In this episode of Boldin Your Money, Steve Chen talks with Jillian Johnsrud, author of Retire Often, about how taking intentional career breaks, what she calls mini-retirements can lead to greater freedom, career clarity, and personal growth. Jillian shares her journey from debt at age 19 to financial independence by 32, and how sabbaticals became a core part of her life rhythm. They explore how mini-retirements can be used not just for rest, but for skill-building, career pivots, and even wealth creation. Jillian also introduces her four-step framework Dream, Career, Money, and Journey offering practical tools to help anyone take time off with purpose, not regret.
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Transcription
Introduction (00:00:00):
This episode is brought to you by the Boldin Financial Planning platform formerly NewRetirement, create a financial plan for free at Boldin.com.
Steve Chen(00:00:09):
Welcome to Boldin Your Money, the podcast. Today we have Jillian Johnsrud joining us, and Jillian is an author of a new book called Retire Often. She has and is a champion of many retirements and sabbaticals. We originally chatted with Jillian back in 2020, and I’m super curious about what’s happened in the interim. So with that, Jillian, welcome to our show. We’re super excited to chat with you today.
Jillian Johnsrud (00:00:37):
Yeah, thanks so much for having me back.
Steve Chen(00:00:39):
Yeah, so I would love for you to give a couple minutes on where you are today and your journey to this moment in time, and then we’ll jump into the main topics.
Jillian Johnsrud (00:00:50):
Yeah, I think on the financial side, I, I’d grown up without a lot of extra, but then I got married at 19, the ripe old age of 19, but my spouse at the time, and I had like $55,000 of debt and we both went into low earning professions, so that’s always a fun combination. So we never anticipated to retire early. That actually seemed like crazy talk. So instead I was like, ah, if we’re not going to be able to do that, this idea of sabbaticals or mini retirements felt possible. It felt accessible. And so that kind of was the plan initially just out of the gate. And as it turned out, by the time I was 32, we had become financially independent. So that was a happy surprise, but this idea of mini retirement still was a lot more appealing to me. That rhythm of life, of periods of work and periods of rest. And yeah, it still resonates with me.
Steve Chen(00:01:56):
I mean, it’s amazing to start at 19, kind of getting married and starting your life and negative net worth, did you have this vision of, okay, we want to be financially independent, and did you know about it? Were you financially literate at that point?
Jillian Johnsrud (00:02:10):
No, not at all. My first kind of financial goal as far as that goes was maybe we could be able to retire by 60 instead of 65. And I had seen my spouse’s parents, their health decline, and they hadn’t been able to work for as long as they anticipated they would be able to work. And it was just a really stressful situation and I thought, this is a better plan. What if we try to be ready by 60 versus 65? And it honestly felt incredibly ambitious and a little out of reach. I wasn’t sure how we were going to do that, but I bought my very first personal finance book when I was 19, and then when I was 20, we moved to a town that had a library Growing up, we didn’t really have a library, and I started reading nonfiction and I started reading about a book a week, a couple books a week, and I did that for 20 years. So now I’ve read a thousand nonfiction books. But that was how I built my knowledge of personal finance and investing. And when you read that much nonfiction, you kind of have to read all the genres, just not enough of one genre. So that’s kind of how I learned about most things in life.
Steve Chen(00:03:28):
So you weren’t super targeted strictly on personal finance, but it was like you’re just reading a ton. So then
Jillian Johnsrud (00:03:35):
I literally just go to the library and get a little basket and walk from one end of the nonfiction area to the other every single row and probably grab a book from every row. So there were some weeks, I definitely read seven books.
Steve Chen(00:03:51):
What drew you to personal finance? Because obviously you zoomed in there, have built a whole persona and become an author yourself, which is congratulations and amazing. I mean, it is amazing to go from 19, which is pretty formative time in your life to whatever, 12, 13 years later and you’re financially independent, which is something most people barely get to when they’re 60 years old.
Jillian Johnsrud (00:04:19):
That motivation and initial interest for me came about, I was probably about 12. My mom was in her second marriage and it awesome. It didn’t feel healthy, didn’t really feel safe. And I went to her and I was like, yeah, we can’t do this. I don’t really care where we go, but we shouldn’t stay here. And I was like, yeah, I’ll get a job, I’ll work whatever, we can live in a little apartment. And my mom’s a very practical woman and she just looked at me and was like, Jillian, I can’t afford to race three kids on my own. We don’t have that option. And being an optimist and an idealist, it was crushing to me. And so I went upstairs to my bed and I just cried hot tears into my pillow. I was so devastated. But it was also a little bit of an epiphany of, oh, money gives you options.
(00:05:14):
Oh, money gives you choices. And in that moment I was desperate for more options and more choices and I was like, I never want to be in this spot again where I can’t make healthy, safe choices because of money. And so really for me, that initial motivation was really out of, I want more options in life and this is how I’m going to go about it. So I just started saving a lot of money. I worked after school, I worked over the summers. By the end of my senior year, I had saved $8,000 and I lived on my own whole senior year as well and paid my bills. And so that motivation right out of the gate was there of I want some more options in life.
Steve Chen(00:06:05):
This is so interesting. I interviewed this woman, Brie, who lives in our town way back, this was back in 2017. She had saved a hundred thousand dollars in high school. It was crazy. Same thing, but working, starting to invest and and it was a similar kind of like, I should connect you too, just motivation. I mean, she’s probably, I’m sure she’s mostly in her mid twenties now, but I should check in and see what she’s doing. I just remember hearing about her and thinking, this is incredible, who does this? But yeah, this internal motivation, and I think these stories that people have from their early lives about wanting to get this lovable control is such a huge driver. How did it play out? I mean, I dunno if you’re willing to share this, but I’m curious how it played out with your mom and what happened.
