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Dear Quota Team,
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Ok, this might be a completely bizarre question, but I think it’s perfect for your newsletter. I have been in sales for close to twenty years, and in that time have held almost every level of position. I’m currently a sales manager in a niche industry, and do quite well. 
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My question is about a friend of mine. I’ve known him since high school. Most of us have stayed in touch and talk regularly. My friend got into sales about five years ago after he saw how successful I’d been and how it allowed me to afford a great house and lifestyle.
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The problem is that he seems to be terrible at sales but doesn’t seem able to admit it to himself. He has worked for seven companies in the last five years, and there seems to be no end in sight. When I talk about it, he talks about sales as if there’s a light at the end of the tunnel, and as if he is close to getting that “perfect” sales job that he’ll stay and succeed in.
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From what I can tell, he barely closes any deals. He is a really nice guy which I think helps him land these jobs, but he’s also kind of mentally disorganized and somewhat unreliable, which I think is a big part of the reason why he fails. 
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I kind of want to tell him that he should find another career. I want to do this for his own good. We’re all in our forties now and most of us have our lives more or less figured out, but he keeps flailing. Should I have a talk with him where I give him some advice, or should I let him figure things out on his own. It kind of hurts me to see him wasting his time like this. Any advice?
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Empathetic in New Jersey
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Dear Empathetic,
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You’re a good friend and you mean well, but since your friend didn’t come out and ask you for advice, this is a bit of a tricky situation to navigate. 
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You should start by finding out if he wants your help. Ask him how work is going, then ask how you can help. Tell him you want him to be happy and successful and since you’ve been at it for a lot longer, maybe there are some tips you can give him to help him make it work.
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If the conversation goes in that direction, maybe try approaching it from a 'coaching' perspective, or a way where you both talk about what you're good/bad at in sales. Just make sure you don’t come off as condescending or a know-it-all, since any advice from that perspective is likely to be ignored. 
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As far as telling him to try another career, you can only do it casually, in the form of a random suggestion. “Hey, I actually know someone who’s doing really well in _____. Might be something worth checking out.”
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Giving unsolicited advice is always difficult, especially among friends. But your heart is in the right place, and you might end up making a difference in your friend’s life. Oh, and one last thing: just because somebody doesn’t take your advice right away doesn’t mean they won’t. Sometimes people push back and argue, then walk away and eventually realize you were right. Good luck to you and your friend!