Dear Carolyn: My longtime best friend, Mary, has been complaining about her financial situation. She is self-employed and only works part-time, by her choice. Another friend of ours is a professional business coach and has offered many times to help Mary set up a formal business plan and to help her learn to market herself more effectively, but Mary doesn't want to put in the effort.
Lately, Mary has been talking about taking on a second job but has no idea what she wants to do. She refuses to work for someone else because she only wants to work when she wants. She is not comfortable using most technology and has zero desire to earn a degree.
I know I can't force Mary to do anything, but I don't know how to keep sympathizing with her when she can't seem to grasp that making more money might mean doing something she doesn't like or on someone else's terms. How can I kindly tell my friend there are no well-paying "work when you feel like it" options?
— Free Spirit's Friend
Free Spirit’s Friend: I don’t think it’s free-spiritedness anymore when you’re chained to it.
“I’d love to be wrong about this, Mary, but from my perspective, you have a lot of energy to complain about your situation, but very little when it comes to doing something about it. That strikes me as a more reliable source of unhappiness than money shortages or having to report to somebody else.”
If I ever write to you guys for advice on why people don’t like me, send me this.
And yes, you can also just say to Mary, “In my experience, there are no well-paying ‘work when you feel like it’ options. If you find one, though, please let the rest of us in on it.”
Re: Mary: The "free spirit" could suffer from depression. It may be that she is simply unable to move forward to other things, instead of merely unwilling. It's hard to articulate that or admit it to yourself or others when you're the one suffering from clinical depression.
Anonymous: True, thanks. ADHD can also produce this kind of paralysis. And anxiety.
I do think friends can serve a useful purpose even in these cases — by not merely suggesting things that will surely be ruled out for whatever reason.
Instead, they can prompt her. “What do you think you’ll do?” And, “That’s a tough one. Any ideas?” “That sounds frustrating. Have you asked anyone for help?”
Etc. However you phrase it, be warmly, firmly relentless in shifting the responsibility for problem-solving back where it belongs, with her.
That can include, where appropriate: “Have you ever been screened for anxiety or depression?”
Expressing sympathy is not the only way to be a supportive friend, especially when you don’t actually sympathize. Sometimes, the kindest position to take is that of affectionate mirror — reflecting her complaints back on her — and, when that phase outlasts your patience, affectionate brick wall: “I love you like a sister, but I can’t talk about this again.”