Today, we chat with Chad Dickerson, the former CEO of Etsy and the current head of Strong Back Open Heart (his own executive coaching practice). In this episode, we learn how he uses OmniFocus to help manage his workload and bring order to his life.
Chad shares personal insights he's gained as a CEO, including the importance of living an authentic life and staying true to oneself. We talk through the belief that personal improvement doesn’t happen by accident, and how the right productivity habits can keep anyone optimally engaged.
Some other people, places, and things mentioned in this episode:
- Chad Dickerson
- Strong Back Open Heart
- Randy Hunt
- Peter Drucker
- Getting Things Done
Andrew J. Mason: You're listening to The Omni Show where we connect with the amazing communities surrounding the Omni Group's award-winning products. My name's Andrew J. Mason, and today we hear how Etsy CEO, Chad Dickerson, uses OmniFocus. Welcome everybody to this episode on The Omni Show. My name's Andrew J. Mason, and today we have Chad Dickerson. Chad runs his own executive coaching practice, Strong Back Open Heart, where he works with CEOs, other C-level execs, and teams to help them grow themselves and their businesses. He's done coaching work with 30 companies to date and is generally working with about 15 clients at any given time. Chad was the CEO of Etsy from July, 2011 to May, 2017. He helped lead the company in its mission and growing it into a global community of creative entrepreneurs and their customers. Chad, we are so, so honored to have you with us today. Thanks for joining us.
Chad Dickerson: I'm excited to be here.
Andrew J. Mason: It's so funny. I talked to Randy, who we had a couple of episodes ago, "Hey, do you have anybody you recommend that loves OmniFocus or Omni Group products," and he's like, "Yeah, I do. Actually, the CEO of Etsy was using OmniFocus." I was like, "I would be interested to talk to him."
Chad Dickerson: Yeah, this is one of my favorite topics. Yeah. I spent a lot of time talking to Randy about it over the years.
Andrew J. Mason: It's funny. I'm reading on the blog more about yourself, just trying to get a feeling for your bio as I'm preparing for this interview. And I do want you to share more about your role as CEO. That's fantastic. But I love that the whole CEO executive coaching was just a small slice of the things that you shared about yourself. What else besides those roles would people want to know about you if they got to know you better?
Chad Dickerson: Yeah, yeah. I think it's pretty easy to kind of know someone by their LinkedIn profile or their resume, but there is so much more to a person. And so outside of that, which anyone could look at, I think one of the things that I really spend a lot of time on is music. I was kind of a happy guitar player for probably, and still am, 20, 25 years. And over the past few years, starting the pandemic or just before the pandemic, I started taking piano lessons and that led me to a bunch of music classes. So I've learned how to play piano and I've got better at guitar and piano. So spent a lot of time on music and recording just for fun. I'm not trying to be famous or anything like that. And then I think the other thing is my background. I grew up in North Carolina. I'm a dyed-in-the-wool Southerner. I lived in the South coast since like 1995, but it's a huge part of my identity. Both sets of my grandparents were tobacco farmers, and almost pretty much all of my relatives still live in North Carolina. So yeah, I still have kind of a deep connection to that world even though I live in New York, which is almost the opposite of my childhood.
Andrew J. Mason: It's funny. I got this sense, and I'll go ahead and call it out here also with the interview with Randy Hunt as well a few episodes back, even though there's kind of a larger than life role, you know, CEO, you both sound really down to earth. I don't know why, but I guess I was expecting sound bites. I was expecting really polished kind of clippable audio bits here that, honestly, it's a little bit disarming because it's like I have a human in front of me here. This is fantastic.
Chad Dickerson: Yeah, I think I try to live life really authentically. I think there's always pressure to do things that maybe aren't true to yourself, and yeah, I've tried to resist that with some success and some failures along the way. But I think it's really important to be who you are and that's actually a pretty common topic in my coaching conversations with CEOs.
