Max At 40

AUTHOR’S NOTE: Having recently turned 40 years of age, I want to take an opportunity to write this letter to my 20-year-old self, sharing thoughts and lessons I’ve learned over the last 20 years. I realize this isn’t my usual fare, but the moment is still significant enough for me that I feel compelled to use the opportunity to reflect and share my thoughts.

Feel free to skip this entry if it’s not what you subscribe to my Substack for. I won’t take it personally. But I hope you’ll read it and find meaning in it. So, here it is.

Dear 20-year-old Max,

Remember when age 40 seemed so far away? Well, here we are! It’s 2026 and you’ve turned the big four-oh! So right out of the box, the good news is that you’ve made it this far! The older you get, the more you realize how living a long life is no guarantee, and that it really takes lots of work and some luck, unfortunately, to stick around for the long haul. I can’t help but think about how human life expectancy was once only about as long as I’ve been alive. I’ve outlived Jesus, for one. For what it’s worth, I’m as old as John Lennon was when he died. It’s sobering to think about, but it also makes me even more grateful to still be here.

I know, from where you’re at, you probably weren’t thinking about what life at 40 would look like. You probably instead have lots of ideas of what your life is going to look like five, at most ten, years from now. All I can tell you is this: it’s going to be a roller-coaster. Emotionally as well as literally. You may not feel like you’re doing anything all that important, and looking back on it, I don’t think I made much of a difference. But you tread water, weathered the storm, whichever term you want to use. That’s not nothing.

Here in 2026, you’re doing well for yourself. You have a great career. You even have a budding writing career, though honestly, it’s still kind of stillborn. You’re not wealthy, but money isn’t a big problem. You’re enjoying life, for the most part. You’ve visited over a dozen countries, most of them in the most recent several years. All things considered, you have a lot going for you. Rest assured - your struggles will all pay off in the end. You made mistakes, sure. But you eventually make all the right choices. Be proud of that.

Now, I know that on some level, that sounds disappointing. I get it. None of your dreams come true, unfortunately. But if nothing else, know this: you’re in a better place now at age 40 then you were at age 30, and most certainly age 20. Not everyone can say that. Sometimes, better than before is the best there is. You’ll learn that as you make it to where I am today.

Now, for some bad news. I hate to do this, but I’d be remiss if I didn’t take this opportunity to warn you of what’s to come. I know my 20-year-old self would absolutely want an idea. That way, he can prepare himself. So, here it goes. In a few short years, you’ll undergo the biggest test of your life. I won’t sugarcoat it: the floor will give out on you. You’ll end up questioning everything about yourself, every choice you ever made, and your pride will take a massive hit. And you’ll need to make a major decision about the direction you want to take in life.

I wish I could tell you not to even go down the road you chose for yourself. But I can’t do that. I know my stubborn 20-year-old self wouldn’t listen, anyway. So, instead, I’ll say that when it does happen, close that chapter quickly, and move on. In the long run, things will work out. It won’t feel that way in the moment, no. You’ll feel a level of despair and hopelessness you can’t fathom, not right now. But understand that overcoming challenges like what’s to come is what life’s all about. In the end, it’s not the failure you’ll regret. It’s the time wasted that you will.

When you undergo this crisis, I ask one thing of you: don’t blame your family, especially your mother. They may not always agree with your life choices. But nobody else in this world is more committed to your success, roots for you more, than they are. And it’s when you undergo this test of character and will that you’ll learn the hard way the importance of family.

Your mother’s still here, by the way. Your relationship with her remains as strong as it ever was. Be grateful for that.

Which leads to my next point: a man is nothing if he’s not there for his family. And a few years after getting past that challenge, you’ll have to be there for them through tragedy. It’s going to be tough. But you’ll be strong and carry on, like a man should. You’ll look back and won’t help but be proud of how you were the person you needed to be when your family needed it most. I know you won’t believe it now, but trust me: it’ll make all your sacrifices, all your unanswered prayers, worth it. If nothing else, you won’t need to look back with regret and shame that you didn’t live up to your commitments as a family man.

A few short years after that, you’ll then meet a man whom you won’t know for long and quickly forget his name. All I can recall is that he was tall, late-40s, early-50s, and Italian. The reason I mention him is because he’ll tell you something that’ll change your life. I’m not kidding. Somehow, you’ll get into a conversation with him about how your life hasn’t worked out, how you don’t know what to do with yourself. He’ll reassure you that everything will work out, to just keep on grinding, that everyone finds their place in this world.

You won’t like hearing it at the time. You’ll even feel frustrated. You’ll ask him, “How would you know?” He’ll reply, very simply, by saying, “Because I lived it.” I can’t even begin to tell you how much that woke something up inside of me. It was in that moment that I realized how little I actually knew, that there truly exists an understanding only time can deliver. That’s what he was offering me: wisdom. Not knowledge.

With that wisdom, you’ll make a series of choices over the next several years that’ll change your life. Don’t get it wrong - you won’t run into great riches or anything like that. Not yet, anyway. But after years of struggle, you’ll finally find a direction in life, and a place in the world. Sure, it wasn’t the life you expected, nor was it the one you even truly wanted. But there are people out there who go their entire lives without finding any direction in life or place in the world. You will. Be grateful for that.

As for finding love, I wish I had good news to report to you there. I regret to inform you that “40 Year Old Virgin” wasn’t just a movie, not in your case. You thought that 20 years is a long time, that eventually, it’ll just happen on its own. You thought that, by 40, you’d at least have been in one relationship. Unfortunately, it won’t happen. You were the “incel” before the term ever became part of our popular lexicon. When it comes to love, life still rewards the attractive and socially adept. You’re still neither. At this point in life, it’s just fact.

