Dear Prudence,
I’m in my late 20s and my father is in his mid-60s. He’s recently moved to a new state and has decided to try his hand at real estate. My problem? Dad has been a stay at home dad/essentially retired for my whole life. He is a total dreamer and a sweet man, but he is completely unprepared for the current workforce, let alone a competitive field. He is also somewhat delusional when it comes to his own skills/abilities. He doesn’t understand marketing/social media and thinks he can be successful without it. He refuses to create accounts to promote himself locally like his other colleagues. He is completely puzzled by all but the most basic computer programs and websites (I still have to explain how to search for stuff on YouTube and we watch videos together every day). He has poor eyesight, but won’t wear glasses/contacts for fear of seeming “old.”
I am a typical millennial who works in a fast-paced tech profession, and his lack of computer skills is alarming to me. I offer to help him with various things, but that just highlights how little he knows, and I’m feeling a sort of secondhand-embarrassment on his behalf. He won’t take classes to “brush up” (i.e. gain computer skills) because he says “he can figure anything out.” I’m scared he’ll crash and burn because he’s just not quite able to compete. I live across the country from him but stay in touch daily. How can I help him succeed and not seem like a doddering old man?
— Old Dad, New Career