Andrew J. Mason: And thank you for that. And I am interested though. I love hearing about the business world. Do you mind giving just a couple of sentences as to what you did in your capacity as CEO of Etsy?
Chad Dickerson: Yeah. So I joined Etsy in 2008 as the CTO. It was a company of about 40 people. I wouldn't say it was unknown, but it was fairly... It was always kind of like, if it was a movie, it would've been like a cult classic that not that many people had heard of. But it was definitely on the rise. The company been around at that point just under three years. I came in and engineering infrastructure and everything needed a lot of work, and the company was growing and had a really great future ahead of it. So I spent the first three years there building out the engineering team. And in summer 2011, I was actually promoted to CEO when the founder stepped aside. So then I ran the company for six years and we took the company public. And at that point, it was a NASDAQ listed public company and a thousand employees. And I think we were doing somewhere around $400 million in revenue. That was the run rate. So it was a real company. And in the end, and I've been very honest publicly about this, I was replaced. I wasn't necessarily the right person to grow a public company. And so, one of the things I learned from that experience, which was a difficult experience, is knowing when to step aside I think is really important. So that is something that comes up a lot in my coaching conversations because no matter what you're doing in life professionally, it always ends. Like, if you're a sports star, it ends. If you're a CEO, it ends. And so I think managing those kinds of transitions becomes the most important thing.
Andrew J. Mason: That's so cool. And I love that you're having this conversation with the awareness that that slice of a person's identity is just one piece of a much larger pie.
Chad Dickerson: Absolutely.
Andrew J. Mason: Let's go ahead and shift over to the Omni Group. Do you have any recollection as to when you first used OmniFocus or talked to anybody at the Omni Group?
Chad Dickerson: I do. Fortunately or maybe unfortunately, I'm kind of digital packrat. So I'm the kind of person who keeps lots and lots of old emails. And so I was curious, like, how did I come across OmniFocus and Omni group, because it's had such a important impact in my life. So I went back. I started blogging in 2001. So that was like 22 years ago. And my current blog goes back to 2005. So basically I read the book, Getting Things Done, in 2006. So almost 17 years now. And I've been reading Merlin Mann's 43Folders blog and tracking Merlin really closely. I think Merlin even today is a fairly cool guy in a lot of ways; also a musician. And so Merlin talked a lot about GTD. And I just started at Yahoo at that time and I think integrating kind of like a new environment. It was the largest company I'd ever worked at. And I was working in a job that was very cross-functional. Like, I was working with teams all over the world. So I think I needed some way of organizing my life even more than usual. So actually, I had forgotten this until I looked back into my archives, I ran a speaker series at Yahoo. And I was so excited about GTD. And Merlin... I actually invited Merlin as a speaker in 2006. So right when I was getting into GTD I kind of invited Merlin. And I looked back at the Omni Group's history and I realized, I didn't realize this until recently, Merlin was one of the designers who was brought in to help design OmniFocus. So yeah, I feel like I tapped into the main sort of mother lode of GTD and OmniFocus because I just happened to be crossing paths with Merlin back in that time. And so I had already read the book. And what I was really looking for was some... The GTD book has such a strong philosophy. I was looking for some kind of software that sort of was very opinionated and baked that philosophy into it. And I started using OmniFocus the year it came out. I think it might have come out in January of 2006. I think I started using it in June and I've used it ever since. It's been a part of my life through jobs and getting married and having a child and all those sort of things.
Andrew J. Mason: That's awesome. And one of the things Randy actually mentioned a few episodes ago was that having this long uninterrupted history of relationship with the software gives you this unbroken timeline, this kind of rich past that you can pull from to make future decisions or look into.
Chad Dickerson: Yeah.
Andrew J. Mason: Has that been the case for you?
