"Mom struggles"

I've been struggling lately. I don't know if it's the upcoming surgery that has me more contemplative.  I've been thinking about Michael, myself, our relationship, and his future. I'm an enabler. I have a hard time telling Michael "no" when he asks for something, but especially since Amanda died. I know there were many times when Amanda was still alive that she'd ask for something (i.e. to have her nails done), and we said "No" when it would have been just as easy to say yes, even if it hurt a little financially at the time. Since Amanda died, I look back at all of those lost opportunities for the relationship to be built, those times to connect. Not that we should have said yes to everything and spoil her, but what really would it have hurt to say yes more than we did?  And so I have some regrets and I don't want to have those with Michael, BUT...

Michael is my baby...he will always be my baby, but he is not A baby, and I need to let him fall sometimes on his own without trying to swoop in and prevent...what?  Financial hardship of his own making? Him feeling the repercussions of poor decision making and lack of planning?  What I'm really preventing are learning opportunities for him to grow, to feel the sting and say OUCH! I shouldn't do "that" again.

In the last two months or so, we've spent a lot of money on Michael. Now granted, we CHOSE to do this, so he could go see his father and sisters.  We feel that was important. But see, it wasn't just the flight and travel money, then it's money to make up for his lost work when he gets back. It's hey, I forgot I need my meds, may I please get some money? And I rationalize, well those are important, so here's the money. And then it's that he needs contacts. Again, I rationalize the importance of those and purchase his eye appointment and 2 years of contacts....but the last time I bought them we were leaving NC and I told him he had two years to start budgeting and saving for the next go-round. Fast forward two years and there I go paying again. And it's gas money sometimes, and his check was short so can I help him pay rent? There's a litany of occurrences.  He always expresses his great thankfulness, so there's that, but...he's 26 now.  Yesterday he texted me this sweet note but was asking if I would "help" him get his fishing license so he could take Sara out on a boat fishing at River Park North. I lied to him and said I didn't have the money. I felt terrible for lying to him and I thought saying No might split me in two. Then I worry about, well is he going to put it on his credit card and just add to his debt then??  He likes to go and do like we all do, but he doesn't have the income for it...at all.  So since I'm connected to his checking account and I can see when he's gone to Christy's Euro Pub and blown money that, had he planned ahead, could have been used for X, Y, or Z, and then he asks me for money, it bothers me.  So I'm not mad at myself for saying No, (I mean clearly I say "yes" too much!), but then the guilt starts of....would I look back on this if something were to happen to him and regret it? In this instance, I definitely think not.  It's just a struggle. Letting go. Needing him to grow up, but then I've been preventing that in many ways. I mean, he pays his bills, gas, etc., 99% of the time, he just needs to learn to budget and plan ahead.  Part of me thinks...well geez, at 26 I had a 2-year-old and a 7-year old....but he's not me, and I've been enabling this behavior of spending all I have and then asking mom when I can't do _____.