Shawn this is a great topic. I was raised in a household where both parents worked 9-5 gigs and never promoted the entrepreneur lifestyle, although my dads family were business owners he never tried to adapt. I'm not sure what the turning point was for you but I never liked the fact that someone else could control my income and fire me for whatever reason they liked. I never wanted to feel like I had to kiss a** in order to feed my family which is what I saw my dad do but he made it through and stayed on the same job for 31 years. But he was very unhappy. I decided I wanted to be different and have more control over my life.
One thing I have learned is that you will always have people who are waiting for you to fail and can give you a million reasons why something wont work but this is where you have to dig in deep and push onward. I have also learned that most people who are trying to shoot down your ambitious goals are the ones who are afraid to try these things themselves. I have several "friends" and family members who are college educated and feel that what I'm doing is foolish and up until recently felt that getting a "steady" job was the way to secure a good life but since the crash of the economy their viewpoints have changed and seem a little more interested in real estate investing.
When it comes to obtaining,maintaining and expanding a Wealth building mindset here are a few things that have worked in my favor:
1) Stay away from the "nay-sayers". I dont mean cut them out of your life just dont discuss your business goals with them. Period.
2) Educate your self. The worlds of real estate and finance are constantly changing therefore I have learned the more I educate myself on different aspects of the business the more confident I feel about pursuing certain goals.This can be done by reading, listening and networking on awesome sites like BIGGERPOCKETS.
3) Surround yourself with like minded people. You will no doubt need someone to talk with when that "blockbuster" deal falls through but it needs to be someone who can relate to your frustrations. But beware just because someone is an investor does not mean that they wont try to discourage you. You have to learn the difference between someone who is offering constructive criticism and someone who is jealous and trying to pick you apart. Also these colleagues dont have to be involved in real estate. Most business owners experience similar problems.
These are just my personal thoughts on the subject but there are many investors on this forum that can offer some great advice also.