Most upsells fail because they sell more information when buyers already have it. Instead, offer acceleration (faster results), accountability (coaching or audits), or personalization (templates, community, custom plans). Shift from teaching to doing.
Chapters
Here's a mistake I see in a lot of funnels. The upsell is just more of the thing they already bought. They buy a $7 guide, then the upsell is a $97 course on the exact same topic, same idea, just longer. And that usually doesn't convert that well because the buyer doesn't need more content. They need help getting the result. So a better upsell is usually one of 3 things: something that gets them there faster, something that keeps them accountable, or something that feels more personalized— templates, a community, a coaching call, an audit, a custom plan. That's what tends to convert because at that point they already believe in the topic. What they want now is the easier path. So don't sell them more information. Sell them a faster, simpler, more supported way to get the outcome.