Yesterday, when an extended family member said he realized that his high school degree won't be good enough to meet their aspirations and he is beginning to think about college or trade school. It took a few years for the realization to settle in.
What it made it better was my teenager who is in many ways similar and likely to take the same "path less traveled" got to hear the conversation.
I also did not go directly to college after HS either, uncertain what to do with myself. Have been encouraging our teenager to at least be thinking about the future.