Good question.
Is aviation a perfectly safe career path that will lead to lollipops and rainbows on the back of a unicorn? No, very few careers are this day an age, unless you're selling feet pics. Apparently it's a lucrative market, according to a mate.
Could you get 90% of the satisfaction from owning/flying your own aircraft privately? Definitely. But there might be that little ear worm asking you "Do I actually posses the talent to be in command of the jet?". You are in the position where you have to ask yourself if you are comfortable with that ear worm. With 350 hours of private flying, you no doubt have a passion for aviation. It comes down to your personal motivation. Do you look up at an airliner and think 'cool' or do you really dig late afternoon circuits in a lightie before retiring to the hangar for refreshing cool beverage. The real answer to that will tell you what you want to do.
I have been flying professionally for almost 2 decades and grew up in an aviation family, so I was probably doomed from the start. It has been an amazing journey and even in hindsight, there is little I would change. Except for maybe my first marriage.
j3