
Jia Jiang explains his four-step framework for making discipline and success easier.
You’ll Learn
- The problem with hard discipline
- How to make your goals feel easy and enjoyable
- Two handy tips to defeat procrastination
About Jia
Jia Jiang is an award-winning speaker, entrepreneur, and the bestselling author of Rejection Proof. As a keynote speaker, Jiang has spoken at corporate and industry events and in front of 400,000+ live audiences. His TED talk has millions of views and is ranked in the top 1% among all TED talks. Jiang is also the owner of Rejection Therapy, which helps people overcome their fear of rejection and develop mental resilience. His work has been featured in Time, CNN, Today, Business Insider, The Guardian, Wired, and more.
- Book: Easy Discipline: An Unconventional Way to Achieve Ambitious Things
- TED Talk: What I Learned from 100 Days of Rejection | Jia Jiang | TED
- Video series: 100 Days of Rejection Therapy
- Substack: Easy Ambition
Resources Mentioned
- Book: How to Win Friends & Influence People by Dale Carnegie
- Book: Go for No! Yes is the Destination, No is How You Get There by Richard Fenton and Andrea Waltz
- Book: Made to Stick: Why Some Ideas Survive and Others Die by Chip Heath and Dan Heath
- YouTube: Caroline Girvan
- Game: Slay the Spire II
- Past episode: 016: Going for No with Andrea Waltz
- Past episode: 1167: Mastering the Three Elements of Charisma with Olivia Fox Cabane
Thank you, Sponsors!
- Shopify. Start your free trial at Shopify.com/awesomepod
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Jia Jiang Interview Transcript
Pete Mockaitis
Jia, welcome!
Jia Jiang
Thank you for having me.
Pete Mockaitis
Well, I’m excited to be chatting. Your name has come up a few times over the years with How to be Awesome at Your Job, guests sharing transformational things they’ve read or tried. So I must start by hearing the tale of your 100 Day Rejection challenge.
Jia Jiang
Yeah, so I’ve been wanting to be an entrepreneur for all my life, but I had to delay it for a long time because I was kind of afraid of rejection. You know, I was afraid of failure, I was afraid of rejection for my family.
Eventually, I started my company at age 30. But then, as soon as I got rejected for funding, the first thought that came back to my mind was, “I’m not good at this. The guy, the potential investor, he knew much more about business than I did. So if he didn’t like my company, maybe I should change my idea or even not do this altogether.”
And that’s really a signal to me, it was like, “Man, I’m really afraid of rejection. Like, that’s a loser thinking. No people who are successful at anything can think like that, that they just wanted to quit after a rejection like that.”
So I said, “Let me overcome my fear of rejection.” Like, that’s my number one goal, overcome my fear of rejection. But I want to do it in a fun way. I’m like, “What can I have fun with rejection?”
So I started this project called 100 Days of Rejection Therapy, where, every day, I would go out and get rejected on purpose. And now I film myself doing this using my phone, and I made my first vlog. So, you know, I would go out and, like, I would ask a stranger for 100 dollars. And then the next day, I would go to ask for a burger refill after getting a burger for lunch.
Then there’s another day, I went out and I asked, I went to Costco and asked to speak on their intercom. I got a “no.” And then another day, I went to a PetSmart to ask for a haircut, to get a haircut. I asked for a German Shepherd cut, and they said no.
But I didn’t die, you know? At the beginning, I thought I was going to die. But not only I didn’t die, it was pretty fun. I had a great time, you know, and I had a good energy, you know. I was easygoing, I was making jokes. And then people started to say yes to me.
So my most famous video is, one day, I went to a Krispy Kreme Doughnuts shop and asked them to make me donuts that look like Olympic rings. There’s no way they’re going to do that, right? I’m just going to go in and make a joke.
And the donut-maker took me so seriously and, fifteen minutes later, she came up with a box of donuts that looked like Olympic rings. And she was like, “This is from me. This is my pleasure.” So she gave it to me for free.
And that video went viral. And that’s why a lot of people probably recommended my name to you, probably saw that video and saw my TED Talk later on, talking about it. So, yeah, that’s 100 Days of Rejection Therapy. It was a lot of fun.
Pete Mockaitis
Well, it’s fun and it’s viral. Can you tell me, was it transformational for you?
Jia Jiang
Yeah, on a couple of levels, first of all, at the beginning, my goal was I want to come in and just ask and I don’t know what’s going to happen, right? But then I found people started to say yes to me. And I was like, “Wow, the world is different than I thought.”
I thought the world is according to a script. You ask for hard things, people say no. You ask for easy things, people will say yes. As it turned out, when I had this mindset of, “I won’t take myself too seriously, I’m going to have fun. I’m going to just go confront these fears and with a fun attitude,” that the whole script flips.
Sometimes it’s the hard request, the audacious ones that get yes, because people are curious. But also, because of me, right? I’m very relaxed and I’m fun-seeking. In that way, I exude a type of energy that people don’t push back to, right?
Sometimes if I come in really hard, people feel cornered, and they will say no to me. But if I come in very relaxed, then people would be like, “Ah, okay, maybe I’ll say yes.” So to me, it’s just a great lesson. The world is very different than I thought.
So I started teaching other people to say, you know, one, don’t be afraid of asking. Secondly, try to have fun when you’re asking. Try to have fun in whatever you do. The result will surprise you.
Pete Mockaitis
Certainly. Well, so that’s a nice mindset, worldview, to not only enjoy life more but get better results. I’m also curious to hear, now how does rejection land for you. You’ve now had the 100 Days of Rejection Therapy, and I imagine subsequent rejections over the course of life and business. Tell me, how is a rejection feeling nowadays?
Jia Jiang
Yeah, instead of seeing rejection as a failure, now I see this as a start of a negotiation. I started just to be like, “Okay, cool. It’s fine I get rejected. But can I try something else? Can I ask for something else?” And I would try to ask for different things in a very fun way, in a very relaxed way.
So I no longer see rejection as a sign of signal failure, signals end. I see this as a signal to ask for more, to keep asking and have more fun to do this. So, yeah, that’s a complete mindset shift.
Pete Mockaitis
Oh, that’s great. So it’s no longer a crushing emotional situation. It’s just like, “Oh, kind of interesting. Let’s try something a little different this time.”
Jia Jiang
Yeah. I mean, sometimes it’s like a negotiation, right? It’s like, you know, “Hey, what can I do? I can’t do this. Can I do that? If you don’t like this, why don’t you like it? Okay, I learned a little more any way I can get yes.” So I started having this dialogue with the person who rejects me.
Pete Mockaitis
I dig that so much. And, I’m thinking, it totally checks out with psychological research on exposure therapy. And I lived it myself with my first book. Back in the day, I sent out a whole bunch of one-page query letters to publishers and agents, and then they would come back. And I was actually wonderful to have the experience of being rejected over 100 times via letter because I could choose, “When do I open these letters?”
It’s like, “Ooh, I’m feeling down right now. Meh, let’s maybe wait till after lunch.” And then, “Okay, now I’m ready to face this letter. Oh, and it’s a rejection. Oh, and it’s another rejection.” And, sure enough, having lived that exposure, afterwards, rejections seem like no big deal. It’s like, “I’ve been through this over a hundred times. Is that all you got?
Jia Jiang
I love your approach to it because you kind of took control of this thing. When people get rejected, they feel they lost control, right, other people are telling them what to do. But you took control of this whole process, “Even though I got rejection letters, I get to decide when to open them. I get to have the mindset that, hey, these are fun. These are, like, things that are helping me to overcome that fear,” so you decide.
This mindset is all about initiatives, right? Who’s taking initiatives? Who’s doing what to whom? If you let the world do rejection to you, then you can feel very down. You can take it very personal. But you go to the other route where, like, “I’m going to do this to rejection. I’m going to have fun with rejection.” So who’s taking the initiative, like, determines how you feel and what’s your next step.
Pete Mockaitis
Yeah. I love it so much. We had an earlier guest, Andrea Waltz, who talked about go for no. And so it changes your whole perspective if you’re having fun with it. And, sure enough, along the way, you get some yeses, and they’re surprising, and it’s fun.
And then it just sort of changes the whole equation, it’s like, “Oh, okay. All I need to do is ask a hundred people. And then, you know, one to six of them will probably say yes. I only need one. All right. Well, let’s get to it. Away we go.”
