You might be better off using an inconspicuous trellis of some sort. I saw a tip somewhere suggesting attaching a board at the top and bottom, painted to match, and then stringing wire or line between them for a vine to climb without damaging a wall.

Like carol said, but with fishing line.

Ivy climbs by use of holdfasts or aerial rootlets. It needs a textured flat surface to climb so things like trellises or fishing line don't really work - they just don't have enough substance or width for the rootlets to grasp and take hold.

You may need to tie the ivy tendrils to the column temporarily with some twine (wrapped around the entire column). Once these tendrils sense the solid surface, they will start producing the stem rootlets that will help the vine adhere. Once it adheres, it will continue to do so and to climb and you can remove the temporary twine.

If you see Ivy in the wild it will start to climb only via the new growth at the tips. Older stems like these won’t attach themselves easily. I’d be inclined to clip back a few stems and guide the resultant new shoots to the pillar. Or you could stick some existing shoots to the surface temporarily with tape and wait for growth at the tips to attach themselves. As GG said Ivy will not easily climb trellis and will fail completely to stick to fishing line.

I will try to anchor a few lines and see how it goes.

You won’t get much new growth to climb the wall if they are left in the pot. Plant in the ground!

It is planted in the ground. The pot was cut in half, inserted into the ground to deter the lawn service folks from slicing across with their weed eater edger tools.

> pot was cut in half, inserted into the ground to deter the lawn service folks

That may be an insufficient measure; they find it difficult to resist opportunities to destroy or mangle.