You Can't Afford to Give Up on Yourself

Thoughts on restarting, over and over.

I’m in the middle of reading Ryan Holiday’s recent newsletter as I write this.

I’m highlighting pieces of it. The part that got me to open this Substack and write after this silence was this:

“The purpose of any piece of writing at all is not the end product on the page. It’s the person YOU are on the other side of having done it. It’s the thinking long and hard about something. It’s the slow, tedious, difficult work of figuring out what you actually work. And the equally hard work of finding the words for what you think. AI can give you an essay, an article, a book, or a briefing. What it can’t give you is the person you can only become by doing the writing yourself.”

— 39 (Or So) Lessons On The Way To 39, Ryan Holiday.

You see, I haven’t really stopped writing. I’ve just become a lot better at refusing to pursue my own curiosity in the name of building systems.

That paragraph hit me like a bag of wet salt, in the face—upon waking up. It reminded me of the unease I had been feeling as I watch tutorial after tutorial on Claude, perfecting my prompting and agenting skills:

No matter how great AI gets at writing, the value of writing was never in the input, or the output—it was (and remains) in the transformation of the writer.

I love to write. I won’t stop. But if I neglect the true purpose of writing, then it won’t be long until I forget why it matters to me.

So, I opened Substack. And wrote what you’re reading. All of it, in one sitting.

Don’t worry, I won’t leave you hanging. There’s a lot I want to say, but I don’t have the time to say it; we’ll see as the days go by. For now, here’s a loose structure.

4 parts:

1. What I’m thinking,
2. What I’m working on,
3. What I’m proud of, and
4. Your invitation.

Sounds very “me” centered, doesn’t it? I can’t promise you’ll learn anything. But I can promise you I’ll give you something to think about :)

Let’s get started.

What I’m Thinking

1. It is important to be skeptical about AI. Not just healthy skepticism, but the kind that you have for a doctor who looks like a drug addict when you have a bullet in your chest. Okay, maybe that’s too dramatic. The point is, if you understand AI and what it can do, the more you learn, the more skeptical you become. You need this to use it well.

2. Is it possible to be wealthy, happy, and have a great family? I think so. I just don’t know how. But from my reflections, if I accept a reality that hasn’t happened just yet, I’m more likely to be okay with it and make a way for it to happen. But if I refuse reality and ask outrageous questions, I may just get the kind of answers that people consider outrageous—like getting everything I want because I refused to settle for less.

3. Life happens in seasons. You can’t try to do it all at once. You must accept and/or choose the season you’re in. Sometimes it will happen to you. However, you can also choose it. Either by what you consume, do, or reflect upon. Reflection, especially at the start and end of the day, matters because it can clue you in on what season you’re in and if you’d like to continue. At the start of the day, you get to look forward. At the end of the day, you get to look back. It doesn’t mean you won’t have moments during the day to do it; it’s just more convenient (or accessible) around these times.

What I’m working on

1. My YouTube Channel: I haven’t published in a while. And the last time I did, it was a while before that one. I’ve thought long and hard about what my problem is, and inconsistency seems to me the primary weakness. However, I can see how consistent I am in other areas of my life. My marriage, for example. And I realized that I haven’t taken YouTube (and my gifts in general) seriously. I am consistently on the lookout for how to be a better husband. I’m reading, learning, paying attention, and talking to my wife. But when it comes to writing, YouTube, my business, I don’t approach it with the right energy. When I realized this, I honed in and started sealing some cracks. I don’t want to talk more about it for now.

2. My health: I came across a recent article by Tim Ferriss in which he discusses the implications of AI for the non-fiction writing business. That led to reading an article about someone who lost 70lbs in about a year. And that led to a confirmation that the new experiment I was running on myself was totally worth it. I’ve gained a lot of weight over the past 5 years and haven't been able to shed it. This has also been a product of inconsistency. But finding my way —a way that works for me—has proven to be the way.

3. My faith: I’ve given 3 Sunday sermons at my local church so far, and each time I do, I’m reminded of how much I still have to learn about God and how to listen. I try to always wrap my goals (writing, AI, health, business, family) around a stem of faith. Because ultimately, what’s the point if I get all that and lose my soul? I hate sounding preachy. And I hate people who do. Hate is a strong word, I know. But softening the blow doesn’t change my feelings about it. Faith is personal. It comes by hearing, which is why studying, hearing, and community matter. But no one is holier than another —especially not me. And the more I think about how much work I have to do, the more humble I become.

What I’m proud of:

1. Sticking to an eating window: In the past, I’ve often given myself reasons to eat whenever and whatever. And to be completely honest, it’s not really that bad. It’s only bad relative to what good needs to be and my own personal standards of what healthy living looks like. I’m proud of my ability to acknowledge I’m hungry and then remember why I’m doing it in the first place.

2. My AI skills: I know. Incredulous, considering how this letter started. I stay skeptical of AI, but I am improving my skills in how to use it. In fact, I actually think that I can teach now. So, if that’s a part of me you’d like to experience, sign up here.

3. Hiring people to work with: I have hired a couple of people for my business. It’s something I’ve never done, and my wife takes the credit for getting me to see the value. I don’t yet know if this will pay off, and I’m treating it like a slightly expensive experiment — which, I think, is what we all do with life anyway.

4. This podcast with Coach Chanty. She’s such an amazing host. She wasn’t afraid to ask questions that got me thinking - and you know I love to think.

Your Invitation

In 100 years, you and I will be dead. I know, dark. But you know this.

We often refuse to consider the implications of our meaninglessness because of the slight “so-why-bother?” that it may surface.

But I think that’s only half the reflection.

What if you lived past 100? Just what if. Consider it.

What would you like to have done by then? Dream. Think. Write.

Go bananas—or oranges if you prefer.

Now, if you had only 10 years to do it, what would it take?

See you next time.