Dear Me,

I should have written this letter to you a lot sooner. But I wasn’t ready – I should have been. I should have been nicer to you growing up. You weren’t fat, or ugly. I should have been nicer to a lot of people. David didn’t deserve for me to pick on him so much, and Lindsey just needed a friend. I should have been her friend. I should have stayed out of trouble. I should have stayed away from boys and partying. I should have studied harder in high school. I should have kept up with the track team. I should have listened to Mom. She was always right.

I should have gone to a different college; the one I really wanted, but it wasn’t Dad’s top choice. I should have told him how much it mattered to me. I should have chosen a different major, maybe then I would not have dropped out. I should have waited to get married and have kids. I should have gone backpacking in Europe first. And skydiving. I should have gotten to know you first. I should have put you first, maybe then I wouldn’t feel so lost. 

I should have taken the other job; the one that was a little less money, but man I would have been so much happier. I should have spoken up in that meeting. I’m so tired of getting walked all over. I should have talked to HR about Tom in accounting. Man, he sure said some inappropriate things. I should have slapped him. 

I should have seen that my husband was having an affair. I should have seen how much our arguing affected the children. I should have never married him. I should have married Michael instead. I should have known. I should have done a lot of things differently. 

But, I didn’t. And I’m writing you this letter to tell you it is okay. It is okay to make mistakes, to miss opportunities, to have a past littered with things you might regret. It is okay to let go of all of those things, too: to stop focusing on your past, and to live a life of fulfillment and forward direction. 

Show yourself some grace, damnit. Forget the past. That was then, and this is now. Accept the past for what it was, and embrace what is coming in the future! Forgive yourself and let go of what weighs heavy on your heart. Ditch all of these ‘Should Have’ shenanigans and take control of what lies ahead. You are strong, you can do this. I believe in you. 

All my love, 

Me