A little hard-up for productive work, this week, I found myself sailing close to the wind.
While I promote the idea of taking a risk, it’s different when said risk is loaded with caution, from souls, wiser and older. When the popular opinion is ‘sounds like a scam’ I should run for the hills, not step into the cuck boots and all. Alas, I did the latter.
Now that I have completed and submitted the assignment, payment hangs in the balance due to a requirement that I was not made aware of at the outset.
High seas
Like many English idioms, “sailing close to the wind” hails from the high seas. In its original sense, it described a sailor’s art of navigating as near as possible to the direction of the wind — a tricky move, requiring precision and nerve. Too close, and the sails lose power; too far, and you drift off course. It was a delicate balance, and the metaphor stuck.
‘Nauti’cal but nice
By the early 1800s, the phrase had found its way ashore. No longer just nautical, it came to describe anyone skirting the edge of rules — be they social, legal, or moral. It suggests cunning, but also risk.
Today, it’s often used in politics, business, or everyday conversation:
- That email felt like it was sailing close to the wind legally.
- They didn’t lie outright, but they certainly sailed close to the wind with that pitch.
It’s a phrase that captures both admiration and unease — a compliment with a raised eyebrow.
And back to me, it seems my risk has not paid off and I went sailing close to the wind on a very tiny boat.
I fell on my sword: idiom usage
