Inspiring topic and post you've created. I was for some part of my life also risk avoiding. Postpone buying a house, stay longer with my employers than good for me. A couple of years ago I changed my career completely, took the opportunity to let myself go with a package and started a self employment life. Very exiting, but also scary. I manage my fears by thinking positive, not looking back at my decision, take it as it comes. Last years I had my ups and downs, but I love my freedom I created. I can enjoy longer vacations, can decide to sleep in on weekdays and so on. At times when things get rough, I try to look for solutions and most of the time there are solutions, maybe not always those you like, but hey, nothing is always 100% sunny. Of course I still have my fears, but so far I'm able to manage them providing me overall a better life than before the change from being an employee to be self employed.
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Looks like you have done really well in managing those fears! Thank you for sharing.