A Tactical Guide to Winning Scholarships

Preface

This essay was in response to an email from a friend of my mother requesting tips and sources with which to help her son apply to scholarships in his senior year of high school. It has been slightly abridged from its original version.

I. Introduction

I have put the time into writing a brief essay here, firstly because I genuinely enjoy writing and I think I’m good at it, both of which are critical to writing essays. Secondly, I wish I had had someone to explain these things to me. I did not follow this procedure when I applied, but if I had, I would have won more money, or at least wasted less time. The scholarship game is solely and entirely about winning, and if it is not played to win then it should not be played at all. This essay is a tactical guide for applying to scholarships during the junior and senior year of high school.

II. Game Theory

Applying to scholarships is a numbers game, but not in the sense that a shotgun apply-to-as-many-as-possible strategy is optimal. Using the formula…
Expected value = award amount * number of scholarships / number of applicants
…you can see that the best scholarships are not the largest ones, but typically the ones with the least applicants. Therefore, despite the list I include below, your son will probably not do particularly well by shooting for all of them, especially since that would be exhausting. The highest expected value scholarships will most likely be ones offered by, in the following order
  1. Any professional organizations or unions your family is involved in
  2. Your High School
  3. Your School District
  4. The State of Washington
  5. Your son’s most likely college
  6. Federal
  7. Foreign governments
  8. Nationally organized faith, ethnic, political, or other organizations, corporations, or scholarships applying to specific academic fields.
Scholarships from professional organizations are basically the only scholarships you can expect to get, even if they are not often more than $1000. The applicant pool is often only a few people, so the odds are very good. School and school district scholarships are similar but your success might be linked to your GPA compared to your classmates and your reputation around school and among your teachers. The great State of Washington actually offers a large number of scholarships and these tend to be for substantial amounts of money. A large number of people apply, but they also have enough funds to distribute multiple of the same scholarships. Sometimes these scholarships will be restricted to Washington residents and/or people attending Washington public colleges. I recommend applying to every scholarship in these categories for which you are eligible. The odds are good enough that you, on average, if you are a good writer, and have good grades, and put effort into it, will probably make more than minimum wage.
The second half are not worth as much. College-specific scholarships are often not available until you are properly enrolled, but check anyway. Sometimes scholarships are worked into the college application process. Federal grants are similar to state grants: big and numerous, but they tend to be heavily need-based. If you are poor, adult, orphaned, veteran, married, have kids, or otherwise fall into a category the federal government sponsors, these are much more valuable and do these first. They can potentially pay for your entire schooling. However, need-based scholarships are beyond the scope of this essay and my expertise.
Foreign governments are hit and miss. Check with your embassy if you are a foreign national. If you wish to study outside the US, certain governments are happy to sponsor Americans into their universities, notably Japan.
Miscellaneous national scholarships are by far the easiest to find and generally what people think of when the topic of the scholarship grind comes up. However, they are extraordinarily difficult to win on account of the massive number of applicants (since they are easy to find and frequently compiled on scholarship lists) and usually lack multiple prizes. In my opinion, these are the least efficient scholarships.

III. Time management

When applying to colleges, often essays can be recycled between colleges if the essay prompts are sufficiently similar. Hence, the marginal effort for each next essay gets lower with each new college. The 12th essay is a lot easier to write than the first. This advantage exists in scholarship essays, but to a lesser extent. Organizations like schools and the government are likely to have sufficiently generic essay prompts that essays can be recycled, even from college applications themselves.
If I recall correctly, I could write about 100 words an hour out of high school. At that rate, a 500 word essay takes 5 hours, plus another 3 for identifying the scholarship, editing, filling out the scholarship, and various forms of procrastination, for a total of around 8 hours. Consider the expected value equation: if the scholarship is for $1000, there is one scholarship available, and 100 people apply, you will be, on average, winning $10 for working 8 hours, or $1.25 an hour. You would be better off flipping burgers. But that’s actually an overestimate. In reality, you do not have an average chance of winning. If you are average and write an average essay, you have a 0% chance of winning, because the best essay has a 100% chance of winning, and then you get squat. So if you’re not willing to do your research finding relatively obscure scholarships, and willing to put in the time to write literally the best essay, applying to scholarships is a massive waste of time. To some extent, quality over quantity.

IV. Battle Plan

Doing things in the right order will keep you from missing opportunities and keep you from wasting time on less lucrative opportunities. First, spend as long as you can tolerate finding every possible scholarship you qualify for and order them in a spreadsheet that includes:
  • Application URL
  • Due date
  • Essay prompt
  • Essay word count
  • Any extraneous requirements
  • Prize amount
  • Number of prizes
  • Your subjective estimated number of applicants
Once you have found every essay you conceivably qualify for, arrange them in order of expected value (hint: use Excel’s data sort function). This is going to a hand-wavy estimate at best due to the estimated number of applicants, but it’s the best we got.

V. Scheduling

Rather than work on the highest expected value scholarships first, I recommend committing to a set number of applications, then committing to writing that many applications. This way, you can work in order of upcoming deadlines rather than expected value without risking missing any of the highest value scholarships because you were working on something else. Hopefully not too many deadlines overlap. At this point I recommend putting the deadlines in your calendar. It’s possible to write an essay a week on top of a typical high school course load and extra curriculars. This is probably pretty hard. One a month is probably pretty easy. How ever many you attempt, having a set goal and grinding towards it predictably does wonders for morale. It lets you know when you’re done and how far you have left to go.

VI. Writing

Writing well is extraordinarily difficult and I can’t teach it in an essay. However, here is the short list of things to remember:
  • There is no excuse for poor punctuation or grammar.
  • Follow the dang prompt.
  • Avoid cliche topics.
Most importantly, have someone proofread and edit every essay. This is the single best way to improve your essays and writing skills. Additionally, it lets the writer share the burden. Even a classmate is better than nothing but an experienced writer is best. Having two different people read each essay is likely optimal as they will notice different aspects. Current or past English teachers are excellent for this job. Parents are not unless they have an unusually good relationship with the student, and are actually competent writers themselves. By far the most common and efficient method for collaborative editing is to use MS Word’s track changes and comments features. This is how I and most scientists write research manuscripts together.

VII. Incentives

So how do you get your student to spend weekends grinding essays instead of WoW mobs? And how do you get them to write good essays, not just crap to check boxes and get you off their back? Teenagers are frequently poor at making long term investments. You can use any stick and carrot you want but it won’t produce winning essays if the student is trying to please you but not trying to win. If your student is paying for their education alone, this problem kind of solves itself. But if you intend to pay for your student’s education but also want your student to win any scholarships possible, there isn’t much incentive there to put real effort into the essays. This is why (in this situation, which you may not be in) I recommend the following policy:
For any scholarship your student wins, promise them a percentage of the winnings immediately, in cash, with no strings attached. Somewhere between 10 – 50% will probably produce results. $100 cash to a teenager is a lot of money while $1000 in their parents’ bank account is an abstraction.
There are a lot of things that can motivate people. Duty to family is a great one, and if your son is willing to write ten thousand heartfelt words to make their parents’ lives easier, then you have done an anomalously good job parenting. But the only incentives you can always manufacture are greed and fear, and fear is detrimental to the creative writing process.Trust me; I’m young enough that I still hang out with teenagers.

VIII. Conclusion

Winning scholarships is not about writing the most essays, but about grabbing the lowest hanging fruit as quickly as possible. Not everything out there is worth pursuing. Approach it haphazardly and you might polish your writing skills, but you won’t make much money on it, and it will take you a very long time.

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