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Scholarship FAQ: Expert Advice to Start Your Search With Confidence

How, when, and where should you start your scholarship search to win big? Find out all the answers from a professional scholarship strategist now!

Jean O’Toole is a scholarship expert. As a scholarship strategist for Connections101, she offers students motivational tools for scholarship searching, and her strategies get results—she worked with one student who won $190,000 in scholarships, plus 41 seniors from one school who collectively won $5.6 million in free money for college!  

She’s also the author of Scholarship Strategies: Finding and Winning the Money You Need. In her book, Jean explains how students can take a smart and organized approach to applying for many winnable scholarships, laying out 25 clear strategies and identifying 15 ways to reduce college costs beyond scholarships and traditional financial aid. 

Below, Jean has answered five frequently asked questions about starting your scholarship search, including when and how to start, where to find scholarships, the most efficient search strategies, and her top application essay tips. Read her advice below, and look out for another Q&A with Jean on scholarship myths next week!  

When should I start my scholarship search?

Students at any grade level can and should start their scholarship search; there are even scholarships for kids as young as five or six years old who are in kindergarten! Scholarships from companies, organizations, individuals, and foundations are private monies, and they get to decide who and what they want to honor with their scholarships, so it’s important to read the application requirements such as age or grade level.

For example, the Doodle for Google Competition is for students in grades K–12 and honors creativity with an annual award of up to $30,000. Scholarships for younger students can be awarded with a check sent directly to the student so the money can be saved, invested, or used for current educational expenses. Scholarships may also be awarded as a bond that will mature when the child turns 18. And sometimes awards are held in an account until the student is enrolled in their chosen college or university; then the money is sent directly to the school.

How do I start my scholarship search? 

Students often miss out on scholarships because they focus only on opportunities that relate to their grade point average, extracurricular activities, community service, and/or career goals. As a first step in the scholarship search, try creating what I call a “Personal Search Engine List.” This list should describe all activities, interests, and accomplishments from your life along with what you want to accomplish in the future. It should also include your “ready-to-go materials,” such as papers, projects, essays, or poems that were completed for class or club assignments to be used for potential scholarships. Let your Personal Search Engine List become your map for money. It’ll guide you to opportunities you can and should seek out. 

Related: How to Start Your Scholarship Search

Where do I find scholarships?

There are four main places to find scholarships: through your school, through your family members, in scholarship book directories, and with online search engines. High school students should regularly ask their school counselors for any available opportunities; I call this “Getting Out of the Waiting Game.” College students should proactively ask their financial aid office, their field of study’s department, and alumni offices on campus about any new scholarship opportunities. You should also ask family members to find out if there are scholarships available through their companies or professional unions. Utilizing the index of scholarship book directories can help you quickly identify scholarships that correlate with your Personal Search Engine List. Finally, there are many online scholarship search engine websites.

What scholarship strategies are the best use of my time? 

One smart strategy is to search for scholarships that make use of papers, projects, essays, and other assignments you’ve completed as homework in the past. The time has already been spent, so new material doesn’t need to be created. Another strategy is to contact scholarship committees to connect with them and ask what they’re looking for in an ideal candidate; this allows you to better craft your application materials. (Plus, they might remember your initiative when your application is received.) The greatest strategy is to gather criteria information about scholarships that pertain to students a year or two older than yourself. By knowing the criteria in advance, you can make informed choices for the next year or two on how to use your time outside the classroom to qualify for the most opportunities in the near future.

What tips should I keep in mind for scholarship application essays? 

The key to standing out and impressing scholarship committee decision makers is to include what I call a “Why you?” statement. Students mistakenly assume that this is a sentence stating an obstacle they’ve overcome and how it’s made them who they are today. But the “Why you?” statement shouldn’t focus on the past; it should focus on the future. Try crafting a sentence that explains what type of impact you plan to have on lives other than your own once you finish your college education. Scholarship committee members generally prefer that their scholarship monies impact more than just one individual. The “Why you?” statement should be incorporated into all your scholarship applications in some way, not just applications with essay requirements.

Related: 10 Tips to Help You Write a Winning Scholarship Essay

The CollegeXpress Team wants to say a big thank you to Jean O'Toole for answering such important questions about scholarships for students. These awards make a huge difference in being able to pay for college, and equipping yourself with the most knowledge possible can help you win more and stress less.

Ready to begin? Start looking for awards using our Scholarship Search tool, and find more expert advice about paying for college in our Financial Aid section.

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Ana Sophia Garcia-Cubas Assemat

Ana Sophia Garcia-Cubas Assemat

$10,000 Scholarship Winner, 2020

CollegeXpress has been an instrumental resource for my scholarship search and has given me the opportunity to try my best so I can graduate from college debt-free.

Maurice Whan

Maurice Whan

$2,000 Spring Scholarship Contest Winner, 2021

This year has been tough for my family and myself, so receiving this scholarship has been a blessing in disguise! CollegeXpress has been an excellent resource in helping me prepare financially for college. Thank you again for this amazing opportunity!

Mataya Mann

Mataya Mann

High School Class of 2022

To say that CollegeXpress is a helpful tool would be an understatement as it is much more than that. Before finding CollegeXpress, all I knew was that I wanted to go to college, it was going to be insanely expensive, and I felt lost. CollegeXpress has given me access to resources such as helpful tips for applications and scholarship [opportunities], and helped guide me in a direction where I feel confident moving forward and pursuing a career. CollegeXpress has helped instill a spark in me that makes me want to continue and supports me in doing so.

Keaun Brown

Keaun Brown

$2,000 Community Service Scholarship Winner, 2020

As I transition to furthering my education, I can say with certainty that it simply wouldn’t be possible without the help of generous organizations such as CollegeXpress. Those who initially founded CX had no idea their platform would give a plethora of information to a first-generation homeless kid native to the ghettos of over half a dozen states. Everyone at CX and Carnegie Dartlet gave me a chance at a future when the statistics said I had none. And for that, I thank them.

Heaven Johnson

Heaven Johnson

Back to School Scholarship Winner, High School Class of 2023

I’d like to thank everyone on the CollegeXpress team for their generosity. Not only have I been awarded this scholarship, but CollegeXpress makes it easier to apply and gives amazing tips for schools and scholarships. I am extremely grateful as this will help with my schooling and allow me to be able to enter into the field I’ve been dreaming of all my life. 

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