Jia Jiang
You can ask more people, right? You ask more people, you can ask differently, the same person differently. You can ask again that person more times. You can change your location, even your environment to ask, right?
Sometimes you’re at work, you ask for something, “Oh, it didn’t work. Okay.” You ask again. Then the next time, where you go to, you have a beer or somewhere. You ask again, right? Under different circumstances, you ask.
So there are all kinds of levers you can pull after getting rejected. But most people will just get rejected, they’re like, “Oh, man, that sucks. That’s the end, right?” But shift your environment, shift whatever, right? You can try it again, so.
Pete Mockaitis
Well, Jia, I’m going to try a hard segue here. Sometimes the rejection seems to come from within. We want to do a thing, and we just can’t muster the energy, motivation, discipline, gumption, whatever, to get her done. Your latest book is called Easy Discipline: An Unconventional Way to Achieve Ambitious Things. Ooh, that sounds real nice. Lay it on us, how do we make discipline easy?
Jia Jiang
Yeah. So for most people, we try to think about discipline as a combination of willpower and pain tolerance, right? So I grew up in China, and I grew up with this idea called chi ku. In Chinese, it means eating bitterness. It means you have an ambitious goal, right? But to achieve that, you got to eat more pain, eat more bitterness than other people.
If you eat bitterness, you’re going to eventually find your way to success. And that’s called Chuku. But the problem is I suck at eating bitterness. I don’t like eating bitterness. And it’s against human nature because, like, your motivation runs away. You start something, then, very quickly, you learn you don’t like it but you have to keep doing it because you want to succeed, you want to achieve your goal, right?
So if you let the outcome you want to achieve provide the motivation for you to keep going, that will run out in no time. And then you’re going to start not liking yourself. You get disappointed, you lose confidence. You’re like, “I’m not made for this. What’s wrong with me?” That’s a loop that a lot of people have.
You see every year, people, there’s about half of the American population make New Year’s resolutions, right, “A new year, I’m going to lose weight,” “I’m going to find a new job,” “I’m going to make more money in the new year,” and all that, “Find love.”
And then, by February, it’s done. Like, only 9% of people who make New Year’s resolutions keep them throughout the year, by the end of the year. Why is that? Because we set these outcomes we want to achieve, and somehow using this outcome to motivate us and it doesn’t work. It works for someone, I’m not saying for everyone, but most people, it doesn’t work.
And I call this bare knuckle grinding through your way to success, hard discipline. Easy discipline, on the other hand, is later on I found in life, because I failed all my life, like most of my life, because I tried hard discipline, and I was just hating myself.
And then I started trying easy discipline, which was, “What do I like to do?” Instead of just thinking about the outcome I want to achieve, “Can I find things I like to do? Can I just start with easy? If something comes to me easily, I would just do it anyway,” right?
Like, I used to love playing video games. And I played for a long time, video games. And that wasn’t discipline. No one’s telling me that, you know, “Wow, you’re very disciplined in playing video games,” because I just love doing it.
But why when it comes to work, something that’s important, we feel like we have to feel like a prisoner, we have to feel hard, we have to endure the pain to actually achieve those outcomes? What if you just have that same mindset of, “How can I play? How can I turn my pursuit, my work into play so I can keep going?” And that’s what easy discipline is about.
Pete Mockaitis
Well, that sounds delightful. And I have often wondered this. Indeed, I, too, enjoy video games. Recently, “Slay the Spire II,” it’s so good. And I will play it for more than maybe I want to, maybe more than I plan to over the course of a week.
And I thought, “Boy, if only doing the things that, you know, build wealth, health, spirituality, other goals, felt as appealing and fun to me as this video game, that would be amazing.” And so tell us, is that possible, and how?
Jia Jiang
A hundred percent. I’m not saying everything can be turned into video games-type of addictive, right? But it can get to, it’s just, I mean, there’s a spectrum, right? On one hand, it’s just dreadful. You do the work, you’re just like, “I got to do this, my goodness.” On the other hand, it’s just so delightful you cannot stop.
Most of our work, somehow, at this lower end of that spectrum, if you can just move that to the middle even, right, make this somewhat fun, make this be like, “Oh, I had a great time today working. I can’t wait to do it again tomorrow,” then that’s how you become much more successful.
I’ll give you an example. For a long time, I didn’t like exercise. Because the idea of me going to the gym to exercise, it was dreadful. And I tried it, you know, I bought gym memberships and I used it for a couple days, and they just go to waste.
I would go to the gym, and go there and sit there to see, “What do I do, man?” I’ll see all those machines, “That guy looks good. He’s doing this. I’m going to do that a little bit. And this guy’s doing this, I might do that a little bit.” Like, afterward, I was drained. I’m like, “Why do I have to come in for a buffet of movements, none of them I like?” And then, because of that friction, I don’t go anymore, right?
So I was like, “Okay, how can I remove all the frictions, and turn that into something fun?” The turning point is I started, I’m sure you’ve heard of this, P90X was actually a big turning point for me.
I started doing it because the guy, Tony Horton, he was the trainer on the DVD, right? And he was fun, and I didn’t have to think what to do. If I didn’t have to think what to do, just tell me what to do, and I would do it, and the workout is hard.
And then, afterward, I feel good. My body started to change. And then I started doing that again and again. I started doing different programs. Now, I follow this woman called Caroline Girvan. She does that on YouTube, all for free. I just follow what she does, you know, and I can’t wait. Sometimes, I feel if I don’t do it, I feel bad. And then I bought a Peloton, and I just follow Peloton. Like, they just tell me what to do, there’s programs.
So I removed all the frictions, and not only frictions, those exercises turn into fun. And now they became what I do every day. I turn this type of thing to exercise. I became a better worker, a better salesperson by using easy discipline. I became a better father by doing easy discipline. So I turned all kinds of goals I have in life that I’m not good at into something that I enjoy. And now I have a great time in everything I do.
Pete Mockaitis
Well, I like that a lot in terms of you identified a friction point, “I don’t know what the heck to do,” and then you found a solution, “Ah, the P90X guy tells me exactly what to do. Friction resolved.” And then you do it, you feel good, you see a result, and then you look forward to it.
So it’s a very beautiful pathway by which momentum is liberated and grows. I dig that a lot. So this is a nice contrast to, you say that bullying ourselves doesn’t get the job done. Talk to us about that, the alternative approach that’s not going to work.
Jia Jiang
Yeah, the alternative is like, “I know this is hard and I’m going to do it because I’m a badass,” right? You have this mindset.
Pete Mockaitis
David Goggins style.
Jia Jiang
I’m not going to try to mention him, but I actually see a lot of people who are falling into that type of mindset. The thing is, it can work. That’s the thing. It can work, but not in the long term. Over the long term, we burn out. Like, there’s a short-term success and long-term success, right?
If you bully yourself, you’re like, “I’m going to do, like, three months of David Goggins.” Most people can’t do it. Some people can. A few can. But the thing is, you can’t turn that into a lifestyle. You just can’t.
In my book, I write about Sisyphus, in the Greek mythology, the guy would push up a rock out up a mountain just all day, and then the rock will roll back down, right, Sisyphus goes back down and keeps pushing.
And most people feel like Sisyphus because you’re always going to be pushing. The gravity is always against you. However, I have an alternative version of that story. I’m like, “Why does he keep doing it? If he has no choice, then he’s dead already, he has no free agency. But if he has free agency, that means he must go back. He must be the person who goes back down and does it.”
“And why does he do it? That must mean he likes pushing rocks, right? He’s having a good time, and that’s why he enjoys it, even though it never gets to the top.” So I was like, “Okay, how can we flip that script in our lives, in our work, for us to enjoy the work rather than just thinking about the results, just the top?”
So that’s also the cover of my book. That’s actually my T-shirt, you know. I have this, like, this guy just floating upward with a rock rather than pushing upward. So can work lift you up rather than actually push you down?
Pete Mockaitis
Well, that’s fun. I was looking at your book and your book cover, and, yeah, “Oh, I see, that’s Sisyphus, except his rock is, like, a helium balloon floating upward.” And it’s sort of easy and enjoyable because, hey, we love balloons. My kids, they can’t get enough with a balloon and go wild.
Okay. Well, you’ve got a whole framework. So how about you walk us through that? And then I just want to go example, example, example, right, in terms of, like, “Okay, that works great for exercise. Cool. But how do I deal with email? I hate email. How do I deal with…?” Well, fill in the blank.
