#158: Prioritize the Biggest Rocks (and Don't Feel Guilty if You Never Get to the Small Ones)

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This is a podcast episode titled, #158: Prioritize the Biggest Rocks (and Don't Feel Guilty if You Never Get to the Small Ones). The summary for this episode is: On this episode, DC and Adam dig into the next lesson DC wishes knew when he was younger – how to prioritize what matters most and why it doesn't actually matter if you never get to any of the "the small rocks." In other words, do the one thing that will move you closer to your goal. That might take five minutes or it could take many days. Either way, this method of working is the anti-checklist. Tune in to find out why. Required reading for this episode: The 7 Habits of Highly Effective People by Stephen Covey The ONE Thing by Gary Keller and Jay Papasan Like this episode? Be sure to leave a ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ review and share the pod with your friends. You can connect with DC and his co-host, Adam Schoenfeld, on Twitter @dcancel @schoeny @HYPERGROWTH_Pod

Adam: Okay, we're back.

Speaker 2: And we're back. Seeking Wisdom is here. Are you ready to set it off, Adam? What are we talking about today?

Adam: I'm ready. I like that because I'm like, " We're back," all quiet. And then you bring it. We're talking about the sixth lesson that you wish you knew when you were younger, which is prioritize the biggest rocks each day. And I love the second part. Feel no guilt if you never get to the small rocks.

Speaker 2: Oh my goodness. I love this one. This is a great one. And we've touched upon this a little bit in some very, very old episodes, and this is something important. Don't forget if you're listening to Seeking Wisdom, if you're a new listener, if you didn't listen to the old archives to go back to the early archives of Seeking Wisdom and listen to some of the classics. Back in the day we used to call this digging in the crates. What we meant by that was the early DJs in hip hop would spend a lot of time trying to find beats and samples by spending lots of times digging in milk crates. And those milk crates were filled with old albums. And so they would go in different houses, go in different locations, go to different people's houses and dig in the crates all the time to try to find the best beats that no one else had found before. So if you want to find the gems that you may have missed in the past, some of our best episodes, some of our classics, go dig in the crates, find those early Seeking Wisdom episodes. And you'll find one that was where we covered the book, The ONE Thing, and that one thing it really shaped my mind. That's a book that we would give out to everyone who joined Drift from the very, very early days. And the idea behind the one thing is very similar to the ideas of Stephen Covey if you read the Seven Habits of Highly Effective People where he talks about big rocks and small rocks and the idea that if you took a large jar and you filled it with frocks, you could fill the entire jar and think about the jar as your day, right? You can fill the entire jar with tiny little pebbles, even sand, right? So those are tiny little small tasks, or you could fill it with big rocks and then fill around the big rocks with tiny pebbles and sand if you had extra space. And The ONE Thing talks about this in a different way, and he says like, " Look, the most important thing to do each day is to think about the one thing that you can do each day that will have the biggest impact, that will move you further towards your goal than anything else. And sometimes that one thing can take five minutes and sometimes it can take many days, but that's how you prioritize your day." It's the anti- pattern to a checklist. And one of the things that for me was a problem using checklists and using every type of software, imaginable paper checklist, all these different systems, planner, checklist planners, all these different things was that by definition if you put something down in a checklist, that everything that you put down feels the same priority because it takes the same amount of space, right? So something super important, then yes, you can label and you could give priorities, you can do all this fancy stuff, but really each thing that you're putting down really is of the same size and weight. And that fools you into thinking that if you spent all day checking off things on your list, that you were somehow productive, where all those things might be things that did not move you further towards your goal at all, but they were things that felt good because you checked something off the box. So to me, it's important to go away from that pattern of prioritizing that way and to prioritize only the biggest rocks each day, like in the Stephen Covey example, like in The ONE Thing example. And for me, that's all I think about. And I was talking to someone recently and they were telling me about all the things that they had to do each day. And then they asked me, " Oh, okay. How do you prioritize things each day?" And I was like, " Actually, I only focus on one thing each day." And so I wake up the night before. I think about it in the morning. I think about it as well and think about like, " What's the most important thing I need to get done today?" That might be in the scope of work. It might be in the scope of life. It's just one thing. I don't have one thing per life, one thing per work. I just think, " What is the most important thing that I need to get done today that is going to move me further towards the goal that I have set for myself for that timeframe." And that's how I prioritize. That doesn't mean that I only do one thing each day. It means that that is the only thing that I care about and that I have any... Anxiety is the wrong word, but put any pressure on myself to make sure I complete. Then once that thing is addressed, and I try to address that as quickly as possible on the day, if possible. Sometimes that's impossible. Sometimes that happens to be a meeting or a call that's scheduled later in the day. But I fill the rest of the day with other smaller things that I need to get done or I feel like I can fit into that space. It's a very different way of thinking versus thinking of, " I had seven things to get done today," or, "I have 10 things to get or three things." I only have one thing. And it releases that anxiety, that guilt that you give yourself when you have this long laundry list of things to do in a given day. And it's been fundamental, I should say, for me this big change. The impact that it's had in my career since I started to move this way versus focusing on lots of little tasks and checklists and stuff like that has been massive. And so it's something that if you're listening to this and you're not doing this, I would suggest that you spend some time experimenting to see if this can be a more effective pattern for yourself.

