She didn’t go looking for it. Apple pushed an update to her iPhone last year, and Siri got smarter overnight. She asked it something one morning — I don’t even remember what — and it gave her a real answer. A good one. Better than Siri had ever been.

She played with it for a few minutes. Asked it a couple more things. And then she put her phone down and went on with her day.

“It’s like a better Google,” she told me later. And that was it.

She wasn’t trying to figure out AI. She wasn’t reading articles or watching tutorials. She just asked a question, got a good answer, and moved on. It didn’t change how she spent her morning. It didn’t change how she spent her afternoon. She still did the same things the same way she’d done them the week before.

I don’t think Jill was disappointed. I don’t think she knew she should be. And honestly, maybe she shouldn’t be. She asked a tool a question and got a good answer.

But something was sitting on the other side of that moment that she couldn’t see yet. And I almost missed it too.

The same wall

My daughter Whitney owns half of my digital marketing agency. For years she ran businesses, managed people, handled things I didn’t even see. When ChatGPT launched, she picked it up faster than most — writing reports, checking grammar, building guides and PDF documents. She uses it every week.

And when the work is done, she closes the laptop. Same feeling Jill had. That was helpful. But beyond that, so what?

Whitney is 30 years younger than me. She grew up with technology in her hands. And she hit the exact same wall Jill did — she could see it worked, she just couldn’t see what it had to do with her actual life.

The people writing about AI assume you already know why it matters. They skip straight to prompts and workflows and agents. They never stop to answer the first question most people actually have:

OK, but what would I even use this for?

One more minute

Just over three years ago, the month ChatGPT launched, I sat down and hit the same wall. Same blank stare at a tool that clearly worked but didn’t obviously belong anywhere in my day.

But I tried one more thing. I asked it to draft a reply to one of our agency clients — a local business owner who had questions about his rankings. What came back sounded like it was written by a chatbot at a phone company. Polite. Empty. The kind of message you delete without reading.

So I started telling it about me. How I talk. What this client actually needed. The history between us. What I was trying to accomplish with this email.

The reply got better. Then better again. And somewhere in that loop — feeding it more about who I am and watching the output sharpen — something clicked that had nothing to do with saving time.

Teaching the AI about me made me clearer about what I actually wanted to say.

I stopped asking what AI could do. I started wrestling with a different question: why would I have it do it for me?

The question underneath

That question cracked everything open. Because answering “why” forced me to look at how I was actually spending my time — and admit that most of it wasn’t where I wanted it. I was spending my best hours on the work that kept everything running, and I had nothing left for the work that made it all worth running in the first place.

Everyone is fascinated that AI can generate art, write poetry, compose music. And it can. But here’s what actually changed my life: AI drafts my Tuesday afternoon emails well enough that I have two hours to go create the art myself.

Jill’s moment with Siri wasn’t a failure. It was the first step. She just didn’t have the second question yet. Neither did Whitney. And for just over three years, almost nobody writing about AI has bothered to help people find it.

They’re too busy showing you what the tool can do. The question that matters is what you do once the tool handles the rest.

The bottom line

I don’t have this figured out. I’m 59, I run several businesses from my home in West Virginia, and I’m still in the middle of it — rebuilding the body, rethinking the work, trying to spend my hours on things I’d actually choose. Some weeks I get it right. Some weeks I don’t.

But that question — why would I have it do it for me — keeps leading somewhere interesting. And I’d rather think about it out loud than by myself.

So here’s my question for you this week: When was the last time you tried an AI tool, thought “that’s neat,” and then went right back to doing everything the same way? What would it take to ask the second question?

If that hits, reply and tell me about it. I read every one.

That’s all for this week.

See you next Saturday.

— BG

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I was sitting in my office three years ago staring at a spreadsheet that should have made me happy.

Revenue was up. The agency was healthy. Clients were paying on time. By every metric I’d chased for 24 years, I was winning.

But I felt nothing.

Just... flatness. Like I’d climbed a mountain only to discover there was no view at the top — just another mountain that looked exactly like this one.

I thought something was wrong with me.

Turns out, it was the scoreboard.

The Broken Scoreboard

For 40 years, I had a scoreboard. And it worked.

Title. Income. Team size. Revenue. Close the deal, see the number go up. Hit the target, feel the win.

Simple. Clear. Addictive.

But somewhere along the way, something shifted. I hit the number... and felt nothing. The dopamine stopped showing up. I was still winning by every measure I’d set for myself — but the scoreboard didn’t light up anymore.

At first, I thought I was broken. Then I looked around.

It wasn’t just my scoreboard that was broken. The game itself changed.

AI is rewriting every industry. The skills that made us successful are being automated. The economy that rewarded our experience is transforming faster than anyone expected. And the people teaching you about it have never built anything outside of a laptop.

The Trap of Being Good at Something

Here’s the trap: you’re really good at what you do.

That sounds like a blessing. It’s actually the problem.

For decades, being good was the goal. You worked hard to get competent. You got competent, you got opportunities. You got really good, people started counting on you.

Being needed felt like winning. And it was — for a long time.