The thing, cold calling, you said sales, you know, “Hey, there’s a thing I need to do to get where I want to go, but, ugh, dreadful is where it lands on the continuum, far from delightful.” So maybe walk us through your framework, and then let’s just apply it again and again and again so that folks feel like, “Oh, okay, let’s get after it.”
Jia Jiang
Okay, so my framework is called EASY, so E-A-S-Y. E stands for enjoyment, right? That’s what I was talking about, “How can you turn your everyday work into fun, into more enjoyable than before, and use that enjoyment to fuel you rather than just you trying to be a badass?”
So in my book, I wrote about 12 different tools to how do you achieve easy, right? I’ll tell you one. One of the things that you want to have more enjoyment is you can be a game-changer, right? If you don’t like the game you’re playing, you can try to change the game.
For example, so you talk about this idea of making sales calls, right? If you are outcome-oriented, “I’m going to make the call,” you’re going to make the call and someone will slam the phone in your face. Some people will talk to you, give you a minute of their time, and then afterward, you may succeed or not, right?
There are more rejections than success, of course. Nowadays, people don’t pick up phones anymore. It’s tough. It’s really tough. But what if you changed the game? Instead of saying, “I have to make that call. My goal is to actually make the sales. By the end, I have a contract,” or whatever, the next step.
You’d be like, “What if I change my goal just to understand that person? What if I want to have a good conversation? Can I have an actual conversation with a person that actually shows who I am but also let me learn what that person is going through? Maybe have a game to be, like, I want to find that person’s biggest problem. Whether or not I sell to that person, I don’t care. But let me change the game.”
So now you start shifting games, right? So I’m someone who very much doesn’t like talking to people. I don’t. I don’t like making these calls. But I love solving people’s problems. I started performing the role of a therapist or a consultant, that helps me a lot. Now I’m having fun, because now it’s a different goal from the goal that I didn’t like.
So you can do roleplay and change your game. Call that a game-changer. That’s how you make your work more enjoyable.
Pete Mockaitis
Okay, So could you give us an example there with regard to throw a role play in there and, suddenly, a conversation that was not so fun is more fun.
Jia Jiang
Yeah, absolutely. So I used to be terrible at sales calls. Meaning, some people, like I’m great at speaking. That I know. If you get me on a stage and get me in front of your audience and talk about rejection, I can tell a great story and inspire your audience and get a standing ovation. Like, I can do that.
However, getting on sales calls is a different thing, right? Sometimes the potential client, they’re like, “Huh, this guy is interesting. I see his video. Now I got three to four potential speakers. I’m going to interview all of them to see if they’re actually crazy in real life, right? Are they who they are on the videos?”
I used to hate those calls because my mindset was, “Okay, how can I get the other person like me the most? And what do I do? And what thing does he or she likes to hear? Let me try to do a word salad or try to contort myself into a way that they will like my answer. Then, hopefully, they’ll hire me.” And that’s a terrible mindset.
I was tracking myself, “What’s my sales success rate?” I was at 18%. Like, I was getting rejected for most, like almost every time, but 18%
Pete Mockaitis
And they found you. They found you.
Jia Jiang
They found me. Exactly.
Pete Mockaitis
You’re on the short list of finalists and there you’re only getting 18%. Okay.
Jia Jiang
Yeah. And I was like, “Well, I’m the rejection guy. I mean, I can take a rejection, that’s fine. But, man, this seemed like a drudgery.” So I started changing my two mindsets, right? The first, I’ll tell you, is “How do I have more fun? What if I changed my goal? Instead of thinking about how do I make them like me, what can I say to impress someone, let me be a consultant. Let me come in and maybe ask you questions.”
“What’s your business like? And what’s your goal? Why did you actually pick me as a candidate? Like, why? What are you trying to achieve? What is the everyday struggle of your audience member, of your association member, or as an employee who attends this event? What’s the day look like? Huh?” Then, right away, the dynamic changes.
Now I’m asking really good questions, and they would feel like, “Oh, this is a good question,” and they started telling me. Then I started getting a lot of information. The more information I get, the better solution that I would provide. So I do a role change, now I become a consultant on sales calls.
Boom! I had a better time. I like it a lot more. I’m no longer so afraid because now I’m just asking questions. There’s nothing wrong with asking questions and trying to understand the other person, right?
So that’s one thing that I can do to dramatically increase my…I do two things. I’ll tell you another thing, too, my other two things. But with the combination of these two things, I was able to get to 94% of success rate.
Pete Mockaitis
Hotdog!
Jia Jiang
It was dramatic. I mean, I track everything. And then after, I was like, “Man, I’m great at sales calls.” So that’s the first thing I did. So it’s, like, the enjoyment will make me like it more.
Pete Mockaitis
Well, what’s the other thing?
Jia Jiang
The other thing is the A, right? A stands for artistry. So E stands for enjoyment, A stands for artistry. What does artistry mean? We’re not talking about, like, drawing stuff and singing stuff, but we’re thinking about being present.
So, again, the reason I used to hate these sales is because I just didn’t like it. I didn’t like people that much, you know? I read How to Win Friends and Influence People at a pretty young age. It tells you how to make friends, right, is to be genuinely interested in other people.
I wasn’t. I was just not. I don’t like people that much. But then one day, I went to Japan. I did this traditional tea ceremony. If you’ve ever been to Japan, I highly recommend it, traditional Japanese tea ceremony.
So, basically, you’re in a room with a host, right? The host will make tea for you. And every movement and every word she says is very present. Like, that moment is, you feel it’s almost like essential, if not spiritual experience when you’re there by drinking tea.
It’s never about tea. It’s about being in the presence of another person, and you giving your best. And the Japanese have a word for this called Ichiko Ichie. It, literally, translates into one time, one meeting. It means that every time we meet, that’s the only time we’re going to meet.
Even though we might meet again, Pete, again in the future or wherever, right, this moment will never be replicated. So, because this is a unique moment, I better be fully present, I better be giving my best. I translate this into the artist mindset because that’s what artists do. Artists take whatever the world gives to you and you make art in that moment. So nothing is perfect but you go deep with this moment.
Now how do I translate to sales calls? When I take the artist mindset into my sales calls, I’m no longer afraid. I just go deep. Everything the other person says, I reflect and I talk back. I dig deep into that conversation and forget about trying to impress someone. I forget about I’m trying to be good.
Every time, you know, if I get picked, I make over $20,000. I mean, let me forget about that. Let me just be having the best conversation. Let me give you my best. By having that mindset, the artist mindset, my goodness, I become a much better conversationalist. People like me more.
The result is people like me more, people buy me more, and I turn these sales calls into little pieces of art. And that’s how I went from the combination of both, right, the role-playing, the change of role, but also trying to make art. And I went from 18% to 94% of closing rate.
Pete Mockaitis
And so when you’re making art, it’s funny. I’m kind of feeling internally the shifts in terms of a lot of good things are happening automatically, like embedded within that notion, making art, just there in terms of like, one, yeah, you’re not thinking about yourself, the self-consciousness just disappears.
And just imagining, like, Bob Ross, or whomever, you know, with his happy little trees on the canvas, just that mindset and that groove, it’s calm, it’s present, it’s curious, it’s fun, it’s peaceful. And so it’s like, all that at once, in terms of I’m thinking about just, you know, charisma.
We recently had Olivia Fox Cabane on the show, and wow, you’re getting a lot of those internal vibes right, right away, just by imagining making art. But what is the art that we’re making? The art is, “I’m trying to craft a beautiful conversation, connection, understanding.” What is the art we’re crafting in this conversation?
Jia Jiang
Sometimes there’s no result, you know. I mean, you’re having a conversation where you want to be your best self. Like, the vibes, that’s all it matters. In the end, this is what easy discipline is about. If the vibe you have internally is right, you do the best work, and the other person feels it, right?
If you feel your vibe is right, very quickly, the other person is like, “Ooh, you know, this dynamic changes.” When you just think about, “I’m an artist now,” this whole dynamic changes between us, even having this conversation right now.
You start feeling differently, I start feeling differently, and then the result will be, when people are watching this, when people are listening to this, you can feel it, too, right? The vibe just changes, the feeling is good, and you get into the flow. When we get in the flow, whatever that comes out, it’s art, you know? It sounds very woo-woo, but it’s true.
