How can I support my boyfriend who’s feeling lost and insecure about his career and finances?

My boyfriend (29M) – (I am 25F) has been struggling lately with feelings of inadequacy and financial insecurity. Although he’s not in a bad place financially he went to private school and university he feels like he hasn’t achieved enough for his age. He doesn’t have a stable career that he enjoys, and he’s becoming increasingly anxious about turning 30 without feeling fulfilled.

He talks often about wanting to move abroad to start fresh and find something better for himself, but he can’t afford to make that happen and feels stuck. He’s constantly stressed about money, even though from an outside perspective, he’s doing okay. It’s really weighing him down.

We had planned a week-long beach trip during our annual leave to relax and recharge, but he canceled last minute. He had been hinting that he was unsure about going, but I didn’t realize he was seriously considering backing out. When he told me he couldn’t afford it and would rather stay home to save money, I felt disappointed. He told me I could go without him, but honestly, I don’t want to go alone, and it’s a bit late to make new plans with friends.

He’s extremely insecure about his situation, and it shows. He’s said multiple times that I deserve someone with a better car, someone who can spoil me more, and that all of his friends are richer or more successful than he is. It’s hard to hear him talk like that because I don’t see him that way at all I love and value him for who he is, not for what he owns or earns. But his self-esteem is so low right now that it’s affecting how he sees himself in our relationship. He’s the kind of person who doesn’t easily open up. I’ve tried gently asking what’s bothering him, letting him know I’m here for him and creating a safe space to talk but he shuts down and insists nothing is wrong, even though it clearly is.

I really care about him and want to be there for him, but I’m not sure how best to support him when he’s not willing to talk. How can I help him feel better or at least feel supported, especially during a time like this?

TL;DR:

My boyfriend (29M) is stressed and depressed about his lack of career progress and financial insecurity, feeling like he hasn’t achieved enough by almost 30. He canceled our planned vacation to save money and doesn’t open up easily. He’s very insecure he’s said I deserve someone with a better car or more money, and that all his friends are doing better than him. I want to support him, but I don’t know how. Any advice?