Version 4.0

by | Jun 14, 2025 | Version 4.0 | 2 comments

What a difference 40 years makes. I mean, 10 years ago I couldn’t string a cohesive sentence together because I was half drunk half the time. The rest of the time I was busy convincing myself I was great without actually having done anything great.

Twenty years ago—somehow—I was in college. I don’t know if back then I thought I knew what I wanted out of life, but I can tell you now, I didn’t have a clue. I think I wanted to be famous, and it was for all of the wrong reasons.

Looking back 30 years, I was 10. The adults around me were my age now. I have vivid memories of each fearing their journey over the hill. Mid-life crises were a real thing in their minds. Now we have quarter-life crises, but that’s not the tale I’m here to tell.

What strikes me the most, in retrospect of course, is how resigned to life these memories feel. Like 40 was it—nice knowing you. I can coast now, get fat, let gravity have its way with me. The perception of 40 just felt different back then. But again, so did everything.

Contextually, it wouldn’t surprise you to learn I’ll be turning 40 in just shy of two months. What might come as a bit of a shock is how excited I am for it. Age is but a number, of course, of course, but from a symbolic standpoint it’s like the much-anticipated release of Book Four in an epic 8 (hopefully 9) part series.

This is where it gets juicy and good. Our main character has come of age, he’s survived the mistakes of his youth, and has finally positioned himself to be a force of nature. Will he be a force for good or for evil? Only time will tell.

But like all good stories, we need to understand where we’ve been to set a foundation for where we’re going.

At 29 I was working a job I hated. You don’t even need specifics—just know I was working for someone else and I wasn’t happy. At the time I was bouncing between $30,000 and $50,000 positions, and let me tell you, I felt like I was rolling in that 50K.

Despite the internal perception I was doing just fine, I had no savings, no retirement plan (like no 401K or any clue how or if I was going to retire), and I’m pretty sure I didn’t have health insurance. I was living on a prayer, which makes me chuckle as I write this, since my religious beliefs are … limited.

A theme is going to start to emerge—just bear with me for one more paragraph. Being poor sucked for sure, but it was the symptom of a much larger problem. I wasn’t a good person. Maybe it makes more sense to say it this way: I wasn’t good at being a person. My problems weren’t mine, I had no accountability, and my ego was the dominating force in my life.

Book Three opened at the height of nirvana. Vibes were immaculate. Problems of the day were still easily erased as night left my inhibitions behind. It wasn’t perfect, but it was working. New characters were introduced, others duly departed, and life felt like it was good enough. Good enough for all that I thought I was capable of.

That was until a crack began to form in my rationalizations. It was small at first, hardly noticeable at all. In fact, it would have been downright irresponsible to pay it any mind. So I held my current heading toward mediocrity until one evening when friends and I sat around a table of beers. It was a networking happy hour, and we were happy networking with ourselves.

I don’t remember why I blurted this out, but as my eyes wandered the vast young professional landscape, I said to my friends (or to no one at all), “I wish I had my shit together.”

That crack? It’s starting to glow now.

Looking back, I’m not even sure what I meant. It was such an amorphous comment I’m surprised it shot out of my mouth rather than dribbled down my chin.

And yet it was enough to cause a rift in my blissful, willful ignorance. There’s this wild thing that starts to happen when you stop doing what everyone else is doing. For the first time in my life, I started believing in myself rather than hoping others would believe in me.

Do you know what self-belief does to a person? The next 10 years of my life tell that story.

From comfortably numb to critically sober. From poor to rich. From weak-minded to strong-willed. From pencil pusher to maestro of my own orchestra. From grasping at straws to designing the perfect life for myself.

It’s easy to use words like suddenly and overnight when looking back at a decade of life (which honestly gives pangs of nostalgia), but the honest truth is there were countless times I threatened myself with giving up, with pouring a drink or taking the easy way out and getting a real job.

So why didn’t I? That’s what I’m here to uncover.

These are the letters to my former self. I hope they benefit you as well.

2 Comments

  1. Michele Clarke

    Trey,

    Can’t wait to read more. Thanks for your vulnerability and transparency. You indeed have much to offer this world!

    Reply
    • Trey Kauffman

      Your support is awesome, Michele, thank you so much! 😊

      Reply

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