Pete Mockaitis
Yeah. And then there’s also the internal state, because, I think, in my early days of podcasting, my vibe was different. It was still of service, but it felt a little bit more, I don’t know, aggressive. I mean, I don’t think I was ever mean.
But it’s like, “Okay, the clock is ticking. You have a ton of wisdom. We have a limited amount of time. Give me more wisdom. More, more, faster, better. What else? What else? Example. Story. Illustration. Tactic. You know, it’s like I want it all. And I want it fast because the time is ticking.” And that’s not a great vibe.
Jia Jiang
Because you had a goal, right? You had a goal, it’s like, “Oh, my goal is to get as much stuff from this person as possible and still stick into this little time we have. Let’s just keep go, go, go.” And when you have that, the vibe is not right.
And there’s no art being made by saying, “Go, go, go,” right? But real art is made by, “Oh, that’s interesting. Hmm.” Maybe pause a little bit, like, “I like what you were saying. My feeling’s different.” So that’s really making art. And that always produces better conversations. and most people enjoy it more.
Pete Mockaitis
Certainly. And so then, when you say artistry and making art, we don’t want to over-fixate on the product or the output so much as being in the vibe of we are creating something beautiful here now. And in so doing, that’s just good for everybody.
Jia Jiang
It really is. You get in flow and, usually, the best conversation of two people is just forgetting about themselves. They’re forgetting they’re in a conversation. They’re just, like, deeply immersed. And the thing is, their curiosity just pops up and you hear other people’s point of view or story. It brings the story out of yourself. You start responding with your own story. And then that’s two people co-creating art, right?
And I started having that mindset in everything I do.
Pete Mockaitis
Yeah. All right. Let’s hear about the S, systems.
Jia Jiang
Yeah, the system. So I tell the EASY is like four different characters. If the enjoyment is this happy go-lucky guy, that feels all good, the artist guy is like deep, right, very present. System is another character. He’s, like, very systematic, you know? What can I say?
I call this system smart. System smart is basically you try to figure out where you are, what you’re trying to accomplish, what your weaknesses are, and try to shape the environment that gets you to do more better input to get to the result.
Most people try to do work and take actions to achieve the outcome. System, meaning what can you engineer with your environment and your everyday activity, so you can actually manufacture better input that leads to the outcome? I’ll give you an example.
Okay, I learned this concept from Jim Collins, right? You know, he’s very prolific. He still keeps writing, and people ask him, “How can you be so creative and prolific? What’s your secret?” And you would think it’s like some sort of meditation, maybe some AI before anyone else had it.
And he’s like, “I have a stopwatch.” People are like, “What?” “Stopwatch.” So, it’s like, he has learned that the most creative and successful people in his endeavor, they spend at least 1,000 hours a year in 365 days to do creative work.
So he has a stopwatch, so every time, every day, when he had a conversation, when he started doing research, when he started thinking, when he started writing, doing creative work, he will start his stopwatch. And then when he’s done, he clocks out, right?
By the end of the day, he writes that number on a spreadsheet. And this spreadsheet go back to decades. He does this every day and all he makes sure is, he goes back to 365 days and it’s over a thousand hours, so cumulatively. And he said he’s never been under a thousand hours.
That’s his system. He has a system that kind of enables him to track the fun thing he loves to do. So that system works for him. I’m not saying it works for everyone. But it got me thinking, “Wow, what can I build, a system that fits me so I can be my best?”
So one of my biggest problems is this, right? Phone and also the computer. I get distracted all the time. I doom-scroll all the time. And because the world, nowadays, this whole world is engineered to distract us to get our attention. And for a long time, I didn’t like it. And, I mean, like, I want to be able to have better control of my own mind.
So I was like, “How can I have a system where I can be away from my distraction? I don’t have to find my distraction.” So every day, to write, I would go drive 45 minutes away from where I live, to this place called Half Moon Bay in Northern California.
I would park my car on the beach, overlook this ocean, and I sit in my car and write. That’s my office. I get the most beautiful view. I think I have the best office view in the whole world because of that place I park.
And then I don’t bring my phone. I don’t have my phone, so I don’t have data. I don’t have hotspot. I have none of that. I just have my computer without internet connection so I can just write, so I can fully focus.
And if my family needs to reach me, I wear my Apple Watch. I can take calls on the watch, but it doesn’t do hotspot with my watch. So I built a system for me, for me to be at my best to get the input. If I can be good at my input, the outcome is amazing.
So ever since I started building the system, my productivity just went way up. So that’s an example of system thinking, how to build a system for you to have your best work.
Pete Mockaitis
Okay. And then the Y is yourself.
Jia Jiang
Y is called yourself. And this is more like a long-term thing. I grew up in Beijing, China. I met Bill Gates when I was 14. I heard him speak. I was mesmerized by him, you know, and I was mesmerized by his entrepreneur story, this idea of using technology to change the world.
So I wrote a letter to my family, telling them, “Hey, I’ll be the Chinese version of Bill Gates. By age 25, I’ll build the biggest company in the world and buy Microsoft.” I did write that letter, my family kept it for me all those years.
And then how do I do it? I’m going to replicate Bill Gates’ life. He went to school, and then he studied computer science. I’m going to study computer science. I couldn’t go to Harvard. I came to America, right, but I didn’t get to Harvard, but I’m like, “I can go to school early.”
So I went to school at 17, I go to a college. I was like, “I’m going to finish college in three years. I’m going to come off a boy genius. I’m going to then start building my company and, very quickly, I’ll be the next Bill Gates.”
Well, the problem is I’m not Bill Gates. That’s the problem. Like, I don’t have his mind. I don’t have his interest in programming. I hated programming, and then my college was miserable. Instead of spending, like, three years to graduate, as I thought, I spent over five years. I’m not ashamed to say it because I was not a good programmer.
Even after college, I started finding jobs and I sucked at my jobs. And I worked really hard. I’m just trying to push up the rock on the hill, right, doing programming every day. Then one day, my boss called me in, he’s like, “Jia, consider yourself fired.” Okay, that’s not a good start of a conversation, no matter how you cut it, right?
But then he said, “Hey, we really like you. We see how hard you work. We like how you treat people, how genuine you are. How about we rehire you? We’ll put you in another job. How about we call this thing…?”
So they came up with a new job title called client services engineer. I’ve never heard of that job title before, I’ve never heard that since. But he’s, like, “How about you serve our customers and write a script for them, rather than writing our main software?”
And then my whole life, my whole career trajectory changed that day because I love that new thing. I love solving problems for people. I love helping them. And then I became better. I no longer felt like I was a loser. I was never fired again since then. I was having a good time. And this is called yourself.
A lot of times, we have a goal that’s from outside that either someone put it in us or we install that in ourselves. But I was, like, “Instead of having that goal, what if you actually learn who you are, and then have that dream come out of you?”
So right now, I don’t even follow that tech entrepreneur dream anymore because that’s not who I am. I’m really good at writing. Now I know I’m really good at writing, I’m really good at speaking. So I said, “What if I build my dream out of that? What if I can be a writer for the rest of my life? I’ll be happy.”
So I didn’t like myself that much before because I couldn’t get that goal, but now I love myself and I’m excelling in the things I do because I’m doing who I am. That’s yourself.
Pete Mockaitis
Cool. Well, excellent stuff. Well, I’d love your take now, it seems like these are some big ideas that we can put into practice in all kinds of different contexts. I’d love to get your pro tips for when you’re in the heat of battle, there’s a thing you know needs doing, and now is a fine time to do it based on the calendar and opportunities and availability, and yet, “Ah, I don’t want to,” what do we do?
Jia Jiang
Try to turn that, somehow, turn that into a game, okay? Turn that into a game to see, okay, by the way, I faced this. I still face this every day. Sometimes the most important thing you know is important, and because you’re so delaying it, that feeling of delay actually makes this thing worse, right? And so you turn that into a game.
You’re like, “Okay, what can I do, and just give myself 15 minutes, just do this task? What’s the best I can do in 15 minutes? Let me contain it. All right.” Whatever that comes out, it was, like, you know, your 15 minutes is a very short amount of time, right? It depends on what the task is. But I try to contain it.
I’m like, “I’m going to go nuts in the next 15 minutes. Let me start my clock. Just 15 minutes, go nuts on this to see what kind of art I can create.” That’s the artist mindset, right? And then whatever it is, it is. And then, usually, when I get started, when 15 minutes is done, a lot of times I’m not done. A lot of times I’m like, “Actually, I’m in the zone. Like, I’m in the zone.”
