I'm assuming you're based out of Canada. Where abouts? I'm in Calgary and find myself in a similar position, however my situation may have more flexibility.
I'm 37 and my wife is 33. Our family net worth is in the mid 7-figures. I’m in middle management and she’s a sub-specialist physician with annual income in the 7-figures—income is high and stable. We have two children and one on the way. We have been discussing the possibility of me leaving the work force to be a stay-at-home dad and managing the ‘family office’ when the third arrives. I use the term family office loosely as we only have four corporations within the family that serves various functions.
Part of me managing the family office would be to actively trade with a small portion of our portfolio. Our portfolio has been very passive historically but I’ve been becoming more active with a microscopic part of the portfolio (<5%). The active part of the portfolio has been very successful to date. I’m not a day trader, but more of a options position trader. I average 20 trades per week which includes all legs of spreads. If I were to quit my job, I’d be more active with a larger percentage (25%). Replicating my performance with a larger allocation would easily replace my lost income. But as they say, past performance is not an indicator of future results.
Another driver is lifestyle. My wife gets home before me during the week, helps out with homework and ferries the kids to various after school activities. Being a stay-at-home dad, I can help out around the house a little more, particularly during the week.
Back to the OP, I have no desire to join a prop firm. I feel I don’t need the leverage a prop firm can provide and being a solo retailer allows me to keep costs down. But I certainly see the social appeal of being around other traders to share ideas. I wish Calgary had something like that (of quality).