Debt Regrets

What is your biggest debt regret?

My biggest debt regret was not a single instance but a series of mistakes that all stemmed from a lack of boundaries. It was the inability to say No, the fear of consequences if I did say No. The lack of boundaries manifested in many different ways in my life, but here are two relevant to money:
* The fear of missing out: making plans with friends and going to expensive restaurants and places, even when I didn't have the money for it. * The fear of someone else's reactions: buying things for them that I didn't agree on out of fear of being guilt-tripped.

Through these regrets, I learned ways to spend time with friends that didn't involve spending money that I didn't have. I got comfortable with the idea that I won't be able to do it all right now. I learned that my friends will still be friends even if I didn't have the money to do all sorts of things with them. I learned that someone else's reactions are about themselves and not about me. I learned to be okay with someone else's reactions. I learned that guilt is a powerful motivator and if someone is guilt-tripping me about something, it's probably not a healthy dynamic and that I am out of alignment with what I actually want. 
What are your biggest debt regrets? What are the lessons that you learned?

Do any of these resonate with you or leave you with more questions? Comment or DM me! I'm working on a library of resources and want to know the areas where you'd like guidance.