To get over procrastination, the best thing is just get started. Sometimes you can’t even get started. That’s the biggest friction. But when I have this container, just 10, 15 minutes, that’s it. “Let me dig deep. Let me have fun in the next 10, 15 minutes and I’ll have a coffee.” And then you get started, right? And then a lot of times, you’ll finish a task, and a lot of times you’ll do a good job.
Pete Mockaitis
Okay, understood. So just getting started gets the momentum going, certainly. And then, any pro tips on, in fact, the getting started part?
Jia Jiang
Yeah, I mean, I have a secret. Sometimes just getting that is hard. I totally can understand. I call my wife, I was like, “Can I borrow you?” She was like, “What do you need?” I’m like, “Can you sit with me for 10 minutes? Just watch me and do this.”
And then it doesn’t have to be your wife. It can be anyone. It can be my son. I could get my friend. And it’s like, “Hey, are we friends or what?” They’re like, “Yeah, we’re friends.” “Can I borrow you for 10 minutes?” “For what?” “Just sit here with me, watch me get this started.”
And sometimes that’s it. That’s crazy. It’s just, like, you fire up that Microsoft Word or Google Sheet, whatever you’re doing, right? You fire it up, start doing, that’s it. You get started. Having that person to get you sitting here with you, you get it started.
Pete Mockaitis
Okay. Very good. Well, Jia, tell me, anything else you want to really make sure to mention before we hear about some of your favorite things?
Jia Jiang
A lot of times, when we’re trying to achieve something, right, and we think worse. We think we have a lot of flaws, and I used to think I had a lot of flaws, I still do. But I used to think those flaws are just there, just obstacles stopping me from achieving my dreams.
But now, those flaws are treasures, they’re assets, because I get to learn myself, and I get to bring them and try to build systems around them. And I wouldn’t be able to write this book, Easy Discipline, without those flaws. This book is all about my flaws, the how to actually turn your flaws into your treasures, into your advantages.
So whatever flaws you think you have, whatever part of you, you don’t like yourself about, switch it around. Think about those, start using, start mining those flaws, start just turning them into good stuff, and you’ll like yourself a lot more.
Pete Mockaitis
All right. Beautiful. Thank you. Well, now could you share a favorite quote, something you find inspiring?
Jia Jiang
I found this quote, and it’s from Charles Bukowski. And he was like, “Who you were before the world told you who you were supposed to be.” And I love that quote. But I even made some modification on that quote, “Who you were before you told yourself who you were supposed to be.”
Pete Mockaitis
Okay. And a favorite study or experiment or bit of research?
Jia Jiang
So one of the books that really inspired me was a book called Made to Stick. It came out about 20 years ago, still one of my favorite books by Chip and Dan Heath. They write about how ideas travel.
So there’s tons of research in there. One of them is saying, when you can make an idea more surprising, the idea will travel farther. So when you make the idea more emotional, it goes farther. So, yeah, it just tells that sometimes how you tell stories, the stories you tell determines how sticky, how influential it is.
Pete Mockaitis
Okay. And a favorite tool, something you use to be awesome at your job?
Jia Jiang
Drive every day. I manufacture a commute to a place I write. And during the commute, I listen to audiobooks and nothing else. I get myself in the mood. I get myself inspired. So when I stop, just ideas pop up.
Pete Mockaitis
Okay. And is there a key nugget you share that really seems to connect and resonate with folks, you hear them quoted back to you often?
Jia Jiang
“Rejection is like a chicken. It’s either yucky or yummy. It depends on how you cook it.”
Pete Mockaitis
Okay. And if folks want to learn more or get in touch, where would you point them?
Jia Jiang
You can search me on Substack, and I write. I definitely write every week and sometimes more.
Pete Mockaitis
Okay. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?
Jia Jiang
Find one thing that you love the most. Just figure out one thing. What’s that thing that, of all the things you do at your work, you love the most? And then you tell yourself, “What if you just go even deeper on that thing? How about you go nuts on that thing and maybe you do nothing but that thing that you love the most for your work for a day to see what happens?” And maybe that thing can become the foundation of your work.
Pete Mockaitis
Okay. Jia, thank you. This is fun.
Jia Jiang
I had a great time. I had a great time. Thank you for having me.

DJ DiDonna makes the case for why taking more extended time off helps professionals get further in their careers–and shares tricks for actually snagging that time.
You’ll Learn
- How to convince your boss to let you take a sabbatical
- How sabbaticals act as “regret insurance”
- How to plan a truly fulfilling sabbatical
About DJ
DJ DiDonna is a senior lecturer of business administration at Harvard Business School, where he teaches MBA courses on entrepreneurship and building meaningful professional and personal lives. He has spent his career translating social science research into real-world tools for positive change. In 2019, DiDonna founded The Sabbatical Project to define, explore, and research the role of sabbaticals in modern life. He has helped organizations around the world—from nonprofits to Fortune 50 companies—design and implement sabbatical policies.
His work has been featured in The Atlantic, Harvard Business Review, Time, Fast Company, The Wall Street Journal, and The New York Times. Previously, DiDonna cofounded EFL Global, a fintech company that enabled more than $2 billion in capital to underbanked businesses and individuals across twenty countries before its acquisition in 2018. DiDonna earned his MBA from Harvard Business School. On his sabbatical, DiDonna walked nine hundred miles on pilgrimage in Shikoku, Japan, helped lead the Wilson Sheehan Lab for Economic Opportunities at his undergraduate alma mater, Notre Dame, and unskillfully remodeled his kitchen. Outside work, you can find him plotting how to be in the Big Outdoors.
- Book: Big Time Off: The Transformative Power of Sabbaticals and How to Take One by DJ DiDonna
- LinkedIn: DJ DiDonna
- Website: TheSabbaticalProject.org
- Website: djdidonna.com
Resources Mentioned
- Tool: Voice Dream Reader
- Book: The Three-Body Problem (The Three-Body Problem Series, 1) by Cixin Liu
- Book: Working Identity: Unconventional Strategies for Reinventing Your Career by Herminia Ibarra
Thank you, Sponsors!
- Shopify. Start your free trial at Shopify.com/awesomepod
- Monarch. Get 50% off your first year with code AWESOME at Monarch.com
DJ DiDonna Interview Transcript
Pete Mockaitis
DJ, welcome!
DJ DiDonna
How are ya? Great to be here.
Pete Mockaitis
Doing well. Doing well. I’m excited to talk sabbaticals. First of all, we’re going to use that word a lot, what are we talking about here?
DJ DiDonna
So it’s funny, when I first took my sabbatical, I instinctively called it a sabbatical and I didn’t know what that meant. I think a lot of people use it because it lends this prestige from academia. It lends this prestige of, like, here’s an identity that you can have when you’re doing something very uncertain and you’re oftentimes giving up your identity.
And so, you know, I created one, take it or leave it, but intentional extended leave from your job. So, “When you’re away from your job, are you not looking for another job?” which is what we tend to fill in the space with. “Is it a time that’s hopefully measured in months, not days or weeks?”
And you can do work, but it can’t resemble your routine job. So no little consulting projects, nothing similar, but people will do things like try to write a book or get certified in yoga or scuba. I remodeled a kitchen, which might sound like work to folks, but it’s like intrinsic work of your own choosing.
Pete Mockaitis
Okay. Well, that sounds nice, and we’re going to get into the practicals and the pushbacks and the constraints and the difficulties soon enough. But, first, let’s hear, tell us, I mean, they sound like a swell time. Can you share with us any surprising discoveries or key benefits that we should know about?
DJ DiDonna
I think anyone who’s been on a vacation knows that vacations are great and you can easily imagine that a longer vacation would be even better. The reason I set out to do this research and write this book was because the profundity of the kind of changes that I experienced, identity changes, life changes, the joy, the density of memories from that time were such that I was like, “Okay, something very different is going on here.”
And so when I spoke to other people for the research, I realized that there’s something deeper on a personal identity, “Who are you? What do you value?” that is changing in a way that just is not happening with shorter breaks. So that was surprising that it wasn’t just, you know, my personal experience, but universal across everyone that I spoke to.
But the other thing I think that’s counterintuitive based on how you framed it is that sabbaticals can be really tough. I think, a lot of times, you’re getting to sabbatical land burnt out or it’s catalyzed by some crisis, like a personal crisis, a work crisis, a relationship crisis, a health crisis. And so you’re having to work out a lot of stuff, and the vacuum of your responsibilities and how you spend your normal day allows a lot of big thoughts to come in.