Chad Dickerson: In fact, one of the things that I keep as a, I think it's a custom perspective, I've been with the software so long I almost forget what's a built-in perspective and what's the custom ones, but I think this is the custom one and I have a completed perspective. And so occasionally I will shift in an up perspective and look at projects that I got done and all the tasks that were done. And it's helpful. It's really helpful at the end of a year when you want to go back and kind of see how you spent your time in the year. It's funny. I get the prompt. I can't remember what the prompt is, but it asks if you want to archive some of your stuff going back. And I always say no. So my OmniFocus database goes way, way back. I was looking at it recently and it was like a walk down memory lane.
Andrew J. Mason: That's got to be a huge database. Oh my gosh.
Chad Dickerson: Yeah. Yeah. It's significant.
Andrew J. Mason: So talk to me about width of usage. Some people go really deep on one project or one slice of their professional life. For some folks it's all over the place, personal and professional life. Where does it show up for you in your usage of OmniFocus?
Chad Dickerson: Yeah. For me, it's a record of everything. I mean, I'm self-employed, so I don't have to worry about sharing confidential information that are anything like that. So I've kind of full control over my life. I'm also on three nonprofit boards that are really active, so there's a lot of work there. So you mentioned in the intro I coach usually inside about 15 companies, I'm dealing with usually about 15 CEOs. So it's 15 CEOs for my work, executive directors at three nonprofits, the music stuff that I work on, like guitar, piano. So I use it for all of those things. A very common thing that happens is I'll do multiple coaching calls in a day and I'll promise to send something to a client. For example, there's a very famous essay by Peter Drucker called Managing Oneself that I often recommend. And right when I hang up the Zoom call, I go to OmniFocus and add, "Send this email to this person," because it's very easy even for something that simple to like... You know? Your phone rings, the doorbell rings. And so I really look at OmniFocus as it's gone. Yeah. And so, OmniFocus is the brain. It's like the reliable brain. I've used it to manage the building of my coaching website. Way back when I got married in 2007, I used it to help plan my wedding. And one tiny use case that's super important to me is, we all sign up for like trials for software or a streaming service and it's like what week free or 30 days free, I have a workflow where as soon as I click that I put in OmniFocus the day before the trial runs out. I recently signed up for Showtime. And it is cancel showtime if not using by today. And that feels like a gift to myself every time I land on the day. And I feel like that little investment, it's super helpful. I use it for everything. I use it... I have it installed on all my computers, all my mobile devices. And I use it as much as my email [inaudible 00:11:44].
Andrew J. Mason: So cool. And I'm sure you've gotten some variation of this question before in executive coaching, but what do you say to the person who maybe they have a realization that they should be doing something in the area of project or task management, but they've just kind of reached that space where it's, "I'm keeping more things in my head than I can handle and it's starting to leak out the other side of my head, and I need something more that's not working for me now"? And so it can be as specific as OmniFocus or more broad like Tasker, or productivity in general. But what's a great first tip that you would give somebody? The low-hanging fruit. Just what's something that you're like, "If you haven't done anything yet, go ahead and do this"?
Chad Dickerson: Yeah. And by the way, this comes up in my executive coaching conversations because think of the word, "executive," it's all about executing. And executing depends on ordering tasks and thinking about what's most important, what's not. The first thing I recommend to people is to read the David Allen book. I think it feels odd sometimes when I suggest that someone read the book because they feel like they're overwhelmed with tasks and then I tell them, "Well, now you need to read a book." But when I do that, and I do that pretty frequently, I send them the diagram out of the book that shows kind of like the inbox and all the sort of, it's probably got a name, but I think you know the diagram I'm talking about. And if anyone's listening wants to know about it, look for the kind of inbox or something like that. So I tell them to read that. That's my first bit of advice. I also say that it's easy to think about these things as a solution, but I think of them more like a practice than just practices like meditation or exercise. They're things that you do on a regular basis. And sometimes there are periods where you don't do them and maybe you kind of fall off the wagon and then you go back. I encourage them to think about GTD and OmniFocus specifically as something that just like if you're trying to run a marathon. You start running by running 100 feet and then you run 200 feet and then you run a mile. So don't feel overwhelmed. I think that's an important message because the thing that you're trying to get out of is trying to be overwhelmed, so you don't want to be overwhelmed by the tool that's supposed to relieve you from the sense of overwhelm. So those are the main things. I guess one more thing. Even though the book, the David Allen book, I think, encourages you to carve out a day or half a day and get everything into the system, and that's what I would actually recommend if you can do it, but I think a good way to start would be to pick a project and use OmniFocus for that project just to get used to the interface and everything. Because I hate dumping. If you read the book and then dump everything in OmniFocus, it might seem a little bit intimidating. I realize that's like a conflicting bit of advice. I think if you can do everything all at once as described in the GTD book, but for most people that's intimidating. So one project would be a good place to start.