Adam: So what are the counter forces? Is it just guilt? What is it that prevents us from doing this even though we know and we know logically that this is a better way? What prevents us from actually doing it?

Speaker 2: I would say I don't think that everybody knows that this is a better way. I think it's obvious when you talk about it or it's at least logical when you talk about it. But I don't think it's how most people think because it's not how most people were taught and it's not the current way that we reinforced the idea of productivity in our culture. And so I think we have created a cult of productivity. There are some books, I will say, that talk about this like The ONE Thing and Drucker and Stephen Covey, like we just mentioned, but there are probably a hundred times more books, a hundred X more books, especially more recent books, that talk about productivity, talk about checklist, talk about getting more things done in a shorter amount of time, right? Everything from Checklist Manifesto, which is a good book, but for our work all of these productivity guides. There's hundreds and hundreds, if not thousands of these books. I think that is the current thinking and current thing that people are talking about in our culture. And I think this is very different. This is going the opposite way and not thinking about productivity, but really thinking about impact and leverage. And those are very different things than productivity.

Adam: Can you talk more about the guilt aspect, the feeling of guilt if you never get to the smaller rocks? And specifically, I'm curious, what if there's another person on the other side of that small rock?

Speaker 2: There often is. You have kids, I have kids. And so when you have people on your team, and the same for me. So there's almost always someone else on that other side, right? One, I will say it's not easy. Nothing is. Nothing is easy. It's simple. The concept is simple, but it's not easy. There's always someone on the other end who's going to be pulling for your attention. But I think that is the point. It's not supposed to be easy. Along with productivity, another false idea that we have that's popular now is that things shouldn't be hard, that you shouldn't go through discomfort, that you shouldn't go through this, that things shouldn't be painful. It shouldn't be difficult. That if they were right, if you were doing it correctly, then it wouldn't be painful. I don't believe that. I think a lot of things are going to be painful. And I think feeling this guilt that you get from this idea that you may be letting someone down is real. And I don't think it gets necessarily any easier. I think as you continue to focus on your big goals, big rocks, and you get closer to knocking off more and more of your big goals, then you can have that to counterbalance in your own mind and say like, " Okay, I am making something visible. I am making massive progress towards the thing that I think is most important." And so I think at least for me that helps somewhat, but I think on the day- to- day, not getting back to that at email, not checking off that small task that maybe someone else is waiting for, there's an incredible of guilt that's associated with that. And I think we have to wrestle with that. I wrestle with that all the time. And I won't say it gets any easier except for when you're making progress towards your goal.

Adam: Yeah. How do you set that expectation with the people around you? I mean, how do you say this to them directly without hurting feelings or making it clear what your big rocks are and this dynamic of how you work?

