It can be tough to know what to say when someone close to you has lost a job or gotten a terrible diagnosis.
When my mom died, I was taken aback by some of the things people said. They were trying to be supportive, to connect with me in my time of grief, but sometimes it just amplified the hurt I was already feeling.
I liked this LA Times article headlined, How not to say the wrong thing. It follows an easy formula: comfort in, dump out.

Draw a circle. This is the center ring. In it, put the name of the person at the center of the current trauma. For Katie’s aneurysm, that’s Katie. Now draw a larger circle around the first one. In that ring put the name of the person next closest to the trauma. In the case of Katie’s aneurysm, that was Katie’s husband, Pat. Repeat the process as many times as you need to. In each larger ring put the next closest people. Parents and children before more distant relatives. Intimate friends in smaller rings, less intimate friends in larger ones. When you are done you have a Kvetching Order. One of Susan’s patients found it useful to tape it to her refrigerator.Here are the rules. The person in the center ring can say anything she wants to anyone, anywhere. She can kvetch and complain and whine and moan and curse the heavens and say, “Life is unfair” and “Why me?” That’s the one payoff for being in the center ring.
Everyone else can say those things too, but only to people in larger rings.

Here’s one caveat I’d add. I found it irritating when people offered consolation that was supposed to make my mom’s death seem like a good thing — she’s not in pain any more, she’s in a better place, she loved you a lot. And I do understand that they were trying to help, so I took their words in the spirit of loving kindness they were intended.
None of that took away from the hurt I was feeling, though.
So I’d specify that comfort in should probably be things like “I’m thinking of you,” or “Can I bring you dinner?” as opposed to inadvertently sounding like you’re minimizing the hurt. “You always hated that job,” might be true but it doesn’t help if you’re worried about paying the rent.
Comfort can take many forms, as long as you’re reading the situation right. When a friend lost both her mom and her dad while she was pregnant, I said perhaps too directly, “That sucks.” She thanked me and said she’d had so many people trying to cheer her up that she was relieved to have someone acknowledge her pain.
I’d encourage you to read Susan Silk and Barry Goldman’s whole article on the LA Times site, which includes this stinging anecdote about why it’s important to get comfort in/ dump out right:

“It’s not?” Susan wondered. “My breast cancer is not about me? It’s about you?”

Related articles

• Someone you know ill? Watch what you say, and to whom – Los Angeles Times (bikerdownministry.wordpress.com)
• Foot-in-Mouth Avoidance: Master the Kvetching Order (blogbyben.com)
• The kvetching order (kottke.org)