The honest answer to "when should I upgrade" is never "when a plan feels expensive relative to what you're making from it" — it's when you hit a specific limit that's actually costing you something. Upgrading before that point is paying for headroom you're not using yet; waiting past it is quietly losing sales or data you'd have kept otherwise. The clearest signal is hitting your block limit. If you're deleting an older link every time you want to add a new product, you're not just inconvenienced — you're actively removing things customers might have clicked, to make room for something new, when the real fix is simply more room. A second signal is your analytics window running out. If you're on a plan with 7 or 30 days of retention and you want to compare this month's performance to last month's, a longer retention window on a higher plan is the only way to actually see that comparison instead of losing the older data before you can use it. A third, less obvious signal: you're managing more than one page's worth of content through a single account. That's not a sign you need more blocks, it's a sign you've outgrown a single-page plan entirely and need Agency instead. The safest way to know for certain is to actually use the 30-day trial on the plan you think you need — no card required — and let your real usage over those 30 days answer the question a feature list alone can't.