I have created a cms static block having some text lets say "hello Worls". . I created a widget which is using that block. I have specified in the fronend to dispaly in the home page and left column. I have a 3 col layout for the home page. I am using Magento 1.9 and it is not showing up even after I clear my cache. and then select the Preview option.
Your steps are seems correct and you've clear cache as well. let me draw flow here and do cross check with your steps Or create new one.
1. Create static block and make sure status is enable. (CMS >> Static Blocks)
2. Create new widget and choose your theme and assign All store view or choose your store.
3. from Layoout Updates tab, choose Display on; in your case choose "specific page"
4. From Page drop down choose "CMS Home page" and from "Block Reference" choose "Left column"
5. From "Widget Options" tab you need to choose your statick block.
6. That'it and save and check on FE.
Hope it helps you, good luck
P.S:- By following same steps you can also show static cms pages.