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You’re doing a lot of things yourself and you know you should be systematizing and automating things, but you’re just not in a place where you can invest yet.

The question you should be asking is: “What things should I be automating in my workflow and business that I don’t know to automate?”

Fortunately, a Community member asked it for you and that’s exactly what we get to in this episode.

I share several of my favorite tools, shortcuts, and workflows and how I use them to maximize efficiency and get a ton done.

I guarantee even seasoned productivity pros will get something out of this episode, but if you know you’re not as efficient as you need to be or if “automation” is a strange word for you, this episode is going to change your world.

Highlights, Takeaways, Quick Wins
  • You’re doing a lot of things you shouldn’t be doing.
  • Don’t wait until you get overwhelmed to start looking into automation.
  • If you do the same thing more than once, you should automate it.
  • Automating is a small investment in your time and your future.
  • Every second you save by automating something means you have more time to spend earning money and creating value.
  • Dedicate keyboard shortcuts to your most used apps.
  • Minimize the time you’re switching between the keyboard and the mouse.
  • When you write down your process, you open yourself up to the opportunity for others to help you shape that process.
  • Don’t automate the things that should be personalized.
Apps Mentioned
Show Notes
  • 14:20 Sean: Getting to the point where I have a great team means I’ve had to hire but I also embrace a mindset of automating things. You’re doing a lot of things you shouldn’t be doing. For this episode, I’m going to assume you’re not in the position to hire yet and that you’re doing things you shouldn’t be doing as often or you’re doing things manually.
  • 15:09 Ben: This isn’t something where you’ve been in business a little bit and you’re finally to the point where you should be automating things. From the beginning, you should be actively looking for things that you can automate.

Don’t wait until you get overwhelmed to start looking into automation.

  • 15:33 Sean: Charli asks, “What are things I’m doing now that I should have automated already? I can’t think of anything I do that’s automated currently so I’m sure I’m behind.” Here’s my rule of thumb: if you do the same thing more than once, you should automate it—not more than twice, six times, or 50 times. Someone else said, “I feel like the automating tools I can install require a significant amount of time to learn and get used to. Isn’t it counter productive?”
  • 16:17 It’s common to feel like you could do something five or 10 times in a row in less time it would take to slow down and automate it, so isn’t it counterproductive? If you’re doing it more than once now, you almost certainly will do it again in the future. Automating is a small investment in your time and your future.

Keyboard Maestro

  • 16:52 Everything won’t be specifically Mac focused in this episode, but the top three apps I recommend for Mac are Keyboard Maestro, Alfred App, and TextExpander. Keyboard Maestro records sets of actions to which you can assign a hot key. If you’re transferring files, importing footage, exporting things, or you’re doing the exact same thing more than once, you’ve got to find a way to automate it. If you always export your Premiere project and select the same preset then enter the same bit rate before you click export, that’s something you can automate.
  • 17:52 If it’s something sequential or repetitive, you can automate it. With tools like Keyboard Maestro, it’s simple. You don’t have to know programing or anything; you simply hit record, do your thing, stop the recording, and assign a hot key. You can then go in and edit that or do more advanced and custom things as well. You’ve got to ask yourself: am I doing something the same every single time, multiple times? Sometimes that’s even within running a macro. If you have 100 photos and you want to apply the same preset to all of them and save it as a .jpg at 10-quality in photoshop, you could run a macro on that.
  • 18:40 You could run a .jpg and then run the macro, then go back to your finder window and grab the next file, run the macro again, and think you’re being efficient. Well, that’s not as efficient as you could be. You’re going back to finder, selecting the next file, importing that, and then your macro! Why not create a macro that goes to finder, moves your selection down one, imports it into Photoshop, and then runs the shortcut for your other macro.

Alfred App

  • 19:30 The other one I like is Alfred App 2, which allows you to open apps, find files, and search the web. You may already use Spotlight for that, but I think Alfred is way better. You can use workflows, perform conversions, grab things from your clipboard, and even do math with it. I write so many titles—at least one to three every single day—and I can never remember words like “of” and “an” that aren’t capitalized. You shouldn’t have to think about that!
  • 20:27 Alfred has a workflow that will convert the case for you. You type whatever your topic is, copy it to the clipboard, run Alfred, type “case”, and hit enter to convert it to Title Case. I even set up a macro to select the text and run the macro! It will copy it to the clipboard, run Alfred, type “case”, hit enter to convert it, and then paste the result.
  • 21:10 Ben: That seems like an insignificant thing and people might be wondering if it actually saves time. Let’s say combined, it saves you 5 seconds a day on average. That doesn’t seem like much but it does add up over time. If you multiply that time over the course of a year by how much your time is worth, then you can estimate that’s how much money you’re saving if you wanted to assign a value to it. It’s definitely worth it, even if it doesn’t seem like it with something so minute.

