Jimmy Wales reveals the foundational principles around trust that helped build Wikipedia.
You’ll Learn
- How trust helped Jimmy achieve 52X productivity
- The common assumptions that erode trust
- How our systems encourage mistrust
About Jimmy
Jimmy Wales is the Cofounder of Wikipedia and the Wikimedia Foundation. Named one of Time’s 100 Most Influential People, he has been recognized by the World Economic Forum for his contributions to the global public good. He lives with his family in London.
Resources Mentioned
- Study: “On the Folly of Rewarding A, While Hoping for B” by Steven Kerr
- Study: “Guarding the Firewall: How Political Journalists Distance Themselves From the Editorial Endorsement Process” by Gregory Perreault, Volha Kananovich, and Ella Hackett
- Tool: GPT-OSS
- Book: The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change by Stephen Covey
Thank you, Sponsors!
- Monarch.com. Get 50% off your first year on with the code AWESOME.
Jimmy Wales Interview Transcript
Pete Mockaitis
Jimmy, welcome!
Jimmy Wales
Hello. Nice to be here.
Pete Mockaitis
Well, I’m excited to chat with you and get some insight into trust. That’s something we’re big into here, so why don’t we start with, could you tell us your story of how Wikipedia came to be? And I know we could do that for hours. So, let’s do the five to 10-ish minute version of that just so we can get situated in context and piggyback off of some things.
Jimmy Wales
So, I had the idea for a free open source, freely licensed encyclopedia, written by volunteers more than two years before starting Wikipedia, and I was very excited to get started. I thought it was such an obvious idea, lots of people would be doing something similar. So, I just got started. I didn’t really know what I was doing.
And went out and hired an editor in chief and we set up a seven-stage review process to get anything published. And, in retrospect, I realize now the entire system that we built just screamed, “We don’t trust you,” because that seven-stage process, you had to send in your CV to prove you were qualified, and then we would take your draft and send it out for review to the most prestigious professors we could find and so forth. We were being more academic than Britannica.
And I realized it wasn’t going to work when I thought, “Well, I could try to write an article about Robert Merton who had just recently won the Nobel Prize in Economics for his work on option pricing theory.” And in grad school, I had published a paper on option pricing theory, the mathematics of it, and so I knew his work very well.
And when I sat down to write, I had this enormous feeling of writer’s block because it was very intimidating. They were going to take my draft and send it to the most prestigious finance professors they could. I hadn’t been in academia for a few years at that time, so even though I was familiar with his work, it was a very scary thing to contemplate.
And that was when I realized, like, “Oh, this isn’t going to work. Like, it doesn’t feel good. It isn’t fun.” So, one of my employees, Jeremy, came to me and showed me the Wiki, the concept of Wiki, which had been around for several years. So, a Wiki is just a website anyone can edit. And the word Wiki comes from a Hawaiian word wiki-wiki, which means quick. So quick collaboration is the concept.
And so, a Wiki is a website where you can just quickly write and share and so on, which was pretty radical. I mean, these days we have Google Docs and everything else so it doesn’t seem as radical but that wasn’t really a thing back then. And it worked. Within two weeks, we had more work done than we had in almost two years. It was really quick.
Pete Mockaitis
52x, there you go.
Jimmy Wales
Yeah, because we had this community that had grown up for two years, and we had the mailing list, and we had spent two years talking about an encyclopedia, talking about how to build it, what it should be like, neutrality, all of the kind of values of Wikipedia. But we had created a system that didn’t trust people and, therefore, didn’t make any progress.
People were very intimidated, it wasn’t very fun, so even though people liked the idea, it didn’t really move forward. But that act of opening up and just saying, “Okay look, everybody just come and write. We’ll figure out as we go along. We’ll need to…” Well, in the early days, I assumed we were going to need to assign someone to be the editor-in-chief of the, I don’t know, the American history section. And I still had a top-down mentality in the early days.
But after a short period of time, it was like, “Oh, that doesn’t seem to be in any way necessary or even useful to have someone like that.” In fact, the community looks after each other and monitors each other, and so on and so forth. So, the whole journey there was really about realizing, like, you can trust people and that’s the way to make progress.
Pete Mockaitis
This is fascinating stuff and, boy, from seven stages of approval to seven rules of trust, that’s kind of a fun little parallelism there.
Jimmy Wales
Yeah, the other day, I never thought of this, somebody the other day said to me, “Oh, so the first system was like the seven rules of mistrust.” I said, “Oh, yeah, I didn’t think of it that way, but that’s actually quite good.”
Pete Mockaitis
Well, so your book is called The Seven Rules of Trust. I’d love to hear, any particularly surprising or fascinating discoveries you’ve made about human beings and trust along your journey or in putting together this book?
Jimmy Wales
I think there’s a lot really. I think one of the keys is, I think, it’s rule four in the book, is give trust to get trust, that by being trusting, then people will trust you. And I think that’s a little counterintuitive or a little surprising to people, although it actually isn’t, I think, once you really think about it.
If you think about how you conduct yourself in relationships and things like that, if you approach someone and you trust them and you make it clear that you’re trusting them, they’re very likely to reciprocate because humans are like that. People are very pro-social and they like that kind of environment.
So, in a workplace, the kind of manager who trusts the employees to get the work done tends to be rewarded with employees who are trustworthy and who work to get the work done because they’re like, they appreciate that. And if you approach the employees with a really, like, an aggressive sense of mistrust, well, they’re probably just going to work to rule at best. They’re not going to trust you in return. They’re going to say, “This person is really being a jerk.”
You see these stories from time to time, sort of post-pandemic stories about people working from home, and then some kind of software installed on your work computer to monitor whether you’re at your keyboard or not. And I’m like, “Man, quit that job. That is so toxic. Like, that’s completely absurd.”
And, actually, if you want employees to give it their best, the best way to get that out of people is to say, “Yeah, you’re to work from home? You know, we’ve got a lot of work to get done. That’s the important thing. Organize your day as you see fit. If you’re away from your computer, give me some time back later. Let’s be flexible. Let’s be trusting of each other.”
And I think people really respond well to that. And they respond the opposite way when you show them mistrust.
Pete Mockaitis
Yes, that really does resonate. And I’ve had that in my own experience. I heard a fun turn of a phrase. I believe it’s a malicious obedience or malicious compliance.
Jimmy Wales
Yeah, malicious compliance. Yes, I’ve heard that.
Pete Mockaitis
It’s like, you know, you say they work to the rules, like, “Oh, this is a rule, huh? Okay. Well, I’m annoyed and irritated with you, and this is the rule. And I know this is going to cause a little bit of trouble, but I kind of like that. I’m taking some gleeful delight in obeying the rule but causing a little bit of trouble, like, ‘Well, I’m just doing what I was supposed to.’” And, yeah, that’s not what we’re going for.
Jimmy Wales
Yeah, totally. Totally. And so, it’s a healthier way to live, among other things.
Pete Mockaitis
Okay. Well, you mentioned one of the rules. I’d love it if we could, in fact, have perhaps a one-ish minute overview of each of the rules and then we’ll dig in a little bit from there.
Jimmy Wales
Sure. Well, I mean, I don’t necessarily have them all memorized in order, but I can do my best, or maybe we just start digging in.
Pete Mockaitis
I have your table of contents up.
Jimmy Wales
Oh, that’s cheating, you know. So, I’d say the first rule, “Make it personal.” And so, the idea here is that trust is won and lost in an individual human mind. And so, there’s a lot of different things I mean by that, but in particular, it’s about empathy, like thinking about that other person, thinking about, “What do they need from me in this situation? What will help them to trust me that I’m going to do the things I say I’m going to do?”
And it’s an encouragement that we maybe not think too much about statistical measures and playing the numbers. Certainly, because I come from the consumer internet world, there’s a lot of emphasis placed on A-B testing. You A-B test and you see, “Which of these two patterns gets us a higher checkout rate at the end of the visit to the website?”
