Hi! I believe I can be of help with this issue.
First, let me say I can imagine how distressing and frustrating this situation is for you. You're on meds (I assume as you're seeing a psychiatrist) and you're in therapy but that hasn't led to resolving the problems. You have a family that loves you (they will miss you, after all) but that didn't lead to answers that were clear to you.
You are clearly a highly intelligent person as well as a well educated one. You present your problem with a mood and language that the Existentialist philosophers and the existentialist psychologists (I'll metnion Viktor Frankl later on) would call a crisis of meaning and purpose. This is often expressed as feeling there is nothing that one can do or could do that would be more than a pretend mask over the depression and negative reality perceived.
But before we begin focusing on meaning and purpose in life, I need to explore with you the possibility of you having treatment resistant depression (TRD). One problem with labeling someone with TRD is that the next level of treatment psychiatrically is ECT, electro-convulsive therapy. Right, "shock treatment". It isn't the same today as the horror movies of the 50s. However, even though doctors might deny it a bit, there are real side effects, especially some short term memory loss issues that are common. Not always, and perhaps not even the majority of the time, but relatively common. However, ECT does offer relief to many people with TRD and they feel more alive than they ever did before.
Given that you have the financial means, there are also treatment centers in some univeristy hospital settings and other respected locations that your doctors can help you choose that treat TRD with intensive inpatient strategies, various medications and therapy. This may also be worth your considering and discussing with your psychiatrist and therapist.
And then there is the issue of meaning in life. This is a decision you have to make. If you feel this is a lifelong problem that might be based in brain function, then stick with the options above. If you feel that it is a long term lack of passion in your life that causes your depression, then we can look at the ideas below. In essence, you have to make a call here if you think it's a lack of passion in your life causing depression or depression causing a lack of passion in your life.
One approach would be to take some months to try the meaning oriented approach below and see if it lifts you out of the dark pit of depression. And if not, then perhaps the TRD approaches above would be the next step afterwards.
Let's start with Man's Search for Meaning by Viktor Frankl. He was one of the young Vienna psychiatrists before WWII (it was a HUMAN pursuit then, not a medication writing practice as it is now) and wrote this book after coming out of the concentration camps. It has gone through so many printings there's one every few years. It was included in the list made of the 50 most important books of the 20th Century. Here's the Amazon page:
The reason I started you off with Frankl is two fold. And neither is that you will become either Sister Theresa or run for president, though you are welcome to do the latter if it strikes you as worthwhile. First, though, is to get you thinking in those existential terms. I don't get the sense you are religious, but if you are, then the equivalent would be getting you thinking in terms of personal communication with G-d, which is a framework for meaning and purpose in a religious framework.
So, the first goal is to be thinking in terms of existential meaning and purpose. The next goal is to get you thinking in terms of the VALUE of giving. This was very missing in your narrative. You talk of giving only in terms of your ability to give through their collecting on your insurance. That's trying to get out of the dark pit through "the back door". That is a shame as you are clearly a giving person. Yet you deny the pleasure and significance and meaning of your giving and the meaning of wanting to give and the meaning that your giving to your family and to others can have in the world. Not just insurance money. That's not the giving they need nor the giving you need.
That was the second goal, and the important part (in my view) of your getting meaning focused therapy: to begin activating your giving system and the ameliorative effects that giving can have on one's depressive symptoms. When one is able to feel the importance of another's (a loved one's) betterment, of doing something for them, this by itself provides footholds and handholds for the climb out of the pit of darkness.
Let's start with some self work. I imagine you've tried books. But I want you to try some more. I want you to read two types: the motivational classics and two books by Martin Seligman on happiness. Because you are so focused on your unhappiness and on your lack of motivation and clarity that you can't hear how you are already valuing giving and the needs of your loved ones just in your concern for their being taken care of with your insurance money. So here are the books for after Frankl:
Learned Optimism: How to Change Your Mind and Your Life by Martin Seligman.
Authentic Happiness. This is Seligman's most famous book. It began a whole field in psychology called Positive. Don't dismiss the power of working on happiness, please. Once you've conquered the value of giving and its importance in your life, happiness reading comes next.
Now for two motivational classics. If you have already read them, work on happiness and read them again. I think very highly of the first book on my list, which is a real classic: The Seven Habits of Highly Effective People by Stephen Covey. It is assertiveness thinking, but it is adult thinking all the way and is the book that has helped more people than probably any other.
The second book is by Anthony Robbins. He's one of those speakers who fills up huge auditoriums. For a reason. He's a terrific speaker and writer. The particular book (if you like it, try his others): Awaken the Giant Within.
You can find both of these books easily on the internet with little investment.
You may surprise yourself at how effective changing your outlook will be by just paying attention to people like Covey and Robbins and others you may find to your liking, instead of paying such exclusive attention to your own repeating thoughts of negativity and fear of taking a chance! I don't want you to minimize this.
You're in therapy, but if this is not meaning focused therapy, then here is the web address for Psychology Today's therapist directory. You can sort by zip codes and when you see someone who seems like they might be helpful (they show you a photo of the therapist!) look at the listing and see if they list humanistic therapy in their orientations. Make sure to interview the therapist and that you feel like he/she is intelligent and wise enough to be of help to you.
The idea here isn't that these types of therapy are magic. It's that I want you to find a therapist who will form a strong therapeutic alliance with you and will help you look at the sources of your lack of confidence and fear of risk. You need to explore this if therapy will be ultimately worthwhile. And one more point: I want you to make sure that the therapist you choose works from within a religious orientation as well.
Okay, I wish you the very best!
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