I just wanted to throw in my 2 cents here, because, despite myself, I fall into the depressing to read/self pitying trap now and again, but not nearly so often as I used to.
Something I have learned the hard way is that there is no more surefire way to make yourself unduly miserable than to compare yourself to other people. Now, naturally, you are going to do it anyway, and to be fair it's necessary, but you have to take a couple of cold hard shots of reality first:
1. You are you, I am Me, etc. Whatever happens to anyone, good or bad, is a combination of many very complex and intricate factors, some of which correlate very strongly, some of which do not, and some of which cause others, etc. For all intents and purposes, you lead a singularly unique existence. That's not to say your existence is fundamentally non-comparable to others (we all have to drink water for example), but rather your comparability to others is bounded.
2. You never, never get the full picture of anyone else's life. Even people who are freaking married to another person for decades who sleep in the same bed find out things (Good Bad or Innocuous) about their spouses they had no clue about. I'm sure we don't have the full measure of MMM's existence (and this is not because he is being deceitful, it is because he cannot exhaustively write down absolutely all of his experiences as a human being because no one can, also he writes in character).
Some years ago, I was very jealous of someone I knew who didn't have to work and just seemed to indulge in my hobbies all day. Then I found out he was on disability and a structured lawsuit settlement because he had been badly injured through neglect, lived in constant physical pain, and couldn't really leave his house without extensive preparations. At that point I was no longer jealous at all. That's an extreme case, but it's a good example of the principle.
The point being, even in more typical cases, we don't get a good picture, a true picture, of what other people's lives are actually like. I have known people who the popular media portray as miserable who were serenely happy and I have known people who had amazing careers, experiences, etc. but who were some of the most maladjusted, self loathing and depressed individuals I have ever seen.
All that is compounded by our own cognitive biases and predispositions to focus on negative experiences in our own life and the positive accomplishments and happy times of others. Your own human nature compounds your existing problems, it is the nature of solipsism.
I'm not going to lie, it's a little deflating to realize what I could have accomplished by my age (I'm 35) and realize I kind of threw my life away because I made mistakes, and other people who were smarter than I was are set for life and having an amazing time that I will never have. It's a little depressing to realize I will never leave the US, I will never own rental properties, I will never be successful in business, etc. It can get you down.
On the other hand though... so what? Most people don't accomplish any of those things either, and some of the people I've been the most envious of have done nothing that seems all that grand or prestigious. And most of those people just stopped giving a flying fuck about meeting metrics that are traditionally used to judge how accomplished somebody is.
Also... who says? I never thought I'd be where I am today. Sure it's not where I wanted to be when I was say 15 (I really, really thought my life was going to go much better than it did lol), but it's a damn sight better than where I thought I would be when I was 25 and got my cold shower of how much reality sucks and how the real world doesn't care one bit about me, my wants or dreams, or even if I live or die.
And do you know why it's better? Because I made it better. And I keep making it a little better, every day. Sure it sucks it's not as wonderful as it could possibly be, but why waste time wringing my hands over it? It's useless and a waste of my time and energy.
You have to learn to feel guilt, and not shame. The difference is, guilt is "I did a really bad thing" and shame is "I'm a really bad person".
If the latter is true, you probably need some serious help with mental health issues. That's not meant as a slight to anyone, that's a serious problem that needs to be dealt with.
But for most of us, the truth is, the former is accurate. We're not any better or worse than more successful people, we just made poor decisions. That's bittersweet news because it means your past opportunities are all shot and you're never getting them back, but it also means you can, you know, STOP doing that stupid thing that cost you so much and not have to carry that weight around any more.
You have more power over your life than any other entity; there are some people making a lot of noise and wasting a lot of effort right now you I sorely wish would realize the implications of this. That's the cold hard truth and I hate to invoke a cliché but the truth shall set you free. Well, it'll set you freer, bit by bit, as you figure the truth out and how to act on it constructively would be more accurate.
It is what it is, take it one day at a time. Serenity is key.
I had a discussion once when I was starting to climb out of my financial hole with a coworker. We made about $1.50 an hour above minimum wage. At the time, I was saving about 8% of my gross income. So not very good. This coworker asked me why I bothered, and pointed out unless you're saving half or more of your income it's not going to change your life very much because it'll be decades before your saving and investing gets you anywhere.
The thing is, he was right. But that doesn't matter, because even if I couldn't manage (still can't) to save literally half, I will have more options in life at some point in time using the principle to the extent it is possible in my circumstances, and I now save far, far more of my income than I ever thought possible, so who is to say one day I won't get there?
All this to say, when I read something like MMM, I don't try to take it as a literal roadmap. I'm not that person, I didn't have the same life, etc. However, are there things, principals and ideas here that do apply to my situation that will make things better? Of course there are. The key is figuring out, where am I personally, and how can I get closer to the goal I wish I had.
Very few things in life done by anyone are instant runaway successes and history will vindicate that (the telegraph was nearly abandoned as a useless technology at one point). Most things and people that succeed do so by iterations over a prolonged period of time. You have to accept that modest and small improvements which come gradually are probably going to be the best you can do, but at least these things have a tendency to compound and establish inertia. I have noticed that just as foolish things I used to do seemed to cluster around one another, wise things I started doing seem to cluster as well.
Anyway I went way off base there but all that's to say I try not to read blogs critically and not so literally.