How have I and How should I handle this?

My fiancé (33) and I (30) have been together for 8.5 years and yeah we had the basic arguments and life changes. He lost his job 2 years ago, he works in tech and AI is happening.

For the first 6 months - I was all for letting him chill and coast on the severance. I wanted to give him his time and encouraged him to take a trip and have fun. But I also made a spreadsheet and applied to 75+ jobs for him.

Months 6 to 9 - his severance ran out and he told me not to worry about it. He was dipping into his savings. And I told him it’s time to actively start looking for jobs. I and a friend applied for about 100+ for him. He got a few interviews but it didn’t work out. He personally applied for 20ish job. During this time I proposed to him, because ya know… for better or for worse.

Months 10 to 12 - I told him it’s time to ask his parents for money. It took a lot of convincing but he did. The credit card is in my name and during this time it accrued 20k in debt. My job gets busier and I tell him he needs to take over applying.

Months 13 to 16 - I tell him maybe it’s time to pivot. Tech isn’t working out and we need money and we can’t rely on his parents indefinitely. His parents give him $2.5k a month so half the rent plus $350. The debt is $27k. I take out a personal loan to cover it. Tell him to not worry about it and I’ll handle the debt. Just reduce spending. By the end of this time, he’s avoiding his parents calls so I have to talk to them.

Months 17 to 19 - it’s really time to pivot. My job is getting harder he’s failing all of the interviews, if he gets any. He comes around to the idea of going into a new field all together, but he needs to take classes. He takes 2 months to mourn his old career path and while he’s doing that I enroll him in college and select his classes. I map out what can happen for him, but he doesn’t really understand it. I ask him to do research. He uses chat gpt for 15 mins and now he’s “good”. The debt on the card is going up again. His mom tells me that I’m making this too easy for him.

Months 20 to 23 - I finally got him to take the pivot seriously, but now he’s dragging his feet. Which would be okay, but there’s literal deadlines. If he can’t do something I will do it if I can, but there are things he can only do, but he procrastinates. And guess what, he doesn’t clean or research, but he is on season 2 of Madman.

I’m so tired. My motto in life is “it will be fine” or “I got it”. I’m great at calming him down when he’s sad or anxious. But I’m kind of struggling. If I ask him to do something I give it a month, and after that I get serious about it. And then his reaction is that I’m unreasonable. He often tells me that I don’t give him any “grace,” but I feel like that’s all I do.

He’s my best friend and I have no intention of breaking up. I’m just struggling. And while he takes his time to figure things out, I see some of my dreams disappearing.