What are some reliable telltale signs that you're life is progressing or improving?

I think you need to look at it the opposite way.

Having a bird’s eye view is going to be too subjective and really difficult to measure.

Instead, breaking down your areas that were fucked up and see how far you’ve come. Some will be measurable; some will not.

I like to categorize my goals by mind/body/soul. Maybe you can use this is a template

Emotional control - When I came here I was a raging alcoholic. In hindsight, alcohol was a symptom. My problem was emotion and impulse control. Since using the headspace app and joining an accountability group (less feeling|more doing), I am less reactive, maintain a fairly even mood and am so much more confident in myself.

Gym - I weighed 130lbs and my max bench was 135 when I walked back into the gym a few years ago. Today, I’m 190 and repping 250-260.

Job/Finances - I was stuck in a job that payed ok but I hated it. As a way to cope with anxiety/depression/divorce, I racked up a shit ton in credit card debt. I busted my ass by re and revising my resume and practiced interviewing. I’ve been in my new job for a year now and received roughly a 20% increase from where I was. I’ve eliminated $10k in debt, built a sizable savings account and will be paying off my car next month. I don’t worry about money anymore.