A philosophical question, you say. Then I'll give it a philosophical answer. Well... I've questioned my gender my entire life, or at least since I was in pre-school. I felt that "girl" was the last thing I could ever be, gender-wise. I though for sure I was a guy in my teen years and transitioned as a young adult. I was comfortable and felt empowered as a man. Then ten years later it turned out I was a cis woman all along.
Being on testosterone helped me in the past but ever since I went off it 6 months ago, I've been loving estrogen. Gender aside, both hormones have been both amazing and disastrous for me personally. Especially for my mood. Neither cured me from any of my actual issues. But figuring out my truth set me on the right track.
So now I'm detransitioning and slightly miserable about that, but I really love being a woman, for the first time ever in my life.
If you ask: can a person be trans without having questioned their gender? I am simply bouncing it back by asking: can a person be cis despite having always questioned their gender?
My personal experience answers "yes" to my own question, but I cannot answer yours. However I can imply that it might be just as possible, considering our scenarios are completely reverse. But then being cis is not the complete reverse to being trans, and there's always more to both than the gender aspect. There is also a certain amount of overlap, which most people seem to either overlook or be unaware of.
I think a more important question is: what do you want with your life? instead of just looking at the two boxes cis and trans. I had to do a lot of deep digging through my mind to find my answers. I'm suggesting you do too.