Should You Automate Your Online Business?

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Industrial machinery with a large gear

The age of automation marches on with fresh fuel from AI tools, inflation cost-cutting, and what seems to be a genuine and growing desire to spend less time working and more time living.

But just because something can be automated doesn’t mean it should be. Automation is a tool, and at its core the entire point of automation is to replace labor. I’m not someone who thinks we should do this without thought: often, automation proponents believe replacing all labor is the same. Get rid of it. Why bother paying for people when an app can do it for a fraction of the cost?1

But some actions, I believe, should not be replaced. They are human work, and they need a human to do them.2

Automation stems from the desire to do more. We can’t escape that. The first time we really see automation as a concept is as part of the Industrial Revolution, where time-saving emerged as a capitalistic device to create more monetary value by speeding up production and reducing human labor costs.3 When we situate automation within this historical context, it becomes reasonable to interrogate our own desires to automate. Why are we told that this is the thing that you must do to grow your business? Who benefits when automation is the default? Who is hurt? And what do we gain or lose through automation?

In Which I Am A Hypocritical Fool

Many years ago, a small business owner on Instagram had an account that I noticed was growing very quickly. She had good photos and solid copy, but the speed of growth was wild for the field of work she was in. Within months she had tripled what it had taken me years to do, and I booked a consult with her since her other job was as a social media manager. I wanted to know the secret!

And the secret was…automation. She ran a complex bot software that followed, unfollowed, engaged, and even watched Instagram stories on her behalf. She backed it up with real, valuable content. But she had skipped to the front of the line by automating the human actions of Instagram, leaving everyone to think that she had earned her rarified status through hard work, deep interaction, and seemingly endless scrolling time.

(Reader, I must confess that I hired her to do the same for me, and my account got restricted within days. That’s what I get for doing something that grossed me out because I thought it was necessary to compete.)

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I’m not so worried about the illusion of hard work. The idea that we need to work hard in prescribed ways in order to earn our right to exist or be worthy or whatever is a bad idea and a deep societal rot that directly leads to disenfranchisement and murder4. But the fact that what was automated were the very tasks that implied sociality, that created the relationship between the account and its followers, that traded on the parasocial relationship to make people think she was avidly engaging with their work…that bothers me.5

And that is the core of what bothers me about automation as a whole: why are we using it to do things that others will expect are human?

Automating Humanity

To some extent, what is expected to be human is a moving target. There was a time not that long ago that getting an email from a business that used your first name may have made you assume that it was personally sent to you. Now, many people know that’s an automation, and one that businesses (including mine) use to try and get past Gmail filters to escape the Promotions tab purgatory.

Is that harmful? I don’t think so. I don’t really care. You can see pretty easily that emails are from mailing lists (unsubscribe button, usually sent via the software’s address). It requires some level of knowledge, but a knowledge that is increasingly common.

The chat therapy company that used GPT-3 to craft responses to users without disclosing that automation was driving their breakthroughs? Perhaps more nefarious.

Some automation use cases are better than others. Over in Think Tank we just beta launched our new mastermind feature. I ran the process manually, but now can automate all but one step. The one step? Actually matching members to the right group.

There are ways I could automate it (for example, everyone with revenue between $X and $Y are in Group A), but the group creation is the most human element of a process designed to create deeper human connection. I looked at the groups holistically, taking into account not only revenue but also goals, business model, and time zones! Is there a script that could do that? Probably. Could ChatGPT take a stab? Sure. But there’s no way to account for the human knowledge of it, the intuitive hit that two people might really get along, or that another two people might butt heads in a way that could become unproductive for the group. That knowledge only resides in my head, and short of writing a full personality and history brief on every member (which…no thank you) for a program to parse, cannot be outsourced to an automation. It had to be me.

And that’s ultimately where I think automations shine: making it easier for us to do the truly human work. To make the connections, leverage the intuition, and activate the creativity.6

What To Automate In Your Knowledge Work Business

I have a simple rubric, then, for automations. I suggest automating:

  1. Something you wouldn’t have bothered to do or been able to do before because of time constraints
  2. Something that someone would have done that truly is dull as fuck with little or no redeeming value for the laborer
  3. Something that makes it easier for you to do the human-only things

Without automation, it is unlikely that I would have tried to create a small-group, customized mastermind feature for a program designed to hold 200 members. The first time would have been fine, but to manage changes, to keep track of member status, to add new people…nope. But with some Airtable7 and Zapier magic, I can run this program in the background while I show up for the most important part: the matchmaking.

The dull stuff, well, that’s where automation really shines. Everyone has a different definition of dull. There are folks who love spreadsheets and folks who gouge their eyes out at the sight of a cell. But some things really don’t need to be done by a human, and if those are automated, they can free those same humans to do more engaging work. For example, downloading and uploading Zoom calls. There was a time when this was manual work. Record the call to the cloud. Someone downloads the video. That person uploads the video to the host. That’s like an hour of work that requires no skill and is not engaging and is not creative. Now, Zoom connects with so many platforms that any video recorded to the cloud can automatically sync to a host. The video just magically appears where I want it!

That kind of automation frees time for the human-only things.

And what the human-only things? That’s for you to decide. But for me it’s the creativity, the ideation, the connection. I automate in order to show up more fully with my clients and members. I automate so I can be present. I automate so I can have more free time, because to me that is true abundance.



  1. See the Writer’s Guild of America strike demands which include a hard line against AI.

  2. And while I’m here for a utopian argument that all work should be automated, without a theory of liberation behind it that creates abundance and ease for all humans, it’s just labor suppression.

  3. This is actually what the Luddites were fighting against, btw. They didn’t hate technology: they were protesting manufacturers with shady labor practices. After I wrote this I saw that Luddites are apparently having a moment; Brian Merchant from the LA Times has a great thread about it here.

  4. RIP Jordan Neely

  5. As I said, I tried to do the same. No angels here.

  6. This is one of the reasons I am so blah on generative AI: these corporations are trying to further commodify and even replace the human work.

  7. this is an affiliate link I get Airtable credit please use it I need my Airtable fix thx

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