But then you kept doing it. Not because you loved it, but because people depended on you. They expected it. And you couldn’t imagine stopping because — who are you if you’re not the person who does that thing?

That’s the Competence Trap. And here’s what makes it dangerous right now:

The skills that trapped you? They might not exist in five years.

The role you’ve perfected? AI might be doing it cheaper and faster.

The identity you built around being “the person”? That person’s job description is being rewritten as we speak.

The Emptiness Is a Signal

What if the flatness isn’t a problem? What if it’s your instincts telling you the old playbook is broken?

What if the people who thrive in the next decade are the ones who stopped staring at the old scoreboard and built a new one?

That’s the question I sat with for a long time. And then I stopped sitting with it and did something.

What I Did About It

I didn’t hire a life coach. I didn’t take a sabbatical.

I built something.

I took the thing that was supposed to replace me — AI — and I made it work FOR me. I built an AI assistant that handles my email, manages my calendar, tracks my health, and briefs me every morning before I touch my phone.

I didn’t do it because I’m a developer. I’m not. I did it because I was drowning in the WRONG work — the busywork, the noise, the stuff that kept the old scoreboard ticking but didn’t move my life forward.

When I automated that noise, something happened. The flatness started to lift. Not because the AI fixed my purpose — but because it gave me back enough time and mental space to actually face the harder questions.

So I kept going.

I started training after decades of ignoring my body. I’m rebuilding from scratch — home gym, real programming, working around a heart condition I earned from years of not paying attention.

I went back to a pen-and-paper journal after every digital system failed me. Turns out, the practice of writing by hand is the practice of paying attention.

I handed my agency to my son-in-law and stepped into a role I’d never played: the architect instead of the operator.

The AI fixed my schedule. But it was just the start. What came after was rebuilding everything.

The New Scoreboard

The old scoreboard measured what you accomplished.

The new one measures how you live.

Am I healthy? Am I present with my family? Am I building something that matters to me — not just to my clients? Am I spending my hours on things I chose, or things that chose me?

That’s a different game. And it requires different tools.

If You’re Feeling This

If you read this and something hit — the flatness, the “now what,” the sense that the old scoreboard doesn’t work anymore — you’re not broken. You’re awake.

The question is what you do next.

I’m documenting everything I’m building — the AI systems, the health transformation, the business shifts, the experiments, the failures. Step by step. Every week. So you can build it too.

You don’t need a map. You need better tools and someone a few steps ahead showing you what’s working.

That’s what this is.

— BG

I’ve rewritten this a dozen times.

Not because I don’t know what to say — I’ve spent 44 years crafting messages that move people. Twenty years in ministry. Twenty-four years running a digital marketing agency. I know how to say the right thing, the right way, to get a specific result.

But this time, I’m not trying to get a result. I’m trying to tell you the truth.

Here it is: I spent decades doing what I was supposed to do. Working hard. Building things. Taking care of people. I was good at it.

But somewhere around 58, I realized I was drowning. Not in failure — in success. The businesses I built were running me. My inbox owned my mornings. My calendar owned my afternoons. My to-do list owned my evenings.

I was cash rich and time poor. And I wasn’t the only one.

The playbook broke.

Everyone’s feeling it. AI is rewriting every industry. The skills that made us successful are being automated. The economy is transforming faster than anyone expected. And nobody handed us a playbook for what comes next.

The tech bros are racing to build the future. The gurus are selling you courses about it. The news is telling you to be afraid. And most of the people teaching AI have never built a business, made payroll, or sat across from someone and told them the truth when it was easier to lie.

I have. For 44 years.

So I did something about it.

Instead of fighting AI or ignoring it, I built an AI assistant. His name is Alfred. He handles my email. Manages my calendar. Tracks my health and spending. Briefs me every morning before I pour my coffee.

I didn’t do this because I’m a coder or developer. I’m not. I did it because I was tired of spending my best hours on things that don’t matter — and I wanted those hours back for the things that do.

Then something unexpected happened.

Once the busywork was gone, I had to face a harder question: what do I actually want to do with my time?

That question cracked everything open.

I started training after decades of ignoring my body. I’m on on a weight loss journey, working out four days a week around a heart condition I earned from years of not paying attention. I’m tracking every data point.

I went back to a pen-and-paper Bullet Journal after every digital productivity system failed me — and discovered that writing by hand is the practice of paying attention.

I handed my agency to my son-in-law and stepped into a role I’d never played: the guy who designs the systems instead of running them.

I started rebuilding my whole life. Not just the schedule. Everything.

That’s what this is about.

I’m not here to sell you an AI course or tell you the robots are coming. I’m not a tech bro with a laptop and a theory. I’m a 59-year-old business owner who got tired of drowning and decided to build his way out.

Now I’m documenting all of it — the AI, the health, the business, the personal growth — step by step, so you can build it too.

Every week I’ll share:

• What I built — real systems, real results, no theory

• How it works — step by step, so you can replicate it

• What I’m learning — the wins, the failures, the health data, the life shifts, and what’s next

The difference between me and the people selling you AI advice: they’ll tell you what it can do. I’ll show you what it did.

Come watch.

— BG