Many endeavours in my life required lots of determination, bravery, pushing myself, even though I sometimes didn't want to. It was rewarding to overcome obstacles, and find creative ways to solve problems. 
Last few years I've taken a different approach. I know my rough direction, but leave things open and flexible. And when something isn't working as smoothly as it could, then consider stopping, and work on something else (often related) and then later try again or I discovered a different way that was more optimal to achieve the same goal. 
To my surprise I've achieved more in the last few years than I have my whole life! This includes financial, personal, work related, almost every measure in my life. I'm happier  less stressed, I've got more energy to focus on important things.
Don't underestimate letting things happen, and not be so adamant to force something when it's not flowing.
Also when you progress in one area of your life (often personal/ relationship with friend or family) it has a direct effect on something that seems like there is no connection logically and vice versa.
Basically I found being less rigid suddenly attracted more opportunities that I would normally never consider possible. 
You definitely on the right track! You will be pleasantly surprised. 😲