Andrew J. Mason: That's excellent. And what about the rest of your software ecosystem? For some people, OmniFocus is, what I call, one link in a much larger chain where there's mail or Obsidian or plugins that are just kind of daisy chaining it together as part of an overall workflow. Or is it just OmniFocus? But tell me a little bit more about how everything fits together for you in that workflow.
Chad Dickerson: Yeah. Most of what I do is just interacting with OmniFocus from my brain to OmniFocus. And I would say I mostly use the forecast view, that I'm always kind of looking out in the next week or the next month. I tried... This is probably ancient history now, but I used to use the mail.app on Apple and there was a plugin, and I don't remember who made the plugin, it might have been Omni Group, called Clip-o-Tron. And it would allow you, kind of with a right mouse click, to push something into OmniFocus. I used it for a while, but I found that it's better just to cut and paste because I think that... I feel like it needs to be a little bit difficult to get into OmniFocus. Because if it's going to get in OmniFocus, I'm going to do it. So I like a little bit of friction there. The Clip-o-Tron worked fine. It probably worked too well. But I found myself just easily dumping emails in OmniFocus. And there's a lot if we Google about this, but I think using email as a task manager is generally not a good thing because it's a media where anyone can assign you a task at any moment just by sending you an email. I would say one thing that I use that's kind of maybe not directly connected to OmniFocus, but I would say spiritually connected to OmniFocus, and I can't remember how I started using this, but I'd used a piece of software called DEVONthink, which is like a document database and clippings. And you can basically put anything into it and it creates a searchable database of, mostly PDFs for me, but we can drop all kinds of things in there. We can talk about this for hours, but sometimes people say, "Well, why don't you just use Spotlight on the Mac?" I feel like DEVONthink is this nice contained world. It's walking into a library. And Spotlight is just like the whole world, not the library. DEVONthink is really helpful because I find that I have a task for January 31st every year to look to make sure I have all the W2s and everything for kind of like the US tax filing that happens in April. Because I organize things really well and DEVONthink... I find myself looking at OmniFocus tasks that are related to like information gathering. And I look in DEVONthink to make sure they have all the information gathered. But I've been using DEVONthink probably as long as OmniFocus. And I have a ScanSnap scanner. And so there's less and less paper in our lives, but I still get paper. And I have this workflow of scanning the paper, putting it in DEVONthink. And then later on some task will come up in OmniFocus that requires me to pull documents out of DEVONthink. I was really proud. About a year ago, I was applying for a mortgage, and I managed that in OmniFocus. But I had done a really good job of scanning and tracking documents, so I was able to pull together all of the crazy documents that you need for a mortgage in about 20 or 30 minutes. So I felt very proud of that.
Andrew J. Mason: Full disclosure. My own OmniFocus database, actually you were speaking to this metaphor of the library, having stuff just in the library versus the entire world, and then the mental hurdle there, I do the same thing. I have actually all my reference in OmniFocus and I just have a high level folder called reference and then projects, and then everything just kind gets dumped in there. And the database gets big, but it's a really cool way to do things.
Chad Dickerson: So you can search external documents in OmniFocus? That's something I didn't know.
