Dear Anna,

I’ve been with my boyfriend for three years, and I love him — he’s funny, supportive and kind. Right now, we’re living at my sister’s place while saving for our own apartment. He’s 29 and I’m 27. I work full time as a freelance writer and make a comfortable living, but his part-time retail job barely covers his own expenses, so moving out feels like it’s slipping further away. He’s tried a lot of different things — short courses, odd jobs — but nothing sticks. He says he wants to find a career, but he doesn’t know what path to take and has no degree, certifications or family support. I keep thinking a tech role would suit him, but I don’t want to micromanage his life. How can I encourage him to take the lead and figure out his next steps? — Not Your Career Coach

Dear NYCC,

Y

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