I started as Thief. Started with Pickpocketing and when my thieves had 6 stars in stealth and combat, I moved into scouting and break-ins. I also trained regularly in Handicraft, eventually mastering the profession and upgraded my starting building into a Thieves Guild with all extensions built.

All of this took many years and every now and then my opponents will be building new buildings, and getting new titles and public offices. My coffers are not exactly overflowing but I can afford a villa now and again.

I think my foundation is pretty solid. But my guy is still single. I tried to court the rich and powerful ladies, took me like 8 years to find out he got rejected. I used rings during elections but so far all attempts at public office failed.

Looking at it, it seems like my guy has enough to live on but nowhere near taking over anything. How can I turn this whole thing around?