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3 Smart and Easy Strategies to Win More Scholarships

The key to winning scholarships is just a little extra thought and strategy. If you want to win more free money for school, use these three smart tips to do so!

Summer is a great time to focus on searching for and completing scholarship applications because students don’t have the burden of also trying to balance schoolwork. Getting a jump start on the scholarship search can help a student qualify for more opportunities in the future and open the door to massive college cost savings for their family. After working with hundreds of schools and thousands of students over the past decade, I have found these to be the three easiest steps any family can take to give their student an edge and advantage to becoming a successful scholarship recipient.

1. Learn about local scholarships

Most school districts have a “senior awards night” or some other kind of annual event where local scholarships are awarded to graduating high school seniors from local companies, organizations, and individuals. Contact your high school counselor’s office and request to be emailed the program from last year’s event. This will give your family a list of all the local monies that were given away. As these scholarships are only open to local students, you’ll have fewer competitors and a statistically higher chance of winning. Although many local scholarships may be smaller amounts, students can accumulate these awards into thousands of dollars, so it’s definitely worth applying.

Related: Ultimate Scholarship Guide: Searching for Scholarships

2.  Find out who won last year and why

Most companies and organizations that offer scholarships will post on their websites who their recent scholarship recipients have been and why they were chosen. Many also post the winner’s submission if an essay or creative work was required. Students can also gather this information from the school counselor departments or online community forums and keep it in mind as they’re applying.  

3. Find out who the decision makers are for each scholarship

Some local scholarship recipients are chosen by a faculty member or members of a school, whereas other local scholarships may have their own committees to review applicants. Find out who the decision makers are for each of the local scholarships, then reach out to that decision maker with two goals in mind. First, you should thank the decision maker for their efforts in making scholarships available for local students; second, you should ask what they’re looking for in an ideal candidate. Asking this simple question will already define you as motivated, determined, and driven—which makes for an incredible first impression.

Think about it like a job search

Professionally, we encourage individuals to research and prepare to be the ideal candidate for an internship or job. Students can give themselves an advantage by taking a similar approach to the scholarship search. By learning in advance what scholarships are available and what the criteria is for the opportunity, students can strategically direct their limited time and energy outside of the classroom to qualify for as many scholarship opportunities as possible. 

Related: How to Apply for Scholarships the Right Way

With the student loan debt crisis in the United States having reached over $1.5 trillion (surpassing US credit card debt), it’s important that families are empowered to take a proactive approach to finding scholarships from companies, organizations, individuals, and foundations. Every student should start their money mission as early as possible. Use your summer break and these three strategies to give yourself an edge to success in your scholarship pursuits.  

Start searching for scholarships you’re qualified for using our Scholarship Search tool!

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About Jean O'Toole

Jean O’Toole is an educational consultant and author of the bestselling book Scholarship Strategies: Finding and Winning the Money You Need. Over the past 15 years, she has helped tens of thousands of students in the United States. Individuals collectively have been awarded millions of dollars by applying Jean’s scholarship strategies. In 2008, Jean co-founded Connections101, a company specializing in providing motivational tools for scholarship searching. It is her goal to empower students to design their paths to their future without college debt. Visit Connections101.com for more information, and follow Jean on Facebook, Twitter, and Instagram.


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Priscilla Yeboah

Priscilla Yeboah


Throughout my search for colleges I was afraid and timid, but I finally found the college that was fit for me, and luckily, I got accepted. One of the most influential things that’s helped me a lot was the articles and advice on CollegeXpress. It’s helped me a lot and benefited me as a senior to make the right choices in life. Thank you!

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Ana Sophia Garcia-Cubas Assemat

$10,000 Scholarship Winner, 2020

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High School Class of 2021

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