Here are some thoughts on creating portraits that feel true and transcending norms in photography:
Capture authentic emotion and connection - Try to go beyond surface level smiles and make the subject comfortable so their personality and essence comes through. Capture them candidly engaged in something they enjoy. Connect with them as a person first before photographing.
Focus on natural light and minimal retouching - Natural lighting flatters most subjects and avoids the artificiality of complex setups. Embrace imperfections and refrain from over-retouching. Keep some flaws to maintain a raw, authentic feel.
Break compositional rules - Play with unconventional framing like extreme closeups, unusual angles, or off-center placement. Break the expectation of central, head-on positioning.
Experiment with grain and texture - Add film grain or embrace noise to create a grittier, analog feel. Avoid glossy, highly processed looks.
Use alternative processes - Try developing prints with cyanotypes, salt prints or hand painting for organic, unpredictable results. Or use toy cameras, pinhole cameras etc.
Photograph moments unposed - Capture glimpses of real emotion and activity. Posed portraits can feel forced. React to genuine interactions and fleeting expressions.
Overall, embrace rawness, imperfections, and the unexpected. Photograph with a documentary sensibility rather than seeking perfection. The most compelling portraits often subvert or transcend conventional techniques to capture a true essence.