Answer: Although your feelings are understandable, you have absolutely nothing to be ashamed of. In fact, you should feel proud of yourself for holding down two jobs and keeping it together during difficult times.
Remember that Steve’s success doesn’t make him a better person. If he was faced with your life circumstances, he might not cope as well. And even though things seem to be going smoothly, he may have problems that are not apparent on the surface.
If you want to avoid detailing your personal history, just provide a short and simple summary. For example: "Frankly, the past few years have been pretty tough. But the good news is that I'm employed, I have supportive friends, and I'm working towards a better future."
Then shift the focus to Steve: "Being a motivational speaker must be interesting. What do you enjoy about it?" Or "Tell me about your family. What are all your kids doing?" If Steve is a talker, he may happily take over the conversation.
On the other hand, you may find that you want to share some of your story. If Steve is a true friend, he won't be judgmental. And if he’s judgmental, then he's not a true friend.
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