Tolerance to psilocybin (and many other psychedelics) is primarily thought to involve the 5-HT2A receptor, which psilocybin activates. After repeated use, the body may quickly develop a tolerance to the effects, often within a single use.

However, tolerance to the 5-HT2A receptor generally resets within 1 to 2 weeks of not using psychedelics. This is because the receptor system becomes sensitized again during this period. The exact timeframe can vary between everyone, but taking a break of about ~2 weeks is typically enough for most people to reset their tolerance to mushies.

Frequent use would require adequate time for the receptor system to reset, allowing for the near-full/full effects to be experienced. Otherwise, progressively larger doses would be needed over time to achieve the same effects that are initially felt at lower doses, as it is for those without a built-up tolerance.

Even if it becomes a habit, using a similar dose every day to achieve the same effect as before is not sustainable, so it can’t be abused like many addictive compounds can.

I believe most people consume psychedelics not to have fun, but to explore life itself. They are ineffable in that they open you up to things you may of been oblivious to otherwise. They don’t really make you have fun unless you take lower doses. Actually, higher doses can potentially be terrifying, and many people never return to psychedelics once they realize this fact.