How to win scholarships

Ask The Expert: How Can I Win Some Scholarships?

Question: I start my sophomore year in college after this summer, and I already have thousands of dollars in student loans. I’ve applied for scholarships that my school lists on its website, and I’ve applied for like a dozen. Haven’t won anything. Are scholarship just scams?

— Peter in Michigan

Howard Dvorkin CPA answers…

Howard Dvorkin on how to get out of debt fast

As a CPA and financial counselor for nearly three decades, I can tell you this: I’ve seen a lot of “scams,” but scholarships haven’t been one of them.

I’m a big believer in scholarships — because I’m an even bigger believer in getting money for free. However, there are some general rules and even some counter-intuitive advice for winning scholarships.

First, you should read 5 Really Dumb Reasons Why You Didn’t Get That Scholarship, because asked financial officers for the silliest reasons students don’t win. My favorite: Missing the deadline. That happens much more often than you’d think. I’ve seen it repeatedly with the two scholarships has bestowed. (More on that in a moment.)

If there’s a smart reason students don’t win scholarships, it’s this: They aim too high. I’ve seen students brush off $500 scholarships and spend hours applying for $5,000 scholarships. I suggest the opposite: Spend less time applying for smaller scholarships.

I’m a passionate advocate of applying for small scholarships. Why? Because there’s no limit on the number you can win. So three $500 scholarships can pay for a year’s worth of textbooks (which averages $1,146 at public schools). Smaller scholarships often have fewer rules, which means less time applying for them. Also, because the amounts are small, so is the competition.


That’s why I decided to launch The Scholarship For Aggressive Scholarship Applicants at only $500 — but award it every two months. Instead of spending $3,000 once a year, I’m giving money to hard-working students every eight weeks.

Even better, I purposefully set up the scholarship to emphasize effort over grades. Of course, I believe grades are important, but many other scholarships already reward high GPAs. I wanted to stress hard work.

That leads into my final piece of advice: There are many scholarships that reward many kinds of effort. Don’t narrow your search. Focus on what you excel at, and then search for a scholarship in that area. That’s how to win scholarships more often. For example, check out’s extensive list of The 21 Weirdest College Scholarships Ever. There just might be something for you.

Lastly, read about the previous scholarship winner, announced just last week. You can also apply for our next scholarship.

Have a debt question?

Email your question to and Howard Dvorkin will review it. Dvorkin is a  CPA, chairman of, and author of two personal finance books, Credit Hell: How to Dig Yourself Out of Debt and Power Up: Taking Charge of Your Financial Destiny.

Posted in: Ask the Expert, News
Tagged with: ,