A couple of prompts for this list including a survey by Bloomberg about financial security and the following quote I saw. This list is a series of questions to do a self assessment of actual freedom.
1. What day is it?
This is from Mark Baker and essentially not knowing what day it is can be considered a sign of freedom. You're doing what you want to do everyday.
2. How much trouble would you be in if your primary income source disappeared tomorrow?
Take this as being about several things including having money in the bank, having multiple streams of income or having optionality to go find something else in short order.
3. Do you need an alarm clock?
This is about owning your time, setting your own schedule
4. Can you move the bag of concrete?
This is just an example for physical capabilities. Hoisting a 300 pound thing into the bed of your truck won't be doable for too many people but a 60-80 pound bag of concrete or 5 gallons of something or the big bag of dog food, not relying on someone else to move 50 pounds is how to think of this one.
5. What constituencies do you answer to?
I answer to clients of my day job as one constituency for example and I have to have a radio on me at all times for fire department calls for service. These truths detract from my freedom quotient (making up a term). Channeling Ayn Rand, does it matter that I enjoy doing these things? The answer is reasonably subjective.