I know that’s not what you wanted to hear. Believe me, I know. It sucks. And I don’t have any useful advice to offer, except maybe this: it’s easy to be liked, but it’s hard to be loved. So don’t ever fall into the trap of thinking it’ll happen “when the time is right” or something stupid like that. Love is something to pursue. Maybe some of us aren’t meant for it. I’m increasingly becoming resigned to the fact it’s the one blessing I’ll miss out on, unfortunately. But again, it won’t ever happen on its own. Keep that in mind going forward.

Let me now share the five most important lessons I’ve learned in these four decades of living. One, always make choices you can live with, that you won’t need to explain to anyone later, including yourself. Life is hard enough as it is. Don’t do anything to make it harder. This doesn’t mean don’t take risks in life. You’ll absolutely have to. I wish I’d taken more risks earlier in life. The key is to take calculated risks. You can explain those. You can’t explain recklessness or doing something you knew was wrong. Live your life with honesty and integrity, always.

Two, remember that when it’s all said and done, the only thing anyone remembers about anyone else is how that person made them feel. You can’t control what people think of you. But if you treat people with fairness and humility, nobody will remember badly of you. They say that if you don’t have a few haters in life, you’ve done nothing with yourself. That’s true, too. Still, do the best you can to make it so people remember well of you. Even if your relationship with someone might’ve been rocky, let their last memory of you be something positive. It’s the only legacy anyone truly leaves behind.

Three, I mentioned earlier that it’s easier to be liked than to be loved. Well, it’s also hard to get anyone to truly care about you. That shows the importance of family. But it also shows how important a robust social life is, how it’s something money cannot buy. The happiest people on Earth are part of strong families and communities. That’s a demonstrable fact. It’s going to be hard for you to have this for yourself. Find it wherever you can, if you can, however. I still haven’t found it myself. Maybe I never will. But it might not be too late for you.

Four, and you’ll hear someone say this, when it’s all over, we don’t think about all the money we made, all the success we’ve had in life, none of that. All we remember are the people we knew, those who meant anything to us. If you want to be around for them, then don’t neglect your health. I can’t stress this enough. You’ll be fortunate to make it to 40 without any major health problems (not yet), Max, but there are no guarantees in life. You’ll lose people along the way to health problems, you’ll lose many more thereafter. It’s tough to enjoy life when you can’t move around, when you’re in and out of the hospital constantly, when death is constantly in the room with you. Stay active, hit the gym, eat as healthy as possible. It truly is everything.

Five and finally, just enjoy life and let it surprise you. You’ll endure so many disappointments along the way, it’s just not worth it to get so obsessed with career, money, etc. Don’t get too wrapped up into politics, either. Trust me, the country is going to go through hard times. It won’t be the same place it was the first 20 years of your life in a short time from now, trust me. If I told you what it all looks like in 2026, you wouldn’t believe me.

So just let history unfold, look out for yourself, and remember that life is rough, but still worth living. Don’t miss a World Cup. Travel the world when you can finally afford to do so. It’ll be among the best memories you make for yourself. By the way, your favorite baseball team will finally win a World Series. There are so many wonderful experiences up the road, so stay on it!

Looking back, I think what strikes me most is to think how I lacked confidence in myself. Yet, here I am. How’d I make it so far, so successfully, without confidence? Maybe it’s because you, in fact, believed in yourself. You believed in yourself more than you know.

Make no mistake, though - you need success to be confident. But you also need to be successful to be confident. It’s less about what everyone else thinks of you. It’s what you think of yourself. But to think highly of yourself, you need wins under your belt. And you got them.

You did do it right, Max. Now it’s time to get to the task of living. I don’t know what I’ll have to say to you in another ten or twenty years. I certainly didn’t know what my 40-year-old self might say to my 20-year-old self. Now I do. The lesson here is that life is a mystery to be experienced, not solved ahead of time. If we all knew how it ends, would we really want to go through it all?

It calls to mind a song that’ll become a hit in just two years from your time, “Roll With Me”, by Montgomery Gentry:

Who knows what’s up ahead
I think I’d rather not know instead

So now I’m slowing it down
And I’m looking around
And I’m loving this town
And I’m doing alright
Ain’t worried about nothing
Except for the man I wanna be
I’m thinking maybe its time
To be living the rhyme
When I’m singing a song
About nothing but right
And it sure would be nice
If you would roll with me

I can’t tell you how much that song meant to me, how those lyrics still sustain me to this day. So hold onto something like that if you’ve got nothing else. And just roll with it. Maybe even find someone to roll with you.

Anyway, don’t let anything I’m saying get too deep inside your head. Focus on the present, focus on where you’re at currently and what you’re doing. I wish I’d done that more back in your time. Don’t forget what I said here to you, certainly, but don’t fixate on it too much, either. Let it serve as a guide, not a checklist. Make it something you can always come back to when you feel lost. Let it be the light in the darkness, at the end of the tunnel. All I ask is, don’t be in too much of a hurry to get to where I’m at.

In the meantime, remember that I’m always praying for my past self. I hope you’ll pray for your future self. Whenever you get here, just get here in one piece. I can’t wait for you to see how it all turns out. Meanwhile, I’ll get on moving myself, and I hope to have even better news to report to you in another ten, twenty years.

Good luck, God bless, and happy birthday, Max.

If you ended up reading this entry, thank you for letting me share my thoughts with you. What about you? Have any of you passed 40 years of age? What advice would you share with your 20-year-old self if you could? Share your thoughts in the comments.

Max Remington writes about armed conflict and prepping. Follow him on Twitter at @AgentMax90.

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