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Peter Boumgarden: If I'm going back and forth between a couple meetings and then I've got a break for a T-ball practice and then I got to finish a few things and then take a flight out, it could be very easy for me to say, "What did I do today?" But if I have a script that pulls at the very tail end, and if I'm active in OmniFocus checking things off that shows me at the very tail end of the day, actually I did finish seven things. Then it gives me a sense of saying I actually did do things that I didn't realize or I maybe even forgot about, that allows you to go into the next day or even that evening not being like, "What have I done in this day? And I need to kind of get caught up tomorrow." Which can create a certain kind of spiral. So I think automating the reflective component, at least in terms of pulling completed tasks and then forcing myself to say, "All right, what are some takeaways from that?"

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 hear how Peter Boumgarden uses OmniFocus. Welcome everybody to this episode of The Omni Show. My name's Andrew J. Mason and today we have Koch Professor of Practice for Family Enterprise in Washington University, Peter Boumgarden, and we're learning how he has implemented OmniFocus. Peter, thank you again for joining us. We're thrilled to be able to have you chatting with us today for a little bit. Thanks for hanging out.

Peter Boumgarden: Yeah. Thanks, Andrew. Looking forward to it.

Andrew J. Mason: Well, talk to us a little bit about your role as professor of Family Practice in Washington University. What does that look like day-to-day? What are the kinds of things that you get to do with students and just maybe flesh a little bit of that out for us?

Peter Boumgarden: Yeah, happy to. So my world in academics has kind of evolved from the time where I was an early stage assistant professor to now. So I spent my early years at a small liberal arts college, Hope College in Holland, Michigan and I was teaching and research and doing all that sort of stuff. And then when I got tenure at Hope, I had a sabbatical year and was really thinking about the blend of things that I wanted to do. And so I came back to where I did my PhD, WashU in St. Louis into a role here. And it was intentionally a role that allowed me to do a decent bit of work in the practice, hence the language of practice, the practice of business and organizations. And so took that role in 2018 and then a couple years later took over the directorship of the Koch Center. And so the Koch Center is a center that focuses on privately held companies, so imagine that's everything from a family business, mom and pop shop, all the way up to Walmart owned by the Walton family through a series of trust, though it's publicly traded. So we look at things like that from a research standpoint. We do quite a bit engagement with students on those issues. So they might be current family business owners or owners in businesses. They might want to buy a company. This is the language of entrepreneurship through acquisition, going out and buying something. So that ends up being a good focus of our work. And then we have some stuff as well on everything from family foundations and philanthropy to family office and investment. So think of that as being kind of the core work that I do. And then I also lead at the university level WashU's approach to undergraduate education at the university writ large. So that's a co-led with a colleague of mine and what we do is we're kind of rethinking the strategy of higher ed, especially in light of all the disruptions of AI and other such things. And so that's the role that I had in the Provost Office is the assistant vice provost of Undergraduate Education.

Andrew J. Mason: Man, okay. Heck of an overview. Thank you for that. And also really exciting to hear the multifaceted-ness of your role to be able to be focused internally with the students as far as externally looking a couple, I don't even know if it's a couple of years, but a year, a year or two out into the future saying, "Okay, what does this look like as we continue to rethink and retool this entire landscape and how all of that goes?" How have you found the challenges that all of that brings to you? Not only just the future looking stuff, but also the engagement with the students at that level. I picture very much to be akin to landing a plane or surfing a wave. There's so much stuff happening, but it's also, I'm sure, very fulfilling work as well.