Every second you save by automating something means you have more time to spend earning money and creating value.

  • 22:15 Sean: You can do basic or slightly complicated math right in the Alfred App window. It’s amazing the kinds of custom workflows you can make. You can go on the Alfred forums and nice people will make you workflows. When I was doing a lot of designing in Photoshop, I liked to use the golden ratio in my designs, so I asked someone on the forum to make me one. Now, all I have to do is press G + a number and it gives me two options: the golden ratio number that’s higher than my number and the one that’s lower. From there, if I hit enter, it’ll copy it to my clipboard.


  • 23:17 Another one is TextExpander—it’s dynamic snippets for your most commonly typed words and phrases. For example, I use this a lot with emails and other things. Internally, we use Infusionsoft and we talk about it a lot. “Infusionsoft” may not seem like the most difficult word to type, but when you’re typing a word out hundreds of times a day, there’s no reason to type out the whole thing. I just type out INFS and it expands to the word “Infusionsoft” capitalized and ready to go. Same with “Sequence”—it’s not a fun word to type so I use SQ. Use this for anything you’re typing a bunch!
  • 24:14 is “SWCOM” and to input my email address, I type “@@”. When do you ever type two @ next to each other? I use TSM for, “Thanks so much for getting in touch,” which I like to start my emails with. If I want to say the person’s name, I type TG and, “Hi [Name], thanks so much for getting in touch,” comes up; there’s even a way to do fill-ins there. To start an email, I just hit my keyboard short cut, R, to reply, then TG, type their name, press enter, and I’m ready to finish that email.
  • 25:24 I offer a 30-day money back guarantee on sales and I already spent the time to write a polite refund email. When I have to give a refund, I don’t want to have to go through that emotional experience every time so I just use that template. That way, I don’t have to think about being polite when I’m frustrated someone is asking for their money back, I just write it once. When I use that shortcut, it says, “Hey [Name], thanks so much for getting in touch. I’ve refunding the [blank] as requested. Hope you have a wonderful day.”
  • 26:53 The cool thing is when I trigger this, I get two fill-ins: their name and what they purchased. I can even set a default to “the purchase,” so if I wanted it to be generic I can do that. If I want to fill it with something specific like “class” or “membership”, I can do that really quick. These are just helpful tips to stop writing things multiple times.
  • 27:26 Ben: If you’re someone like me, I have a little bit of stubbornness when it comes to doing this because what I’m doing is “working”, but that’s what has kept me from making some upgrades to my productivity. Where I have taken the time to automate things, it gets a little addicting. You start messing with stuff and seeing how it makes things more efficient, which can be fun. Then, you look for other things to automate. There’s that resistance you’re going to experience because you’ll have to take the time to do it, learn something new, and if you don’t have a Mac, you’ll have to research and find counterparts that will work well for you.
  • 28:38 Sean: I don’t know if you can teach this, but the biggest thing is having the mindset. A lot of people get stuck in what they know works and they’re afraid of not knowing something. It’s uncomfortable and they don’t want to be uncomfortable. You know you can bring up Finder if you grab your mouse, look for where the pointer is, drag it down to the bottom of your screen, mouse over to it, and then click on it. Ultimately, you have to learn to do absolutely everything on the keyboard and everything on the mouse and minimize the transition period between the two—don’t go back and forth!

Keyboard Shortcuts & BetterTouchTool

  • 30:05 If you’re not aware, CMD + TAB brings up an app switcher. While you’re holding CMD, you can press TAB and go through each of the apps, but you can also press CMD + SHIFT + TAB, and it will go backwards. If you’ve got 20 tabs open and you missed the one you wanted, you don’t have to go all the way back around, just go backwards. This is still slow though, so dedicate keyboard shortcuts to your most used apps. I like having a full-size keyboard because you have more keys to do things with. CMD + F1 through F11 are my most commonly used apps:
    • CMD + F1 = Chrome
    • CMD + F2 = Photoshop
    • CMD + F3 = Illustrator
    • CMD + F4 = TextMate
    • CMD + F5 = Messages
    • CMD + F6 = Wunderlist
    • CMD + F7 = Skype
    • CMD + F8 = Scrivener
    • CMD + F9 = Logic
    • CMD + F10 = iTunes
    • CMD + F11 = Community Chat
  • 31:35 At any point, I could click on the app, open Alfred and type “Chrome”, or I could CMD + TAB to it, but I don’t have to do any of that. No matter what window I have open, I can keep my hands on the keyboard and go straight to that app. Then, if I want to come back to the previous window, I can hit CMD + TAB. You can do something like CTRL + F for Finder.

Minimize the time you’re switching between the keyboard and the mouse.