Okay, that’s valid. I’m not saying don’t use A-B testing. A-B testing is super valid. But layered on top of that, you also have to say, “But how is somebody going to feel when they get through this? Are they going to feel like this is a great relationship, like we’re a good company to do businesses with? Or, are they going to feel like, ‘Oh, my god, this is a nightmare,’” even if you somehow got them to the checkout.
And where you really see this a lot of times is when you try to unsubscribe from something, there are so many dark patterns there, which I’m sure if all you do is A-B testing, you say, “Yeah, look, if we do it this way, make it clear, obvious, honest, simple, for people to say cancel their subscription, then when people start down that path, even though we give them some reasons along the way and we offer them a discount, we make it easy and 40% of them still quit.”
“If we send them in an endless loop and then force them to call us on a phone later, then only 3% quit.” And you think, “Oh, great, well, we’re going to do the difficult way.” No, you’ve just undermined trust. You’ve just undermined any chance of ever getting that customer back. You’ve undermined your reputation, the word of mouth. I mean, it’s just super toxic.
Pete Mockaitis
Yeah, they’ll hop on Reddit, trash you.
Jimmy Wales
Yeah, people go crazy about that kind of stuff. I mean, I personally just can’t stand it, and I sort of have my own internal blacklist of companies I’m never going to deal with again. And so, that’s the kind of thing where, you know, don’t just look at the numbers. Like, make it personal. Make it personal. So, be positive about people, so assume good faith is a classic Wikipedia rule.
I’ve talked about this a little bit already, that under rule four be trusting but here, you know, it’s like it’s a good bet if you meet somebody, and whatever they’re doing, they’re probably a decent person. If you meet a thousand people, 990 of them are going to be fantastic people. Probably nine of them are going to be annoying, but they’re still not malicious. They’re just like annoying people. And then maybe one in a thousand is somehow actually being malicious.
And so, it’s a very small number of people. And so, being positive about people and designing whatever your process is or your life or whatever around that premise of saying, “Oh, look, I’m just going to assume most people are going to be good. They’re going to do the right thing,” that actually works really, really well. And then we talk in rule four about the reciprocity piece of that. One of the reasons it works really well is because people like to reciprocate that.
Rule three, create a clear purpose. That one’s fantastic. So, this, really, when people say, “What do you think is the one rule of trust that has been really instrumental to the success of Wikipedia?” And I would say it’s this. Wikipedia, the goal of Wikipedia is a free, neutral, high-quality encyclopedia, and that’s what we’re here to do, and that defines everything about everything that we do.”
And what does that mean? It means when we come to decisions, we’ve got a North Star, something to guide us, we know what it is that we’re trying to do, we have a good purpose, and we’re able to follow that purpose. And it gives everybody an organizing theme. And a lot of times, people don’t sense that kind of clear purpose. And they’re not really sure what the point is of what they’re doing.
And, frankly, this is, I believe, one of the problems with a lot of social media is because the company’s purpose is, frankly, it’s just show as many ads as possible and get as many clicks on ads. And if that’s their core purpose, they lose sight of a lot of things about what users really want to need out of a social media platform. And they, instead, optimize for addiction, outrage, clickbait, etc., which, as we know, is pretty toxic and not very healthy.
And so, having that clear, good purpose is really important for success. Skipping four, because we did four already, rule five, I think this chapter is titled something like, “Your Mother Was Right,” and this is about be civil. Be nice, be kind to other people. Disagree respectfully. You focus on ideas. No personal attacks, is one of the core rules of Wikipedia. It’s just useless. It violates our purpose, which is to write an encyclopedia. And it isn’t practical.
And, obviously, we see this in all kinds of ways, in all kinds of places, in all kinds of businesses, that being nice to other people is actually a fantastic way to get things done because people are like, “Oh, yeah, this is a nice person. This is great. I’m going to do what I can to further this. It’s a relationship with this person or with this business that I like, and I’m going to cherish that.”
Be independent. So, this is, maintain freedom from undue influence to build credibility. In this case, the Wikipedia reference I would get is we’re not funded by governments, so governments have no influence over what we say and what we do. We aren’t funded by a handful of billionaires or one billionaire. I mean, you can imagine how that might end in tears. We’re funded almost exclusively by the small donors. The average donation of Wikipedia is just over $10. But we do have some…
Pete Mockaitis
I’ve seen your messages, Jimmy.
Jimmy Wales
Oh, yeah, you’ve seen the messages, yeah. And this is why it’s really important. It’s important for our intellectual independence that we have the ability to say, “You can come and offer Wikipedia a million dollars to change an article, and we’re just going to go like, ‘Sorry, that’s not what we do. We’re not desperate with that.’”
And the way it normally happens, it wouldn’t be that blunt or brutal. It would be, if we had one major donor who is funding 80% of our budget all the time, then, wow, you would have to really listen to that one donor, and you would really have to kind of worry about what they think about the content of the articles and things like that, in a way that I think could easily be unhealthy.
As opposed to we have to worry about what the general public thinks, that everybody thinks, and we need to appeal to the widest possible audience so that everybody can go, “You know what, that Wikipedia is a great thing. I love it. I should chip in.” And so, that independence is part of why people trust us.
When you’re reading Wikipedia, you know, for example, that no government can force us to change an article. And they’ve tried. We were banned in Turkey for three years and we fought all the way to the Supreme Court in Turkey and won. Meanwhile, for three years, we were blocked in Turkey and we didn’t give in. And that’s kind of just we’re very principled. We’re very independent in that way. Because for us, that value of independence, that intellectual independence is really core to our whole mission. We have to fight for that.
Pete Mockaitis
And I’d love to comment on that. I think it’s so wise and true that we should take a look at that. And, you know, I don’t think it’s conspiratorial to just assume that when there’s a substantial flow of money from a concentrated source, whether it’s an industry or an individual, that will influence the editorial choices of something.
So, for like TV news, I mean, I’ve noticed a pattern of who tends to advertise a lot on TV news, and I don’t want to, you know, be a tinfoil hat conspiracy person, but I got to imagine that has an impact on what stories they choose to pursue and which ones they don’t. I will tell you, I have, you know, a couple major customers, and when I’m getting pitches, that say, “Oh, hey, we’re going to totally make fun of one of your major customers. Would that be sort of a fun little episode?’
It’s like, “Well, maybe,” but I already don’t want to do that. I mean, I also don’t think it’s valuable, but I will admit, like, my financial influence is impacting what I choose to do, at least a little.
Jimmy Wales
Yeah, that financial influence over the content. Now there are ways around that. I used to be on the board of The Guardian newspaper here in the UK, and that’s a really interesting structure because The Guardian is owned by a non-profit trust.
I was on the commercial board, so the operating company that actually runs The Guardian, but the editor-in-chief of the newspaper is hired by the other board, by The Scott Trust, by the non-profit board, and we, you know, the commercial board, had no authority to fire the editor-in-chief or to change any editorial policies.
And so, that was a really strong firewall, backed up by the legal structure, there just wasn’t any way. Now that doesn’t mean that the editor-in-chief completely doesn’t care about the commercial situation. They have to. I mean, newspapers are in dire straits and all of that. But I kind of like that, that sort of independence. And so, when we say be independent, that doesn’t necessarily mean, “Oh, well, anything done for money is bad because it’s all going to be corrupt.” I don’t believe that.
But I do believe that there is that potential, right? Then you do have to think about, “Okay, how do we design this situation so that it’s quite clear that, you know, our…” A typical kind of example, like Google has always been good about maintaining the independence of the search results from the ads. So, you can pay money and get to the top by paying for an ad, and it’s clearly marked as an ad.
