I am currently in the midst of an unbelievable streak of luck; I have won over 150+ contests (skill-based *and* random draw) since October 2013. I discovered the amazing world of Rafflecopter and Giveaway Blogs and have been a contest hobbyist since then.
My strategy is three-fold and simple:
1. Just Enter! Don't let the number of existing entries or the method of entry intimidate you. Enter and enter as often as the rules allow. I personally spend about an hour entering giveaways per day, 1/2 in the morning and 1/2 in the evening. The old adage is true, "You can't win if you don't enter." Even though the new saying around my house is, "Thousands will enter...Adrianne will win."
2. Think Like a Winner! Even though I have a long-standing reputation as a sardonically irreverent cynic, I put forth every iota of positive energy in my being into each contest entry. For really big contests, I like to meditate on the following:
I can win this because I am worthy to win this. Positivity IS my luck.
3. Share the Wealth! I often enter contests with other recipients in mind. I won many of my daughter's Christmas gifts this past November/December. Paying it forward is half the fun of winning, and it keeps the goodwill and positivity out there in the Universe.
Friends and family tell me that I must be lucky, that they "never win anything." And my response is simple: It's not just luck You must enter to win!