I almost made a terrible mistake last week.

Last week, I considered automating something that keeps me connected to my readers.

Here’s what happened:

I was going through the responses to The Saturday Solopreneur, and I had more kind reactions from readers than usual. Folks who said the newsletter was meaningful to them, or just wrote in to tell me that they started a business after reading my content. I try my best to reply to meaningful messages from readers, but responding takes a lot of time, and I was getting ready to travel, so time was a bit tight.

So, I started doing some research on how other creators and writers handle a situation like this. It turns out that a lot of people build canned “positive replies” as Gmail templates and then use those to respond. And of course, that would be much more efficient than writing back to everyone from scratch.

But as I thought about it, it just didn’t feel right. Replying to people sharing real gratitude with a copy-paste message seemed like a terribly inauthentic thing to do. I realized that when you optimize the most human parts of your business, you risk removing the very reason people connect with you in the first place.

And in this new world where AI is everywhere, I’m appreciating (more than ever) the little slices of human connection.

Don’t automate everything

The internet loves automation. Everywhere I look, someone’s offering some sort of automation to “10x” whatever it is you’re trying to do.

And don't get me wrong, a lot of automation works really well. I use content scheduling software, email automation, and Zapier to do some of the mundane work in my business. These tools are great at handling the boring stuff, so I can focus on what matters.

But I realize there’s a fine line between helpful automation and soul-sucking systemization.

I know someone who built a high-revenue course business using AI to automate everything from sales and onboarding to “personal check-ins.” He told me he doesn’t even know if his course is actually helping people; he just sees the revenue number going up.

And while revenue is increasing in the short term, he runs the risk of optimizing himself into disconnection.

Some things are worth doing the hard way

I can’t reply to every single message I get. But when someone shares a breakthrough after taking one of my courses or reading something I published, I try to respond. Not because it’s scalable, but because these connections are valuable to both of us.

And honestly, I still can’t believe so many people care to read what I write. The fact that anyone would take the time to both read my content and write me back is pretty incredible. I still feel that way after six years of doing this stuff.

I take a similar approach to this newsletter. It’s written from scratch each week, and I don’t A/B-test subject lines; I simply choose what I think best represents the writing. Sometimes the emails flop, and sometimes they land. I’m okay with both outcomes.

The human parts of my business aren’t inefficiencies. They’re features.

Choose your trade-offs wisely

I’ve seen folks automate their way into businesses they barely recognize. They started out helping real people, solving real problems. Then they “scaled,” and now they don’t know if their work still matters.

Systems replaced connection, and metrics replaced mission.

That’s the cost of automating everything.

Don’t get me wrong. Not everything needs a manual touch. But I’m trying my best to be intentional about what stays human:

• I automate course delivery, but reply to student wins.
• I use content schedulers, but write the posts myself.
• I systemize operations, but keep the creative work messy and real.

A good blend between manual work and automated work keeps you close to the business and close to your readers and customers.

The best question you can ask

Before building a new system, ask yourself this:

“Am I eliminating friction? Or removing the human touch?”

If it’s friction, automate it.

If it’s the human touch, take a pause.

Because your business, no matter what it is, doesn’t need to be a flawless machine. It needs to stay alive. That means keeping the parts that give you energy, and letting go of the ones that drain it.

Some conversations are worth having. Some messes are worth keeping. And some things should stay delightfully, inefficiently human.

The fun part of managing your own business is that you get to decide. And you have the opportunity to be totally intentional about how to set things up!

And that’s all for today.

See you next Saturday.

P.S. If you're interested in building an online business that lets you stay connected to your customers while automating the mundane and boring parts of your business, consider my flagship course, ​The Creator MBA​.

It's 111 lessons behind the scenes of building an online business from $0 to 8 figures in revenue over the last 5.5 years.

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