Peter Boumgarden: Yeah. I think I'll answer from two angles. One is really focused on the student side and then another of it is actually a little bit more germane to today's discussion around task management. But when it comes to the student side, the thing that I found is somewhat interesting is my role will involve very different types of students. I teach, for example, one class called Markets and Morality, which is co-taught with the chair of the English department here and there it's 18 year olds wrestling with big questions and reading complicated texts to explore some of the moral challenges inside the market. And at the same point, I might fly to Shanghai a couple weeks later and work with our executive MBA and be dealing with questions about how they're managing as a 45-year-old senior leader in an organization, the transformation in front of them. So again, it's this interested, complicated task that I'll be working with everyone from an 18-year-old to an MBA that's 25 thinking very vocationally about their work and then all the way up to senior executives and the work that they do there. And so the particular challenges that that leads to around technology and AI, for example, which is a big focus of our work for the undergraduate side is very different. If you're 18 and you're thinking about being a computer science major, you're looking at the 20% dip in computer science majors from last year to this year and you're wondering, should I code in the same way? In contrast, if you're pretty senior in your organization, oftentimes you're thinking about how does the nature of work going to shift moving forward? What do I outsource versus what do I augment? How do I prevent myself from losing an independent voice as everyone starts to sound more and more similar with AI and language? So that ends up being like a really fun engagement because some of those engagements are very existential, "What do I do with my life?" And others were much more tactical and pragmatic. But to the point about task management, one of the things that's increasingly challenging, even more so than when I started using OmniFocus some 12, 14 years ago, is the nature of those tasks is pretty different. So even today, I was prepping, for example, for a talk on private equity and healthcare in New York tomorrow. So I had to do some deeper dive research. I then had a meeting with a couple senior university leaders about a big part of our undergraduate work. I then had to kind of juggle some things personally when it comes to all things prepping for things coming in the next couple of weeks and then I had to do a little bit of grading. So like four different things that have different types of tasks and nature of the work. So without the right kind of system in place, I ended up being pretty lost and therefore needing it even more when I started at the very beginning.

Andrew J. Mason: Man, fantastic. I mean, a lot of challenges and a lot of exciting opportunities there. I wish we had the time to really dive into some more of that, but right now what I just kind of latched onto that you just shared was the context switching, how that's the name of the game in order to be at the level of productivity that you find yourself. Let's do a little bit of a parallel track here. Do you have any recollection as to when you first came across Omni Group or OmniFocus more specifically? Was there just like a moment in time, "Oh yeah, that's the day that I remember seeing them," or just kind of there was this growing awareness over time all of a sudden it just shows up in my radar and suddenly becomes the thing that I use?

Peter Boumgarden: Yeah. I was looking back at this in preparation for this interview and I was looking back at my first email from Omni Group and it was in 2011. So now 15 years later-

Andrew J. Mason: Oh my gosh.

Peter Boumgarden: Summer of 2011. And I was thinking back to where I was. I was a first year assistant professor, I was probably 27 years old. I had just moved from a pretty focused type of work. I was working on a single dissertation and a couple studies into then at that point managing a couple different research streams. I was doing some bit of work with, or starting to do some work with companies directly, so kind of corporate engagements as well and then obviously juggling six courses or six sessions of a course in a liberal arts environment. And so my guess is looking back in time, it was probably a point in life where I'm like, I have too many balls in the air and I'm having a hard time keeping in my active memory the different things that I need to do and why. And so that was when I first purchased the software. I would say for the first several years though, I was probably off and on in usage. I didn't have an overly clear use case about how it fits into other tools that I used and therefore what I would do is I would kind of dump everything into it, use it for a couple of weeks and then kind of fade away for a while and then feel overwhelmed and hop back into it again, restructure and do that. So I would say it's been more of the last eight to 10 years in particular that figuring out the work stream, the workflow has been really critical and it's become all the more important because though it was complex when I was a 27-year-old assistant professor, it's become more complex in different types of roles and engagements than I had back then.

Andrew J. Mason: I think of somebody that is coming into what we would consider to be a career age and they're starting to get the idea that, "Ohm no, the swath of my commitments is much more varied invest than what I had originally given any attention to." What advice do you have for somebody that knows they need to be doing more to keep track of their ideas, but maybe through your unique perspective, because you do have engagement with all different age range, all different types of career paths, just kind of your unique perspective or take on a first piece of advice for somebody that's like, "Okay, I do feel overwhelmed, I see more to do than I know how to do and I need to do something"?

