I like this particular interpretation of the etymology of risk from Rolf Skjong (shown below), who talks about the story of Odysseus sailing through the Strait of Messina in The Odyssey written by Homer. When Odysseus had to sail through the Strait of Messina between Italy and Sicily, he was in a predicament.
If Odysseus tried too hard to avoid the monster Scylla living on the rocky cliffs of Italy, he and the men on his ship would be further endangered in becoming swallowed whole by Charybdis, the whirlpooloff the coast of Sicily.
If Odysseus tried too hard to avoid the whirlpool Charybdis, he would inadvertently be pushing himself and the men on his ship closer towards Scylla living on the coast of Italy, making it easier for her to pluck and gobble up all the men on the ship.
The story may be the origin of the phrase, "between a rock and a hard place".
Per Mr. Skjong :
ETYMOLOGY OF RISK: Classical Greek origin – Nautical Expression – Metaphor for “difficulty to avoid in the sea”
The term risk may be traced back to classical Greek ριζα, meaning root, later used in Latin for cliff. The term is used in Homer’s Rhapsody M of Odyssey “Sirens, Scylla, Charybdee and the bulls of Helios (Sun)” Odysseus tried to save himself from Charybdee at the cliffs of Scylla, where his ship was destroyed by heavy seas generated by Zeus as a punishment for his crew killing before the bulls of Helios (the god of the sun), by grapping the roots of a wild fig tree. In the classical text there is an antique painting of Odysseus riding a turtle (that happened to be on the cliffs) and the fig tree on the right.
Latin and vulgar latin (resicum, risicum, riscus : cliff, récif, Felsklippe, is the direct formal origin for italian (risico, risco, rischio), spanish riesgo and french risque. English borrowed it from spanish, german from italian and both were confirmed by the French risque of the 18th century. Dictionaries confirm that the Latin word comes from a Greek navigation term rhizikon, rhiza which meant “root, stone, cut of the firm land” and was a metaphor for “difficulty to avoid in the sea”. It might be of a certain interest that these lexical borrowings happened in the end of the middle-ages, when mentalities woke up and people dared to discover the world. So that from the 16th century on, the term got a benefit meaning, for example in middle-high-German Rysigo 1507 a technical term for business, with the meaning “to dare, to undertake, enterprise, hope for economic success”. 
The Strait of Messina that Odysseus had to navigate with Scylla on one side and Charybdis on the other, as shown on Google Maps, between the boot of Italy and the island of Sicily:
We like to say at our company: “To manage liability and asset risks adeptly is to sail unscathed between Scylla and Charybdis.”
What this means to us is that risk is present on both sides of the balance sheet, but to use each side optimally is something most companies and investors do not do.
The left side of the balance sheet consists of assets. If you deploy capital and overpay in the purchase of these assets, you've increased your asset risk significantly and severely diminished your ability to generate equity value using the right side of the balance sheet.
The failure of the hedge fund LTCM, which sought to profit off of slightly mis-priced assets using 100:1 leverage, is exemplary of this scenario. The hedge fund under-appreciated the risk of small mis-pricings (i.e. basis points) going the wrong way, and they blew up.
The right side of the balance sheet consists of liabilities and equity. For us, we focus on the management of liabilities. If you overpay in the sourcing of your liabilities, you've increased your liability risk significantly and severely diminished your ability to generate equity value using the left side of the balance sheet.
The primary modus operandi of most P&C insurers is exemplary of this scenario. They push so hard and consistently in generating significant amounts of liabilities, which are sourced at high costs of capital and managed at high leverage ratios. They've become hamstrung in their ability to create equity value using the left side of the balance sheet - they leave little room for error or any semblance of risk-taking in their asset management strategy.
But if we can balance the management of both asset risks and liability risks, then we think we can optimally create more equity value than others by crossing the proverbial Strait of Messina unscathed.