  • 32:07 The keyboard is really powerful because you have all these shortcuts, but I also like doing gestures on the Magic Mouse for Mac or a trackpad. Some of the gestures are built-in, like a two-finger or three-figure swipe, but there’s also a program that links to all these apps: BetterTouchTool. This will change everything for you. You can customize anything you can imagine. The Magic Mouse is touch sensitive, like an iPhone screen, so you can map taps using one to three fingers to something. You can map a three-figure click or two-finger swipes in any direction.
  • 33:31 You can even do two or three-finger tip-tap left or tip-tap right, where you rest your fingers on the mouse and tap one of them. It gets even crazier: you can then customize those with modifier keys. Once you run out of all those, you can then set to holding down SHIFT + CMD while you tap. It’s infinite. You can map them to your whole computer or specific applications. Here’s a specific example of how powerful this is: I’m in Chrome with a bunch of tabs open and I decide I no longer want a tab open, so I hope you know that CMD + W will close your current tab.
  • 34:19 I hope you’re not trying to find that tiny x. You want to close the current tab and your hand is on the mouse, so don’t move over to the keyboard for CMD + W, use your mouse with BetterTouchTool. I have two-finger swipe down on the mouse mapped to close the tab. If I accidentally close a tab, then CMD + SHIFT + T will bring back a recently closed tab in Chrome, but I also have it mapped to two-figure swipe up.
  • 35:39 Ben: I don’t doubt that Sean has some kind of photographic memory thing going on with this stuff, but the more you do certain actions it becomes muscle memory. You get used to doing it and then the more your muscle memory takes over on certain types of actions then other types of actions, though new, are more easily acquired. It’s really just a matter of practice. That’s a hurdle a lot of people don’t get over—things not coming easily to them in what they consider to be a reasonable amount of time.


  • 36:47 We got into this topic when we got coffee the other day and I was telling Sean how much time I waste paying my water bill because I have to put in all my information and I can never remember the password to it so I have to go look up the password. Once I finally get into the site, I have to enter my payment information because they don’t save that either. If I’m upstairs and don’t have my wallet with me, then I have to go downstairs to get it, go back upstairs, and by this time the site has timed out. I can’t remember what the password is again so I have to look it up again, then put in my payment information. I always check to see if they’ve added an auto-pay feature and they never have.
  • 38:39 Sean: Why do you not use 1Password? We don’t do sponsors here, I’m just sharing what apps are great. This is the benefit of having great products—they sell themselves. You don’t have to pay people to talk about the products. Good products sell themselves when people know about them (Related: Lambo Goal e020 10 Steps to Launching an Online Course). You can’t just make a good product and expect it to sell itself, people have to actually know about it. The hard part is getting people to know about something in the first place.
  • 39:39 Ben: When it’s excellent and people experience it, people talk about it.
  • 39:43 Sean: We’re just sharing tools that can make your life better. 1Password is a program on Mac, Windows, and iOS and you enter a single master password—there’s a Chrome or Safari extension. Whatever form you’re on, you can use a keyboard shortcut to bring up 1Password, enter the master password, and it will autofill any login you’ve ever made. 1Password can manage all different passwords. Each of these passwords could be completely random, crazy characters, that you could never memorize. It’s very secure and you only have to memorize a single password.
  • 40:52 You also don’t have to enter it every single time you login, you can set a timeout period. If you’ve entered your master password and it’s within five or 15 minutes, any other time you want to fill something in, you just have to hit the keyboard shortcut. That way, if you step away from your computer for a few minutes, it locks. No one else could come along and use the shortcut. It’s convenient but also really secure. Also, all of this syncs to your phone and it utilizes the iPhone’s touchID, which means you can now use your thumbprint to log in to Safari or 1Password supported apps. Why are you typing your password on your phone? Use your fingerprint!
  • 43:02 Cory: I use 1Password everyday. It’s very useful.

