The author of Schott's Original Miscellany, a noted compendium of lists, shows you how.

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Credit: Kate Sears

Lists seem to be more central to our lives than ever before―from our own obsessive to-do lists to the structure of the human genome or Google’s cataloging of the World Wide Web. But the urge to collect and classify is hardly new, nor is it always magnanimous. For every Ben Franklin listing his rules of civilized human conduct, there is a Joseph McCarthy listing his enemies of the state.

Here then are some of the lessons from lists past that I think about when assembling my own and examining those of others.

1. Ask for help. Since list writing is often undertaken in an overwhelmed state, why do it alone? In 1964 Deborah, duchess of Devonshire, wrote to her friend Patrick Leigh Fermor to ask for his assistance in compiling a rather unusual list: whimsical titles for a set of fake book spines that would cover a secret library door in Chatsworth, the duchess’s stately home. Fermor obliged with a list that included Military Dilemmas, by Major Crisis; Consenting Adults, by Able N. Willing; and In the Soup, by A. Crouton. If a problem shared is a problem halved, a list collaborated on is a list enhanced.

2. Fear not the short list. It is notable that Paul Simon’s 1975 classic “50 Ways to Leave Your Lover” actually lists only five methods of abandonment. Although Simon is blatantly guilty of fraudulent misrepresentation, there’s no doubt the song would have been unbearably dull had he enumerated the other 45 techniques for ditching a paramour.

3. Go on, be vengeful. It’s gratifying to vent your spleen with a list of bilious retribution. In the unlikely event you’re stuck for inspiration, turn to Gilbert and Sullivan’s 1885 comic opera The Mikado, in which Ko-Ko has “a little list of society offenders who never would be missed,” including “the idiot who praises with enthusiastic tone, all centuries but this, and every country but his own.”

4. Proceed with caution. In his Jeeves and Wooster novels, P. G. Wodehouse introduced the Junior Ganymede Club, a secret guild of valets and butlers. The club’s Rule 11 required its members to keep lists of (often compromising) information about their employers―a source of endless confusion and mayhem. The modern-day moral? Be sure to erase perilous lists, like those of last-made cell-phone calls, most-recently-visited websites, and whatever you wrote after reading No. 3.

5. Think big. When the shopping has to be done, a shopping list is called for, but dedicated list writers should tackle weighty subjects once in a while. Historians still debate Edward Creasy’s classic 1851 list, Fifteen Decisive Battles of the World: From Marathon to Waterloo. And the relentless flow of rich lists and tabulations of the “new establishment” surely owes everything to Mrs. Caroline Astor’s 1892 epic compilation of “the 400,” a Who’s Who of New York high society during the Gilded Age.

6. Think small. When examining a daunting to-do list of your own, there’s no shame in tackling your most achievable tasks first. As Virginia Woolf declared, “Let us not take it for granted that life exists more fully in what is commonly thought big than in what is commonly thought small.”

7. Savor sevens. Some of the most magnificent lists are heptads, including the seven sins, the seven virtues, and Shakespeare’s “Seven Ages of Man.” To understand why sevens are so powerful, we can turn to Cardinal Robert Bellarmine (1542–1621), who gave this reason for omitting the eight beatitudes from his catechism: “Nobody can remember more than seven of anything.”

8. Embrace the back of the envelope. The best lists always seem to be those jotted down on the nearest thing: a receipt, a cocktail napkin. One of the most famous lists in British politics was reportedly penned by Michael Heseltine, who, while a student at Oxford University, is said to have mapped out his life on the back of an envelope: millionaire, member of Parliament, minister, cabinet, Downing Street. It is interesting that he achieved all but one of those enveloped ambitions―he was beaten to the top job by John Major in 1990 and had to settle for deputy prime minister.

9. Reconsider the vertical. Given that few of us think in rigid sequence, why do we inevitably start lists at the upper left-hand corner of a piece of paper and continue down in a neat, linear cascade? Varying the format can make a list far more useful. Start in the center of a page and write items in spatial relation to one another, so that you create clouds of related tasks; draw a Venn diagram for party invitees so you can note how people will interact. During the 18th century, sailors in the British navy would sign petitions of grievance in a circle so that ringleaders could not be identified. (From this, the term “round robin” is derived.)

10. Avoid the trap of 10. Just because 10s can be ticked off on one’s fingers and toes does not mean that long lists should be artificially compressed to a decade, nor short lists padded out to reach this symbolic number. In biblical hermeneutics (yes, those), the number 10 represents the perfection and completeness of the divine order―as in the Ten Commandments. So lists of 10 should be left to God, David Letterman, and, of course, Real Simple.