Jillian Johnsrud (00:07:00):
Yeah, eventually she was ready to leave, but it took a lot of years and so I think that clarity, the first year my ex and I were married, someone just randomly said to me, I had never heard of financial independence. I don’t think it was really an idea. I’m 42 now. This was a long time ago, 23 years ago. But someone randomly said to me, Hey, so I mean you guys have been living on your own and paying all your bills when you get married, you should just save one of your incomes or just save half of that and then as you get older, if you want to have kids or buy a house or whatever, you’ll just have some more options. And I think just that word options, I was like, Ooh, I like that. Yep, that sounds great. We should definitely do that.
(00:07:52):
And so that was all it took just one person casually saying two sentences to me and that became the goal. Let’s try to save half. And like I said, we didn’t go into hiring professions, but figuring out how to pay off those debts. I realized very early on when I was about 20, 21, it can be really tough if you grow up poor. I felt a lot of shame around looking poor. I really didn’t want to look poor, but I realized because I realized I don’t make enough money to be rich and look rich, I’ve got to pick one of the two. There’s not enough cash here to do both. And so I kind of optimized for being rich, and now I feel like there’s actually three options. You can look rich, you can be rich, or you can experience a rich lifestyle, and sometimes you make enough money to do all three. Sometimes you got to pick one. Sometimes now I’m like, I get to pick two, I get to be rich and I get to have a rich lifestyle. I still don’t look rich. My minivan’s like 20 years old. I think pity people still pity me a little bit when I pull up in it.
Steve Chen(00:09:11):
I think that’s a strong signal though. You see this, I remember being in San Francisco and seeing this written down and then noticing it that very often people that have money, they drive kind of crappier older cars or they’re not spending money on stuff like that, like a depreciating asset. And then you’d roll around and they start noticing, oh, here’s someone in the nice house, but their cars seemed like really old or whatever it is. And it’s also all relative. It’s so interesting. It’s, I think everybody’s kind of indexing on this upper middle class lifestyle that, hey, this is kind of what success looks like and whatever house, certain kids, certain school districts, whatever it is, wherever you live, and then spending to keep up with the Joneses, and that makes it really hard. And then Mr. Money Mustache comes along and he is like, Hey, you got to save this high savings rate. It’s all, it’s basically the savings rate relative. It’s really the savings rate. If you can save half of whatever you’re making and you’re able to live on the other half, then you can pretty quickly. You did get to financial independence at that lifestyle. And then it depends on are you happy at that lifestyle? Does that meet your needs? But so many people don’t understand that.
Jillian Johnsrud (00:10:28):
Well, one of the things about mini retirements is you can use ’em for a lot of different functions. So especially if you’re early in your financial journey, you can use them as wealth building activities. They don’t all have to be travel or adventure. The house sit actually I’m in right now was a mini retirement project about 12 years ago. Me and my spouse at the time, we took a month off. We bought this house, we renovated it ourselves, got all the basic stuff done, got it rented and used it as a rental for seven, eight years, and then five years ago moved into it, finished renovating it, but I’m kind of a number geek, so we paid a hundred thousand for it initially. We’ve put another a hundred in, it’s now worth 500,000. So that month off, yeah, it probably cost us a few thousand dollars. We didn’t get paid that month, but we’re $300,000 richer because of it. And so I think frontloading some of these mini retirements for things that can accelerate your career or can accelerate wealth building activities, especially if you’re at the early stages of your financial journey, it can make a lot of financial sense.
Steve Chen(00:11:43):
That’s super interesting. Do you have other examples of, I hadn’t thought of it this way because when I was getting ready for this, for this, I was thinking about, oh, take a sabbatical, take some time off and chill out. I think that’s how most people think about it, but you’re kind of flipping it on its head, and that example makes a lot of sense, but yeah, are other examples of how people do this use their time that way?
Jillian Johnsrud (00:12:06):
I mean, on the professional side, a lot of people use a mini retirement to get additional training, additional certifications, improve their soft skills, really recover from burnout so they can show back up at a hundred percent and kind of be a little bit more of a rockstar. Oftentimes people use a mini retirement to try to find a better job. On the other side, there’s a lot of cultural influences there. When someone takes off work to go do something fun where everyone kind of in your network subconsciously wants to pull you back into work, they’re like, ah, they’re having too much fun. Let’s get them back into being employed. And so people are often surprised that they get a lot more job offers while they’re on mini retirement than they ever did while they were happily employed. Nobody ever thought of them for the job while they were happy at their job.
(00:13:04):
So that can be one of those things. Or professionally, a lot of people, especially in their forties, late thirties, early fifties, they’ve done their career for a long time and they’re looking at, I’ve probably got another 15, 20 years. Is this what I’m going to do for the rest of my life? Is this the one thing I’m going to do? And if by your forties or fifties you’re further along in your financial journey, I talk about this as kind of the first chapter, the first chapter over your career, you really need to optimize for earning the most amount of money is making that financial progress, paying off your debt, starting to invest. But if you’ve made a lot of financial progress, that’s not necessarily what you need to optimize for in the second chapter of your career. And I see a lot of people, they’ve gotten some financial momentum and they take this mini retirement to reimagine, what do I want to do professionally?
(00:14:04):
Do I want to make a pivot? Is there something else I would enjoy? Are there other things I could optimize for? Could I optimize for coworkers? I enjoy more? Could I optimize for a better work-life balance? Could I optimize for more creative or interesting work or work that leverages my skillset in a different way? Could I optimize for something that’s less stressful or I have more time with my family or it’s more flexible for me to travel? And it’s tough to do that. It’s tough to reimagine that when you’re in the thick of your current job and just so overwhelmed and maybe burned out and focused on what’s happening in front of you.
Steve Chen(00:14:42):
Yeah, that totally resonates. It does feel that that’s how most people go through their life. They’re like, Hey, they’re pattern matching. I don’t know the world I run in. It’s like, Hey, in my high school, 95% of people went to college, four year schools, and they went to pretty good schools, and we were all kind of on this train of like, okay, we lived in a middle class, upper middle class town, but we were kind of trained and almost indoctrinated. Then you’re like, okay, get through school and then you’re either going to go to grad school or you’re going to need a job, and then you’re going, and then you kind of heads down trying to make money, go through your life, get married, have kids, all that stuff. I mean, what percentage of people do you think do this that they find the space to pull back a bit and think about it more holistically before the traditional 55, 60-year-old timeframe when you’re like, okay, for whatever reason I got laid off or I have enough money, I’m going to think about it now.
