When we write business plans, we end up guessing rather than collecting information. This makes us look at risk in terms of what we could possibly gain, and then all the things we need to get right. We see what we have to put on the line.
This is risky, so flip it!
Experienced entrepreneurs do it the other way. They take small risks that they can easily afford to lose, and even if they lose, they come out ahead with better information, connections or resources for the next bet.
Pick goals in a way where you risk an affordable amount of time or money. What can you aim for now, with what you've got?
What do you need to reveal about the that direction to know if there's risk in it? What will this information cost to get? Can you afford to get it? Can you afford not to?