Missing Pieces: ‘Clever Endeavor’ Is Pun for the Whole Family

In Missing Pieces, we explore the thrift store shelves, searching out games from yesteryear that trigger our nostalgia, pique our curiosity, or just make us say, “What were they thinking?!”

Clever Endeavor

Channel your inner Hobbit (or Gunslinger), and tackle these tricksy riddles. First one to the middle of the board wins in this two to eight player, race to the end trivia game crowdsourced from some of the greatest minds of the ’80s.


The box contains instructions, a game board, eight tokens in a bag, 25 Venture cards, and 475 Clue cards. Also included is a printed sheet of every clue contributor and their hometown.

How to Play

Setup is straightforward. Unfold the board and place a token on the “Start” space for each player. Remove the shorter Venture cards from the box and place them off to the side, face down.

Play begins with the youngest player reading clues from the a card drawn from the deck of clue cards. Clues may be read in any order, and since scores are based on how many clues it takes for someone to guess, the clue reader should try to pick the most difficult and obscure clues first. Whenever another player knows the answer, they shout it out. If they are correct, they will move their token a number of spaces based on how many clues it took them to figure it out. To determine the number of spaces to move, subtract the number of clues given from seven. So, if the person guessed correctly on the first clue, they would move six spaces. If all six clues are read and nobody answers correctly, the deck is passed to the right and the next player reads a new clue. If two players shout out the answer at the same time, another card is chosen by the same reader.

Answers from left to right: Drum, Dumbo, Pope John Paul II

During the first few rounds, the player’s token will advance through white, blue, yellow, and orange zones of the board. Within any of these areas, players can take up to two free guesses at any clue. All subsequent incorrect guesses are penalized by moving the player’s token backwards one space. Once the player has entered the red zone, there are no free guesses. Any incorrect guess results in the player’s token moving backwards one space.

There are five squares in each player’s area that contain a black triangle. If a player lands on one of these spaces, either when moving forward after answering a clue or moving backwards after a wrong guess penalty, that player must draw a Venture card and follow the instructions on it immediately. Here are a few examples:

There is also one square in each player’s area that may trigger flashbacks to when the kids were toddlers playing the interminable Chutes and Ladders. If a player happens to land on the square with the arrow, they must move back to the square the arrow is pointing to.

To win Clever Endeavor a player must move their piece up the path and into the Winner’s Circle. Once inside the circle, if they answer any question correctly, they are the winner. However, whenever a player is in the Winner’s Circle, they many not answer until after the third clue has been read. All other players can, of course, answer at any clue. Also, a player in the Winner’s Circle can move out of the Winner’s Circle by making an incorrect guess at a clue.


“A boy who could answer a riddle was a boy who could think around corners.”

— Vannay, Stephen King’s Dark Tower series

The first strategy is that you have to get your brain into a “riddle solving” mode. Clever Endeavor is not quite a trivia game, inasmuch as the winner shouldn’t be who has the most obscure knowledge and knows the answer, but rather who can figure out the answer. In fact, when playing with my family, we generally just discarded any card that it might be questionable whether everyone knows it (e.g. the third card in the photo above). Listen closely to the words used. If the clue is, “A pioneer went around me, but mariners left me behind,” you should be asking yourself, “Why did they say ‘mariners’ instead of the more common ‘sailors’?”

Also, don’t be afraid to use your free guesses. There is zero penalty for being wrong twice early in the game, so you may as well say what you’re thinking. You might get lucky.

Finally, don’t lose track of where you are on the board. Twice in the first game we played, I forgot that I was five spaces away from the “go back” arrow and answered two questions in a row after only two clues.


The only fun thing about Clever Endeavor are the clues, and unfortunately they can be very hit or miss. The gameplay mechanics are the typical boring “move a token around until you win” mechanics used by countless other games, and the addition of the Venture cards to add randomness to the game is more annoying than equalizing.

When the cards are on point, clever, and simple is when this game is the most fun. Unfortunately, for nearly every Dumbo card where everyone laughs and appreciates the cleverness, there is a card where all six clues are read, the answer is given, and everyone sits around staring dumbly at each other asking, “Who the $&#* is Calamity Jane?!” (or Joan Crawford, Jackie Gleason, or any number of other dated celebrities).

One interesting fact about this game is that it was crowdsourced over a decade before the term “crowdsourcing” was even created. In 1988, the creators of the game put out ads in Mensa Bulletin, Harper’s, The Atlantic, Writer’s Digest, and other publications popular to the wordsmithing community asking for entries. They received over 25,000 clues for the first edition. I can’t help but wonder how successful another campaign would be, this time using the internet to source the clues. I’d love to see a version specifically for families that is a little more timeless. If they could fill an entire box with clues like the one below, as well as rework the game winning mechanics, I think Clever Endeavor could make a spectacular comeback.

You can pick up Clever Endeavor either at your nearest thrift store – if you’re lucky and patient – or on Amazon – again, if you’re lucky and someone is selling one.

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