Jillian Johnsrud (00:15:55):
I think it’s rapidly increasing. And so I also maybe to take a step back, I define a mini retirement with three characteristics. It’s a month or longer stepping away from your nine to five to focus on something that matters to you. So if you hit those three, I’m like, yep, a mini retirement. And it’s funny, when I talk to people who were maybe going to interview me for about mini retirements, they go, actually after I read that, I was really curious about, I was curious about taking my retirement, but I realized actually I’ve done that. I did that after college. I took three months off and I went backpacking in Europe or after me and my spouse were married, we were going to move across country and I was switching jobs and we took a few months off and we did this really cool road trip.
(00:16:42):
And so I think it can naturally happen whether we know that that’s what it is or not, whether we’re intentional about it or not, there’s periods of life where you might be unemployed or you might have a gap in between. You might negotiate starting your next job a little bit later so you can go do this cool thing that you couldn’t do during your working career. But the other factor is that the economy’s different. It’s just changed a lot in the last 50, 60, 70 years. So this idea that you can have one career at one company for 40 years and then get a pension and retire for the next 30 years, that’s just not the reality we’re living in. For most people. You’re probably going to work in multiple employers, you might work different careers, and you’re going to have these opportunities to take breaks in between these jobs.
(00:17:43):
And for a lot of people, especially if you’re under 40, the wages versus cost of living ratio is a little bit different than it used to be. And so this idea that I’m guaranteed and promised a retirement it’s 60 or 65 might not be a reality. The reality is people might be working till 70, they might be working part-time till 75. Lifespans are also increasing, and I think we have a much better understanding of how to be healthy and active than if I think about my great grandparents. They’re very different than what I do. And so I think this model is what makes sense in our current economy and in our current job market and how we’re actually living our lives.
Steve Chen(00:18:33):
I think it’s starting to happen. I agree with you. As I was prepping for this, I was like, I asked perplexity, how do people do this? Take a sabbatical is what I asked, which they define as more than 120 hours off within a couple months. But anyway, the rate had basically doubled in the past. It’s still not super high. It’s like 7% versus three and a half percent. But while we were talking, this whole being out of work thing as a reframing is interesting. So 75% of people take more than a month to find a job, and tens of millions of people have been out of work in the past decade with COVID and stuff like that. So there is a real rotation. I do see this with people I know, especially as I get older and advance my career or my life, it’s like, yeah, you see more people as they’re deeper in their career, they’re like, okay, I’ve been making more money, but if something happens, I’m out of my job. It takes longer. It takes longer to find those higher pay jobs. And could people be more intentional with that time?
Jillian Johnsrud (00:19:49):
Yeah. One of the things I talk about in the book is this idea of a mini retirement go bag. They used to wash a lot of NCIS and they always had this duffle bag, and so when an emergency came, it had their passport and some cash and their toiletries and a few changes are closed, and they could just grab this duffle bag and in a moment’s notice go off on wherever they needed to go. And we can do the same thing for many retirements, especially those unplanned, unexpected, you get laid off and they’re like, okay, here’s six months of severance, best of luck and you don’t have a lot of notice for this. But in that mini retirement go bag, I encourage people to come up with four or five month long plans, something that’s meaningful to them, something that’s interesting, something, a variety of things that they could do in different seasons.
(00:20:37):
It can’t just be like, I’m going to do a downhill skiing trip. You might get laid off in July, things that they could do at home versus traveling, and if you put in the planning and the emotional energy upfront to what are five cool things I could do? And then set aside a little bit of money for those adventures, then when you get laid off, it’s still a bummer and it kind of sucks, and you go home and you’re grumpy, but maybe in a couple days or maybe in a week, you pull up that word doc and you go, actually, maybe now’s the perfect time to do one of these adventures. And you’re able to emotionally pivot in this difficult situation where if you hadn’t done the planning, you might stay stuck in those difficult unpleasant emotions and not have the creativity or the motivation to come up with a cool plan.
Steve Chen(00:21:29):
I like that idea a lot. This go bag, we definitely talk about in traditional retirement, like, Hey, make sure you’re retiring to something. But
Jillian Johnsrud (00:21:40):
The
Steve Chen(00:21:41):
Idea of thinking through in advance a bunch of things that you want to do over the course of your whole life and doing that early. And I think having the framing of knowing that you can’t always like, Hey, I might want to go climb Everest. Well, it’s 65 or 60, that’s way harder than when you’re 30 or 40. And so if you want to do some of this stuff earlier in the process, you should be pretty thoughtful and intentional about doing it. And I think one other comment I have about this is I do see this where people, they’re like, okay, I got laid off great, I have a minute. But then they’re very worried about getting a job. So they’re very focused on that. And then when they do have the space is when they’re like, okay, find a new job, but I’m going to start two months from now. That’s when they’re like, I feel good. It’s job’s coming, but I can do this. I think it’s getting that framing earlier and being like, okay, actually I got laid up. I can spend some time not worrying about it and maybe taking action with my own human capital.
Jillian Johnsrud (00:22:48):
I think having that plan helps people emotionally pivot. And the other thing is I think the reframing of if you’re going to be, you have six months severance, let’s say you have a job that’s hard to find something at your level, it’s an appropriate fit, and it might take six months. You could stay home and just look for jobs for six months, or you could go do a really cool adventure. You could do some professional development. You could do something that’s personally enriching. And then when you are doing those interviews and people are like, so what have you been up to? You’re like, well, I just finished a cooking class in Italy for a month, and me and my mom, she just retired. So we biked through Croatia for a month. I took this class at the local college for public speaking. You have these things that show that you are interesting and dynamic and motivated and organized and passionate.
