One of the harder ideas to accept, as our kids get older, is that an important part of their learning is what they learn, on their own. For one of mine, a sage person told me, “She has to learn this.” And, “From her own mistakes.” Now, our advice and suggestions need to be oblique, if at all, unless they directly ask. Not easy.
Plus we adults fo see more angles and ramifications. But though we now have them partly launched, they grow at their own pace. OP, I’d think, if you have these concerns, he’s heard that, knows you have ideas. He may come to you for strategy advice, at some point. Or first try it on his own, learn from that.
My other is also not anxious. I just praise and commiserate and she does fine.