Andrew J. Mason: Actually, no. Not external documents. So large HD video files don't show up in there, but I am able to, if I need to screenshot of a receipt or something like that, just grab the screenshot and drag it into the notes icon and pop it in the reference folder. So I can type in Taxes 2021. And then everything that has to do with taxes is in there.
Chad Dickerson: Oh yeah. I think I have actually done that, but maybe I should do that a little bit more. [inaudible 00:19:05].
Andrew J. Mason: No, I've heard amazing things about DEVONthink actually. I've honestly never gotten to try it myself. But let's switch gears. I want to talk about... You mentioned the completed perspective, leaning into forecast. Are there any other perspectives, custom or otherwise, that you really just kind of hang onto for your daily work?
Chad Dickerson: No, I think those two are the main ones. I find the forecast interface is so intuitive of like the calendar layout. Super helpful. And then complete it. As I mentioned, I use that to look back at what I've done. Yeah. One of the things I love about OmniFocus is that you don't really need anything else besides what's built in. And it's like infinitely configurable when you can get by immediately without configuring anything. And it's one of those pieces of software. And this is super rare. I mean, I've been using it for... This'll be like my 17th year. It gets better. Like, a lot of software gets worse. And I find myself being cranky like, "Oh, they changed this menu or whatever." And the release process and how everything's been brought along is really, really user friendly and I really, really appreciate that.
Andrew J. Mason: It's not really my space to say thank you, but thank you on behalf of the Omni Group. I so appreciate you saying that. That's awesome.
Chad Dickerson: Yeah. Amazing.
Andrew J. Mason: Tell me a little bit more about automation. Do you have anything in the space of plugins or coding that you leverage to get work done or even as simple as a repeating task or routine? What shows up for you there?
Chad Dickerson: Yeah. I mean, I have quite a few repeating tasks. Like, I have a weekly task, which is sort mail because there's a desk in my house, I get mail, and it kind of piles up sometimes. And that recurring task I remember a good week to go through the mail if I haven't gone through it very much. I mentioned the automation of preventing myself for renewing subscriptions that are like trial subscriptions and I don't want to renew. But I think a lot of people who are really busy... Like, to some degree, I'm fundamentally lazy. I don't want to think about things too much. So with OmniFocus, I'm always trying to predict my future state of mind. I'm going to forget that I signed up for this trial. I'm going to forget to sort the mail. I'm going to forget a family member's birthday. So I put birthdays in there. But it's in the spirit of GTD. It's very much focused on next action. So it's not, "My wife's birthday's coming up." It is, "Buy card for wife's birthday." It's very action oriented. In that sense, I automate my future brain, my future forgetful brain. And then I'm always trying to anticipate what I might forget to do in the future. And so just today I did something where in New York there's so many great museums and you can be a member of the museum and you get some benefits. And so I join The Met every year and I put a recurring task. Not that they don't remind me, but I put a recurring task in there to make sure that I rejoin The Met every year. So all that stuff, I feel like I have an assistant telling me to do things that I might've forgotten, which is super helpful.
Andrew J. Mason: Chad, I don't think that somebody shows up in whatever station of life that you found yourself in without being at least at some level passionate about productivity or fully releasing or realizing your potential. It just doesn't happen by accident. And back to my earlier comment about having a real person here, just not sound bites, do you mind speaking a little bit to that, just a few words about either being passionate about productivity or being present? Just whatever you've got on your mind there.