Peter Boumgarden: I think one version of this is to think in terms of the hats that you have professionally and personally. And so for me within OmniFocus, those hats end up being kind of broader folders, folder structures for the work that I do. So for me, there's a hat that's tied towards teaching. There's a hat that's tied towards leadership, institutional leadership. There's a hat that's tied towards writing. A hat that's tied towards advising, working with companies. And then a hat that's tied towards personal life. So kind of five hats. And then I think it's then saying within those hats, what are the projects that I have that factor into it? So it could be a particular class, particular client, it could be a T-ball coaching, which I have later on today with my five-year-old son, could be tied towards an upcoming family vacation. So there could be a project that's tied towards a relationship. And then I think there's a piece of saying, "All right, there's all this stuff swirling in your head." This is where I'm going to kind of channel my inner David Allen a little bit. Just get it into that sense and first off, just say, "What is in the system now?" Get it out of the head and just get it all on paper. So that for me was the first stage and I think that would be the first piece of advice I would give to someone is think of your life in terms of roles. For some of you, I think an increasing number of people in today's vocational world might be playing a little bit more of a portfolio career. So not just a single role that you have, but a couple different roles that you have over time, whether it's within a single job or whether it's side hustles or something and then think in terms of the landscape of projects that sit underneath that. So that to me would be the first piece. Then I think there would be a second piece, which I think I really struggled with early on, which is a little bit more of the landscape of what's accomplishable within a set period of time. And so if you think of the first philosophical influence on my thinking was kind of the GTD, David Allen type of thinking. I would say the next layer of thinking philosophically on me has been thinking and learning from the folks in the world of agile processes. So thinking of my life in terms of two week sprints. And so when I go through a review process, I'm oftentimes saying, "All right, what do the next two weeks look like?" There's going to be bundles of open time on there, but some weeks have very few bundles. If I went back two weeks at the end of the semester, it was kind of slotted with meetings. Now we're moving to the summer, so there's more larger swaths of time that are available. And what I do is I kind of plan in terms of three cycles of planning. Cycle one is saying what's possible in the next two weeks, and I'm able to kind of flag all the items that fit into that category. Then my next layer of planning is what's possible today. So today I would wake up and say, "I've got two hours in the morning and then a couple meetings and then maybe an hour at the tail end of the day. I've got three hours of total time." All right, in that day, what's a reasonable amount of things to get accomplished there? And then the last layer that I would say has been influenced by Oliver Burkeman in Four Thousand Weeks as a writer when he talks about the idea of limiting the total number of items in queue and he has an idea of kind of flagging the next three. So what are the next three things that I look at without even going back to the list of the others? And so when I'm really functioning well, I would say I'm basically saying, first off, what can I do over two weeks reasonably? What can I do today? And then what are the next three items on my list? And that becomes kind of this cycle back to the task management side that kind of holds me accountable. But I guess the last point, just to kind of close off the thing about the advice to young people is that's a system that's worked for me. It's based upon the nature of my work and the nature of my obligations. You do not have to at all take my own model, but you should start to think of your life and find ways to kind of not narrowly optimize, but to balance and to think strategically about the allocation, time and tasks. And it's beneficial to have a tool that allows you to do that versus just feeling like you have to do it on a piece of paper or another system.

Andrew J. Mason: Well said. Well said. And just to call out a couple of things, just the articulation of the horizontal versus vertical challenges. Sometimes for me, the challenges early on have been how big of a bucket and how granular the task and deciding how to structure that in a way that makes sense for me across horizontal. And then vertically, how deep do you go in terms of next action planning? And getting to hear how you structure that I hope will be very instructive for a lot of folks. I hope that that's something that they can take to heart if they haven't really started thinking in those directions. Those are transformative ideas, I believe, if they haven't really taken those steps yet. So thank you for that, first of all. And then the second is, do you mind maybe placing OmniFocus inside of an overall software ecosystem in the sense that is there information that comes into it? Is there information exported out of it or is there a corollary software that kind of sits alongside of it? Maybe just kind of describe that landscape a little bit for us.

