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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!

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 anyone can take to give themselves 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 scholarships from local companies, organizations, and individuals are awarded to graduating high school seniors. Contact your high school counselor’s office and request to be emailed the program from last year’s event. This will give you a list of all the local awards 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, you can accumulate these awards into thousands of dollars, so it’s definitely worth applying.

Related: The 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 creative work or an essay is required. You can also gather this information from your school counselor or online community forums and keep it in mind as you're applying. You don’t want to copy what last year’s recipient did, of course, but finding out what’s impressed the scholarship committee in the past can give you insight into what they value and may even improve your applications in case you’re not on the right track.

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 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, people are encouraged to research and prepare to be the ideal candidate for an internship or job. You can give yourself 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, you can strategically direct your limited time and energy outside of the classroom to qualify for as many scholarship opportunities as possible. 

Related: 6 Student Tips to Help You 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 any free time you have plus 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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Lorena Bacallao

Lorena Bacallao

High School Class of 2022

CollegeXpress was the foundation of my college search process. Because of CollegeXpress, I was able to make a more informed and confident decision as to where it was best to pursue my higher education. I have recommended this website to fellow peers and for first-generation students like me. It’s a website I will continue to promote because of how simple it was to use and how many opportunities were offered to me at my fingertips!

Yuhlani Patterson

Yuhlani Patterson

High School Student

CollegeXpress has helped me find so many scholarships that fit me. They match me to colleges I have specific interest in to make searching for colleges way easier and more efficient. CollegeXpress refers me to schools that have my major of interest and backup schools if I want to change my mind. CollegeXpress also gives out their own scholarships, so you have even more of a chance at gaining multiple scholarships. This website has helped me de-stress from the pressure of not being able to afford college, [of finding] what schools are right for me, and how to find easy access to scholarships that most people never knew existed.



High School Class of 2022

My mother signed me up for a couple of scholarship contests through CollegeXpress. I was also able to do some research and compare the different schools on my list. I was able to see the graduation rates and different programs that helped me decide on Adelphi University. I will continue looking for some scholarships for my start in September.

Caitlin Eaton

Caitlin Eaton

$10,000 Scholarship Winner, 2021

I first discovered CollegeXpress during my sophomore year of high school while researching colleges that interested me. My SAT prep class the following year further familiarized me with the opportunities available through the organization. CX has personally helped me by exposing me to a diverse selection of schools as well as scholarships and life tips that have provided valuable guidance in my college search.

This scholarship will help me adjust to college life without worrying as much about tuition. This gives me more room to truly explore and benefit from all aspects of higher education. I plan to study Conservation Biology and work protecting species/ecosystems. I’m looking forward to getting field experience and seeing firsthand the problems research is solving.

Sonny Harris

Sonny Harris

College Student

For the entire year before college, I spent a lot of time deeply considering what major I wanted to go into and how to fund my higher education. After a lot of research, I came across CollegeXpress, which helped me ultimately find a ton of scholarships for which I could apply—and some of which I received! If it weren’t for CollegeXpress, I may not have found those scholarships as they didn't appear on any other scholarship search forum. Additionally, I learned more about the options I had been considering for my major through CollegeXpress’s resources. In the end, I chose to major in Computer Science, as it seemed best suited to me and the careers in the field seemed enjoyable, and I've never been more excited to move into my future! Ultimately, I want to thank CollegeXpress for offering their services. I received enough financial aid in scholarships to fund my entire freshman year of college and even got some money refunded which I used to purchase a new laptop, and I bought all of the books I needed for the semester!

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