Or, I mean, good luck, like the algorithm is the algorithm, and they don’t really, you know, and they keep those teams very separate and they’re quite ideological about that, and I’m glad, and I think they should be. If they started to break down and say, “Well, actually, we’ve decided that in our organic search results, we’re going to start favoring our biggest partners,” I think they would lose a lot of trust, and I think that would be damaging to them in the long run.
Pete Mockaitis
Okay, well said. So, that’s independence. What’s next?
Jimmy Wales
So, the seventh rule is be transparent, and this one’s kind of obvious. I mean, I think it’s one of the things people first think of when you say what makes an organization more trustworthy. And one of things you say is, “Yeah, transparency. Like, I want to understand how it all works, how are decisions made.”
I’ve been encouraging the news media, and there’s a lot of proposals out there, not just from me, from lots of people, and I’m like pointing at those, and going, “Yeah, that’s a good idea,” which is, when you’re writing a story, don’t just adopt that voice of God, voice of the New York Times, “We’re going to tell you like it is. You can trust us. We’re the New York Times.”
You need to show your work. You need to tell us who you interviewed. You need to tell us all the details of the story. If you’ve got multiple sources, you need to talk about that. If there is a source, I mean, this is my personal pet peeve, and some organizations are better than others about this, it’s like, “Okay, there’s a Supreme Court case, okay, it just came out yesterday.” I’m just making this up, but just hypothetically.
And I’m like, “Ooh,” and I see a headline, like, “Ooh, that sounds like an important Supreme Court decision. I’m really interested in that.” And it’s so annoying, it’s like, “Oh, here’s their interpretation. Ah, this will destroy democracy,” or, “Finally, this decision will save democracy.”
And it’s like, “Yeah, but you didn’t link to it. Like, how do I, you know?” Like, now it’s super irritating. Now, it’s not like they’re hiding it from me. I can then go off and Google and find it myself. But that’s like a little small thing of like, “Hmm, if you really believed your interpretation was accurate, wouldn’t you link straight to it and link straight to the quote that would prove what you’re saying?” And that’s the kind of transparency that I think would help to build trust in news and other types of publications.
Pete Mockaitis
Yes, I feel the same way in terms of, because in some ways reporting on a news article can be endless. Like, there are so many people you could talk to, so many rocks you could overturn. But when the story is about a document, or a book, a Supreme Court decision, or a court ruling elsewhere, it feels to me, and maybe it’s just too high a standard, that the bare minimum is, “Did you read the thing that you’re reporting about?” because that’s really kind of finite and approachable, assuming it’s not thousands of pages and all that.
So, yes, I’m with you in showing the work. And I’d also love to get your take on, in some ways, some of these things feel commonsensical, although not always common practice for sure, are there any kind of hidden, mysterious, easily overlooked ways you think that professionals are losing trust, they’re just squandering it, and they don’t even know it?
Jimmy Wales
I think one of the things that we know, just looking at the data, is that there has been a significant decline in trust across most of the world, decline in trust in journalism, politics, business, to some extent to trust in each other, and that this is having some negative impact in society.
One of the examples that we talk about in the book, the question of masks in the pandemic. And, basically, we quote health authorities very early when the pandemic, when the news first started to break, and they basically said, “Don’t bother with masks. Please don’t rush out and buy a lot of masks.”
They gave two reasons. One, they really need it in the hospitals, and, two, they don’t really do any good for you at home anyway. But then, a month later, everybody’s like, “It’s mandatory. You must wear a mask every time you’re outside,” right? And so, suddenly, “When you go out of your house and you’re in any public place, you must wear a mask.”
Well, like that flip-flop caused a lot of people to lose trust. And, in fact, one of the reasons they first said don’t bother with masks is they didn’t trust the public to follow that first warning. They were afraid people were going to panic and buy up all the masks, there’d be a mask shortage in hospitals. And it’s like, no, trust the public, say, “Actually masks are effective if worn properly, etc.”
And at the end of the day, where I get to on masks is like a proper N95 mask, worn properly, by a professional in a hospital setting, they are effective at reducing transmission. I live in London and the number of people who are riding the Tube in London, very crowded, with their masks half-ass on, half-ass off, “Hey, was that really helping? I’m not so sure.”
And that’s what the data seems to suggest, it’s like, “Yeah, good strong effect in hospitals, less so elsewhere.” So, where do you get to on that? That’s a complicated question. But my point here is really about that failure to trust the public resulted in a loss of trust. And I think an example of this, you could also look at a lot of environmentalists who have lost trust by over-hyping concerns.
They don’t trust that the public will believe that there is a problem unless they make it sound worse than it actually is. And then when that’s found out, I remember once there were some emails leaked that were quite, it’s like, “Oh, that’s really awkward. Like, you’re really talking about how to make a scaremongering story, and you’re a scientist. Like, you’re not trusting the public to be straight with them.”
And if you believe, and I think they do believe and I think they’re probably right, like if you’re really straight about climate change, it’s a serious issue and we need to really do something about it. And the best way to convince people of that is not to over-egg the case and create scare stories but to be straight, and say, “Well, look, here’s the problem, here are some mitigations, here’s the most likely scenario, here are some worse scenarios, here are some better scenarios.”
Because I think people just do respond to that and they then trust the scientists. And I think if people feel like, “Oh, the scientists have become politicized,” then they’re less trusting.
Pete Mockaitis
And I’m thinking about just the notion of, as humans, we like certainty and we like our experts, our authorities to just say with clarity and confidence, “This is the thing.” Like, “Oh, okay, that guy really seems confident. I guess I should follow that.” And yet, like, the science suggests that there’s very little relationship between the confidence with which someone asserts something and the truthiness of that something.
And yet, if someone’s coming out, it’s like, “Well, you know what, here’s what we know. Here’s what we don’t know. Most likely it’s probably like that.” That nuanced balanced, hear the uncertain elements, kind of a presentation, over time I’ve come to appreciate that person more. It’s like, “Okay, I feel like it’s more likely they’re telling me the truth. And so, I should latch onto that.” But it seems that the masses go like, “Oh, this guy doesn’t know Jack. Let’s go to someone else who has more confidence.”
Jimmy Wales
Yeah, but you know what, I think the evidence shows the opposite. I think the evidence shows that the mass public doesn’t trust people just because they’re overconfident. And, in fact, that, oftentimes, they see right through it and they see this is a blowhard who’s blowing smoke. And sometimes they don’t care because they don’t trust anybody.
But I think it’s sort of, like, you can get some headway in the short run maybe by doing that, but you’ll be found out pretty quickly because people, I mean, like I trust, like people aren’t stupid, people can see, like, “Oh, actually, you made these claims, but they seem overstated to me. And then I looked into it for five minutes and I’m like, yeah, overstated. And now I don’t trust you.” So, it’s an interesting thing.
Pete Mockaitis
Maybe that gets back to that dark pattern example, in terms of, yeah, that might get you the short-term results of the thing, like, you don’t cancel your subscription or you go, “Wow, check out this YouTuber. Let me forward and share their hot take. They’re fired up.” And then afterwards, you go, “Ooh, actually, oops. Hmm, maybe not so much that person.”
Jimmy Wales
Yeah, you know, it’s interesting, like one of my favorite examples of this is Netflix in the olden days, when Netflix was all about sending you DVDs in the mail. And I think everybody before that, and I’m showing how old I am, but it was a super toxic issue. You go to Blockbuster and then you would return your movie late, and you’ll get these massive penalties.
And, heaven forbid, like the worst thing that could happen to you is you’re cleaning your apartment, and under the sofa, you find, “Oh, yikes here’s a blockbuster tape. How long has that been under there?” And now you’ve got like, basically, the fine is so high, you’ve just bought the tape. It’s $80 or something, and you’re like, “Oh, my God, this is terrible.”