(00:23:45):
Many retirements, they’re not exactly easy to pull off. It takes a little bit of courage and it takes a little bit of gumption to go out and do cool things. It’s much easier to just stay home and do nothing and watch Netflix. So I think there’s actually a distinct advantage to being thoughtful with this time and doing the cool things. And especially if you are in an industry that’s really intense and very focused and doesn’t have a great work-life balance, I think people worry about, well, how am I going to explain this that I took six months off? This is a very work-driven culture here, and I think you are intentional with that narrative and it becomes a work hard, play hard of, I worked super hard at my last job, so I took three months off. I got caught up on all of my personal stuff. I invested in my relationships, I invested in my health, I did cool things, and now I’m ready to go all in again because this is the rhythm that I like. This is how I like to sprint. I like to sprint. I like to work super hard. I like to be super focused. And then in between jobs, I take a break and recharge.
Steve Chen(00:24:56):
Yeah, that’s super interesting. So do you think people should be, it feels like yes, or I guess why should people be proactive versus reactive? Talked about, okay, something happens to you and you’re like, I got laid off. You’d be intentional at the time, but I know that you’re also, you talk about the risk of burnout and you have to invest in yourself and the importance of rest. So what’s your point of view about being proactive and how that should emerge in your life around this area?
Jillian Johnsrud (00:25:26):
Yeah, I think because things are different now, I think it makes the most sense, the most logical sense for a person to say, actually, I think I’m going to take a mini retirement every three or four years, two or three years into my career at a company. I’m going to negotiate a month off. I’m going to negotiate two months off. And then when I switch companies, I’m going to take three months off in between and make that part of the rhythm. And then if are thoughtful about it, the reason I called the book Retire Often versus Take one massive epic mini retirement in your working career is that you can give each mini retirement a different function, a different purpose, a different intention. So in the early ones, maybe make them wealth building activities, maybe make them career building activities, do the affordable, easy, cheap, hyper adventurous things that you might not want to do in your sixties.
(00:26:23):
Do those early front load, all of those. But then as you go through the decades, they can each serve a different function. So by the time you’re in your forties or fifties, if you’re thinking about traditional retirement, start to use those as a test drive of your retirement. When you talk about what are you’re retiring to, don’t just make this theoretical. I’m theoretically going to do this. Do a test run. If you think, you know what, God, I would love to play golf every day. I love golf so much. Take a month off, play golf every day. See how it goes. See what you think about it. If you’re like, I want to volunteer at this organization, take a month off, go do that thing because some of it will be amazing and it will give you confidence to retire and some of it will be a disaster. And then you’re able to learn from that and to pivot and to come up with new ideas and to test run those ideas. So that transition into retirement, you’ve already done it five or six times. It’s as seamless and easy as it’s going to be.
Steve Chen(00:27:28):
Are there communities around this topic where people get together and they kind of share what’s worked and what hasn’t?
Jillian Johnsrud (00:27:38):
I think it’s becoming more popular, and I hope that we’re moving that direction. It’s one of the reasons I host group coaching around it because most people who are doing mini retirements, none of their friends and family are doing it with them. They’re doing it kind of alone. And there can be challenges, there can be fear, there can be things that don’t go as expected, and it is really helpful if you have other people who get it. There’s not many advantages of traditional retirement in my opinion, but one of them is that a bunch of your peers are also retiring, so you’re in this weird life transition altogether, and you can go and get coffee and you can kind of complain to each other of, my spouse is driving me crazy. They’re home all the time. He doesn’t know how to load the dishwasher. But if you are 40 and you try to go to your friend and you’re like, oh my gosh, I am way tireder than I expected. I’m just napping all the time and now I have all this time with my spouse and there’s this conflict and I feel like I have almost too much free time, you’re going to be like, you’ve got to be joking me. You’re complaining about too many naps and too much time with the people you love. You have any idea what I’m living right now?
Steve Chen(00:29:07):
How is the group thing is so interesting. We are seeing this in our communities where we have people in Facebook and people in Reddit that hang out at Bold and they talk about retirement, and they talk about their money and their time. And what’s interesting is there are these emerging, organically emerging groups that just form up themselves and they’re like, we’re going to get together on Zoom or in person and we’re going to do what you’re just described because they’re going through it together and they have different roles and ways of operating. When you’re doing this group coaching, who shows up and are they the same? Are they across these generations and what are some of the big things they’re diving into?
Jillian Johnsrud (00:29:47):
Yeah, I mean, the demographic is probably 35 to 50. It’s kind of that middle career kind of thinking about. A lot of them are thinking about, do I want to make a slight career pivot after this? And for most of them, that’s not something entirely different, but going into something that’s maybe adjacent but maybe a better fit for their interest or their skillset. But I have them basically a lot of the content in the book, we have a workbook, and so there’s exercises. And so once a week we show up and we just share What were your answers? What were you thinking? What’s the plan? And it’s funny because I’m there, but mostly facilitating. They don’t really want to hear my opinion. They’ve heard my opinion. They want to hear how were each other handling it, how are they negotiating this off? How are they thinking about networking?
(00:30:40):
How are they finding another job? How is the budget turning out they thought it would turn out or not, how they thought it would turn out. And then problem solving, I feel guilty taking this $150 art class. Am I missing here? Why do I have so much more scarcity mindset? Or I’m more tired than I expected and I’m feeling guilty about that. I’m not getting as much done as I wanted to get done. So I think it’s really helpful to try to find people who are going through you unique things because that fourth step in the book, I talk about this journey in that it’s really unexpected for most people what this is like. But I liken it to Lewis and Clark on when they were sent out on the expedition across North America, they had never been there and it was uncharted for them.
(00:31:35):
So it was all new and it was all novel, but people had lived there. It wasn’t unexplored just because they hadn’t charted it. Other people were actually really familiar with every part of the country. And so finding the people who have done this, who are doing this and getting some advice and getting some comradery of, wait, what time of year can we cross this river? When’s too soon? When’s too late? That can be really helpful and really reduce, I call it unnecessary emotional suffering. There are things that can emotionally cause us to suffer, but they don’t have to if we just think about it a different way, if we handle it a different way, they kind of evaporate.