Peter Boumgarden: Yeah. I'd say this is the part that's been hardest for me in terms of building is how these tools all relate to one another, but I'll give you at least a current state of the other tools that are in play. So one version ... And I'm in the Mac ecosystem. So one version of the tool that I have would be Drafts as just a core capture of texts coming from different sides of the computer, from a phone, from whatever. And so on version is to say when something comes into my mind, I almost always put that immediately into Drafts, knowing that Drafts could go into something that is a backend storage of that information. So it could be like, I'm going to put that draft of a note that I have on a run, I'm going to add a couple other pieces there, and then I want to capture that as reference material and either hold that in DEVONthink, which holds obviously text, but also PDFs and images and like, or maybe Obsidian, text space only. So drafts is the starting point, reference material that goes into those two different sources. And then tasks, I would then say go into OmniFocus. So there's a certain kind of culling of this, which happens usually at the end of each day where I say, "All right, I've got five random notes here." A couple of these things get deleted because it's just something that I thought was important, but, "Oh, I need to get back to this person on X," that goes in OmniFocus, or here's a podcast that I was listening to that gives me a good idea. So I might be listening to a podcast like this out on a run and be like, "Oh, I should do something with regards to X, Y, and Z." It may not be a task, but it could be something that's a little bit more reference material for something in the future. It could be writing, it could be something for teaching, could be something for a client, that goes into the backend reference material. So think of that as the first bit. Drafts as an entry point going into OmniFocus, DEVONthink, or Obsidian. And then I would say the part that has been an interesting evolution for me vocationally has been that when I was 26, 27, when I first had OmniFocus, I was for the most part an independent actor and so I could get by only having solo tasks. Increasingly now those roles are somewhat shared. So the household is shared with my wife, Kelly, and I have to find some sort of way to coordinate with her. I have a team at the Koch Center, I have a team at the provost office, so there's people that I work with there. And so I haven't quite nailed this down, but what I've found is that I end up using in shared work more something like Trello. So sometimes with Kelly, although we're a little bit less sophisticated on that, but definitely with the team, I have kind of a Trello ecosystem that allows us to identify what are the things that are being worked on now this week, et cetera. My influences there are someone like a Cal Newport and the way that he talks about getting work done in the context of his work at Georgetown and other places. But then usually I'm pulling from Trello sometimes with an API, but usually by hand, into OmniFocus so that OmniFocus still becomes the source of truth. So Drafts in either into reference or tasks, tasks are either collective tasks or individual tasks, but usually for the most part, I don't want to go back and forth between Trello and OmniFocus. I want to have OmniFocus is the place that I look to say, "What do I need to do again this week? What do I need to do today? What are my next three items?"

Andrew J. Mason: That's fantastic. Yeah, that's fantastic. And talk to me a little bit about the automation factor too. We talked about horizontal versus vertical and going deep and wide and the granularity of the information that you capture. I'm sure there's also a lot of pattern recognition that shows up. I also hear a lot of variability in your schedule as well. But I'm sure that there's some tear one off like, "Oh, this is a trip to X and therefore I'll need these five things." Anything like that show up for you where it's as simple as a repeating task or as complicated as some Omni Automation or JavaScript?

Peter Boumgarden: Yeah, I'm not nearly as sophisticated on some of those pieces as many of your other guests, having listened to a few episodes. I would say repeating tasks I'll use at different points. I'll use templates for a type of project that looks similar. So if I'm teaching a class, there'll be some buckets within there that are grading, some buckets that are developing of materials, some research buckets. So I'll use that in terms of the structure. I will say I've increasingly done some automation on the reflective component of this work and so what that's looked like recently is developing a script on Claude Code that at 5:00 PM pulls all my completed tasks from OmniFocus, turns it into a text file that it moves into Day One. So Day One's a journaling app that I use and it'll show me what did I do today and then I have in that template a couple questions of reflection. So what do I want to work on tomorrow? What was the felt experience of this day and what are my key items for tomorrow? And that's been shaped by some of my understanding of the social psychology of journaling, that one of the big reflective exercises there is that in looking back upon the things that you've done, you can build this sense of self-efficacy and I found that. So going to today, if I'm going back and forth between a couple meetings and then I've got a break for a T-ball practice and then I got to finish a few things and then take a flight out, it could be very easy for me to say, "What did I do today?" But if I have a script that pulls at the very tail end and if I'm active in OmniFocus checking things off that shows me at the very tail end of the day, actually I did finish seven things. Then it gives me a sense of saying I actually did do things that I didn't realize or I maybe even forgot about, that allows you to go into the next day or even that evening, not being like, "What have I done in this day? And I need to get caught up tomorrow," which can create a certain kind of spiral. So I think automating the reflective component, at least in terms of pulling completed tasks and then forcing myself to say, "All right, what are some takeaways from that?" Ends up being kind of a five minute activity at the end of the day, but one that helps me close out the day effectively.

