Some of those people aren't "born lucky," they had ambition. They had goals and a plan to achieve those goals. You may have goals (i.e. financially stable) but you don't sound like you have any ambition or any plans. If you do just enough to get by, employers aren't going to go for it. They want "go-getters" and people who want to move up because they know those are the people who are going to do the job well.

Some people are definitely born lucky (Paris Hilton, Walton kids) but most people have put in their time and effort to get a good paying job.

It may suck, but a degree is the most reliable way to move up. It doesn't necessarily show that you know your shit, but it does show that you can take something and stick to it for several years. Jumping from mediocre job to mediocre job won't do anything for you or your resume. You won't be any worse off with a degree, but it's a surefire way to make you more hireable and to get a better job.