> In my first company, they used 10+ year old tooling and imo it was terrible. A very old legacy mess monolith that made adding features pure torture.

Everything becomes like that, legacy, torture, mess. New things comes along, clean, new, solves some problem. Mess dissapears from one place but starts popping out somewhere else but still better than before you think. Wait 10 years and you and you’ve got a completely different mess, lots of people who built it have now left, few know it all but have stopped caring. A new you joins the group. Sees a crazy unweildy legacy system. Sees new technology that solves these problem. Starts over.