Trying to set up a small solo IEM for one guitar

Hi all - first time on this sub, sorry if this is a stupid question or in the wrong spot.

Basically, I am a guitarist trying to set up an iem directly from my guitar to my ears to help hear myself/get pitches for vocal reasons. Most of the venues I play at are small/local enough that they do not have sound guys or even mixing boards. How would I be able to set up monitoring just for my signal?

Right now I am looking at:

• passive DI box at the end of my pedal chain
• connect DI to headphone amp
• connect headphone amp to IEM

I have searched this sub and haven’t really been able to find anyone else trying to do this (I know it’s definitely kind of the sketchy way of doing it).

Is this something it’s even really possible to set up? Any insight or help would be appreciated before I go and spend money on more equipment. Thanks :)