And so people will look and say, “Oh, my gosh, you’re off for three months. You must be having the time of your life.” But, oftentimes, personal development and identity change is hard work and it’s difficult and uncomfortable. So that’s what I would say some of the surprising things were.
Pete Mockaitis
Well, identity change sounds big and it sounds like that can go in very many, many directions. Could you give us an example? And is that a good thing? Maybe I love my identity. I don’t want to change it.
DJ DiDonna
I think that the most important thing is that you are looking at who you are and what your identity is from the perspective of someone that can change it and is in charge, right? I think one of the things you see in the research is that there are some debate about whether you have like a fixed identity.
And so you want to return back, you know, to your identity that might have been obfuscated by, like, hard work or stress or taking a job you didn’t want or being in a relationship you didn’t want. Or is your identity constantly shifting and it’s your job to kind of guide your life towards how you change and shift as a person?
And so I think, in sabbatical, what is being offered is you’re stepping away from your life long enough. People have talked about it as like a near-death experience. You’re zooming out from your life. You’re looking back at how you’ve lived it and how you feel living it now, and what you would like for your life between now and when you die, and getting to say, like, “Do I want to make changes or not?”
And some people are like, “Love my life. Love my work. It gives me meaning. I don’t love going in every day, but that’s a job. But I would like to have stronger boundaries between work and life.” And that can be enough to change your identity, right?
Like, do you see yourself as someone who is a super committed father that picks their kids up every day and coaches the teams? Or do you see yourself primarily as a person that’s doing work and not really of your choosing?
So I think that’s the invitation is just to say, you know, really pick yourself out and say, “What am I doing? And how does that align with who I am and who I’ve wanted to be?”
Pete Mockaitis
Well, it’s intriguing as you describe it in this way. It’s like the sabbatical provides a context or fertile soil for epiphany or revelation, and we sort of have the time for it, as opposed to, a lot of times, epiphanies, even the word implies, “All at once, I realized, ‘What am I doing?’ Or, ‘I had a panic attack and I… no, no more of this.’”
So with the sabbatical, it seems like we don’t have to get lucky or have a strike of divine inspiration in order to come to these major realizations that perhaps we would really benefit from coming to.
DJ DiDonna
Yeah, I mean, I would think about it also as imagine if you could manufacture a scenario that would produce an insight that would change your life forever, right? So if you look at what’s called peak life experiences, like a lot of those are fomented by negative things that happen.
So a health crisis, you know, we’ve all heard about “The Bucket List” or seen it. Like, a health crisis makes you think, like, “What have I been doing and how do I want to change?” And what a sabbatical says is, you know, you can basically carve out time, you know, six months off in the scale of a 40- to 50-year career is like 1% of your working life.
And you can carve out 1% percent and say, “I want to try something on that I’ve always wanted to do. I want to write a book. I want to, like, become fluent in a foreign language or live in a foreign country with my family.” And then just have that experience as opposed to it being an emergency or something that happens to you.
I mean, another surprising thing from the research is that we found that about two-thirds of sabbatical takers, a sabbatical takes them, right? And so it is this fomented by a crisis as opposed to something that’s regularly planned.
And my intention is to identify these kind of inflection points across your life, from gap year early on in your education, to like a twilight career where you can take a pause and figure out if you’re heading in the right direction or not.
Pete Mockaitis
Well, so I think, already, brains are firing off, it’s like, “Oh, it sounds nice, DJ, but no way that I could pull that off.” But even before we dig into some of those particular practicalities, I’d like to get a sense for some examples of these identity-shifting perspectives, insights. Like what kinds of things have popped up for people and how does it go down?
DJ DiDonna
You know, Pete, for the skeptics, just to make sure they get through the episode, right, like take the word sabbatical away and just think about it from the perspective of you, upon retirement, or upon your deathbed, or with your grandchildren, you know, bopping up and down on your knees, like, what is something that you would like to do in your life that doesn’t fit neatly into vacations, that certainly you’ve thought is important so far, but you clearly haven’t made time for?
And so it takes this, like, grandiosity around, like, “Taking a sabbatical is difficult,” and makes it more personal around, like, “I want to go on a road trip with my family to see the national parks.” Right? That’s an often one I hear. Like, how are you going to do that without a bigger container of time?
So I think I would encourage folks to think about, actually, what’s passionate for them as opposed to getting hung up on the term or the amount of time. Because, I think, once you start having this idea and it becomes concrete, it grows and germinates.
As far as the actual tangible outcomes, what we saw is an increase in confidence. So people come back having done a thing that is pretty rare. It’s certainly not the typical story of how we work, you know, at least in the States. And they come back stronger, you know, having healed personally and mental health-wise. And found out a little bit more about their capabilities outside of work.
A lot of people will do some sort of physical expedition, right, like a long hike or get in shape for a marathon or something like that. And that lends confidence about what’s possible. Creativity, so one of the cool things about a sabbatical is instead of doing like a vacation, you’re just being yourself. You’re just being.
And a lot of times that means you’re picking up some hobby that you used to have, you’re tinkering with something that is just for fun, there’s no purpose. And that kind of spurs our creative brands. Like, you’ve heard about the creative process where there’s no bad ideas and let’s get everything out there first and collaborate.
The other thing I mentioned earlier is just about perspective. So because you’ve disengaged from your work identity being governed by your calendar, that kind of thing, for long enough, and people will say it takes about six to eight weeks to fully disconnect, you’re able to get perspective about who you are, where you want to be going and whether how you’re allocating your time and resources is getting you there or not.
Pete Mockaitis
And so could you share some stories of some folks who did this and the realizations that they had?
DJ DiDonna
A couple of my favorite stories, one, there was a family that took a sabbatical on an island off the coast of Norway. So the father had been working in tech, had kind of burnt out, and his wife had taken a few years off from teaching in order to stay at home and raise the kids, right?
So she had wanted to get back into the workforce, he had wanted to take some time off, and so they spent a month above the Arctic Circle off the coast of Norway. She was, like, one of two teachers in kind of a one-room schoolhouse type situation for the island, and he was just experimenting, spending afternoons with his kids, doing little projects and hobbies.
He learned how to fish, learned how to smoke fish, learned how to catch fish, things that just aren’t that seemingly productive. But then he also wanted to go back to his hobby of being a computer developer. He was at management level, and so you’re not really down in the weeds.
And so mobile app development was coming out, this was about 10 years ago, and what he did was he created just a simple kind of text-to-speech app. His father had done work with kind of vision-impaired folks, and so it gave him the idea.
And as a result, he created something, published it on the app store, and it actually started gathering some steam, you know, people paying ten bucks a year. And when they came back to Boston, not only had they completely changed their relationship to money, because they had lived on a relatively meager teacher’s salary in Norway, it gave him the confidence that he could spend another year, a year and a half, building it up to support the family.
He designed the business such that he could take summers off because he was like, “Why would I not spend summers aligned with my wife’s calendar, spending summers adventuring with my kids being present?” And it gave his wife things on the resume and experience to get back into the workforce in the States. I love that story.
I think on the opposite side, it’s also important to know what you don’t want to do. So a lot of people use sabbaticals to test, like, “What’s the counterfactual to the life that I’m living?” There was someone, in the book, who was a career trial lawyer. He studied English in college, always wanted to write a novel, but kind of found himself starting a family early on, wanting to support the family.
And so after 25 years, he took six months off to write. And it allowed him to walk his kids to school, cook them dinner at night, be more present with the family, which his job hadn’t before. But, more importantly, he wrote for about two months and then he printed the manuscript out, tore it into pieces, put it in the trash, and was like, “Actually, I want to go back to being a lawyer.”
And so this concept that, like, part of navigating through life and navigating your identity is, “What are you good at? What are you not good at? What do you like? What do you not like?” And I think about sabbaticals as regret insurance, because you get to try things on for size that you would have regretted not doing at the end of your life.
Pete Mockaitis
Yeah, that’s really cool. And I’m thinking about, well, first of all, I believe that’s Winston Chin, right, who made the Voice Dream Reader, an app that I use and love. And Kwame Christian did, like, a whole episode about how that’s a key part of his life.
DJ DiDonna
Oh, funny.