Steve Chen(00:32:24):
Yeah. One of the insights I got from a friend of mine who was also one of our first folks that used advice in our platform, he’s a doctor, a psychiatrist, and for children anyway, he was like, anticipatory anxiety is the most significant impactful form of anxiety. We all worry about what’s coming and have so much anxiety about it. And then when it happens, you’re like, oh, we’re all still here, but we can’t control ourselves from worrying, having this worry. What about outcomes when people, so they’re in these coaching sessions and engaging and learning about this and going through it. Do you have stories or data about how it helps people? I mean, so financially, and then I’m also interested just on burnout. This is such a work intensive culture we live in, and I think especially millennials and Gen Z are super thoughtful about burnout and being aware of it. Do you see it improving those things
Jillian Johnsrud (00:33:41):
Across every area? I mean, one, it’s kind of intensive. We do 16 weeks. It’s like we’re talking a lot. But yeah, when you put time and intention and effort into something, it typically makes it better. So the plans that step one, the planning gets better, they figure out how to organize it, being more thoughtful of the finances, taking a few of those extra steps in networking or maintaining contact with people during their mini retirement, asking for help during the kind of job hunt process. But honestly, a lot of it is the course correction. It’s really easy if you’ve never done something for it to go off the rails. And I tell people, this is intensive. The workbook’s over a hundred pages. There’s so many exercises, we’re going to spend 16 hours talking to each other, and you could get the mistaken idea of you’re going to have a hundred percent perfect plan by the time you walk out of this.
(00:34:51):
And I tell people, you will not have a hundred percent perfect plan. You are going to have 70% of a plan, and then the other 30%, you’re going to have assumptions of what you think is going to happen and how you think it’s going to go, and those are going to be incorrect. And so the goal is every week, kind of like the scientific method, you’re going to test your assumptions of how you structure your time, of how you budget, how you feel about your money, how you network, all of these things. You’re going to test your assumptions. And at the end of the week, we’re going to do a weekly check-in and you’re going to ask, how is it going? What did I learn? What went well, what didn’t go well? Do I need to have better boundaries with my friends? They keep asking me to babysit their kids. All this stuff that could pull things off the rails, and you’re going to course correct and you’re going to try it again next week and slowly week after week, you’re going to trade some of that 30% of make believe of your plan for actual data that’s real, and that plan should evolve and change as you go.
Steve Chen(00:35:58):
I love talking about planning. I know I want to dive into what you’re doing here. So what do these groups look like? I mean, how many people are doing this at a time? I could see this resonating with our audience,
Jillian Johnsrud (00:36:10):
Our cohorts. We usually on the calls, it’s like five to 15 people, so I try to keep it to where everyone has a chance to share their work and ask questions and give advice. So finding that sweet spot of that group dynamic. And then we do a WhatsApp chat where people kind of continue those conversations and when they’re like, oh yeah, that resource that I shared or that link that, and we throw all of that in there, but in sharing their work and sharing their plan and sharing the parts that they struggle on, they get really close to each other. They develop really strong bonds, and often they keep going afterwards. They still have Zoom calls with each other or they meet up and go on vacation together and stuff, because all doing mini retirement, so why not?
Steve Chen(00:37:03):
This is happening in our little communities, but they’re not organized as, I mean people, I think they are going through this process. Fascinating. So people are, you’re grouping people up, good size, I mean solid. I think the optimal group size, they say like eight people, right? Or whatever. But at five 15, I think it makes sense. Everyone can participate. Then they’re doing 16 hours of training, workbook stuff. What does this cost? Is that something we can job
Jillian Johnsrud (00:37:28):
So affordable? Probably this is not a business savvy move. I’m charging $300 right now, which is like, yeah. So on a business side, let’s not study the economics of this. Let’s ignore all of that for a second. But I love it so much. I love seeing the conversations I love. We show up every Monday night for an hour, and it’s really fun for me. So the fact that it’s kind of a volunteer role on my part, I don’t mind at all. But yeah, I try to make it enough to where people will show up most of the time or else I probably would just offer it for free. I love hosting, but
Steve Chen(00:38:16):
This is where when you’re financially independent, you can kind of really lean into stuff that you love doing and things that I would do for free. I would do this for free anyway. You’re basically think, but then what could happen is you might get a lot of people signing up for this, so they start discovering it, and then it becomes a job. Or then you have to raise prices to keep it manageable.
Jillian Johnsrud (00:38:38):
I think we’ll figure it out. I think could, we could just have a free version if they want to organize themselves, we’ll let them do that.
Steve Chen(00:38:46):
Well, I’m curious. Well, I’m actually really want to dive into, obviously with Bolden, it’s all about financial planning and people are mostly planning traditional things. But it’s interesting, there’s people on our team that are millennials and they’re like, oh, well, they’ll do scenarios like sabbatical in Thailand. And when you’re saying, when you’re talking about planning, sorry, taking a straight this direction, but what are the things that people are considering, the big things that they’re considering in their plan?
Jillian Johnsrud (00:39:23):
Yeah, so there’s the budget. So a little tangent. I’ll talk about the financial planning side because I’ve sat with a lot of people while they run their numbers in financial software and they run both of those scenarios. What would it cost if I take six months off or if I just keep working? And then we have that number at, okay, when you’re 67, and I can never answer this question for someone else, which one is more appealing? Which one do you want more? And so what I have people do is, okay, imagine you’re 67 and you either have 2.3 million and you took these mini retirements, or you have 2.7 or 2.8 million. 2.3 is enough. So that’s a lot of money, different 500 some thousand dollars. That’s a significant difference in money. If you imagine if you visualize being 67 and you can have 500,000 more or less, but when you were 40, you took a big road trip, you took a 10 week road trip with your kids to 10 National park school, they were all still kind of little, and when you were 50, you hiked through Ireland with your parents while they were still with us.