Automating Creates Assets

  • 43:18 Ben: We talked about the “what”, and we could spend the entire time talking about individual things, but I want to go into the why and the mindset behind it. Sean recently switched from MailChimp to Infusionsoft for handling his email automation, memberships, and store. Cory Miller was kind enough to show me a little bit of the backend of what Infusionsoft looks like. I remember Sean saying that he had to spend a couple grand to go through a training course and I was like, “it can’t be that complicated,” but when he showed me the stuff it can do and the ways you can link stuff together, I saw why you would spend $2,000 for training on this software. It was so extensive.
  • 44:59 Sean: Actually, I need to give some backstory about my plans for seanwes before you continue this story. We’re still finishing up the Learn Lettering 2.0 launch and I’ll have an extensive case study on that soon, but we have a certain amount of revenue that will cover payroll into next year. Basically, I was looking at being fine until next year and taking it easy without hiring anyone aggressively, but I realized I’ve wanted to hire someone that focuses exclusively on Infusionsoft, building systems. This is still a decision in the works, but I wanted to bring that into your story. I know you wanted to talk a little bit about that being an asset.
  • 49:16 Ben: You had just said, “This is an asset for us,” and the word “asset” really stuck out for me. Thinking about these automations and the time you’re spending investing in a system, however small or big, that becomes an asset for you going forward. It saves you time so you can earn more money, so you can provide more value. It’s an asset, and thinking about it that way helps me get over the road block of learning something new, spend money on a program, or taking the time to do research. The time I spend doing those things is asset-building, and when you have those assets they continue to work for you. You might have to modify them as technology changes or upgrades, but they become something that adds to what you do.
  • 50:25 Sean: When we talked yesterday, you mentioned outlining your process.
  • 50:33 Ben: It’s not just relying on systems necessarily, but it could be things you still physical do and have created a process for that you follow every time. That way, you’re not wasting time wondering what step to do next. It could be something like writing out your contracts, invoices, or a boiler-plate email. You had mentioned earlier that you spent time writing out that initial refund email and then you don’t have to do it again. You can repurpose and reuse that content.
  • 51:10 Sean: I really like the idea of outlining the process—writing it down—because that can do a lot of things for you. There are a lot of things you’re probably just doing and you’ve found a way that works, even if it’s a terrible process. If you write all that out, it helps you or someone else realize it’s not efficient. Even if you have an efficient process, writing it out not only helps you, but when you start hiring, you have this process and automation you can teach other people to use.
  • 52:20 Ben: It doesn’t have to necessarily be automation specific, it can just be techniques you have for doing things. Here in the Community, someone will ask a question because they’re stuck and want to know how to do something, and someone will chime in with an answer. Then, someone else will say, “You could do it that way, but this is how I do it and it’s a little more efficient,” then everyone gets to benefit from that shared knowledge.

When you write down your process, you open yourself up to the opportunity for others to help you shape that process.

  • 53:08 It’s cool the way that happens. Sometimes it takes me by surprise. I’ll share what I know to answer the question and someone else will chime in and suddenly, I’ve learned something new. Being a part of a community, sharing your process, and asking questions is a great hack instead of finding it all yourself. You’ve got to find a community like this and it’s a great way to help you shortcut some of those things you would otherwise have to spend more time looking for on your own. It’s definitely a worthwhile investment.

What Shouldn’t Be Automated?

  • 54:34 Sean: We got a question from someone earlier saying, “What about things you shouldn’t automate?” That’s difficult, but I would say: don’t automate the things that should be personalized. Don’t automate your voice out of things where you would have otherwise applied it. Where I will draw the line is if I’m replying to people and I’m always using different systems, like the answers to certain questions are always the same. In those cases, I’m ok with someone else coming in my stead to answer those questions using my systems.
  • 55:26 What I’m not ok with is making something that should be personalized, and isn’t a boilerplate response, seem like it’s personalized. I don’t like getting fancy HTML newsletters from a company and then suddenly you get something that looks like it was written in a Gmail compose box from the founder, but it has an unsubscribe button.
  • 56:03 Ben: The equivalent for me is when I check my mail and there’s a piece with handwriting font on it. That does the opposite! That’s not fooling anyone.
  • 56:52 Sean: Ben Flack asks, “What are some dangers of automation and how can I avoid them? For instance automating a bill payment but then having money problems because I don’t think about when the payments happens anymore?” I would say the problems of automation are equivalent to the dangers of having real people to do them. It’s systems and people following procedure and maybe they don’t have all the context that you have to know what to do and sometimes there’s damages as a result of that.
  • 57:40 Ben: Sometimes the technology changes—what used to work doesn’t work anymore. It’s good to be aware of those things but don’t let them keep you from automating things though.
  • 57:53 Sean: I definitely don’t think it should be something that keeps you from automating. It’s a reality but I like to approach things by fixing the actual problem. Let’s prevent the same issue from occurring in the future, then resolve the immediate issue at hand, and move on from it. It’s, “This didn’t go the way we wanted it to. How do we want it to go in the future?”
  • 58:26 I don’t like fixing the immediate problem—that’s a patch on a deeper issue. That’s like saying your automation didn’t work so you avoid using it and do it the slow way. Realize there was a software update and the shortcut you’ve been using has been taken over by the program and it’s going to take you 30 minutes to figure out, but now you know. Now you can update your automation and it’s going to save you those 30 minutes over the next month.
  • 1:00:58 In the chat room, Nathaniel brought up that Gary Vee talks about not automating social media because if a national event happens and your Facebook says something random minutes later, it makes you look stupid. I agree with that; you look like you’re out of touch and it could be really bad.