The eighth question on my list of things to talk about before going into business or starting a project together is: 

What is your plan for success or failure? 

(See post #1 in this series here: https://leighchandler.com/questions-to-ask-before-you-work-together)

Hopefully, you started to have this conversation back at question 1, when you explored your goals.  But it is so important that it deserves its own entry, just in case you missed it (or didn’t go into it deeply because you mostly agreed).

If your project succeeds, what is the next step?  Do you move on to bigger and better things together?  Sell and go your separate ways?  Stick with it until you’ve built something huge? 

How do you measure success, and what are the signals that it is time to cut your losses?  Failure isn’t something we like to talk about, but planning for it takes some of the scary out of it.  Explore the ways you’re willing to sacrifice to make your project work… and the limits to that sacrifice. 

You can’t be sure how you’ll feel about any of this once you get there, but making a firm plan isn’t the goal, you just want to open the conversation.