(00:40:57):
And then when you were in your fifties, you took this break and reimagined your career and you came back to this kind of new reworked career that you’re really excited about. Which one would you prefer? It’s your choice and it’s your life. And you get to pick, do I want an extra half a million dollars, which is not insignificant, or do I want to be able to look back and do all these things that I no longer can do I no longer have access to those choices anymore? Or is it worth, okay, you’re 67, you’re like, ah, I really need that extra 500,000. If you could look back and have, you have five or 10 of these experiences and you feel like you’ve had this incredibly rich full life and you did all the things you wanted to do, how would you feel about working two more years
Steve Chen(00:41:50):
Where I think I know the answer, but I’m curious what you find when you pose this question, and is this kind of what it looks like for most people?
Jillian Johnsrud (00:42:01):
Yeah. Well, so far, a hundred percent, but I have a very biased demographic. I find when people have enough to meet their needs extra doesn’t hold a lot of value, it doesn’t feel very exciting, more money that they probably won’t use. So as soon as they get to, I’ll have enough to pay all my bills. The idea of these memories and these values expressed and these experiences with people they love become much more appealing and much more captivating. And I think especially once you’re to the point where certain seasons of life have passed you by and you can feel that intensely.
(00:42:52):
I mentioned 10 weeks to 10 national parks is something I did with my kiddos, and they’re in junior high and high school now, but when we went, they were all itsy bitsy and we were in a pop-up camper and just exploring the most beautiful places in the world with them every day doing these adventures, and we’re selling our camper this summer. And someone asked me, are you sad? Because for the last nine years, we’ve done a big camping adventure, three, five months, six months every year with them. And they’re like, are you sad that that season’s over? And I am sad? But also we leaned in so hard to that we did all the things. We did hundreds of days of just being with our kids every day and doing these incredible adventures. And it was such a gift to me, and it was such a gift to them that I’m like, I am sad it’s over. But man, I couldn’t have done anymore. We rang every drop out of that towel. And so I think once you’re to the age where you feel that, you look back at those pictures and you’re like, oh my God, that was so fun or that was so meaningful. It makes those future decisions a little bit more clear.
Steve Chen(00:44:16):
I think for all of us, we have to consider this, and I totally see this too, as people age, they become much more aware that time is so much more valuable than money, especially as they have when you have less money and you’re in that scarcity mindset, you’re like, oh, we need money. Got to focus on that and crank and do all this stuff. But then you get older and you’re like, well, you’re not going to take it with you. You can support your kids and everything else. But it’s also interesting hearing you describe it. So you think about a 30 year career, right? Many of us will have 30 year, 40 year careers, right? So you’re working, if you take two weeks off a year, that’s 60 weeks over 30 years, two 30. But many of us work longer. If you took ten four week breaks in that timeframe, that’s 40 more weeks. I mean, it’s a year of time, but it’s not that as a percentage, it’s like 3% or whatever. It’s not that much because one year, one more year out of 30 is literally 3% of your time. That’s the trade off.
Jillian Johnsrud (00:45:25):
This is a great thing to run through financial software. I think most people are surprised how small of an impact it makes, especially if you’re just taking a month off, two months off. It doesn’t massively change your trajectory. Even accounting for nothing else changing, which I’ve, I’ve never seen people take multiple, many retirements and nothing else in their life changed or improved. You create this space and it creates an opportunity for growth and just for new opportunities to happen, whether those are career building or wealth building or both, but it doesn’t have a huge impact. But when you look back on that in the rear view mirror, those ten one month things become the highlights of your life. They’re just epic. And especially compared to two weeks of vacation, because that’s never a two week vacation. It’s always split up of, I took an extra day for Christmas, and then we had this wedding we had to go to, and then we had to travel for this thing, and then my kids had sports, so we took an extra day here to do travel like baseball. It’s never just an epic two weeks in Costa Rica or Italy. It gets divided up amongst all these little things, and then maybe you get one nice five day vacation. So having a month off, you can have incredible adventures, things that you’ll remember for the rest of your life.
Steve Chen(00:46:58):
So a couple of quick thoughts. My oldest kid was like, you experience half of your life by the time you’re 24 in terms of your experience of time, I think is that, and experiences occurs, half of it occurs in the first 24 years because everything’s new where he was using a word. It’s dopamine sensitive. When you’re young, everything’s new, you’ve never experienced it. That’s cool. And I definitely have this in my life where I was felt like time was slower, much more going on. And then you kind of get in this pattern of whatever pattern you’re in. For many of us, it’s working a lot. And then it’s like time flies by. I mean, there are moments, I mean, you’re definitely, if you’re having kids and buying houses or whatever, there are seasons of our lives. But I think that’s definitely true in what you’re proposing, which resonates, is do wildly different things and your experience of time will expand across your life.
Jillian Johnsrud (00:47:57):
Yeah, I feel like by the time I hit 30 or and especially 40, I’m like, I’ve had two lifetimes. I’ve done so much more than I ever thought was possible. And you’re like, oh, time to dream some new dreams. Set up some new goals. I ran through that bucket list.
Steve Chen(00:48:20):
Well, that’s for you. That’s normal for you, but not for most people. But it’s good you recognize it.
Jillian Johnsrud (00:48:25):
Having those mini retirements and having that opportunity, it is compared to a two week vacation, even just a month off is massively different. And you can accomplish so many more significant things and very novel things that yeah, if you’re like, what did I do August six years ago? You’re like, I don’t know. I just lived and cooked food and went to work and took showers. But if six years ago you were hiking the Camino, you absolutely know what you were doing.
Steve Chen(00:48:59):
Yeah, that’s cool. Do you think women do this, think about this more than men or vice versa?
