27. You should’ve known better

Let’s tackle the “I’ve should’ve known better” self criticism when we entrusted the wrong person with our generosity or vulnerability. 

I don’t think it’s fair to blame yourself when things go poorly. Hindsight is 20-20, but in the moment, it’s hard to tell who “deserves” your trust and who doesn’t. 

Questions to ask yourself: 

When  you don’t have the benefit of hindsight, how do you predict a situation that’s going to turn into an “I should’ve known” regret?  

What would it take for you to “know better”? Wouldn’t you have to make a judgment regarding whether or not that person is worthy of your trust, vulnerability or generosity? Is it fair to require that much research before making an effort with someone? 

If you truly should have known better, what does it look like to prove that you do know better now? Does that look like the person you want to be? Does it align with your values? 

What if you can’t change them but you can keep them from changing you? 

What if it’s not that you should have known better, but that you were choosing to be vulnerable and authentic?  



Side quests: 

A short recap of last week’s episode about self-reflection and considering if you’re being authentic or performing a role. 

Walking the walk about letting go of perfectionism and allowing myself to be a work in progress.