Pete Mockaitis
He could see, but he likes having notes read back to him at rapid speed while he’s doing other things. So that’s pretty cool. Hey, sabbatical enriching all of us.
DJ DiDonna
Developed over the winter, you know, dark, dark winter in Norway.
Pete Mockaitis
Yeah. So that’s really cool. And then you’re right, the regret insurance thing is resonating. I’m thinking about, I remember at Bain, they had a program, and they might still have it, they called it Take Two, which is basically this.
It’s, like, you could take two months off, I believe it was unpaid, but you keep your health insurance benefits, and you could just do whatever. And what was interesting is it was a real win-win for the consultants trying something else, like, “I always thought I wanted to work in sports.”
And so then they work in sports for two months, like, “You know what? I like consulting better.” So they come on back and they have that retention of an employee for longer because they could scratch the itch, they could take a look, and they come back and say, “Actually, this is really a pretty sweet gig. Let’s keep doing this.”
And it’s great for the people because, you know, sometimes they do discover just the thing, or they put to rest that lingering doubt. Regret insurance is well put, it’s like, “Ah, I wonder what would have happened if I worked in sports? Well, I know. I tried two months and it wasn’t all I hoped it would be.”
DJ DiDonna
Yeah, I have a fair amount of examples from the consulting field because, as you know, it’s project-based and so when you’re on, you’re on, and you’re on like 11 out of 10. And then when you’re off, you’re totally off.
Like, you’ve finished the engagement and so there’s not work to do that lingers. And I think that the economy is heading more towards this, like, cyclical project-based, like you see it in tech product development cycles.
And so I think, as the economy heads more towards natural inflection points every four or five, however many years, I think it gives you these opportunities to say, “Okay, let me step back and recharge. Let me maybe, right now, right, like let me step back and learn AI from a curiosity standpoint. Like, build something that’s interesting to me,” as opposed to, like, trying to fit it in in everything else that you have to do with life.
And then you’re actually training yourself for the next job. So I like the consulting example and a lot of consultants in the study would use that time off. You know, McKenzie has Take Time, Bain has Take Two, where you would run an experiment.
Someone in the study thought that they wanted to own an eco resort when they retired. Sounds idyllic, right? You live in a beautiful place, and he worked in Costa Rica and in Hawaii over the course of his sabbatical, you know, in the kitchen, in the front office, and he was like, “This is miserable.”
And so it’s this, like, just how can you test different hypotheses about your life so that you’re more fulfilled in the life you choose or the next life you choose?
Pete Mockaitis
Okay. Well, so lay it on us, if folks think, “Yeah, that’s great, but…” where do we go from there?
DJ DiDonna
You know, I think the first step is nurturing that seed of an idea, as kind of woo-woo as that might sound. Like, you really have to think about something concrete. Go to a cafe for an hour, no phone, no music, no friends, and just think, like, “What are things I want to do before I die?”
And I think that’s important because it just makes it more tangible because I think, then, you start to build this intuition, like, “Wait a minute, why can’t I? I’ve always wanted to do this. I’m X years into my life. Like, why have I not done this?”
For me, it was about the spiritual search, right? I felt like I was spiritual. I grew up in a religious household. I wanted to, like, nurture and investigate that side. I felt like it was important, but I wasn’t allotting time to it. And I think it’s something that takes a fair amount of time. So find that thing that is so important that you start to realize, like, “This is not fair. I will not be happy with life if I don’t get a chance to do it.”
The next thing is, I think, take your time scale away from the next 90 days, the next year, and put it into, like, a five-year plan. Of course, a sabbatical is out of reach for almost everybody. If you don’t have a company supporting it with a policy, if you’re talking about taking off three months from now.
But what are you doing in 2032, right? And kind of like plant a flag somewhere in the future that sounds impossibly far away, and say, “I’m taking the summer off with my family in 2032. We’re going to align schedules, we’re going to tell our bosses three years in advance, and it’s just part of how we live our life,” as opposed to waiting until some emergency kind of, you know, clutches you and takes you out of routine life.
Once you do that, then you can financially save 5, 10% a year. You can work out the logistics. Put it far enough in advance that it becomes logistically feasible. Dream and understand what your what the stakes are. Like what does it cost you not to do this over the course of your life?
And then the other thing that’s important, in our research we found that one of the most enabling factors of taking a sabbatical is having an example in your life of someone who has taken it. So ask far and wide, “Is there anyone in my network who has taken extended leave, who has taken a sabbatical?”
I mean, don’t be afraid to post it on LinkedIn. There’s a career break feature on LinkedIn that was rolled out in 2022, and millions of people use it. So that, like, norm around like work devotion, I think, is disintegrating pretty quickly.
But once you can get some advice and some proof and permission that it’s okay to take extended leave from someone you know, the barriers start to break down a bit.
Pete Mockaitis
Tell us about the career break feature on LinkedIn.
DJ DiDonna
So when you’re putting in the employer that you have and how long you worked for them, there’s a career break employer. And then you can kind of say, career break, skills development, personal needs, whatever, whatever.
I thought it’s pretty revolutionary, like, to have every person who’s displaying their resume online include career breaks.
Pete Mockaitis
Yeah, I hear you, in terms of the normative piece, because I think there’s some old career resume advice somewhere, like, “Oh, make sure there’s no gaps in that resume. That’s a big red flag.” I don’t personally evaluate any candidate or talent in such a way at all.
I don’t know if maybe you could demystify some of that for us. If we have these fears about, “What will others say or think or do? Or how will this impact how I’m judged or viewed or evaluated, assessed?” What’s the scoop there?
DJ DiDonna
I think, first of all, like flipping that on its head, if you’re looking at a few different resumes, and one person says something about their life that’s interesting, right, it shows that, so there’s this concept called the red sneaker effect.
That if you have the confidence to dress unlike other people in an interview, or if you have the confidence to say, like, “You know, I took six months off to sail across the Pacific, or to take care of my parents,” that actually sends a signal that, like, “My work will kind of stand for itself. This is who I am as a person. Here’s a tiny glimpse on the resume.” So I would encourage people to think about it like that.
And then, on the negative side, if someone is going to screen you out for taking three months off to care for a loved one, probably not a good fit. You know what I mean? Like, if you’re looking for a signal that the company doesn’t value you as a human being, I think there it is.
And we know that younger generations are more likely to trade autonomy and mission and purpose and flexibility for compensation. And so it’s bubbling up within the economy anyway, as you said, outdated story. And so you can either be a part of this and encourage it and support it, or you can be kind of left behind and, you know, working two jobs and sleeping under your desk.
Pete Mockaitis
And, likewise, with regard to the, “What do other people think?” situation, if you give the boss a heads up, “Hey, three, four years from now, I want you to know I’ve got this sabbatical on the calendar,” how do those conversations tend to go?
DJ DiDonna
I mean, listen, you have to compare apples to apples, right? So in Silicon Valley, the average tenure at a company is, like, two years. And so I think if you’re saying to someone, “I want to stay at this company. I view my tenure here to be long. I like it. I want to grow here. And in four years, I want to take two months off with my family to live in Spain,” I think that’s totally manageable.
Like, people are leaving their jobs. And when people leave their jobs, managers have to scramble and hire someone else. They have to, like, train that new person. People go on parental leave. Like, you have a bit more notice, but maybe five, six months notice.
And so what you’re doing is you’re helping the organization build resilience around, “Can you survive when someone leaves the company?” You’re being super purposeful about, “Here are my tasks. Here’s who I kind of delegate them off to. Here’s how I onboard them back.”
And I think, most importantly from an employer standpoint, it’s an equitable benefit. Like, if you’re carrying water for someone else because they’re on sabbatical, and then you can take a sabbatical, that’s very different than if you’re carrying water because the staffing needs were messed up, you couldn’t hire a replacement, you’re working way more, or someone else goes on parental leave but you’re not planning on having a kid.
So I think it creates this world where, like, our humanity is honored outside of work, as opposed to just pretending like no one ever quits.
Pete Mockaitis
Yeah, you’re right. If you’re hearing that, it might actually be very appreciated by your employer. Like, “Oh, I didn’t realize you were planning on being here for four plus years. Most people don’t. That’s pretty cool. Okay. Well, we could probably figure that out. Sure. Thanks for the heads up.”
DJ DiDonna
Yeah, every company can figure that out, right? Like, companies have to figure out when people leave. They have to figure out when people go on parental leave. And so it’s not easy, right? This is not easy at the current state where there aren’t enabling policies for everyone. It’s not financially feasible for everyone.
