We can follow a guideline until we evolve to an understanding where meditativeness becomes our natural state.
Here is an article with such a guideline.
Some meditation practices are designed to gradually evolve your understanding and state of existence so you are more and more in a state of living with awareness, containing more and more of life within what you experience as yourself. Ultimately you are the entirety of life, but now, you are experiencing yourself as a separate being. Meditation practices evolve the understanding of you experiencing yourself as a separate being to experience yourself more and more as the entirety of life. You are not supposed to have a certain type of experience, the aim is to naturally bring about into your experience what exists as the fundamental truth of life all the time, in an organic way that can start evolving what understanding you already have.
Meditation definitely is not a philosophical/conceptual exercise, but your mind’s understanding naturally evolves as you practice meditation as well. Some ‘meditations’ out there might use concepts/imagination to guide you, they can help with your development too, but not in the way that meditations designed to directly aim for experiencing your true nature, deeper than the conceptual part of the mind. If conceptual/imagination guiding is to be called meditation, then mainstream education/schooling is meditation as well and I think we already have experienced its limitations one way or another. But this type of work must be distinguished from the genuine type of meditation directly aiming to awaken you to your true self, transcending the mind. Every other practice that can potentially help bring a sense of meditativeness, is prone to getting called meditation nowadays. The link I have provided gives a concrete definition of meditation which can help you distinguish/discern.
The article will also bring clarification to what aspects of a meditation practice is necessary to truly awaken you to your higher self/the deeper aspects of yourself, but I think the main purpose of that article is to setup a framework of a basic level of understanding that can be a very concrete starting point. You can start practicing right away using that article and then you will also be able to have insights satisfying your question in an experiential way.