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This is Why You're Not Winning Scholarships

Updated: Apr 4, 2023

As a 7-figure scholarship winner and Princeton University graduate, I know firsthand how much effort and dedication it takes to win a scholarship. I also know that the journey to securing a debt-free degree is not always easy.

Many students apply year after year and still don't receive the financial aid they need to achieve their educational dreams. So, what’s the real tea? Here are five reasons why you may not be winning scholarships and what you can do about it.

1. You're not casting your net far and wide

Much like applying for jobs, applying to scholarships is a numbers game. You need to apply for opportunities strategically and frequently to reap positive results. At its core, scholarships are a competition rooted in personal branding, storytelling, and writing. The better you get at articulating your strengths, interests and story, the more likely you are to be chosen to win free money opportunities. This requires practice, however. The best way to practice this skill is to get accustomed to applying for scholarships. Break up the days that you spend searching for scholarships and applying for scholarships; this will help you have more bandwidth. So, you need to consistently submit applications for various opportunities. Don't be afraid of the grind! Donors want to give you this free money. Get out of your own way!

If you're only applying to a few scholarships, you're limiting your chances of success. 💯 For example, let's say you only apply to 5 scholarships and your chances of winning each one is 1 in 100. That means your chances of winning at least one scholarship is only 5/100 or 5% at most. However, if you apply to 50 scholarships, your chances of winning at least one scholarship increase to 39%. That's a huge difference!

Make sure you're applying to as many scholarships as possible that you're eligible for. Start by using scholarship search engines such as Fastweb,,, and Scholly to find opportunities that match your profile.

2. You're not tailoring your applications to each specific scholarship opportunity

Scholarship committees are looking for applicants who fit specific criteria. For example, some scholarships are only available to students pursuing a certain major, while others are only available to students with a certain GPA or community involvement. Make sure you're applying to scholarships that match your profile and tailor your applications to highlight your skills and experiences that align with the scholarship's goals and values. For example, if you're applying for a scholarship that rewards leadership, highlight your experience as a student council member, team captain, or volunteer leader in your community. 💪🏿

Tailoring your applications allows the scholarship donor to feel like you set aside time to think deeply about the opportunity they're offering you. If you submit an application that is too general or tangentially related to the scholarship, donors are inclined to feel like you’re just applying aimlessly to any opportunity instead of really caring about the one in front of you.

We all want to feel special. So, take that extra time to tweak some lines in your application that speak directly to the opportunity at hand. This is one of the most underrated ways to make your application stand out. People remember people; show who you are through your application!

3. You're not applying for scholarships that fit your profile

It's important to carefully read the requirements and qualifications for each scholarship you apply to. If you don't meet the eligibility criteria, your application will likely be disqualified. For example, if a scholarship requires a minimum GPA of 3.5 and you have a 3.0 GPA, you may want to think twice about wasting your time applying. Instead, focus on scholarships that match your profile and qualifications.

A great way to maximize your chances of winning a scholarship is to apply for scholarships that are incredibly niche and aligned with your identity. Seek out local scholarships since they have less competition because only people in your locality are able to apply. Apply for scholarships for your specific major/career path. Look into opportunities that align with your circumstances, whether that be your gender/racial identity or even if you have experienced a death in the family.

The Dirk Derrick Car & Truck Accident Injury Scholarship is a perfect example of this. This award is specifically for any current or soon-to-be undergraduate student in America who has had their life altered due to an injury from a car or truck accident (be it their own injury, that of a loved one, or an influential individual.) Everyone cannot relate to this experience, therefore there is a smaller number of people who qualify, and an even tinier number of folks who actually follow through to submit this application. This renders The Dirk Derrick Scholarship less competitive than the Coca Cola Scholarship, which is more generally open to high school seniors across America.

As a 2018 Coca Cola Scholar, I can attest to the competitiveness of this scholarship- over 120,000 students applied during the year that I won this scholarship. 😲 Remember that niche scholarships targets a particular subset of people, effectively increasing your chances of winning since everyone won’t be eligible to apply.

4. You're not leaning into your superpower: your uniqueness

Scholarship committees receive hundreds or even thousands of applications, so it's important to make sure your application stands out from the rest. One way to do this is by telling your unique story. 📖 Use your essay to share your personal experiences, challenges, and successes that have shaped who you are today. For example, if you're applying for a scholarship that rewards perseverance, share a story about a time when you overcame a significant obstacle to achieve a goal. To help you articulate your story, check out my "5 Steps to Securing Scholarship Success" e-book, which provides tips and worksheets that offer a roadmap to help you find your voice and coach you through how to write a captivating essay that mirrors what the scholarship is looking for.

5. Procrastination has you in a chokehold

Don't wait until the last minute to start your scholarship applications. Lean into your millionaire mindset and start applying BEFORE the stress starts to hit. Many scholarships have early deadlines, so you'll want to start your search and applications as soon as possible. Get into the habit of applying to scholarships within a week of finding them.

I share over $350,000 worth of opportunities in my seasonal scholarship databases. You seriously don't want to miss out on that type of free money. This will give you plenty of time to craft a strong application and ask for recommendation letters. You’re less likely to let opportunities pass you because you forgot about the deadline, and now you have to cram for an upcoming test or finish tons of homework. Don't count yourself out by being lazy. Get those applications done ahead of time! ⌚ This will also help you avoid the stress and rush of trying to complete multiple applications simultaneously. Haste makes waste, and we have no time for mistakes when it comes to free money OKAYY!

In conclusion, winning scholarships takes time, effort, and dedication. But with the right mindset and strategy, you can increase your chances of success. Remember, the more scholarships you apply to, the higher your chances of winning. Tailor each of your applications to fit the scholarship's criteria, and make sure you meet the eligibility requirements. Stand out from the crowd by sharing your unique story and starting your applications early. With these tips and my "5 Steps to Securing Scholarship Success" e-book, you'll be well on your way to achieving your educational dreams. So don't give up, keep applying, and believe in yourself.

You got this!

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1 Comment

Tanatswa Masikinye
Tanatswa Masikinye
Mar 29, 2023

Hello, do these apply to international students.

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