THE OMNI SHOW

Michael Keithley: I kind of think about it a little bit differently. I don't think about it as trying to be productive. I think about it as a life skill that I have to have to be successful in everything. It's kind of my future self. I'm pre-thinking all that stuff, so that I don't have to think about it in the moment. I don't have to stress about it. I don't have to worry about it when I'm trying to go to sleep or any of those kinds of things.

Andrew J. Mason: You're listening to The Omni Show, where we connect with the amazing community surrounding The Omni Group's award-winning products. My name's Andrew J. Mason, and today we learn how Michael Keithley uses OmniFocus. Well, welcome, everybody, to this episode of The Omni Show. My name's Andrew J. Mason, and today we're excited to learn how Michael Keithley uses OmniFocus. Michael is a distinguished leader and manager with an exceptional track record of forming and guiding technology teams to solve complex problems and achieve business outcomes on a global scale. Michael successfully walks that intersection between CTO and CIO roles and sits on multiple public, private and advisory boards. Michael, we're honored to have you with us. Thank you for joining us.

Michael Keithley: Thank you very much, Andrew. I'm really honored to be on the show. Thanks.

Andrew J. Mason: Well, I said a mouthful there, and I know that that's kind of a really high-level interpretation of your roles. What do you answer somebody who says, "Michael, what do you do for a living?" And you just happen to be in an elevator with them?

Michael Keithley: Well, the simple version is I've been responsible for technology at two different talent agencies, two of the quote, unquote, "big three" talent agencies in the entertainment business over the last three decades. And my specialty, I think really is being at the intersection of Hollywood and Silicon Valley, and I spent a lot of time up in Silicon Valley understanding what's coming and trying to peer around the corner and then translating that into how that will affect our clients or our business models. Think back to Napster back in the day, what that did to the music business, or even think about Netflix and streaming and now AI. Technology has always been kind of disruptive and it's my job to figure that out and help guide our clients and business through that.

Andrew J. Mason: I love that you mentioned Napster, first of all, because it dates me to the inception of publicly available file sharing, but also just because it's a great analogy for what it kind of feels like out there sometimes, it's the Wild West out there. Talk to me more about this intersection between CIO and CTO roles. What are you seeing in the Wild West of today?

Michael Keithley: Wow, AI is exciting and terrifying at the same time for the entertainment industry. Most disruptive technologies have affected more of the blue collar world, less of the white collar information workers, and rarely, if ever, did it affect the creative industry, but I think that's really flipped when it comes to AI and we're starting to see incredible positive use cases, but also ones that are really going to change things, that will either eliminate jobs or certainly change them. And so, there's a lot of angst around it, but there's a lot of opportunity also.

Andrew J. Mason: A lot of the talk that I hear for people is the closed hand around how AI is going to take creative work or take these things away from us, but what are some of the more forward-thinking, exciting things that you hear about AI possibly doing?

Michael Keithley: Well, I think it's, the exciting stuff is all around productivity. Being able to do stuff that required specialist and dedicated systems in the past now moves down to pretty much anybody can do that. And the pace of change, how quickly everything is moving in the AI world is astounding. It's unlike anything else we've seen. If you go back and you look at some of the big revolutions that have happened in technology, you think about the iPhone and the mobile computer and then cloud. Those are big and they're transformative across pretty much everything, in every industry. AI is that on steroids. And so, there are many, many, many opportunities to really do stuff faster, better, cheaper, but it is going to change things and it's going to change jobs, and there's always a lot of friction. And Hollywood has a very unionized way that they do things. And so, that friction, we saw that in the strikes recently and I think we're seeing it currently and we'll continue to see that.

Andrew J. Mason: It reminds me of David Allen's quote about, "There is nothing new except how frequently it is." Something along those lines. It's, "There's nothing new..." He's basically saying the only thing new is about how quickly everything becomes new again. And there's compressions of time where you went from nothing to ChatGPT, and then from GPT to something like Claude to Llama. Those compressions are getting shorter and shorter with each iteration. The curve is kind of going a little ... It feels like there's a freight train on the way and you're getting slammed by it. What are your thoughts there?

