At a friend’s birthday dinner last week, I was once again reminded of how ostracizing it can be to express job-loving sentiments among job-hating people. After I said how happy I was to be back at work after a long vacation, friend smiled politely and remarked that she felt so unstimulated by her work. It was, she said, just a job, nothing more. I pressed her for details and suggested she seek ways to find a greater sense of ownership. She shut me down, and that was that.

Certainly, as someone who’s found myself in more than one not-so-great gig, I can understand how frustrating it can be to have a well-meaning friend try to help me figure my life out.

No one ever really means to be condescending, but it’s damn hard to know how to respond to a close pal’s career ranting. Does he want my advice? Or should I keep my mouth shut and just listen? Should I remind him of the importance of a typo-free resume or introduce him to my acquaintance who has a resume business?

There’s no one right answers, but there are some general guidelines:

When to Just Listen

Compassion for people who aren’t in your position is far more important than you may realize. It’s not helpful to maintain a smug attitude about how great things are for you while your friend is mired in misery. If it’s a venting session and it seems like the person is genuinely glad to get her complaints off her chest, then sit attentively and simply listen. Nothing else may be required from you at this time.

Be open to hearing about the frustrating work situation, but avoid pressing for information if the grievances sound like passing ones. Fleeting complaints may include things related to a long department meeting, the temperature in the office, having to stay late to meet a deadline, a demanding email from a client, and so on.

When to Suggest a Book or Article

Does your friend say he hates his job and then shut down and refuse to elaborate? Things may be worse than he’s willing to say, or he might be at a loss as to how to explain his dissatisfaction, or he may think that talking about it isn’t going to get him anywhere.

If your attempts at trying to get to the root of the problem and get him to talk it out to find ways to problem-solve have been failing, and if listening is pointless because he never really says anything, now’s your chance to offer guidance in the form of a book or article. Maybe you send one on how to make a career transition if he seems unhappy in his current industry. Maybe you put together a list of links to articles on bad bosses and knowing when to stay or leave. No need for a big speech or pretending to have all the answers. There are people who do that for a living.

When to Recommend Bringing in the Experts

Do you feel like it’s been literally years since you heard your best friend say anything good about her job? Do you feel like a broken record with your suggestion that she look for something new? Have your offers to proofread her resume and help her draft a cover letter so she can finally start the search been dismissed? Don’t take it personally. This person probably needs someone outside her circle to turn to for assistance.

It’s the perfect opportunity to suggest career coaching. Your advice about the importance of polishing up the ol’ LinkedIn profile might go unheeded, but similar advice from a professional career expert most likely won’t.

If you truly love your friends and want to help them, you’ll accept the fact that you don’t have all the answers. The fact that you’re happily employed might actually have the effect of making it more difficult for your guidance to be considered. Remember: There’s more emotional intelligence in knowing when to be all ears and when to take a different approach.

Photo of man listening courtesy of franckreporter/Getty Images.