Madcow 5x5

>Remember starting too light is better than too heavy – let it be easy the first weeks, focus on technique and speed, and only aim to break PRs starting week 4. For more information, read Madcow’s original guide here.

I use 3x5 for my big compound lifts then 3 x 8-12 for my isolations

Been there. It sucks if you don't modify it. The idea of doing heavy triples and transferring onto heavy sets of five is ok, but once you start struggling with the triple, you'll miss your monday five. The overall volume is really low, bench especially.

Do some sort of heavy 3x5 with 50-70% warm-up sets beforehand and increase the weight by 5 kg on friday, then decrease it again by 2.5 kg on monday and to the set of five.

Or just get a coach if you're interested in strength training.

>few days ago

It's supposed to be fairly light until like week 4. It will be very challenging once you reach double digit weeks. Made great progress myself on Madcow.

How does one work up to a single in order to get a new 5RM in TM?

Madcow is really good, I made really solid gains on it.
If you just hopped on it, its because there is a 4-week ramp up period. Come back in 4 weeks and tell me thaaat the volume is lacking.
After about week 7, you are dying by the end of each workout

as this guy said, there comes a point where transferring the heavy triple on friday into a 5-rep set on monday is really tough. at that point, deload or add more volume on friday (i.e. another set of 8)

How do you know how long you should go without resetting?

When you start regularly missing reps, its time to deload (or find another program if you're no longer getting PRs after the reset).