I started out by using a free scholarship service, like http://www.scholarshipexperts.com, and then I picked 5-8 to complete each month. I tried to find scholarships that were about something I was interested in or something I was already doing in class. Also, once I had a winning story for the writing contests/scholarships, I submitted the same entry to several. Since 2004, I have won over 15 worth nearly $50,000.
If you like to write, tackle the scholarships that require a high word count. They have fewer applicants than those that require little work. That gives you better odds of winning the scholarship.
I always have someone look at my work before I submit it because I am too attached and make simple mistakes, which is one of the top reasons your application will be rejected. Edit, edit, edit!
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Tamara
The Scholarship Expert