And then when I first heard about Netflix, I’m like, “Oh, that’s going to make me nervous, having three out and you’ve got to send them back, and what if I lose one?” “You can keep it as long as you want it.” “Oh, there’s no late fees?” “Yeah, no, just take three, you can have three. When you send one back, you can get another one.” “What if I lose it?” “Just tell us and we’ll send you another one. Like, that’s it. Nothing bad’s going to happen. Like, we trust you that you’re not scamming us.”
Obviously, if you report, I don’t know what their limit was, but probably after about five lost DVDs, they’re going to go, “You know what, actually, you’re losing too many, so we’re going to cut you off.” But broadly, they were just like, “Yeah, we think most people are going to be honest. Nobody likes a late fee. Have three out as long as you want. And if you lose one, just let us know and we’ll replace it. No problem.”
Wow, like I feel seen, I feel trusted. And that was a big part of why they succeeded, even though sort of ordering DVDs by mail was less convenient than sort of popping by Blockbuster on the corner.
Pete Mockaitis
Yes, it is. It is a good feeling. And I think that, in a way, that’s one of the trickiest potential root causes of this stuff is that there are some things that are very easy to measure, like the behavior that I desire. And then there are other things that are much harder to measure, “How much folks are trusting us and digging our vibe as a brand, as a professional?”
Jimmy Wales
Yeah, definitely.
Pete Mockaitis
And the former is easy to measure, the latter is hard to measure, and so we may optimize for the former at our own expense.
Jimmy Wales
Yeah, and that’s exactly it. So, there’s a very famous management research paper that, everybody learns about in grad school, on the folly of rewarding A while hoping for B. And one of the reasons people reward A while hoping for B is that A is easy to measure. And so, then you reward A, but frankly, then everybody starts to care about A, because that’s what they’re going to care for.
And if A can come at the expense of B, fine, that’s what people will do, because you’ve signaled very strongly. And so, sometimes, you’ve got to have a little more discretion and a little more sort of judgment around these things, which only really works if you’ve got a culture of trust, which is to say, your bonus as a salesperson.
“Your bonus is going to be based on sales, but also this kind of indefinable thing of your customers, how happy are they, are you building the right relationships. Maybe you haven’t closed as many deals as somebody else, but you’ve built relationships, so a part of your bonus is going to be, like, you’re building the base for future.” Okay, how do you judge that?
Well, you’re going to have to trust, and we have to have a culture of trust where I’m trusting you to do all right things, and we’re going to succeed together more if that’s our attitude, if that’s our team attitude of like, “Okay, yeah, of course, we’re a sales team, we got to make the sales, we got to make the numbers, but we’re not overly obsessed with the numbers at the expense of thinking about how do we build the broader growth of our customer base and things like that, even if we’re doing some activities that aren’t going to result in sales this quarter.”
Pete Mockaitis
And this reminds me that my first home purchase was through a Redfin agent, and he informed me that a substantial piece of their compensation is all about the reviews, like what we have to say about the agent. Whereas, if you think about real estate, it’s all about, “Hey, how many deals can be closed and at what price, and get the percentage and move, move, move?” And so, it was a different game. And, sure enough, I was having a different experience in terms of, “Wow, this guy, Michael Linden.”
Jimmy Wales
That’s great. I didn’t know about that. I’m going to read up on that. That’s quite interesting.
Pete Mockaitis
“Michael Linden is really over-delivering. He gave me a ride in the rain one time. This guy rocks.” And that was a pretty cool first-time experience. Well, Jimmy, we’re coming up on time. Tell me, anything else you want to make sure to mention before we hear, rapid fire, about some of your favorite things?
Jimmy Wales
I know, I mean, it’s an exciting time. I’ve been super busy promoting the book, and I’d appreciate it if anybody thinks it sounds interesting, if you take a look. And it’s going to be a fun year for me because we’ve sold the book in 20 languages. So, I’m planning to travel all over the world this year, talking to people about the book. So, yeah, great.
Pete Mockaitis
Could you share a favorite study or experiment or piece of research?
Jimmy Wales
I think my favorite one from the book, and it just comes to mind because I nearly talked about it already, is research that showed that when newspapers endorse political candidates, it not only reduces trust with the people who disagree with the endorsement, they also lose trust among people who agree with the endorsement because now they feel like maybe the paper is always just shilling for their candidate. And I thought that was super interesting. Actually, one of the more optimistic things is like, “Oh, yeah, people are pretty sharp.”
Pete Mockaitis
Okay. And a favorite book?
Jimmy Wales
One of the books that was really transformative, and I’m thinking because this is How to be Awesome at Your Job, Stephen Covey’s The 7 Habits of Highly Effective People. That’s probably why I settled on “The Seven Rules of Trust,” I just like the seven thing.
But that book really taught me a lot and had a big impact on me at a point in my career when I needed to be effective, highly effective. So, I love that book.
Pete Mockaitis
All right. And a favorite tool?
Jimmy Wales
My favorite tool right now is local LLMs, which I’m using for all kinds of fun projects and experiments and things like that, so, yeah.
Pete Mockaitis
Well, that’s so intriguing and we could have a whole other episode about this. But, if I may, can you tell me what is a local model you’re digging and a piece of hardware that folks would need if they’re going to embark down this route?
Jimmy Wales
Yeah, so I’m digging GPT OSS 120B.
Pete Mockaitis
Classic.
Jimmy Wales
So, this is the latest model, free model released by OpenAI, which has gotten a lot of criticism for not releasing very much. And I bought the most expensive laptop I ever even thought of buying in my life, which is the M4 Max MacBook with 128 Gig of RAM, which can run that model quite well. It’s fast and it runs it really well, and it’s quite a smart model.
I’d say just one step behind, not a half step, a full step behind the cutting edge models in the cloud. But it’s really impressive what you can do on a local computer. And I actually think, looking forward for the next several years, there’s going to be an enormous growth and demand for compute on local computers because it’s so possible to do such amazing things that everybody’s going to want it. So, I think that’s a big thing that’s going to happen.
Pete Mockaitis
Okay. And is there a key nugget you share that really seems to connect and resonate with folks, you hear quoted back to you often?
Jimmy Wales
My signature quote, I guess, is, imagine a world in which every single person on the planet is given free access to the sum of all human knowledge. That one puts a spark in people’s eye because they’re like, “Yeah, that’s what the internet should be about. Give everybody access to free knowledge. That’s fantastic.” And obviously that’s the goal of Wikipedia.
Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?
Jimmy Wales
So, I’ve got a little pilot project called Trust Cafe, TrustCafe.io. It’s a social network, but it’s very much a work in progress. I’ve just got a couple of developers working on it, a small community. I haven’t really promoted it that much. I mention it from time to time, and I’m on there. You can come and say hi to me.
Pete Mockaitis
Cool. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?
Jimmy Wales
I would say, take a trust inventory. So, think about all the different aspects of your work life, your home life, all of that. Think about, “What are the things that I could do to help people trust me? And what are the things I can do to encourage other people to be trustworthy?” because I think it will pay huge dividends.
Pete Mockaitis
All right. Jimmy, thank you.
Jimmy Wales
Great. Thank you.
Chris Bailey explains the science behind intentionality and how it can dramatically increase goal attainment.
You’ll Learn
- The 12 main values that drive everything you do
- The simple reframe that significantly boosts motivation
- How to deal with resistance to action
About Chris
Chris Bailey is an author and speaker who explores the science behind living a more productive and intentional life. He has written hundreds of articles on the subject and has garnered coverage in media as diverse as The New York Times, The Wall Street Journal, GQ, HuffPost, New York magazine, Harvard Business Review, TED, Fast Company, and Lifehacker.
The bestselling author of The Productivity Project, Hyperfocus, and How to Calm Your Mind, Bailey’s books have been published in more than forty languages. He lives in Ottawa, Canada. His new book, Intentional, comes out January 6, 2026.