Michael Keithley: It is. And when I try to do presentations or educate folks on this, that's the one message I really want to get through is the exponential growth, and it's kind of like a compound interest or the old saying, "If you double a penny for 30 days, it's worth over $5 million." That's a powerful image for people to think about, and that's what I want people to think about when they're thinking about AI. It is literally going to transform everything.

Andrew J. Mason: Yeah. Let's pause there. And talk to me about how you first came across The Omni Group, or specifically OmniFocus. If you have any memory or recollection about what the world was like then or what you were thinking about or going through at that time. We'd love to hear that and then we'll bring it back around, back to present day.

Michael Keithley: Yeah. I do really remember pretty vividly. And I think I need to set a little context before I tell you about my first interactions with The Omni Group. I've always been a call it time management junkie or task management or productivity, dating back to the Franklin Planner back in the '80s, the analog thing, that really got my kind of juices going. And then when Apple released the Macintosh in 1984, I literally got one of the very first ones and there was no software for that. And I remember my favorite software might've been the very first one I got was something called ThinkTank, which was an outliner, that's all it did. And it really helped me organize and think about and do brainstorming and what we might call mind mapping today, things like that. And then shortly after that, the reviews came out about OmniOutliner and how great that was. So, OmniOutliner was my first interaction with The Omni Group, and that was early, I'm going to say 2005, 2006, something like that. And I had transitioned my outlining from this program called ThinkTank to OmniOutliner. And then, somewhere along the way after that, I tried OmniFocus, the first version, and I didn't stick with it. I don't remember exactly why, but the outliner part of it felt good to me, but it wasn't really there and I still stuck with OmniOutliner for quite a while. And then, a little while later, probably, I'm going to guess, 2002 or '03 or something like that, there was the seminal book by David Allen, Getting Things Done: The Art of Stress-Free Productivity. And that really was making its rounds in Silicon Valley as kind of a thing. And Merlin Mann, 43 Folders, and Inbox Zero, and it just was a whole moment in time and that really got me excited. I was like, "Wow, I finally have found something." And then, I dabbled with a bunch of different things. I remember there was a period in time I was on Evernote and many different task management tools and some mind mapping software, and nothing really stuck. And I think the reason for that is when I look back on it, I view it's kind of like diets. You read about the new diet, use it for a while, it works for a while, but then you kind of fall off the wagon and it doesn't work anymore. And so many of those other tools that I tried were kind of one-trick ponies. And it wasn't until I got to OmniFocus, I believe it was three, maybe two, at the time, where it really aligned with GTD and the philosophies that I found worked, and I've just never looked back. The other Omni product I use is OmniGraffle. Switched from Visio way back in the day. And still use it to this day for presentations and various graphic type stuff.

Andrew J. Mason: I don't think I'm hallucinating when I would say that probably somebody involved in as many things that you're involved in has a lot of spinning plates, maybe a lot of different roles or however you slice that, but what advice do you have for that person that is taking on more responsibility? Maybe they're just starting to have another role show up in their life or additional responsibility for things that they need to manage or oversee. And it can be OmniFocus specific, it can be productivity, it can be paper and pen. I mean, what's your go-to first tip or trick for somebody that is really, "I'm starting to realize I've got more things in my head than I can handle and I got to figure out what to do next"?

