Self Pity is REAL as I hit 8 months without a new role..

Maybe the world's smallest violin is playing right now, I don't know. I truly thought I accomplished something in life by becoming a millionaire at 39. How little and small that thinking truly is has become a harsh and painful reality. I have been in enterprise sales for 11 years with several each at the big enterprise ERP companies. I even decided to explore the overemployed route during COVID and did 2 Strategic AE roles for different companies and different industries. I killed it for both of them for 8 months until I resigned from 1 and did it hitting my quota and maintaining strong relationships. Life seemed great and I took that money to invest as I knew one day it won't be sunshine's and rainbows. As a result I became a millionaire. Problem is that my monthly run rate became significant at $15K/month and I was always making enough to support my life. In January of 2024 I got laid off and thought nothing of it thinking I've saved enough, invested enough, and made decent decisions to hold me out until I find a new role. Fast forward now 8 months later- 2 mortgages of $6K, 2 cars at $4.3K and a wedding I'm now reconsidering every life decision I have ever made. I now realize I made a couple missteps because achieving a milestone doesn't mean sh*t if you don't manage the future properly. I'm sharing this for the younger guys to hopefully learn from my stupidity and to the more successful and smarter reps to give me some advice on how to get back on the horse. I interviewed extremely well with a major tech company and received positive feedback to only get a text from the recruiter 2 days later saying that I did nothing wrong and am amazing but there was a candidate more suited for the role- it was a month process bc the interview process was 5-6 steps with a role play in the end. I honestly feel so deflated and want to throw in the towel. I've got maybe 3-4 months before I run out of runway and don't know what else to do- I have experienced this 2 other times when interviewing and must be oblivious to something. Why is it so damn hard to find a new role?

I've learned to never be comfortable. Always stay hungry. Always look to learn a new skill and understand younger is always preferred over experience in our world. I know I sound bitter but WTF do I do? I feel beat down defeated and have the proverbial chip back on my shoulder to prove I'm good and strong enough. I've never missed my quota but can't even get a recruiter to give me a screen call anymore. Is this what happens at 40? I'll take any advice and jokes at this point.