Speaker 2: Yeah, I think the easiest way for me to do this has been that I make sure that my big rocks go across all parts of my life, right? Whether it's professional, personal, emotional, physical, whatever, all the dimensions in your life, I make sure that I'm constantly rotating my big rocks across that. If I only was focused on one dimension, let's say work or physical and abandoning everything else and never giving any priority to those things, it'll be a very hard discussion to have with people to set that expectation. But if I ebb and flow and I'm able to one day prioritize on this big goal that I have professionally and then two days later focus on this big goal that I have personally, or from a family standpoint or physically, then I think people are more understanding. Again, I don't believe that everyday has to perfectly balance and you have to hit all these major goals across every dimension in your life is impossible. So I think you can spread it over time. And if you use a day as a unit, you can one day focus on this, next day focus on something personal and then vice versa and keep cycling through and keep ebbing and flowing, which is a more natural pattern.

Adam: Yeah. It's funny. Otis and I were having a conversation about this just yesterday, given we're in a weird time right now with the pandemic and everybody's got extra stress at home. Sometimes it's like picking up my daughter is the big rock of the day.

Speaker 2: Totally. And it should be.

Adam: That framing of everything's in one jar versus these separate jars. The rocks and the sand and the pebbles make sense.

Speaker 2: Absolutely. That should be a priority one time. But if that was always the priority, that would also be a problem, right? And so it's this ebb and flow, and life is supposed to ebb and flow. That is the natural pattern. And that is the pattern that I try to follow here.

Adam: Can you talk about how you've built this into the culture at Drift as a leader? We have this principle; innovate, don't invent, which I think it comes from this lesson. How have you really thought about bringing this to the culture that we have at Drift?

Speaker 2: We've tried in a number of ways. One of the mantras that we tried to enforce early on and I try to continue to, and even recently I've been interviewing a lot for senior positions, and we talk about this mantra that we have, which is that every idea that we have is wrong. And so that's something that we try to instill or I tried to instill pretty early. And the idea is that basically to accept that every idea that we ever have is wrong by definition, right? And it is wrong, and it is either 1% wrong or 100% wrong. It's somewhere within that spectrum. And our job is to try to figure out and iterate and try to learn and develop a feedback loop so that we can figure out how wrong we are and we can find the right solution. So the reason that this is important is because it's trying to reinforce that you can't sit around by yourself and believe that you're special and that you're going to develop some idea or ideas that are perfect when they come out. And one of the things that it forces you to do beyond starting without going through the feedback loop is before you even start that what you do is try to rely on history. So we look at people who have done this before, who have maybe had similar ideas, who have executed in a similar space and may have executed on it successfully or unsuccessfully, and we try to learn from them beforehand as a hack towards shortening the feedback loop. So that's one thing that actually happens as a side effect of this idea of that our ideas are always wrong with to go in the feedback loop. Before we go into the feedback loop, we try to force ourselves to learn from history. Another thing that we do at Drift is that we've started with this idea of that everyone within the company is a learning machine, and we reinforce this through having internal talks from guests who come in, having an internal book club, talking about books a lot. This podcast manifested from that idea. And what you're doing when you're doing that and reading books is that in books that have nothing to do with the domain that you're in is reinforcing, again, that you're not special, that you can learn from history and you start to see patterns of where things like the thing that you're trying to tackle have been tackled before. And I'd say the last thing, but there are many other things that we do, is we talk a lot about decision- making, psychology, how that affects our decisions. And again, that pushes us towards a place of the thing that we're trying to work on now might seem special in this context that we're in or new. But if we think about it from the human standpoint, from the human decision- making standpoint, it pushes us back again to learn from history because those patterns haven't changed, right? The technology might and the implementation may have changed, but the way that we make decisions and what we need and what we're looking for when we make a decision to do something as humans hasn't changed. Again, forces us back to learn from history.

Adam: Can you say more about how you pick the other domains that you want to learn from and then the questions you ask when you're doing that? I know your boy Charlie Munger talks about the domain dependency problem a lot and how we get stuck in our own domain in this crazy way. Can you say more about how you do that and how you think about which domains to look at and how you integrate those other domains?

