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Scholarship FAQ: Expert Advice to Start Your Search

How, when, and where should you start your scholarship search? 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. An example of a thorough Personal Search Engine List can be found here

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; my favorite is[CollegeXpress also has a handy scholarship search tool here!] 

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.

Related: Scholarship Search Best Practices You Need to Follow

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.

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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Brooke Maggio

Brooke Maggio

High School Class of 2021

CollegeXpress has helped me tremendously in my college search in narrowing down the schools I’m interested in. Using the college search tool, I was able to narrow down my choices to schools that matched what I was looking for. I also used CollegeXpress for their scholarship search, which helped me find scholarships that I meet the requirements of.



High School Class of 2019

My favorite feature of CollegeXpress is the scholarship search. As someone going out of state for college, I needed all the financial help I could get, and CollegeXpress helped me easily find scholarships I could apply for to help fund my education.

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.

Emilie Delgado

Emilie Delgado

$2,000 Community Service Scholarship Winner, 2013

CollegeXpress has tremendously helped me in my search for financial aid opportunities as I enter my college career. It is easy to navigate and quickly narrowed down scholarships that I could apply for. Being awarded the scholarship will greatly help me in my finances regarding books and tuition. Thank you for this opportunity. Without CollegeXpress, it would have been more difficult to apply. I would recommend this site to everyone!

Sadie Hartmann

Sadie Hartmann

High School Class of 2021

I'm a senior in high school, and CollegeXpress has helped me in so many ways this year in trying to navigate the process of deciding and committing to a university. The COVID-19 Student Resource Center has helped me many times with the most up-to-date and accurate information, along with financial aid and student life [advice]. During these uncertain times, CollegeXpress has been a great recourse to relieve the stress as a senior. Along with the COVID-19 Student Resource Center, I'm constantly using the extremely helpful tools off the site to aid me during this stressful process. Tools like the lists and rankings of universities have been the most beneficial. I've also used the site to receive expert advice on topics like financial aid. Finally, CollegeXpress has helped me easily apply for several scholarships. I'm thankful to be given the chance to win a scholarship to lessen the burden of my college debt.

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