- Book: Intentional: How to Finish What You Start
- Website: ChrisBailey.com
Resources Mentioned
- Study: “An Overview of the Schwartz Theory of Basic Values” by Shalom Schwartz
- Book: Solving the Procrastination Puzzle: A Concise Guide to Strategies for Change by Timothy Pychyl
- Past episode: 572: How Morning Practices Like Savoring and Investing in Calm Boost Productivity with Chris Bailey
Thank you, Sponsors!
- Monarch.com. Get 50% off your first year on with the code AWESOME.
Chris Bailey Interview Transcript
Pete Mockaitis
Chris, welcome back for round four.
Chris Bailey
Round four, Pete. Are you serious?
Pete Mockaitis
It is. It is round four. The last round was, oh, about five years ago, so it’s been a while. But we are using the same pen and the same microphone so I feel like, since I respect you and think you’re a genius, that maybe I, too, am worthy of some sort of props, but maybe that’s reading too much into things.
Chris Bailey
Has the pen helped?
Pete Mockaitis
It’s been pleasant. This is the Pilot Precise, by the way, RT, for those listening.
Chris Bailey
It’s the best pen.
Pete Mockaitis
Yeah, well, you raved about it in a previous episode, and I was like, “Oh, let’s check it out.” It was like, “Yep, I’m just going to buy dozens of these things.”
Chris Bailey
Yeah, I have friends who are into fountain pens and they have all these fancy pen rituals, pencil rituals, all these different weights. They send me these pens. They’re all garbage. I’m sorry if you’re a pen person. They’re all garbage, except for the Pilot Precise V5 RT. Come at me, pen people.
Pete Mockaitis
Noted. We’ll put that in the pulled highlight quotes there. So, well, I want to hear, we’re talking about your book, Intentional. It’s been about five years since we chatted. Tell me, what’s the most powerful thing you’ve learned in your life of productivity over these last five years?
Chris Bailey
About values. Now, before your eyes glaze over, whenever I’ve heard the term values, my eyes have glazed over. I am not exaggerating. When I hear the word values, I think of the corny corporate exercises I’ve done in the past where somebody like brings in a sheet of paper and there’s a hundred values and they say, “Circle the values,” and I like them all, you know, grace, humor, whatever. And there’s very little research behind those.
But it turns out, there is a fascinating body of research behind what we value on a fundamental human level, and that there are 12 main values that drive pretty much everything we do. And that when we don’t want to do something, we’re usually going against the grain of our values. And so, I’ve been into this idea. You know, we’ve chatted about this three, going on four times, this idea of becoming intentional.
I’ve always wanted to write a book on becoming more intentional, but I’ve never found enough stuff around values to share, stuff around intention to share, until I encountered values, which are the research shows, that’s been validated across 60 different countries, hundreds of thousands of participants, full credit where credit is due to Shalom Schwartz for discovering this methodology of motivation, essentially.
It was kind of the missing piece that pieced together all of the things that I’ve been incubating on intentionality over the last decade. And it was an unlock for me. It was as if everything was aligned. And I don’t want to oversell. I don’t think I’m overselling.
Once you see what the values are and stuff and how the different levels of intentionality in our life fit together, there’s beautiful, fascinating science behind it. Of course, we don’t always accomplish our intentions, which is a whole other thing, but it’s fascinating, it’s beautiful, and it’s powerful.
Pete Mockaitis
Well, that’s intriguing. And part of me is tempted to say, “Give me the 12 now. List them.”
But first, you say it’s a big unlock and there’s hard science and research. Can you tell me what are some of the main discoveries of this research and what impact does it make when you apply it?
Chris Bailey
So, there’s different fundamental motivations we have in our life. There are two kinds of axes of motivation that we have that motivates us in our work, in our life, any context that we’re in.
There’s whether we’re motivated to enrich other people or ourselves. And there’s whether we wish to conserve things as they are or improve things as they are. And so, these are the fundamental motivations in our life that our values fit inside of.
And the key to keep in mind is that, with all 12 of these values, we’re all different. Your values are different from mine. Although good pens aren’t a value, but there are associated values actually with a good pen and good microphones. We have the same microphone.
The key to keep in mind is we all have all 12 at a different level. So, there’s self-direction, which is going our own way. There’s stimulation, which is enjoying novelty in the moment. There’s pleasure, which is, you know, sense pleasure, it’s a good meal or a good bath or something. There’s achievement, so accomplishing good things.
There’s power, right, a power over resources and other people. There’s face is another one of the values, which is how we come across to other people. There’s security, so personal security and societal security.
Tradition is another value, so the customs that surround us. Conformity is very, interestingly, to me, a fundamental human value, you know, kind of this fundamental conservation of living within the expectations of other people. Humility is a fundamental value.
Universalism, I find to be a beautiful value, which is protecting and advancing the welfare of people and of nature. And benevolence is the final 12th value, which is kindness and serving others. And so, across, and all these values fit into those kinds of four motivations, ourselves or others, or improve and change.
And so, we all have all 12 in different extents. And anything that we could be doing in the moment, anything we could possibly be doing in the moment, fits inside of these values. A good pen is pleasure. That’s the pleasure value.
Pete Mockaitis
Pleasure. Stimulation. Power.
Chris Bailey
That’s stimulation maybe a little bit because it feels so good. Self-direction, if you chose it yourself. If you heard it from a friend, if everybody you know is using this same pen, that fits with conformity. Humility, using a simple $3 pen, or, however much this costs, instead of a fountain. Everything we do is motivated by these values.
And so, our values are the broadest intentions in our life. They’re what we ultimately hope to accomplish. And so, the more that the goals we have fit with these values, the more we actually care about them. And the more they feel like a natural extension of who we are. And then it goes down to the various levels of intentionality in our life, but this is at the very top.
Pete Mockaitis
Ooh, Chris, you know, as you were speaking, my natural consultant brain, thinking, “Is this a mutually exclusive and collectively exhaustive categorization set? Can I think of anything that does not fall into them?” And, well, I’ve only been thinking for about 40 seconds and I was having a hard time digging one up. So, we’ll say it’s pretty good.
Chris Bailey
Well, I can name one or two. I can name one or two.
Pete Mockaitis
Well, let’s hear it, yeah.
Chris Bailey
Yeah, health is one that doesn’t fit. But these values, they’re a motivational continuum. So, they are what could be possibly motivating us in the moment. And health is interesting. That was a big question I had when I looked at this theory, it’s like, “Okay, where is health in this?”
Pete Mockaitis
I think that’s power. I’ve got the power to get out of bed, the power to have the energy for the day, the power to walk up a flight of stairs.
Chris Bailey
Well, that’s the interesting thing. It depends on the person. So, women are more likely to see health as a pleasure value because they feel good in their body.
Pete Mockaitis
Being in pain sucks. Fix that shoulder with a physical therapist. Ugh.
Chris Bailey
Yeah, yeah, exactly. Yeah, it’s self-direction, right? You can go your own way. Some people see it as that achievement. Other people see their body as an achievement that they can, yeah, bro.
Pete Mockaitis
“Muscle ups, bro.”
Chris Bailey
Yeah, yeah, exactly. So, they’re a true motivational continuum. It’s beautiful that these are what drive everything we do. So, uncovering the ones that actually motivate us is paramount for achieving the goals that we set.
Pete Mockaitis
Yeah, it is interesting because I’ve noticed that I really like feeling like a winner – achievement – and I really don’t like feeling like a loser. And some of this can even be neurotically nonsensical, you know, in terms of, like, if I’m taking out my trash and I can’t fit the week’s trash into my trash bin, I feel like I am being a poor steward of the earth’s resources because it’s like, “Oh, you know, this huge garbage bin wasn’t enough for you, huh? So now the whole world has to see, ‘Oh, that family can’t handle consuming a moderate amount.’”
