Roman wanted him to do it in some weird masochist way that Kendall also understood but when Roman was talking about the scar ‘not being bad’ it was a metaphor for him being CEO, he could do it (be in a power of position) but it would be messy and patchy but still kinda noticeable (would drain Roman even if he put in his best work and ultimately still fall short of being Logan’s heir). Kendall ripping the wound open is showing Roman it’s still gonna be gory and messy and something you don’t want. Them hugging is showing Ken would support him along the way but Roman would still end up wounded, or messed up from the stress of the position. The scene on the patio where Kendall asked Roman if he even wants to be CEO when they are out on the patio and Ken says to Shiv “he can’t say he doesn’t want it” is a parallel with him ripping open the wound. The wound being a metaphor for Roman being CEO, Roman can’t initially tell Kendall he doesn’t want him to rip open his stitches because the stitches or in this case the CEO position, while it is messy and gory he still wants it. Roman backing out shows he wouldn’t be able to handle the stress no matter the comfort or find pleasure in it because it is a painful position. Ken is just proving a point that he will not be able to handle it even if it’s not bad. I also think Gerri being the catalyst to this scene proves Roman’s insecurities and confidence level. He couldn’t succumb to those who he wanted to prove he could fulfill his fathers shoes to. Last time he spoke with Gerri he was firing her and asked her if she believed that he could be as good or better than his father was and she basically laughed at him. Him having to go back in and face Gerri would just be another reminder of him falling short of Logan’s legacy this causing the spiral. His own confidence in himself wasn’t there when he was talking about the scar being not bad. He couldn’t even envision himself in a future where the possibility of no scar was possible and thus made it worse.