How to Figure Out What to Automate

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It’s another Automated Solopreneur episode! Today I’m telling you 4 types of tasks you can automate – as well as questions you can ask yourself to determine what you can automate based on what you do on a daily basis. 

Those 4 types of tasks? 

  • Common, easily repeatable tasks
  • Infrequent tasks that have a high level of effort to do.
  • Tasks that require specific timing
  • Tasks that you cannot forget to do.

In How I Built It Pro, I talk about when you might be automating too much, plus my plans for making the membership more automation-centric. 

Show Notes


Joe Casabona: Imagine being told that you need to get to your wedding, and that’s it. No time, no date, no location, just you need to get to your wedding. You’d kind of feel stuck, right? Surely there are people who know that information you’d think it wouldn’t be part and parcel with “you need to get to your wedding”.

That’s kind of how it feels when someone tells you you need to automate. What should you automate? How should you automate it? And how do you know if you can automate it?

In today’s solo episode, I am going to continue a little series I’m calling the automated Solopreneur, where I talk about how to determine what to automate. In the Pro show. I’m going to talk about a recent automation failure and when you know or how you should know when to quit. And I’ll talk about future plans for the Pro membership. They’re really excited, I’m still hashing them out, I will make them public soon.

But if you want to get ad-free extended episodes of every episode, you can sign up for $5 a month over at It comes with those ad-free extended episodes, it also comes with some special videos that are for members only, and a Friday newsletter, again, for members only. Again, that link is

But for now, let’s get to the intro, and then the episode.

[00:01:36] <music>

Intro: Hey everybody, and welcome to How I Built It, the podcast where you get free coaching calls from successful creators. Each week you get actionable advice on how you can build a better content business to increase revenue and establish yourself as an authority. I’m your host Joe Casabona. Now let’s get to it.

[00:01:57] <music>

Joe Casabona: All right now there are a number of questions that you could ask yourself when you’re trying to figure out what to automate. Those questions really quick. If you want to take a deeper dive, I’ll link to the article, or let me know and I can do an episode on that as well.

But you should ask yourself if a person needs to do the task, ask yourself if you personally need to do it. Look at tools to get some great ideas. We’ll cover tools in another episode.

But the two questions about asking yourself if a person needs to do it and then asking if you personally need to do it will really help you narrow those tasks down. So for example, does a person need to upload my episodes to YouTube? The answer to that question is no. My audio host transistor will do that automatically for me.

How about uploading this audio and preparing show notes for each episode? A person does need to do that because someone needs to write the description and gather the show notes. But I personally don’t have to do that. So my VA does that.

So asking you those two questions will invariably create a list of things for you that you don’t need to do. But aside from that, there are also categories of tasks to help you figure out if a task is worth automating. So those categories of tasks are common, easily repeatable tasks, infrequent tasks that have a high level of effort, tasks that require specific timing, and tasks that you cannot forget about. Those four categories are where you should look to automate.

So let’s take those categories one by one, starting with common, easily repeatable tasks. These are things that you do so often that it’s worth your time for you to set up an automation so that you no longer have to do them manually. And this takes some discretion, right? Because if you have to do a task for the first time, it doesn’t make sense to set out and automate it. You don’t know how often you’re going to do it, you don’t know how long it actually takes you, or if you’re actually going to be able to automate it.

Again, one example of this common easily repeatable tasks that I’ve decided not to automate yet that I’m going to talk about more in the Pro show is detecting churn for members. Because I use ConvertKit and they don’t do that automatically. So I need to ask myself, how often am I clearing the list of non-paying members and is it worth spending that time to automate?

But an example of something that is common and easily repeatable that you could automate is emailing your newsletter subscribers when a new blog post or podcast episode is out. Most email services or email service providers will connect to your RSS feed and send emails when a new item gets published. So you don’t have to do that personally.

Now, if you are doing a newsletter with curation, that’s maybe something that you could automate. But the level of effort is higher for that. What is not higher, though, is automating the actual gathering of things, right? So maybe you use an app like Reader or Readwise to gather notes, maybe you use Feedly, or Feedbin, or Pocket, something like that.

You’re reading an article, and you think, “This would be great for my newsletter,” you can set up an automation using shortcuts or make or Zapier that you send the link, it grabs the important information, and then puts it into, let’s say, a Google Doc, for you to then include in your newsletter. That way, you’re at least not going to all these different sources and trying to remember “what was that thing that I wanted to share with my newsletter?”

So the way I do that is with Craft. I have a Siri shortcut called Clip to Craft. And I can activate it from the share sheet so that if I am reading something, and I say clip to craft, it adds it to a note I have called Newsletter Digest. So that’s common, easily repeatable tasks.

So what you should do here is, as you’re doing something, think about how often you do it, and think about if it’s something that you don’t have to do, and if it’s something that maybe a robot can do instead.

