When I talk with people about the scholarships I received, I often hear, “You’re so lucky.” While I have been very fortunate to be honored by some of the top scholarship programs in the country, it is important to understand that I also received my share of painful rejection letters. Only after high school did I realize how well I had done in the scholarship process, because while I won more money than I needed, I was also turned down for some scholarships I really wanted and worked hard to win. But I still won plenty of college funding because I used a proven method of applying for scholarships: cast wide and go deep.


One of the secrets to my success was to cast my net far and wide. This tactic allowed me to pull in several big fish I never would have caught with just a single line. It also meant if I lost a fish (was rejected by a scholarship), I still had others to take its place. In applying for a scholarship, you are selling yourself on a piece of paper. One scholarship committee could be completely blown away with your application while another could pass over the exact same application. The more scholarships you apply to, the more chances you have of being selected for one. So don’t put all your eggs in one basket. Spread your efforts wide to increase the odds of success.

I was watching a crime show the other day in which the police were interrogating a goofy-looking “ladies’ man.” The cops wanted to know how someone who was socially awkward and not very attractive always ended up with the most beautiful women. He explained to the detectives that it’s a numbers game: yes, he always had a beautiful lady by his side, but to get that one lady he endured rejection by the 20 other beautiful ladies he had asked out before her.

I like to call that numbers game “the multiplicity rule”: the more you put yourself out there, the greater your chances of success. Still, I recommend that you decide on a few key scholarships you want the most—and focus extra effort on them.


As mentioned earlier in this chapter, thousands of scholarships are given out each year. Since you can’t possibly apply for them all, it’s important to find the ones that fit you best, even as you are casting your net wide. It is better to put your strongest effort into a few scholarships that fit you well than to waste weak efforts on numerous scholarships that may not suit you at all. When it comes to applying for scholarships, quality should trump quantity.

Your search can be as broad or as narrow as you choose. There are scholarship programs that receive more than 100,000 applicants each year and have very few stipulations regarding who can apply. In contrast, there are also some very restricted scholarship programs that limit who can apply: for example, if you are Catholic and have the last name Zolp (an actual scholarship for students attending one university in Chicago). Reflect on who you are and what you want, determine your college goals, and then go after the scholarships that fit you best. These “best fits” are your strongest investments in your future—the ones on which you should spend most of your time and energy.

Here are some strange but interesting scholarship qualifiers.

And no, I’m not making these up!

1. Being exceptionally tall

2. Being exceptionally short

3. Loving to vacuum

4. Bagpiping skills

5. Being an organ donor

6. Having a zombie-apocalypse escape plan

7. Duck-calling

8. Being left-handed

9. Having knowledge about fire sprinklers

10. Being a skateboarder