Jillian Johnsrud (00:49:05):
So I think sometimes, especially with depending on the gender roles and dynamics, the impact of burnout can be multiplied for women. If they have the same busy demanding career, the expectations of what they carry outside of that, and sometimes that desire to want to meet all of those expectations and not disappoint people, it can amplify that burnout. So I think men and women both experience burnout, but I see a lot of women, especially in their forties, they’re crispy. They’re burned to an absolute crisp because there’s so many demands. And I just know I have five kids. It’s funny, even between me and my ex, despite how much we tried to create equality in our home, the cultural pushback to that is constant. I remember we used to go to the gym together and we would bring our two little kids in the gym had a rule that they didn’t change diapers, like the parent had to change diapers, and they would always bring the kids to me.
(00:50:23):
And every time I’d be like, Hey, we take turns, we take turns changing diapers. And they would still consistently just bring the kids to me. And I’m like, we’re both here. And I would take the kids to go change their diapers in the bathroom. No one would say a word. And then when it was my husband’s turn, I would see him taking our little girls to the bathroom and all of the old women, because we worked at a gym. It was like all the 70 year olds were just like, he’s just the best. Isn’t he amazing? What a sweet dad. And I’m like, nobody compliments me for, I’m doing the exact same thing here. I get zero compliments. So I think with current gender roles, even if inside your home you try to create so much equality, women just disproportionately usually get asked and expected to pick up that additional labor.
Steve Chen(00:51:17):
It feels like it. Hopefully that’s changing. We’ll see. Not as fast as it should. Do you feel like there’s any downside? I mean, we talked about the financial side. Okay, plan for it. Well actually, lemme back up a second. In your groups, are your groups biasing female? No, it’s 50 50 or whatever.
Jillian Johnsrud (00:51:38):
Yeah, very. Are they
Steve Chen(00:51:39):
Biasing
Jillian Johnsrud (00:51:39):
Male? Yeah, very evenly. Split. Split.
Steve Chen(00:51:41):
Okay. So we talked about the financial tradeoff. Are there any other trade-offs or do you think it’s all upside for people? I guess there’s some career risk, maybe. I dunno,
Jillian Johnsrud (00:51:53):
Career risk, career gain. I mean, I see a lot of people there. Best opportunity to get a substantial raise or to get a substantial promotion is by switching companies. Typically, a long loyalty is not financially rewarded. I had a friend who took a year off and when you went back and got his next job, it was a 50% pay raise, which are like, man, that’s awesome. Great. No, no, no, it’s not great. Because he had been at his last job for 15 years, which mean he had been underpaid significantly for a long period of time. He had left a lot of money on the table by not taking many retirements and switching employers. So that actually massively delayed his path to financial independence because he just stunted his lifetime earning potential by that company loyalty. So is there some risk, but there’s also some upside and there can be a lot of reward in that.
(00:53:02):
So I would say those things in general are an upside. There is a whole bunch of stuff that goes wrong. It’s just never the stuff people worry about. People worry about healthcare and they worry about the finances and they worry about the career. And those feel like the big things. And they’re not the things that go off the rails. Typically, it’s learning how to communicate boundaries to your friends and family work. Oh god, it’s an amazing excuse. Everybody respects it. Everyone honors it. If your mom says, Hey, can you guys stay for eight days over Christmas? You’re like, oh man, we would love to. So sorry. I have to go back to work. So we can only be here for three days. If you’re on a mini retirement, you need to have that conversation. And they won’t necessarily respect your goals and your intentions for your time off.
(00:53:53):
They won’t understand them. So that can go off the rails. Mini retirements can reveal weak spots in our lives. They don’t create the weak spot, but it gives us an opportunity to see where those weak spots are. And that can be a painful revelation. You can learn a lot about yourself. I had a friend who took a mini retirement and he was like, yeah, so I thought work was the reason that I never went to my nephew’s soccer game and that I didn’t learn Chinese and that I wasn’t training for a marathon and I didn’t clean out my garage. And it turns out those were just me. I was the problem. And that’s not when you’ve been blaming work for a lot of the things you’re discontent with and then you remove that excuse and you’re like, oh, I’m the problem. It’s me. That’s not super fun to work through.
Steve Chen(00:54:46):
Well, it’s good that they have that self-awareness to own it and be like, oh yeah, it was actually me.
Jillian Johnsrud (00:54:53):
And in preparing for traditional retirement, I have a lot of people say, what about my sense of value? What about my sense of purpose? If I don’t have this job, what if I feel listless? I dunno how to organize my time. And I’m like, yeah, probably all those things that’s real. And you’ll probably go through it, but we’ve got two options here. You can either figure it out or you can die at your desk. That’s it. There’s only two options. So why don’t we start to figure it out in small doses, figure it out over three months, not when you’re staring down the barrel of 30 years. Because at the end of three months, even if you haven’t figured it out, it doesn’t matter. You just get to go back to work and you got to avoid this problem for another couple years.
Steve Chen(00:55:44):
So I have one more question and then I want to ask you a little bit about your book and then we’ll wrap it up. Do you see this? What do you think it’ll look like in the next five years? Has it changed? I mean, it’s been five years since we jumped on. It does feel like this is changing. It’s sabbaticals. People are more intentional about their time, the culture’s changing. There’s definitely a lot more awareness. We’re in the age of ai. Everyone’s like, oh, I’m going to lose my job to ai. I mean, we’ll see mean we tend to get busier, but I can also see that maybe we go to four day work weeks. I don’t know. Or maybe we go to sabbaticals every three or years.
Jillian Johnsrud (00:56:24):
I put one chapter in the book that’s specifically what are 10 benefits to employers? What if we gave every employee a month off every year? How would that change our companies and change our workplace? And I think my internal optimist, I’m excited and hopeful that with ai, if a company’s like, Hey, we could be 30% more profitable with ai, I said that the cost of this is about 7.5% to give every employee a month off every year. What if instead of being 30% more profitable, we settled for 23% more profitable and we massively reimagined work and culture and life. What if every American had a month off, a month off to travel and go on vacation and boost economies and spend money and have hobbies and improve their health and improve their families and improve their communities? We could massively with this one little bit of technology change. Our every one quality of life could improve. Now we could just make a couple billionaires way more rich or all Americans, our quality of life could massively improve and be different forever moving forward. But I think there are a tremendous amount of benefits to companies. And in 50 years, yeah, I think everyone will offer one. The companies that have the vision and are quick to adapt will have a huge advantage for the next two decades while the laggards suffer or burn down, I don’t care. They can burn down too.