Michael Keithley: Yeah, absolutely. Well, the first thing, as I said, get the book and read that or listen to an Audible or whatever, because I think the GTD system is the only one that's realistic in how we live, especially in today's world and all the things that are coming at us and everything else. So, I would get that and try to understand that because to me, it's the only thing that works over the long run. Then specifically, I would focus on your ecosystem. If you're an Apple person, you want something that works with your phone and your iPad and your watch and your Mac and all those things. If you're Android, focus on that and try to have a system that works with that. And then, there's really two I consider key cornerstone parts of the system that you have to optimize for, capture and review. And you need to have in whatever your system is ... And honestly, it could be paper, okay? It doesn't have to be digital. You have to be able to capture anywhere. I don't care where you are. You could be at the gym, on the road, at work, home, out with somebody else, whatever it is, because stuff comes to you, incoming things come to you that you want to capture, and it has to be simple. And one of my mantras, and this is true in my professional life and my personal life too, is reducing friction and making things simple. And really, Elon Musk has some really inspirational stuff around that too, but reduce friction. So, in capturing, it has to be simple. I mean, every button click or anything you have to do introduces friction. And so, it has to be as simple as possible. And then, the second thing is review and reviewing your system. And whether it's a weekly review like David Allen says, or some other cadence, is less important, but you got to make that a habit. And I'm a big fan of a guy named Charles Duhigg who has The Power of Habit. And in that he says, "You got to create a habit loop." And I remember prior to what I'm about to tell you, it wasn't a habit, okay? And the habit loop is cue, routine, and reward. And for me, I got my wife into GTD and she uses OmniFocus also. We have our weekly review and we both know that when we do that, we get to pick out a really nice bottle of wine and we share a really nice bottle of wine. So, that's the reward that does the cue and the routine, reward. And so, once we started doing that, we sit out in the backyard typically and we have just this killer bottle of wine and we sit down, we do a weekly review, and that's been the key to me over the many years. And so, whatever your version of a reward is and how you can make that a habit, I think is super important.

Andrew J. Mason: That's really fantastic advice. And it's important that we add something, take away something that gets us to do the actions that maybe we don't even want to do, but gives us the results we know we want. Like adding the bottle of wine, I think, to the weekly review makes it that much sweeter. So, that's very cool. Talk to me about the surrounding context of OmniFocus. Probably, a lot of data coming in from a lot of different sources, either actions coming out of it or information from OmniFocus coming out into other spaces. Just paint a little bit more of a picture of the world within which OmniFocus sits for you.

Michael Keithley: Once again, I can't emphasize enough how important simplicity is, and less is more, so don't over-complicate things. And you got to recognize where your ... David Allen calls it stuff, right? Where your stuff comes, where your incoming stuff is. And for me, and I imagine many knowledge workers today, an awful lot of that, for better for worse, is email. And then the web, web pages, you're surfing the web, there's some action or task associated with it. Increasingly, I think social media is another kind of inbox or place that we get that. And then, paper, I still get get snail mail and there are things that I have to do. So, all of that, I need to be able to easily, as simple as possible, capture that and get that in my system. And then, I figure out a different time to be able to process that and think about what to do with it and how to organize it. But it's super important. I have two habits that I think might be somewhat controversial. I don't separate my personal stuff from my work stuff. It's all stuff in my system. Okay? Now, I do have a perspective in OmniFocus, one called work, one called personal, or home and errands and other things, but as far as it's all in my one system, right? And the second one is Inbox Zero, I mentioned Merlin Mann. And so, I process all of my incoming cues, whatever they are, to zero. And it drives me crazy if I have outstanding stuff. Many folks that I've talked to over the years aspire to that and they finally just throw up their hands. And especially email, you have to be really Darwinian. I also use RSS feeds to get blog posts and things like that, and I have to be very Darwinian with that to get rid of the stuff that isn't adding value and unsubscribing to email lists. And it's work. But I find it's the only way that I can have what David says is stress-free productivity. Right? And once I get that all in my system, I don't think about it, I let it go, and I can be present in the moment with my family or whatever I'm doing. And the only way I can do that is to know that I have everything in OmniFocus and I'm not going to drop the ball anywhere.

Andrew J. Mason: You hit a really good point about making things as structured as they need to be, but no more. The thin slicing of could and should. Just because you could have all of these tags and system things doesn't mean you should necessarily. And finding that sweet spot, Brian McCabe, who was just on last episode, talked about it can become an effort in and of itself just to maintain your system, and then, what good is it because you're spending all your time working on it versus in it? So, I'd love to know what is that drive, though, that says we do at least need some guardrails so we can be as effective as we possibly can? Is there a passion there for being productive? Is there just this desire to not leave any wasted potential on the table? What is that for you and why is that showing up in your life the way it is?