Andrew J. Mason: That is wildly fascinating. First person, I believe in our 173 episodes that have ever done an automation regarding reflection, but I immediately see how useful that could be. That's incredible.

Peter Boumgarden: Yeah. Great.

Andrew J. Mason: Thank you. That's awesome. I'm also very interested too, as we wrap up, maybe one more question on just the instructive arc of your life. I mean, it leans very well into the reflective section as well. The sense that as you've moved throughout the story of your career, I know that there's usually an urge to try and make something feel like a story arc that would maybe be compacted into a storyline of some sort with chapters and everything. But as you look back on your previous chapters thus far, are there anything that maybe you wouldn't necessarily classify these actions as a mistake in regards to productivity, but something that would be instructive to you where it's like, "I tried something, it didn't necessarily go the way that I would hope to or expect." And so if you're me and you're trying to make your way kind of navigate your way through the productive landscape, maybe just skip that slice of it. Does anything land for you there?

Peter Boumgarden: There's a stream of research in the organization strategy space that I sit in that talks about the difference between exploration and exploitation. So exploration, the idea is that it's about kind of open exploring of new themes and threads. It's oftentimes correlated with innovation, developing new things. Exploitation is oftentimes like digging deeper into a given area, driving efficiency. So if you take an athletic metaphor, exploitation might be, "I'm going to get really good at running, I'm going to add on miles, I'm going to do my nutrition oriented towards this." Exploration might be, "This summer I'm going to do some swimming, I'm going to do some mountain biking and I'm going to do these other pieces of the equation." So in the context of exploration exploitation, what they find is not surprisingly a posture of exploitation drives efficiency, a posture of exploration drives innovation. And I think applying that to the context of task management, I would say that you can get so focused on the exploitation side of it, or I can get so focused on the exploitation to thus leave not enough space for the exploration built into it. And so imagine it's like, "I'm going to optimize the full system and dive in deeper and make sure that I can drive all the outcomes that I care about." But fail to acknowledge that you have to kind of like react in some ways to these things that are inbound things that seem like a divergence but actually are potentially new pathways. And so I think the high level career lesson that I would have on this is that you want to strike a balance from not being so exploration oriented that it's kind of scattershot. "I'm taking this project and that project and I didn't finish this one and I didn't deliver well on these pieces." But you don't want to be so exploitation oriented that all of a sudden anything that seems slightly off diagonal from your approach is something you don't pursue. Because I think many of the things that I've done over time from a career standpoint that have led to the mix of things that I'm doing now, we're taking things that were slightly off diagonal from the current path. Take this leadership role of the Center. I'm going to kind of take this leadership role around the Provost Office. I'm going to think about AI and learning as tied towards that. Those are all things that I could have kind of too narrowly cut off from the list. So the implications from a system standpoint then for me looking back and for me looking forward would be, how do I set up the system with enough reflection, as I just mentioned, that I'm able to kind of think about the things that are coming to reflect on whether or not that's a good fit or not, but then also that I build enough flexibility into the model that I'm not so optimized towards just getting more and more done in an efficiency oriented way that I actually failed to explore more broadly? So a lot of lessons for organizations on exploration, exploitation, but I think some of the same could be applied for many people when it comes to their career.

Andrew J. Mason: I love it through that lens. That's an excellent kind of sharing how that plays out in that way. I think through David Allen's loose grip, to control is out of control and the ability to have an open hand when it comes to regard to that but not be so open-ended that you don't get anything done either. So much, much appreciated. Thank you for sharing your wisdom, your experience with us today. If folks are interested in connecting with you and what you're up to, how can they do that, Peter?

Peter Boumgarden: Yeah, so I have kind of two public facing writing projects. One is called The Owner's Box. It's on Substack. It's all focused on strategies of ownership. It has a podcast with people like Danny Meyer and Bigelow Tea, Sydney Bigelow and others exploring the strategies of ownership that owners take and then another one called A Rich Life also on Substack that's a little bit more philosophical reflecting on the different threads that one has when it comes to exploring a broader view of vocation and life. So those are the two areas, and then obviously LinkedIn is a great way to connect if you found any of this to be of interest and had any questions.

Andrew J. Mason: That's perfect. Peter, thank you so much for joining us. This has been awesome.

Peter Boumgarden: Yeah. Thank you, Andrew. Appreciate it.

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