And so, it’s like, “But, like, who cares? Like, nobody actually cares.” And yet this is, this is inside of me. And it’s kind of, and I guess there’s maybe conformity, right, “Hey, all of us fit our stuff inside the trash bin.”
Chris Bailey
Yeah, there’s universalism in there, wanting to protect the nature. There’s face, right, looking at how you come across other people. There’s achievement, wanting to crush the garbage down to a certain extent. It’s all in there. And so, this is the fascinating thing about values, is because they’re essentially our ultimate intentions in our life. They’re what we care about most.
But every single intention that we set, whether deliberately or not, because that’s another curious thing, intentions don’t have to be deliberate, they can be automatic. A habit is our brain forming an intention that will do something automatically for us. Maybe that’s too much to get into on the podcast, but in every moment, especially when we make these deliberate intentions, we’re automatically evaluating a series of options before us using our top values as a trade-off.
And so, the values that tend to win out in the moment tend to be our strongest values. It’s interesting. They’re behind the scenes of our life pulling, because, of course, we don’t always follow through with our intentions. Intentionality, it’s incredible, it’s beautiful, but the road to hell is also paved with good intentions. But these values are behind the scenes because they’re our true motivational nature, pulling on the strings of what we will do and what we won’t do.
Pete Mockaitis
Yeah, what’s so intriguing is, as I’m thinking about, yeah, with any goal you could feel them at war. And I’m thinking about, I’ve been on both sides of the overweight threshold, according to the body mass index. And food, I mean, boy, it is stimulation, it is pleasure, it’s so good.
And yet, when I am having, on a hot streak of weight loss, what’s doing it for me is achievement in terms of, I’m tracking those calories, like, “Look at that, another day a deficit. Winning!” It feels good. And so then, they’re at war. It’s like, “Well, do I want the pleasure of this cheesecake or do I want the pleasure of winning a caloric deficit for the day?”
Chris Bailey
Yeah, and that’s the thing with these, like, weight loss goals, is an interesting one because 40% of the world’s population at any given time are trying to lose weight, so about half of us are. But we tend to go about goals like that the wrong way. So, we set a goal, ‘Yeah, I’m to lose 10 pounds this year so I look good, have six-pack abs by beach season.” We have this idea of ourselves.
But a goal like that is built around face, right, the value of face. It’s how we come across to other people.
But if your top value is pleasure, and maybe self-direction or something, a different goal would be better, right? Like, instead of that lose the weight to have six-pack abs by beach season built around face, maybe it’s, like, experiment with three different ways of eating – self-direction – to find the one that’s most enjoyable.
And so, you can have the same set of actions that lead you to different goals, but they are actually motivated. And this is something that is also interesting about intentionality, is there are many, and I love this idea. I love this idea.
So, there are many different layers of intentionality in our life. So, we set intentions across all kinds of different timelines, right? We have our values, which are our ultimate intentions. They last the length of our lifetime. Then we have the intentions that are a bit shorter than that, which are called our priorities. Like, “Be healthy” would be a priority.
Then we have intentions that are shorter than that, still, which we call goals, things we want to accomplish in our life, stories of change that we’re creating. Then we have, you know, we kind of go down in timeline. Then we have the plans that we have. Goals should ultimately lead to the plans that we set.
And then we have the smallest of intentions at the very bottom of this. I call it the intention stack in the book. It’s just, essentially, all the layers of intentionality in our life. And at the bottom, the very bottom, we have the present intentions we have in the moment.
So, somebody listening to this podcast, the present moment intention might be, “Listen to the podcast and enjoy it.” Then the plan might be, it might fit inside of a broader plan, like a chore to wash the dishes or something. Then it might fit inside of a goal, like in, you know, “Learn more about self-development and how to be awesome at my job.”
Then it fits inside of a priority, which is “Make a bigger contribution,” which fits inside of a value of, let’s say, benevolence, helping other people, plus achievement. And so, there’s always this stack on top of what we’re doing in the moment. But sometimes it’s aligned to what we care about. Other times we don’t care at all.
And so, it’s fascinating when you begin to deconstruct intentionality and look at the science of it, what it’s shaped like, and how it works, and how we can kind of, I got to say harness, it’s kind of a corny word, but like harness it to do the change that we want.
Pete Mockaitis
Well, yeah. And I think this is, it opens up, and you called it an unlock. It does open up a lot of possibilities in terms of, “Oh, I wasn’t even thinking about approaching this thing with that value as a lens, but because I’m really into that value, it may well behoove me to explore how can I do such a thing to provide for more humility or universalism or benevolence or whatever the thing is.”
Chris Bailey
Exactly.
Pete Mockaitis
You know, Chris, I want to maybe take a little time out here because it almost feels as though some of these values are good-er, more morally virtuous, right, true, noble than others in terms of, like, let’s say universalism, benevolence, humility. We think, “Oh, what a swell fella, or a gal, who exhibits a lot of those things,” versus, “You know what I’m really about is pleasure and power and looking awesome. That’s kind of what’s important to me.” That almost feels hollow or like a less good life.
Chris Bailey
Yeah, I talk about this in the book, too. My top value is self-direction. It’s not even close. But my number two is pleasure. I love nothing more than to…well, I like self-direction more, but I love nothing second more than to just lie on the couch after a busy day and put on a good show or a podcast, and order some Uber eats, like a big sushi platter and just indulge for the night.
And this was a very reflective process that I went through in piecing together this book is, “Are there good values? Are there bad values?” And I’ve, ultimately, come to the conclusion that, “No, there aren’t good values or bad values. There are certain values that are more conducive to certain goals.” But if you’re able to accommodate the values of others, in addition to the values of yourself, I think you’ll be fine.
Power is one that comes to mind, too, because out of all the values, out of all the listed values, it’s the very least common. It’s at the very bottom across the population level, and, sure enough, it is for me, too. I never want to have power over any other person ever in my life.
But, power, if you look at the world around us, it has a place in what we do. Any organization that has a hierarchy, for example, you have different layers of the hierarchy, and you need power within that organizational structure. Every charity has a CEO. Every nonprofit has a CEO. Every congregation has a priest.
So even the most virtuous of places, these values have a place. Conformity, right, maybe also a frowned upon value. But there’s a great benefit to going along with the expectations of others in certain scenarios, right, for accommodating other people. I’m the most self-directed person you might ever meet. And I don’t want to listen, you know, if somebody else tells me to do something, it makes me not want to do it.
But I remember my grandma telling me, like, “Wash the dishes now,” and I’d do it because I had such a respect for her. And that conformity and tradition, all these values live relative to one another, too, which is interesting. They live right next to each other in these values pie, this pie hierarchy – pie-archy.
Pete Mockaitis
Yeah, I think that is a really intriguing perspective there that these values, they’re motivational forces and they don’t necessarily lead to great or catastrophic outcomes for civilization or humanity when they all kind of come together. And what’s interesting about power is you said, you define it as, it is power over others or yourself or circumstances.
Chris Bailey
Or resources, yeah.
Pete Mockaitis
Or resources, yeah. I’ve got a, my buddy Ronnie, he had a funny saying, he said, “Laundry is power.” I was like, “What?”
Chris Bailey
What does that mean?
Pete Mockaitis
And then I think, one day, I had done all, I mean all of my laundry, and I’m beholding this dresser full of organized socks matched and shirts folded, underwear. And then, as I beheld this arsenal of complete laundry, it’s like, I really did, I was like, I’m ready for anything. I’m ready for anything. I felt powerful in that moment. I understood what he meant.
But I, like you, have no interest in controlling the legions of people. In fact, that sounds like a huge headache, like, “Oh, my gosh, that administrative load would be such a stressor.”
Chris Bailey
And that’s the interesting thing. I don’t want to, like, overload people with this value stuff right now, but I break it down more into, like, you can break down the 12 into 19, actually, of them, where you can break down power, for example, into power over resources and other people. Self-direction, you can break into self-directed thought and self-directed action.
