As someone who has made a lot of mistakes and lost a lot of time, who cannot be successful or retired at a sane age any more because of those choices, I do this all the time. I still kick myself. It never stops. That never changes.
What does change is the further out I go into the "getting my shit together" process is my reaction to it. And something I have realized the hard way is that just because a bad experience is a part of who you are now, that alone doesn't dictate the kind of person you will eventually become. People endure much worse things in life than I ever have and go on to great things.
The other thing I've realized, which goes hand in hand with the concept that the past is not the future, is that you cannot compare yourself to other people for the purpose of making self-judgments. You are a unique being whose exact biological and mental limitations, circumstances, fortunes, happenstance, and experiences are singular. There's no reasonable proxy for you.
It doesn't matter if someone else who never made more than $20,000 a year maxed out their 401k every year or whatever. That person is not you. You should be happy for them without any expectation that their triumph is some kind of personal standard you must now adopt.
Your own cognitive biases are against you too. We, as humans, remember and place much greater weight on our own failures, mistakes, shortcomings etc. but for others we tend to mostly observe their successes, triumphs and most impressive characteristics. It's cruel really. The way we are hard wired to think makes it very difficult to form a balanced self concept sometimes.
It's very easy to look at someone who is far, far advanced ahead of you in some way and feel like you've failed, but the problem is, you're only seeing the end of the movie. You haven't lived their life or understood what it took to get there. You are, in short, comparing somebody else's point "F" to your point "A".
Finally, something I've realized is that attempting FI after you've been a fuck up feels like pushing a boulder straight up a cliff. But it's really not that, rather it's pushing a boulder along a series of gradually sloping ridges to ever greater heights, with a few sharp offs here and there.
When I first started to try to get things together, I tried the approach of saving $1000 first. Before then, I had never had $1000 in the bank. It took me something ridiculous, like 7 or 9 months, to get that first $1000. I felt exhausted and anxious but elated at the same time.
Years later, when I had paid all my debt off, I couldn't stop grinning like an idiot for a week.
But, what's more important is not the temporary high I got. What's more important is every time I hit a little milestone like that (and they do become harder and harder to hit as you go, but you also have more inertia as you go as well), every minute of my life that comes after is fundamentally different and better.
It took a while to realize this. You have to absorb the new experience, make it as much a part of you as the old bad experience.
The point being, I'm well short of my ultimate goal. I may never get there. But pursuing that goal has been its own reward, and unexpectedly now I start running into signs I don't give myself enough credit.
I don't check my balances often, but when I did a couple months ago, I thought my net worth was maybe $40,000 or $45,000.
Wrong. My net worth has crested $100,000.
Now, I could stop here and shrug and say big deal, most of the people reading this have $100,000 they keep around for firewood.
But those people aren't me. I'm not the kind of person who has $100,000 in any way shape or form... right?
I had to stop and add it up again, it couldn't be... but it is. Part of that is the market is sky high right now, but even that doesn't explain why it's so much higher than I thought.
And it was then I had the epiphany that while it has taken me decades to get this first $100,000, under conservative assumptions, pessimistic assumptions at that, the next $100k would take about seven years.
Holy crap. Why do I say holy crap? Because I've learned every time I set one of these milestone goals, I smash the living hell out of it. Even with problems like an unexpected hospitalization a couple years ago.
It's like some kind of bizarre exponential growth. And the more I contemplate my new reality at every point on the curve, the less and less the thought of past stupidity arrests my thoughts. It's just... why think about it so much? I've got better things to think about instead.
I don't know if any of that even makes sense, but that's the best way I know to explain it.