Upload media files

Upload media files in WordPress — with the four heights of help laid out: do it now, make it easier for the next person to accept, work out the right move when you are stuck, and learn the pattern so it stops coming back.

4prompt heights
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The four heights

The same task, four distances: today's deadline, the next reviewer, the stuck moment, the pattern.

Execute — do the immediate task

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Upload 12 photos from last weekend’s pop-up to the media library, name files with the event date…
Upload 12 photos from last weekend’s pop-up to the media library, name files with the event date and photographer (2026-07-12_SummerPop_MayaLopez.jpg), add alt text describing each image for accessibility, and organize them into a new media folder called SummerPop2026. Complete this before end of day so the gallery can go live tomorrow.

Improve — make it easier to accept

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Before I finish uploading the pop-up photos, make approval easy for the marketing lead. Put the…
Before I finish uploading the pop-up photos, make approval easy for the marketing lead. Put the event date and photographer in every filename, write concise alt text that highlights subject and mood for each image, resize any files over 2MB, and mark which three are hero candidates for the homepage carousel.

Decide — diagnose the stuck moment

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I tried to upload the pop-up photos but several are too large and the upload timed out. The social…

Upload stalled because images exceed size limits

I tried to upload the pop-up photos but several are too large and the upload timed out. The social lead, Omar, expects high-res images but the site slows if I upload everything. I don’t know which images need full resolution and which can be downsized. Should I keep three full-res hero images and compress the rest, and which criteria pick the heroes to satisfy Omar without breaking the site?

Become — change the pattern

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Over multiple site updates, uploading unoptimized images creates failed uploads and delays the…

Media uploads repeatedly fail and stall launches

Over multiple site updates, uploading unoptimized images creates failed uploads and delays the homepage refresh. I lose time reconciling file sizes with what marketing wants. What single change to our media workflow will prevent this recurring bottleneck — naming, resizing, or approval gate — and how to implement it so the next upload goes smoothly?

Next to this one

Other website builder work people do in WordPress.

Every task here came from the work, not from a feature list — which is why the prompts name what you want done and never the button that does it. The tool changes; the work does not.
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The rest of the map

Same library, five ways in.