And so, it’s very interesting that there’s this. It’s just a fundamental organization to human motivation that we don’t understand. But when you do understand it and you can fit through these different layers of intentionality, the goals that you have with your values, and then see how those goals connect with the daily actions that you need to take, what you get is your goals become a vessel between who you are on that fundamental level, so what motivates you, and what you do on a daily basis.
And so, we are sharing the fat loss example. Same set of actions, but with a different frame around them, with a different motivational frame around them. Imagine if your goals were all like that. This is actually the thing that bothers me about a lot of goals and goal books and stuff like that, is when you look at the actual research on goals, we have to achieve them by becoming more intentional across the different layers of intentionality in our life.
But we so often see them as static, something that shouldn’t change. But goals should evolve. We should be editing them. We should be dropping them. We should see them as fluid things. And goals, in my view, they’re basically just a story of change that we’re in the middle of creating in our life. And we need to see them as more fluid and ready to change, because so often a goal is really no different from a prediction of what we believe will happen.
Pete Mockaitis
Yeah, well, this is really juicy, and so, conceptually, we can hang here for a long time, but I’d love to perhaps shift gears into, “Okay. All right, Chris, my mind is blown with regard to these values, they’re important, and I should be considering them thoughtfully as I’m trying to go about making stuff happen.” Could you share with us a little bit of the step-by-step in terms of, “Okay, I got a list of values. That’s kind of cool. I got some things I want to be achieving, what am I doing with that?”
Chris Bailey
Yes, okay. So, let’s get tactical with this stuff, because, yeah, we have to be. So, you have your values, maybe you do a values test. I partnered with a company to build a test for the book. You don’t have to take that though, because there are certain ones that’ll kind of attract you more, and others that’ll naturally repel you.
And so, what you’ll find is that, when you look at those 12 values and the pie that they’re a part of, you’ll naturally gravitate to some and be repelled by others. Look to the ones that you naturally gravitate to and pick the top two, let’s say, two, three. Stop there. These are what you build your goals around. And then you have a list of goals, right?
How often do we actually sit down and capture the goals that we have that we’re in the middle of creating? And so, I highly recommend a weekly review where you sit down, you capture, and then you review, on a weekly basis, all the goals that you’re in the middle of creating.
And so, every goal, so in the book, I call it the intention stack. So, at the top, it is values, then priorities, then goals, then plans, then intentions, daily, weekly intentions. And, ideally, during this weekly review, or whatever cadence it makes sense for you to review these goals on, you want to look at both your values, which is the motivational force, and the actions, which is how you actually make progress towards these goals in the first place.
So, I think step zero is realizing that goal attainment, the process of goal attainment, is it’s not 99% action. It’s like 80% action, 20% planning. We need to plan more and act a little bit less, because by planning more, we actually act more over the longer arc of time, especially once the initial burst of motivation wanes.
So, during that weekly review, edit your goals, edit your goals, edit your goals. How can you edit them, like with that weight loss example, how can you edit your goals so that they fit more with what you value, so you actually care about them, right? Because the easiest way to tell if something’s a priority to you is you’ve achieved it already, right?
So, the fact that something is yet to be achieved, probably means, on some level, that it isn’t a natural fit for who you are, because it doesn’t fit with that motivational force, right? We do what it makes intuitive sense to do in the absence of intentional action.
So, during that weekly review, how can you edit your goals so they’re more in line with what you value? And how can you bite off a little bit of the goal until your next review, whatever cadence you’re doing this over?
So, if you’re doing it over a week, what do you want to bite off in the next week? Make sure it’s enough that you can chew, or not too much that you can chew, whatever the analogy is there, and schedule time blocks for it.
Practice intentionality on a more granular level. Set a few weekly intentions. Every day, set a few daily intentions so these intentions can actually flow down into one another. So, edit your goals. And, as well, if you find that a goal isn’t motivating that you can’t edit it to the point that it fits into your life, consider dropping it.
Because then we get a chance to try more goals on for size that are actually a fit with what we want to get out of our life and our motivational nature. So that’s one way is that goal review where we bridge, essentially, who we are with what we do.
Pete Mockaitis
Okay, very cool.
Chris Bailey
There you go.
Pete Mockaitis
And then I’d love to dig into some of your perspectives for, if we’ve got a goal that is not so appealing, well, one, you might learn via the editing process that it needs to be dropped. But before that, do you have any cool examples of folks who were able to just turbocharge motivation and progress by thoughtfully tweaking their goals so they are better fits for their values?
Chris Bailey
This is interesting, right? Because is gray intentionality such a beautiful idea? And then the rubber meets the road, right? The road to hell is also paved with good intention. So, intentionality is both vital because any time we act towards our goals, there was an intention behind it.
But sometimes, it’s also useless because there’s a lot of times when we set an intention only to not follow through, or procrastinate on an intention, or lack the desire to accomplish it. And so, there’s essentially two factors in a goal, in an intention, in something we want to do, that attract us or repel us away from that thing.
So, there’s aversion, which, you know, it’s like, “Get this out of my face, this goal out of my face.” And then there’s desire, which attracts us to a goal. And both of these are forces that work with every single goal that we have. And they’re different over the timeline of a goal, right?
So, if you’re at the very beginning, the very inception of a goal, your desire is going to be through the roof. Your motivation level is going to be so, so high. But then reality sinks in, “Oh, there goes gravity,” and then our motivation level plummets, and our desire can turn into aversion.
So, a lot of it’s like realizing where you are on that timeline of goal attainment. But aversion is a very interesting feeling that we experience along the way, because aversion is what leads us to procrastinate on something.
So, the more aversive something happens to be, which is a combination of “How boring is it? How frustrating is it? How unpleasant is it? How far away is something in the future? How unstructured is it? How meaningless is it?” so lack of connected with our values, the more of these triggers that a task has, the more likely we are to procrastinate on it.
And so, that’s another key is realizing that and understanding what triggers a task sets off. So, if something’s unstructured, like meditation is a great example of this. We were chatting a bit about meditation before we hopped on the horn here and hit the record button.
It’s one of the most aversive things that you can do, right? It’s helpful because it’s so aversive, right? If you can focus on your breath, you can focus on anything. If you can become engaged with your breath, you could become engaged with anything because it’s so boring, because it’s so aversive.
But when you accommodate the fact that it’s so unstructured and unpleasant, by working within the aversion, so a simple example of this, shrink your resistance to it. So, this works for meditation, it works for anything you don’t want to do that takes a little bit of time.
You might have a conversation with yourself like, “Okay, do I want to meditate for half an hour today? No. No, I don’t. What about 25 minutes? No. What about 20? No way in hell. What about 15? Yeah, I could do 15.”
And so, you essentially shrink the task until you no longer feel that resistance level so that you’re at a point where you can get started on the thing. And that increases your desire to actually moving between different levels of this intention stack. You move from that goal layer to that action layer that’s at the bottom.
And so, when something’s unstructured, that’s a sign you need to add structure. When something’s meaningless, it’s a sign you need to connect a goal with your values. Edit it so it’s aligned with your values. When something’s boring, frustrating, it might be a sign you need to step back and plan out on a logical level how you want to become more intentional about that thing.
Pete Mockaitis
And I’m thinking about, well, these procrastination triggers, I think I learned them from you as well as what are the top researchers on procrastination. What was the book? I think we both read it.
Chris Bailey
Was it Tim Pytchyl?
Pete Mockaitis
That’s the one. Thank you.
Chris Bailey
Oh, Tim is fantastic, yeah.
Pete Mockaitis
Yes, and he lists those out, and that’s helpful to think about it on those dimensions. And I guess that’s what, to your point about doing more planning, that’s what you can, you can get kind of meta with this. It’s like, “Huh, I have not done these three weeks in a row. It seems something is amiss here.” And so, rather than say, “Well, I just got to knuckle down and buckle up, you know, to get after it.” It’s like, well, maybe there’s some redesign that needs to be working here, or maybe the goal needs to be abandoned.
