeping the pace relaxed and care-free. Then you can better have the confidence level to enter for that trip to Italy (or to anywhere else) you've always wanted, without having apprehension or unfounded fears stopping you.
By taking small steps over time, you will find that most of the fears that may have kept you from entering in the past will all melt away, leaving you much happier and feeling more fulfilled... with a winning attitude!