like a canoe with a hole in it

“Like a canoe with a hole in it” isn’t a fixed, famous saying, but the meaning is very intuitive and matches how people talk on forums and in jokes about sinking boats and canoes.

Core meaning

The phrase “like a canoe with a hole in it” is usually understood to mean:

• Something that is doomed to fail from the start (a built‑in flaw).
• A plan, project, or relationship that is losing ‘buoyancy’ faster than you can fix it.
• Effort that feels pointless, similar to sayings like “pissing in the wind” or “a Sisyphean task,” where no real progress is possible.

In other words, if someone says “This business plan is like a canoe with a hole in it,” they’re saying it’s structurally unsound: no matter how hard you paddle, it’s going under.

How people might use it

You might hear it in casual conversation or forum discussions as:

• “Our budget is like a canoe with a hole in it – money just keeps leaking out.”
• “Trying to fix this code without rewriting it is like being in a canoe with a hole in it.”
• “Their relationship is like a canoe with a hole in it; they keep trying, but it’s sinking anyway.”

It works as a visual, slightly humorous metaphor, much like other water‑based idioms people reach for when they talk about hopeless or self‑defeating efforts.

Related idioms and vibes

People often reach for similar “futile effort” images, such as:

• “Shoveling sand against the tide”
• “Nailing Jello to a tree”
• “Pissing in the wind”
• “Trying to make a hole in the water” (from Greek, used for pointless effort)

“Like a canoe with a hole in it” fits right into that family: vivid, a bit funny, but ultimately about something that can’t stay afloat. TL;DR: “Like a canoe with a hole in it” is a vivid metaphor for something fundamentally flawed or unsustainable that is bound to fail or “sink,” no matter how hard you try to keep it going.

Information gathered from public forums or data available on the internet and portrayed here.