Chris Bailey
It’s interesting, in writing this book, I chatted with lot of monks, as well as scientists, because monks study intentionality on a different layer than scientists do. They’re not observational, they’re experiential. They observe the causes and effects and conditions in our mind, and we can learn a lot from them.
And one interesting thing that I asked one of the monks, I was deep into the research on where intention comes from, because we set all these intentions, right? And some of them we set automatically, which I call our default intentions.
‘Cause some come from automatic sources. We are on a road trip, we need to go to the bathroom, and so we set an intention at the next pit stop, “I’m going to go to the bathroom.” We don’t even think about this. We do it automatically. So, biological sources, sources to avoid pain and experience greater pleasure also lead to a whole other wealth of intentions.
The lessons we have learned in the past. So, the things we have learned changes, they change our relationship with what we know to be true, which leads us to set an intention differently the next time, whether we do it out of habit or energy, or whether we do it deliberately.
But one source that a monk mentioned that wasn’t in the research that kind of allowed me to piece together other areas of the research was – and he phrased it so beautifully – is our self-reflective capacity.
Our self-reflective capacity, by looking inward, asking questions of our inner world, we are able to set different intentions from the ones that we would do out of biology, or out of basic pleasure and pain, or out of lessons we have learned, to truly go our own way and set the best intentions that lead us to the outcomes that we want, whether we want to be more accomplished at work or lead a more enriching, meaningful life by connecting with our values at work, at home.
We need to tap into that capacity more often. And so, it doesn’t just have to look like meditation or journaling or something. It can look like just going for a walk and then letting your mind go to where “What problems are you in the middle of? How can you solve them with setting intentions that are more conducive to what you want?”
They could look like brainstorming with somebody, so somebody that really gets you thinking. It can look like asking questions of your inner world and looking at what arises out of them. Like, we all have these moments where we go from autopilot mode to being deliberate about what we do.
So, if your whole family was gone for one morning or something, and you woke up and your phone wasn’t there, and so you couldn’t rely on habit in bed and you just laid there. Eventually, a moment would come where your mind would set an intention to do something, where you would set an intention to do something, whether it was a habit or whether you waited for a little bit longer to look at what you truly wanted to do in that moment.
It’s the same like if you’re listening to music and a song ends, pause, and then eventually your mind will set an intention to listen to the next one, which will end up being more enjoyable than the one that you were just listening to on autopilot.
Life is the same way, right? It’s by charting this deliberate course that we experience more meaning because it’s in connecting with that self-reflective capacity that we can be with what we value. And so, our values that compete with one another in each moment, the ones that are truest to us can win out, and then we can truly, truly go our own way.
Tthe truest intentions that we can set, like you were getting at, they come from not just acting, but reflecting, whether that’s on a logical level or on a more intuitive level where we look and connect with that self-reflective capacity that we all have.
Pete Mockaitis
Yeah, I hear you. Autopilot is, in some ways, the opposite of intentionality. I mean, even if we establish those habits intentionally and we’re executing, living them out in an autopilot mode – I’m getting philosophical – on some dimension, the autopilot is intentional, but from like a presentness way of looking at it, it’s not so much.
Chris Bailey
Well, this is why, in the book, I delineate between our default intentions and our deliberate intentions, because we have these default intentions that we have. Habits are great. Habits are amazing. But when you look at an intention as just a plan that we will do something, this habit energy, as I refer to it in the book, and as monks refer to it actually, there’s quite a bit of power in that.
We don’t have to worry about making ourselves a cup of coffee in the morning. Our brain, our body goes through the motions automatically until we’re sitting there like with a cup of coffee. We don’t even have to be fully awake enough to notice it.
But you’re right that, eventually, that moment comes. It’s kind of like the movie montage where, like, somebody’s living their dull humdrum life and the scene is gray and it’s raining outside, they’re going through the same motions. But then, like, boom, somebody dies, or something pivotal happens, where that character has a fit of awakening and decides to do things differently, and decides to go in a different direction from the one that they were going in.
And then like cut to the badass working out montage, or like somebody writing for hours through the night, or piecing together some math problem, you know, something like that. But we all have these similar fits of awakening.
And all that is, is going from the habit energy of relying on our default intentions to the deliberate intentions that we can all set in the moment. Well, here’s something mind blowing about default intentions.
Pete Mockaitis
Oh, yes, please.
Chris Bailey
Our values are constructed out of our default intentions. Like, seeing that in the research, it sent shivers down my spine, I’m not going to lie. It all came together. Our values are who we are on a fundamental human level. They’re what motivate us on a fundamental human level. And what motivates us more than who we are by default? Our default intentions.
And our deliberate intentions, the life we want to live, the contributions we want to make, the work we want to do, that’s the layer of deliberate intentions we layer on top of who we are by default. So, it’s, really, when you look at the science of intentionality, it explains everything that we do, everything that we think, and everything that we are. And molding that is the ultimate skill, I think.
Pete Mockaitis
Whew, that’s good stuff and worthy of chewing on and reflecting upon in depth. I know we’re at our last few minutes, but I want to hear two quick things from you. One, tracking goal progress, something that you’re into, you write about. Do you have any favorite principles or tactics or systems in that zone?
Chris Bailey
Oh, yeah, tracking your goal pace is one of my favorites. So, I use this whenever I write a book, where I make a spreadsheet. Two lines. One is my pace line and the other is my progress line. And it works for any cumulative goal, miles ran, for example. And all you do is you print it off and so you track between today and your target day.
You have a pace, say you want your book to be 70,000 words, so you have the pace line that goes up at this beautiful linear pace. And then you have your actual word count relative to that. Simple tactic, but incredibly helpful for goal tracking.
Pete Mockaitis
I’ve made the spreadsheet myself in many contexts.
Chris Bailey
Oh, man, we’re living the same life, yeah.
Pete Mockaitis
Yeah, absolutely.
Chris Bailey
Same pen, same mic, same sheet.
Pete Mockaitis
And you have said it a few times, and I love it, that any productivity intervention must earn back the time that you spend on it, or else it is counterproductive. Since I like to talk about favorite things at the end of each episode, can you share with us a couple favorite tools, tactics, productivity interventions that just crush it on this metric of yours?
Chris Bailey
Okay, I feel I’ve mentioned this on a previous one, but it’s five years ago, so maybe your listenership has cycled out or something. No, they’re probably still out here.
Pete Mockaitis
Never. They’re still there. They’re still there.
Chris Bailey
Yeah, okay. Hey, everybody, again, I hope you remember me five years ago. Rule of three. At the start of each day, fast forward to the end of the day, what three things will you want to have accomplished? It’s my favorite intention setting ritual. I do it every day, every week, every year, so that when I do my daily intentions, they can feed into the weekly and the yearly ones. They all work together like beautiful magic.
Tools. Tools. Man, you know what? I’m going analog these days. I love having a physical book, because I feel my eyes are glazing over from looking at screens all day long, and just practicing a bit of interstitial journaling between tasks. It allows me to really just reflect for one short little paragraph, “What do I really want to get out of what I’m going to do next?” So, an analog pen, of course, the Pilot Precise V5 or V7 RT.
Pete Mockaitis
Beautiful. All right. Well, any final thoughts, Chris?
Chris Bailey
After looking at the research on intentionality, I used to think intention is beautiful, and you see how complicated it is. And it’s in that complicatedness that I think we see our humanness, right? And so, I really think that it’s intentionality that makes us human.
And by connecting with that, you know, talked a lot about deliberate intent, we got to love our defaults, too. They’re who we are. They make up our values. Love your defaults and then you can layer on even better goals, better intentions on top of those.
Pete Mockaitis
All right. Chris, thank you.
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