Michael Keithley: My passion dates back to high school when I wasn't a great student and as I was going into college realizing that, "Boy, if I don't turn something around to be able to figure out how to do more stuff effectively, this isn't going to end well." And I remember I attended some kind of class that was some version of how to study or succeed in college, and that's what really drilled into me the motivation for this. But I kind of think about it a little bit differently. I don't think about it as trying to be productive. I think about it as a life skill that I have to have to be successful in everything and not drop balls. But it's really being ... And I don't know who first said this, but it's kind of my future self. I'm pre-thinking all that stuff, so that I don't have to think about it in the moment. I don't have to stress about it. I don't have to worry about it when I'm trying to go to sleep or any of those kinds of things. I've already done that and I feel safe and confident that it's in my system and I'll be able to deal with whatever I need to deal with at the appropriate time. And we can't do everything. Life is going to give us ... You have to make choices, right? There's way too much incoming stuff coming at us. So, you have to prioritize, you have to make choices. And to me, this combination of this whole system is what makes that easy for me to do.

Andrew J. Mason: I'm catching in your voice in a lot of your responses, and hopefully the people listening to this are too, the kindness that you have from now Michael to future Michael, that reminds me of that David Allen quote, "Handling things when they show up versus when they blow up." And I feel like there's a key there about, "I'm going to do it now when I don't have to, so that I'll never have to." Just the thought process there is a very, very steadying one. Are there any things that come to mind about actions you've taken in your system that were for the good or betterment of your system, but as you engaged in them said, "You know what? This actually isn't for me. I thought it was going to bear fruit. I thought it was going to be the right thing for me or for my system. And now that I've done it, not that it's wasted effort, but there wasn't anything there for me and so much so that I would probably say it's instructional for anybody who is looking at me as an example to say, 'You know what? You don't have to do that thing or go about it in that way because I think it'll save you some effort.'"?

Michael Keithley: Well, I'm going to be a broken record. Less is more. Simplify your system. Don't over-complicate things. I can't tell you how many times in OmniFocus and other systems, I just overdid it. And tags is a great thing. I am Darwinian on my tags, right? Sometimes I'll start to add more tags or perspectives, and if I'm not using it, I just delete it. And I really try to simplify as much as I can. And then once again, focus on where your incoming stuff is so that you can capture that really simply. And once again, email is probably the majority, or the web, and those are easy things that I can get into my system, know that it's there and not have to figure everything out. I used to try to right at the point in time I was capturing, saying, "Is this a next action? What project does it go to? What focus?" Or, any of those things. And I don't do that anymore. Right? And so, really try to make that as simple as you possibly can and don't overcomplicate. And it's easy and I've done it over and over again, and I relearn that lesson, just the absolute minimum I can get by with is the best system.

Andrew J. Mason: I love it. And one last free-for-all question, but just to have the floor be yours. Any final words of wisdom, your billboard to the world, you can wave a magic wand regarding productivity. What would you have everybody know? If you could just immediately, boom, you all get this and you know what it is that I'm thinking, I'd love for you all to get this one thing. What would that be for you?

Michael Keithley: If I could wave a magic wand, I would somehow get everybody to understand the power of the GTD philosophy. There's a saying that, "To really learn something, you got to teach it." And over the years at work, I've always had classes on GTD and OmniFocus and my philosophy, and I don't know what percentage, I'd say maybe a third of the people really get it and it's transformative. And I literally get decades later, people thanking me for forcing them to kind of get religion on this. And it's one of those things you have to experience it, and once you get that stress-free productivity, you absolutely love it.

Andrew J. Mason: That's perfect. Michael, if folks are interested and connecting with you and being in your orbit and seeing what you're up to, how can they do that?

Michael Keithley: Yeah, I've tried to delete a lot of my social media, but I'm still on X, so it's @mkeithley. And then, LinkedIn is the other one that I really focus on, so it's LinkedIn just /MichaelKeithley. And I check both of those fairly regularly and I'd love to hear from people.

Andrew J. Mason: I love it. This has been really fun, Michael. Thank you so much for hanging out with us. We're so honored that you spent time with us. Very, very grateful for that. Thank you.

Michael Keithley: All right. Thank you, Andrew.

Andrew J. Mason: Hey, and thank all of you for listening today too. You can find us on Mastodon at The Omni Show, at omnigroup.com. You can also find out everything that's happening with The Omni Group at omnigroup.com/blog.