Do you ever find yourself trying to get someone to let go of something, to relax, or something similar, but they don’t? You know if they just didn’t worry so much or stopped caring about something so much, they’d have an easier time with the project, relationship, life, or whatever, but they just don’t let go?
You may be motivated by compassion, but I suspect a lack of empathy may be hampering you. I’ll illustrate the perspective of the person you’re trying to motivate with a story from my life.

Fear of being judged performing in public

This example is about performing in public. I use the context of singing karaoke, but you’ll see it could related to any number of other situations, professional or otherwise.
After business school’s class play, the cast celebrated with karaoke. I had just begun learning the leadership and social skills I write about here, so I was still mortified at singing karaoke (or the hangover after, if I decided to overcome the anxiety with alcohol). Now, of course, I see karaoke as a great tool for improving public speaking. I can’t sing any better, but I don’t feel embarrassed any more.
My friend and classmate noticed I wasn’t actively participating. She wanted me to loosen up and wanted to help. She was fun and outgoing and enjoying herself and wanted me to enjoy myself more.

Trying to motivate

Full of energy she wanted me to absorb, she got all happy on me and tried to get me to get up and dance and sing.
I told her I was enjoying myself and didn’t want to. It’s not that I didn’t want to enjoy myself and participate more actively, it’s that I didn’t know how, but didn’t even know to say I didn’t know how. I mean, I knew how to tell my muscles to jump up and cheer, but I didn’t know how to access the emotions everyone else was expressing. I didn’t know how not to judge myself or be resilient from others’ judgment.
Eventually she happily exhorted me just to yell at the top of my lungs to let it all out. She was so happy and trying to share her joy. I figure she felt if I did one big thing it would break the logjam and I’d get over whatever hangup she figured I had and I’d start dancing too.
If she figured I had her emotional skills and partying experience, her strategy might have worked. Maybe I naturally jumped and sang, but just wasn’t in the mood that night.

What didn’t work

But that wasn’t my condition. Since I didn’t know how to do those things, the pressure only shut me up more. She acted on compassion, but didn’t use empathy to understand what would motivate me to change my behavior.

What might work instead

I wonder what might have worked instead.
I’m not sure anyone could have gotten me jumping and singing. Well, alcohol lowers inhibitions, but I mean something enduring and independent.
My general strategy for overcoming hard problems is to overcome simpler problems and build on smaller successes. That’s worked for me over time — I’ve done karaoke in small groups of friends and built to larger groups and I’ve jumped and sung in other contexts. Maybe one day I’ll sing karaoke in a situation like that and have wild crazy fun with wanton abandon.
In any case, sometimes solutions require knowing the person’s situation, which means empathizing with them.