The next category is infrequent but high level of effort. So conversely, if there’s a task you don’t do very frequently but it takes a long time for you to set up, the automation is worth it because you save the time through context switching and having to relearn your process.

A really good example of this for me is contract client work. I don’t do too much of that anymore but there’s still a process for me where I send a contract for signing, then an invoice, and then onboarding. It takes me more time to figure out the right process because it’s something I only do every few months. Then for me to actually execute the tasks right.

Now, one of the things I have to do is remember which document signature service am I using now. I’ve tried so many from like Newsy to DocuSign, to HelloSign, which is now Dropbox Sign, I think. So I’m like, “Where do I have that contract?” I don’t have an SOP for that. But certainly, that’s something that I could automate, right? And to execute those tasks, again, is shorter. Though, since these tasks also rely on client actions, it could take me time over several days.

But if I have an automation that, let’s say, kicks off when I send the contract and then it picks back up again after the contract is signed to send the invoice, and then once the invoice is paid maybe they get like an onboarding email. That would save me a ton of time, right? Because then I just send the contract and automation handles most of the rest for a while.

So that’s infrequent high level of effort. Again, what I would recommend you do for this is if a task comes up where you think back and say, “Oh, I have to do this every six months, but it takes me so long,” maybe that’s something worth automating. At least automating parts of it.

And the way that I guess I would recommend you see if you can automate it is, write out the SOP. What do you have to do? All right, I have to get my insertion order template and upload it to DocuSign or HelloSign. Then I have to fill in the client information. Then I have to send it. When that comes back as signed, now I have to send the invoice. When the invoice gets paid, now I can add them to the podcast episodes or to the kickoff email. So that is, again, infrequent high level of effort tasks.

Let’s take a quick break to hear from our sponsors.

[00:09:35] <music>

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[00:13:26] <music>

Joe Casabona: So the next category of automatable tasks is they require a specific timing. You can automate these tasks. And you see this all the time when you purchase a digital product. Imagine paying $300 for a course and then having to wait to gain access to it because the seller has to do it manually. That’s not the case in most digital sales platforms now. Once you pay, you get access, or once you pay, you get emailed a download link, you get emailed account information.

But this doesn’t just have to be for digital products. Tweet Hunter, at least at the time of this recording, has a tool where you can tell people to DM you for a free resource and Tweet Hunter will handle the DMing. This is great for automation where you don’t have to watch your social media DMs. But the important bit here is that the DM gets sent automatically but you continue the conversation manually.

The same thing can happen if someone on your mailing list, right, if you say like, “Hey, click here to get my brand new email course on automation,” if someone clicks that link, I want them to get the first email nearly immediately and so I’m going to have an automation setup in ConvertKit that adds them to the sequence where they get the first email immediately. So you want to make sure you’re hitting that instant gratification. So if something requires specific timing where you can’t be there all the time, then consider automating it.

Finally, you want to automate tasks you can’t forget. I like to call these the automatic bill pay tasks—you definitely don’t want to miss them but maybe they don’t happen very often. An example of this is my water bill. It happens quarterly. I forgot to do it one time because I thought my water bill and sewer bill come at the same time. I paid one but I didn’t pay the other. And then, without warning, our water got shut off. So after that and after calling the city and yelling at them, I set up automatic bill pay.

As it applies to my business, one of the tasks for me is to upload workshop recordings for members. So if I do a live workshop for my members, or a live webinar that is for members only, I promise them immediate access once the workshop is done. So I have a simple automation to upload the recordings from my computer to Vimeo. What I could do to take this one step further is kick off an automation that emails them the video link once it’s uploaded. I haven’t gotten that far but they do have access to it once it’s uploaded to Vimeo.

So there it is your four types of tasks you should automate: common easily repeatable tasks, infrequent tasks that have a high level of effort, tasks that requires specific timing, and tasks that you cannot forget to do.

I’ll just say like a few more examples. Again, send an email to your mailing list when a new episode of your podcast drops, send an invoice when a client signs a contract, give users access to a private podcast when they become a member. That’s a really important automation I have in Make. And upload videos from Dropbox to Vimeo is another… that’s another good one that I have. Four types of tasks.

I’ll end on this. If you are doing things like automatic bill pay, you are already automating. So the next step is to look at some tasks. If you have a Mac, I think Hazel is a really nice piece of software you should check out because one of the nice automations in Hazel is to look at your downloads folder and move files based on their file type, or to clean up your desktop at the end of each day. Those are little automations that can make a big difference in your life. So there you have it for categories, how to determine what to automate.

Again in the Pro show, to get the rest of this episode, you can sign up over at for just $5 a month. I’m going to be talking about how to determine when you are automating too much and when to call it quits.

But that’s it for this episode. Thanks so much for listening. And until next time, get out there and build something.

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