I think it might come down to how well you allow yourself to enjoy. With me, enjoyment or fun is secondary. I feel guilty enjoying myself if I haven't worked hard or accomplished something. But I didn't realize how bad it was until I didn't have to struggle as much. When I was in school I used to love the time between semesters or summer break. But that was because I knew I would have to work hard again soon and I was working towards something big. If I don't have a really strong struggle or something big I'm working to overcome, I will not feel good doing anything I like. I will just stress all day. But if you are more comfortable with enjoying life and having fun despite it all (like you would do well in retirement), then you would do better then me with money. I feel like my mom's side of the family which comes from poor eastern europe. I would rather keep things simple and work hard to survive then to live in high culture or spend time trying to do things I enjoy. But everyone is different
I've been working very part-time for a while now and there are a few things that hold me back from enjoying the extra time I have - (1) concern about my financial future when I become a senior - I'm not saving for retirement, I'm only earning enough to pay my bills, and use social services for medication for anxiety/sleep disorders, (2) fear of other people's judgement that I'm not working/earning enough and for using social services.
I can reduce the stress of #2 by not telling people about my anxiety disorder and use of social services, and reducing my contact with people who wouldn't understand. Though can still be triggered just knowing the general attitude of society that is out there.
Either way, I still go in and out of paralysis/fear when I get triggered about those things and shame because of the general attitude in society. When I'm not in fear, and I've been doing pretty good lately, I enjoy being productive with DIY household activities which save me money, organizing, cooking and preparing healthy meals which I would have less time to do if I were working mad hours, reading and learning about political, business, spiritual, and health-related topics and sharing what I learn with others. I enjoy being a bit of an activist for the things I believe strongly. So, with all those things above, I feel content and happy with how I spend my time. I would have less guilt if I knew I wasn't setting myself up for a challenging elder life, and if I could spend and give more generously.
Busyness combined with too much time commitment, is a major trigger of my anxiety, so while technically I could manage to work full-time, I feel so much relief from crippling anxiety (which itself becomes like a full-time job when working full-time), that I really don't ever want to go back. I think with more money, I would do more of what I am doing now and would probably get way more involved in the community and volunteer work if I had financial security because of the reduced shame and fear about my financial state and what I SHOULD be doing.
Hey, cosmosis, since you seem to be in good shape financially but struggling with your time, and I'm struggling with finances and have extra time - in exchange for donations, I would be happy to provide you daily/weekly skype /phone/chat/email support for motivation and encouragement, and brainstorm with you to help figure out what to do with your time and how to feel good about it. I love to help people who struggle with similar problems! Of course I could chat with you on a less regular basis for free, too
Feel free to PM me!