There is much to be said about the struggle for happiness. I do not know where you live, but I know the general consensus of the world is that it isn't really getting better. You have the high inflation rate and the wars, many things that are hurting people of this generation. It is hard NOT to feel rather pained by the issues that are cropping up. I don't know just how well that applies to you, but you did speak of taking less time working so that you could pursuit your interest, which I would only guess is the artistic work you do here. I sympathize heavily, though, with the thought of feeling as if all direction in life came from the desire to make your parents happy. It is a struggle I face myself, in all honesty. There are many things that could be it, perhaps it is slow commissions here on FA. Feelings of stagnant growth? Perhaps I am projecting, but I know when I commission a piece and it doesn't get a lot of attention when I upload that I feel bad about like....not having good enough ideas? Nevertheless, I do hope that you find that happiness that you seek....God knows that I still am myself. Wish I could do more to better help, but I am always down to talk or chatter...I hate seeing people struggle with the weight of the world, and it is a pressure not meant to bare alone.

I was given the things I needed in life, so very little of my achievement feels like it was really earned. Which means I also don't really deserve the gifts I was given either.
Finally seeing how family and money is eroding my judgement regarding investment and empathy.
Can't talk very well in person, can't relate to other's struggles, etc.
I'm in a ditch because I was spoiled, but I can't just give what I have to other's.

Note that medications for depression can have negative side effects (a really common one is becoming suicidal for the first 1-3 months after starting them which is... yeah), but... if you have an actual chemical imbalance, then doing everything right on your end won't fix it because it's a physical issue and you may need to clear up that bottleneck first before therapy or anything else can really have much effect.

That's not necessarily the problem though. Searching for happiness isn't really a great way to maintain happiness. If you pursue happiness, well... do fun things, have a nice car, a nice house, stuff like that, yeah, you may be happy for awhile, but it's kinda empty and hollow at its core.

What you usually kind of really want is to pursue joy, which is a bit weird because usually stuff that gives joy doesn't make sense as something that would make you happy. So... doing things that matter to you on an emotional level but which aren't really "happy" things to do. For example, volunteering time at a soup kitchen is just... more work. But it may make your life have meaning and make everything else you do mean more to you. It doesn't have to be that exactly, but it's a very obvious example of something that makes some people feel great despite it's obviously not something that should make you happy in and of itself.

There are a few things I find that, if I don't get them in my life, I start falling rapidly into depression repeatedly. Namely I need to be productive, creative, social, and to be useful by helping people somehow. If I don't have all of those things, I start breaking down extremely fast. Any pleasures like video games or whatever are a temporary relief at best, they won't have any real effect if I'm missing one of those things.

What that usually means is for stuff like the being useful/helpful, is I usually dedicate a bit of time towards sharing my knowledge and teaching people stuff, contributing to whatever communities I'm in. So I know a ton about game design... I stick around on places like Quora or several game design discords and help answer questions or tutor people so that I can help them out with their projects. Without that, I can't stay remotely sane for long.

Also note I have to be creative though. Doing stuff for someone ELSE is... alright... but they have budgets they need to stay in, deadlines to meet, their own requirements that don't line up with mine. What I've found there is if I stick to only making stuff for other people... it's just not good enough. It's not truly satisfying when I have to cut corners because an employer tells me to, or when I'm stuck within their arbitrary limitations or restrictions. And so I have to do something for myself to let my creativity out or it again goes quickly into depression.

To that end, you've been doing a lot of commission work, but it may be cramping you a bit too in that regard. Or maybe it's what you need. It's hard to tell, I'm not you, but my point would be to figure out what you NEED in your life, not what you WANT in your life, and note that these are often two very separate things that often have almost no overlap weirdly enough. Maybe you have some deep need to have children and start a family and you're not even really aware of it consciously. Maybe you just aren't happy doing other people's work for them and sure it's a money maker but it's not good enough, as in perhaps you need to do something of your own creativity, even occasionally, like setting aside one day per week dedicated to drawing a comic or graphic novel with your own characters or something that you can truly call yours without the restrictions of clients telling you what they want out of it.

I don't know what you need. No one here can know. But if it's not a physical limitation like a chemical imbalance in the brain that requires medication... then it almost guaranteed is something you NEED in your life is missing, and I don't know what that thing may be, or which of those two options may be the case, or that it may actually be both.

I would suggest bringing it up with your therapist though, asking if they have anything for helping with figuring out what you really want out of life, and some sort of plan you can build up to help moving towards acquiring what you need. Or to get an actual psychologist to look you over to see if there are physical issues that need addressed, but either way, there's something that needs addressed there which isn't being addressed, probably something you need psychologically which is lacking. Again, no one here can tell you what that is, but a lot of people fill those empty voids with all sorts of things like religion or drugs, alcohol, you name it. Usually these are just generic bandaid fixes and don't truly solve the issue, so I don't personally recommend relying on an external source to fix your internal problems, but it's something to keep in mind because for some people it's literally what they need.

Anyway, it's probably not going to be a super simple answer unfortunately, but recurring depression usually means you either need something you're not getting, or something is physically broken. I know I'm being repetitive on that, but it really is important to drive that home. The real trick is narrowing down the root cause and tending to it. Maybe something I've mentioned in this is helpful, maybe not, it's wild guesses without more to work with, but hopefully it at least gives you somewhere to start looking.

I do hope you figure it out either way, and will offer what limited help I can on such, but for this kind of issue, it's probably either going to be something you have to figure out on your own, or will need someone who has the medical training to isolate the cause.

Do you have a social life at all? Maybe the lack of social interaction is contributing to how you feel.

Hello there, Mister. Thanks for leaving a comment! My social life is little to nonexistent. I grew up alone the majority of my life and my lack of social interaction has never been an issue to me before. When I first realized I was depressed, I too believed it had something to do with my lack of socialization. I don't have a problem talking to strangers or meeting new people. The issue is that almost everyone I meet wants to be my friend when I don't want to. The few friends I have are all I care about and I don't need, nor want, anymore. I mean this in the most respectable way possible.

will be praying for you

Depression sucks but i know that you're powerful to move through it, and don't you worry.