Chad Dickerson: It's very counterintuitive. So if anyone's listening and thinking about going down the GTD path or OmniFocus path, one reason I'm really passionate about it is being somewhat mechanistic about keeping track of everything and executing everything actually gives me a lot more free time, because I'm not kind of sitting around thinking like, "What am I supposed to be doing? What do I have to do today?" And so it gives me a lot of free time. And I think it sounds probably to some people like drudgery, but it actually... Organizing and staying organized is what gives me the free time to do... What I was doing earlier this morning, I was... I have a recording setup in my basement and I have a friend, and we do this for fun, we try to write songs and record songs. And if anyone's ever tried to do any kind of production, I mean, you do audio production, to get a good 30 seconds of something can take hours of days or weeks. And that works really fun to me and really important. But if I wasn't taking care of my business, generally being productive and paying my taxes and staying in communication as needed with the boards I'm on and that kind of thing, I wouldn't have time to sit in my basement for four hours and listen to that same 30 seconds and do a new take and that sort of thing. So I think one reason I'm passionate about productivity is so that I can have those free moments, free hours that are required to do more creative work. So I think about... It's been a while since I read David Allen's book, the Getting Things Done book, but he talks about this idea of like mind like water. And the way I always interpreted that is when everything you need to do is kind of contained in a system, you don't have, and I think he uses this language too, you don't have these open loops in your head that are distracting you. Like, did I do this? Is everything in place? And that allows you to do creative work, like write songs, record music, or just sit on the couch with your kid, I have an 11-year-old, and watch TV without a sense of worry. So that's why I feel like being productive doesn't sort of condemn you to this existence of just constantly cranking. It actually is the thing that allows you to not constantly [inaudible 00:25:03]. So that's how I look at it.
Andrew J. Mason: Anything along the way in your kind of productivity journey that you wouldn't categorize as a mistake or a misstep, or just something if somebody else were to take the same path as you, you'd kind of look back over your shoulder and say, "You know what? You can just skip that piece, but keep going"?
Chad Dickerson: Yeah. I mean, I think the first thing would be being intimidated by the idea of getting organized, and so therefore not getting started. So yeah, I think the biggest mistake you can make is not to get started. I honestly don't even know how people who don't have a system get along in their lives. Like, there's no way I could do it. So yeah, I think if you're thinking about being productive, being more productive, being more focused, I think not getting started is a big mistake. And again, I would encourage people to read the David Allen Getting Things Done Book because it's super helpful even if you only adopt parts of it. Like the concept of a next action. Like, always thinking in terms of action. The other maybe related to not getting started as a pitfall, I think, is trying to get started too fast. And so your workspace is full of papers and everything is a mess. And you tell yourself, "I'm going to get started. I'm going to be productive by the end of the week, and it's already Wednesday. And if I don't, I'm a terrible person. And I'm condemned my whole life to always be kind of a mess." So I think giving yourself some time to kind of get ramped up. And again, I mean, I'm repeating myself about the David Allen book, but I think when you read Getting Things Done, there's kind of like an initial process you can go through, which is super helpful, kind of sorting through your inbox and organizing things. And then something that I haven't honestly been that disciplined about, but I think I do it often enough, just like the idea of a weekly review, kind of a meeting with yourself. And so again, just getting started I think is really important because if you get the system down, there are all kinds of places where you can catch yourself. If you're getting wobbly, you can kind of right the ship. But again, it's a very good life. I feel like the best times in my life were when I was getting a lot done, everything I had was organized. And yeah. Mind like water. You can focus on living your life and being present with people and doing creative work when all of that stuff is taken care of.
Andrew J. Mason: Chad, this has been a phenomenal conversation. Thank you. Thank you so much for your time. If folks are interested in staying in your orbit and connecting with you and finding out more about what you're up to, how can they do that?
Chad Dickerson: Sure. I mentioned earlier I have a blog that's been running since 2005. And so if you go to blog.chaddickerson.com, there's an about me page. There's an email on that page which says hello at chaddickerson.com. And that email comes straight to me. So that's a good way to reach out. And then my various social media links are on there as well. But I enjoy getting emails from people I don't know who are doing interesting work, and am always excited to see one of those emails pop in my inbox.
Andrew J. Mason: That's perfect. Chad, thank you so much for joining us today.
Chad Dickerson: Thanks, Andrew. I really enjoyed it.
Andrew J. Mason: Hey, and thank all of you for listening today too. You can drop us a line on Twitter, @theomnishow. You can also find out everything that's happening with the Omni Group at omnigroup.com/blog.