Re: What is your biggest obstacle to achieving financial freedom ?
~ Exactly. It can be very stressing. I can write a book about how stressing it can be to run your own business. I wouldn't recommend, especially to young people, even if they think that they have enough money for that, to open their own business. If you are young and have money, you should invest in your education. If you want to be financially independent in the future, don't risk all the money you have with opening your own business while uneducated. The probability of you losing everything is very high in that case.
Truth be told, not everyone is suitable to be a business owner. I once started a wine business two years after I graduated from college, with money I borrowed from my parents. Unfornately it ended up as a failure and I have learned great lessons from that experience. Looking back, I actually don't regret on that "experiment" although I lost much money. Now I am living a comfortable life and keep all lessons in mind. It is just best to know who you are and what you really need.
First off, I agree that when we try to do something and then fail in the end, it can be a good lesson for us, a better one than that derived from some lectures. Also, it's good that you borrowed money from my parents, and not from a mafia.
To be honest, I'd like to read more about your "experiment" with a wine business(Where was it? California?). Please, if you have time, tell us about it.And, as far as I understand, you have achieved financial freedom yourself(or, you are very close to it). So, what is your answer to the question in the OP?