But, again, like, looking at the trajectory of the paid parental leave movement, and the US is still the only high-income country in the world that doesn’t have, like, government-supported paid parental leave, but it’s increased over time. I think 40 states offer paid parental leave. And then if you apply to a job that doesn’t, it’s a bit of a head scratcher.
So I think the evolution of sabbaticals and sabbatical policies, I see taking that same trajectory, which is just, “Wait, I can’t take three months off every four years?” Like, it’s not a lot of time.
Pete Mockaitis
Okay. Well, tell us, any pro tips, top do’s and don’ts to keep in mind as we start walking down this path?
DJ DiDonna
I think the first thing is to make sure that you are sufficiently disconnected from your routine life. So if you’re stepping away from work, and you’re coming back to your job, making sure that auto-away messages, emails are being deleted, like, “I will return on X date,” making sure you have support inside the organization to say, like, what’s the break-the-glass moment where, like, “If someone reaches out about this, like, here’s my phone number, but otherwise, no.”
If you’re leaving a job, I think the way to be disconnected is, like, don’t post about it on LinkedIn, don’t tell people you’re taking time off. Just do it. You can post at the end and say, “Here’s what I learned, and many of you might have noticed,” but no one notices. Like, everyone is focused on their own life.
Most often, you’ll hear, like, “You were gone for six months? Like, oh, my gosh, it felt like you were just here yesterday.” People are busy. And that second aspect of disconnection is making sure you’re gone long enough, right?
So, again, best practice, if you can take three months or more, awesome. If you can’t, take as much as you can. I think that it’s like a gateway drug where you take a month off, and you’re like, “That really flew by, and I didn’t get to do 90% of what I wanted to do. Maybe next time in five years, I’ll take more time off.” But just start to experiment with, like, why it’s so different to take extended leave off.
And the other thing, I would encourage people to take that time to get a coach, right? A coach or a therapist to try to, like, process who you are, and use that opportunity to grow as a person. And then, finally, a lot of people shift directly from, like, work-productivity mode into, like, life-productivity mode, and they’re like, “All right, I’m done with work. Now I need to become fluent in Portuguese,” or, “Now I need to do this project I’ve always wanted to do,” which is understandable.
But I encourage people to take a beat. Take a couple weeks, just heal. Get out of your head into your body. Do things like ceramics or yoga, like things that don’t just, like, swap out one brain thing for another, or one laptop thing for another. Like, return to kind of being human again, return to body movement, all that kind of stuff, music, right?
Pete Mockaitis
Yeah. And what you’re saying about the gateway drug and our beliefs and associations, I think, somewhere inside of us, I think we have kind of a belief that, “If I disappear for a while, you know, disaster will strike,” or, “If I can disappear for a while, then I guess I’m not all that essential.”
And so I’ve heard, talked to people who are taking paternity leave who have said such things. And I remember, I, one time, went on an eight-day silent retreat. And so my phone was totally off, and so I had this extensive email autoreply, as well as voicemail.
And it’s like, “Hey, if you need this, ask this person. You need this? Ask this person. You need this? Ask this person. If you really need something and it can’t wait, you know, here is the number of the retreat house.”
And I guess you can already guess, DJ, how many people felt the need to call the retreat house over eight days? Zero. And so, yeah, the world continues, and yet, we are also missed at the same time, you know?
DJ DiDonna
Yeah. I think that, listen, silver lining from COVID was that we all, especially knowledge workers, right, we found out that you actually don’t have to be in the office to get most of the work done. We had the technology to do it before that, but this kind of, like, forced us to say like, “Oh, my gosh, we can’t be in the same room. How do we get the work done?”
And so I think taking time off can be the same thing. It’s like, “How do we get this done when they’re not here?” Like, what changes when you step away from the office? I think we’re scared of change, we’re scared of uncertainty, you know, understandably, especially this kind of like age of AI.
But at the end of the day, like, you’re replaceable anyway. Like, no company, at least not any good ones, fail because one person leaves, right? And in America, you know, you are employed at will, right? And so you can be fired, for the most part, for no reason.
And so I think you have to, like, lean into that and be courageous, and say, like, “How can I arm myself? How can I improve myself in this age of uncertainty?” And in order to do that, it’s making sure you’re healthy and whole, right, you’re not burnt out, you have energy to kind of persist.
Making sure you have creative ideas for yourself and what you want to do in the future, and making sure you have confidence about what value you offer, like, “Oh, I got fired,” or, “That company shut down, like, I can find another job,” because you you have to, and that’s how the world of work is now. Like, no one is watching out for you and saving up for your retirement for you, unfortunately.
Pete Mockaitis
All right. Well, now could you share with us a favorite quote, something you find inspiring?
DJ DiDonna
A quote that I have in the book that really stuck with me is Wordsworth who says, “To begin, begin,” right? If you want to have the life that you’re not going to regret, if you want to check things off your bucket list before it’s too late, you got to begin.
Pete Mockaitis
All right. And a favorite study or experiment or bit of research?
DJ DiDonna
I think this concept of how you rest and recover. So I think everyone thinks that the best way to rest and recover is by doing nothing. And what we found in kind of drafting off other research is that, actually, engaging in activity that’s intrinsically chosen is a great way to recover.
So you don’t have to just sip coconuts on the beach. Many type A achiever people are, like, concerned, like, “What would I do on sabbatical? I’m going to be so bored.” You can do work, but it’s work of your own choosing. It’s intrinsically motivated. It’s something that matters to you. I thought that was a pretty empowering study to read.
Pete Mockaitis
All right. And a favorite book?
DJ DiDonna
Anything by Herminia Ibarra, Working Identity is a really good one. And I think anything by Johann Hari, I think, does really good kind of journalistic investigative work. I’m reading The Three-Body Problem right now, which has been on my shelf forever. So I’m a sci-fi person as well.
Pete Mockaitis
Okay. And a favorite tool, something you use to be awesome at your job?
DJ DiDonna
I don’t want to say what everyone says about using Claude Code, but it’s been pretty incredible to go through all of my notes over the ten years kind of investigating sabbaticals and help surface and identify people that I’ve spoken to who might be interested in the book. It’s been really nice to have like an assistant through the process.
Pete Mockaitis
And a favorite habit?
DJ DiDonna
It’s honestly doing the dishes in the morning. That sounds really lame, but I actually learned to love it on a meditation retreat. We should circle up on our meditation retreat experiences afterwards.
Pete Mockaitis
Well, let’s hear a smidge more. Learning to love it in what sense?
DJ DiDonna
I think appreciating something like washing dishes as, like, work for the household that adds value, and also work where you can just focus on nothing else. There’s, like, a Nintendo Switch game which is about power washing.
Pete Mockaitis
Yes, it’s a top seller.
DJ DiDonna
Which is crazy, but I get it, right? I mean, you wash dishes, you kind of give that gift to your family, you leave the kitchen better off. It’s the most kind of mid-40s dad thing to say possible, but there it is.
Pete Mockaitis
And is there a key nugget you share that really seems to connect and resonate with folks, they quote it back to you often?
DJ DiDonna
I think people talk about the cost of a sabbatical, the price, you know, “Does it affect your retirement?” I think it’s, “What’s the cost not to?” So, really, asking people, like, “What is the cost of living your life without pursuing your dreams, without identifying things on your bucket list, and going after it?”
Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?
DJ DiDonna
TheSabbaticalProject.org. If you search sabbaticals and DJ, I’m all over the internet. This is not the identity that I thought I would have, but here we are. And I am on LinkedIn a lot as well.
Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?
DJ DiDonna
I think, even outside of sabbaticals, this annual reflection of really looking back and saying, like, “How was my year? What do I want the next year to look like?” But I think one thing that people don’t do, you know, I teach at a grad school, and when you apply to college, when you apply to grad school, you have to fill out these applications and these essays, “What are three things, three mistakes, three successes? What do I want to do after I graduate from this place?”
I think, often enough, we don’t apply to the next four or five years of our life. So I kind of encourage my students, I’ve created a template where it’s like, “All right, four years from now, like what life are you applying to? Like, no one’s going to read the essays,” but as opposed to just like a one year frame, I like that four year apply to life.
Pete Mockaitis
Beautiful. Well, DJ, thank you.
DJ DiDonna
Great to meet you.