Speaker 2: I'd say it's kind of like an anti- pattern. For me, I don't sit beforehand and think about, " I want to learn X, Y, and Z. And so I'm going to find other domains where they've learned something similar or have gone through this issue." What I do is I find other domains that interest me, right? And points in history, characters in history. I'm really geeking out on Andrew Carnegie right now, which is a whole another podcast, which is just an aside, but I'm really geeking out. I'm going deep on him. But I'll find figures that I find interesting. I'll find time periods that are interesting. I'll find just entirely new categories of ideas or topics that are interesting to me. And I will start reading those and spending time there more from an enjoyment standpoint. When I do that and I go across those things, you'll observe that the same patterns appear throughout all different contexts and time and events. And then it's there that I start to do this thing that we talked about, this processing and synthesizing across. And then I can see, " Oh, wait a second. I wasn't necessarily looking towards reading, let's say, Andrew Carnegie's biography to solve this problem that we have now, but I'm picking up things here because he went through something very similar from a human dimension that might apply, might help me in this thing that I'm thinking about here." So I hope that makes sense. It's really like you're not screening in the beginning. You're learning from other people and other time periods in history. When you do that, you'll see the thing that we talked about, which is the way that we make decisions hasn't changed. And because of that, you can see some patterns in the past of choices and then side effects or effects that happen from it, and you can start to apply those to the things that you're struggling with today.

Adam: I love that because it takes the pressure off versus thinking like, " I have this problem. I better go study these certain domains." You get to just start from curiosity of, " Oh, I'm interested in 17th century history," or, " I'm interested in architecture," or, " I'm interested in how stand- up comedians built their craft, right?" And you could go study any dimension and then start to see forward how those apply into the situation you're in.

Speaker 2: Totally. As long as you're open- minded and you're looking for it, right? You're looking, you can see it. I'm geeking out on Andrew Carnegie. And one of his first quotes that I was reading in his book was that he said... He was talking about the steam engine and basically investing in that area, which was an earlier area that he was focusing. The thing he said that really stood out to me was that he knew not one thing about steam engines, but he chose to study the more complex and more relevant topic, which made all the difference, and that is studying people. That is how he succeeded in that industry not knowing one thing about steam engines.

Adam: I Love that one. All right. What else do you want to share about learning from history? Anything else that you want to leave the listeners with today?

Speaker 2: The most important thing for me is to get through to your thick skulls and mine that we have to learn from history. That there's nothing that you're facing that someone else, probably lots of people have faced in an entirely different time and context. Learn from those people. Don't do what I did, which is learned through brute force and pain and have to learn everything firsthand. Go out there and learn from them. Be better, be smarter because of that. Go out there. You're not special. You're not a snowflake. Someone else has gone through this before. Get it through your thick skull. You can do this. And while you're thinking about that, don't forget to leave a six- star only rating for your boy, boys in this case, with my boy Adam here. And you do that by going to Apple Podcast, Spotify, wherever you're listening to this. Hit subscribe if you're not subscribed already. Leave a six- star rating. Leave a little note there about a book that you're reading or some way that you're learning from history and teach me something so that I can get smarter here, all right? Six stars only. The universe is only six star podcast Seeking Wisdom. And we're back.

Adam: We love those six- star reviews. We read every one of them. Thank you everyone for leaving those. For DC And hopefully Apple, we'll get that bug fixed. I don't know what's going on. Boom, we're out.


On this episode, DC and Adam dig into the next lesson DC wishes knew when he was younger – how to prioritize what matters most and why it doesn't actually matter if you never get to any of the "the small rocks." In other words, do the one thing that will move you closer to your goal. That might take five minutes or it could take many days. Either way, this method of working is the anti-checklist. Tune in to find out why. Required reading for this episode: The 7 Habits of Highly Effective People by Stephen Covey The ONE Thing by Gary Keller and Jay Papasan Like this episode? Be sure to leave a ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ review and share the pod with your friends. You can connect with DC and his co-host, Adam Schoenfeld, on Twitter @dcancel @schoeny @HYPERGROWTH_Pod