Steve Chen(00:58:13):
I mean, I do believe that we’re more innovative with more rest or more balance in our lives. So it’s interesting. While I was listening to you, I was also looking up in Europe versus the US because Europe has this thing of like, Hey, they get 25 to 30 days off a year, and I think they usually take it, but they still feel vacation deprived versus the US is more like 15 to 20 days. And I feel like many Americans don’t take the time.
Jillian Johnsrud (00:58:42):
And in the book I proposed kind of this extreme idea of almost forcing everyone, it’s mandatory. It’s it’s not a benefit, it’s not an option. It’s mandatory because it changes the dynamic. So one benefit I outline is that in every company and every team there is someone who is exceptionally knowledgeable. They gather all the information and they let everyone around them be slightly incompetent and they do all the things and they take care of all the things, which is awesome because they’re a rockstar. But that actually makes for fragile teams. That makes for fragile companies. When one person hoards all the information, and we know that we should be documenting, we know we should be cross-training, but we don’t have the motivation and the deadline to do it. But if Sally’s going to be out of the office for a month, you know that we’re going to get this done.
(00:59:34):
We know exactly when she’s leaving. Everyone needs to be, everyone needs to share this information, she needs to document this process. And that makes for more resilient companies. But you also have the benefit. Okay, so what if you’re thinking about promoting Peter into Sally’s role at some point? Awesome. We’re going to promote her, but you’re not a hundred percent sure if Peter’s going to be awesome at it. Well, hey, Sally’s leaving for a month, so why don’t we give Peter 60% of her job and just test it out. See how he does? It’s a really low cost way to provide people extra training, extra development, extra opportunity to stretch those skill sets and just see how perform. And if he sucks, next year when Sally takes a month off, we’re going to try someone else until we find the perfect fit. And so there’s all these ways that companies end up being stronger, being more profitable, being more productive, because they institute this.
Steve Chen(01:00:32):
That really resonates. Actually, it’s super interesting. This exists in our company too. We have people that know everything, but then do they become an actual gating function? Like, oh, you can only go as fast as this particular people and it doesn’t change and you want to force change. So I think that’s,
Jillian Johnsrud (01:00:53):
And those high performers you have to kick out. They won’t leave because they’re too important, they’re too essential. They know it. That’s why they do it, because they want to be so essential. They want to be such a high performer. They’re not going to just go on vacation for a month and chill out. So you have to forcibly remove them for a month. Be like, thank you so much. Because they work at 110% all the time and they’re at the greatest risk of burnout. They’re at the greatest risk of collapse. So you want to protect your highest performers. They are doing three people’s jobs. But that’s another great benefit for Sally. He’s doing three people’s jobs because everyone else is doing 80%. Kick her out for a month, make everyone else do their whole darn job by themselves. Don’t let her help everyone. And maybe when she comes back, they’ll just keep doing their full jobs. She will not take on. So you can just give her whole brand new job because now she’s not doing 10% of everyone else’s job.
Steve Chen(01:01:53):
Yeah, a hundred percent. It’s super interesting to think about this. And now I’m going to go, I’m think about the data and ask ChatGPT a bunch of questions about this topic. This is really interesting. Alright, well look, I know we’ve gone long. I do want to, as we close, we would just love to hear you riff a little bit about the four steps on your book, the Dream Career, money and Journey. Maybe you can give us kind of a quick summary. We definitely want people to check out your book, retire Often, and we’ll put a link to it. I think it’s a retire often.com, right? People can go there and find out. But yeah, I would love to hear you just give a quick overview of what people will find there.
Jillian Johnsrud (01:02:34):
Yeah, the book and the Four steps is, it’s really, I’ve been coaching and teaching about this for almost a decade now, and I’ve heard every fear, I’ve heard every objection, I’ve heard every concern that people have. And the great thing about one-on-one coaching, when you’re sitting across from someone, you cannot give them fluffy answers. You cannot be like, just go talk to your boss. It’ll be awesome. They’re like, exactly what do I need to say? What exactly do I say? What does this conversation sound like? And so in the book, I go through all of the tools, all of the prompts, all of the exact scripts. How do you time the emails, how do you plan the conversations? How do you plan the budget? Exactly, how do you pull this off? So while I hope it’s very inspirational, it’s super practical if you actually want to know how to do this, walk through every single thing.
(01:03:31):
And so we start with that planning and all the different ways to think through the planning, how to create phases, how to know which mini retirements to front load versus to save for later. Thinking about where you are in your financial journey and your physicality, how healthy you are. We go through all the career stuff, like how to have these conversations, what do they sound like? How do you craft your mini retirement story? How do you network, how do you find that next job? And then all the financials from how do we budget for it? How do we think through the cost? How do we cap the budget? I usually encourage people to set a maximum spend of 50% of your take home pay per month towards a specific mini retirement adventure. Which is why mini retirements can be affordable for anyone. Whether you bring home 20,000 a month or 2000 a month because how much you’re going to spend is proportional.
(01:04:28):
And then, yeah, that chapter or that step four is just like, here’s all the things you’re not expecting. All the amazing things. If you’re on a trip, what are all the musty highlights? What’s going to be the best part of this? And what are a couple things to avoid or what are a couple things to watch out for? And like I said, with the Lewis and Clark, they had never been out there. They didn’t know any of this. It was all new to them. But SAA had been there. She kind of knew what the deal was. And so they found someone who knew what was going on and could help them navigate that better. And I feel like that’s my role in this.
Steve Chen(01:05:09):
That’s awesome. Alright, well, Jillian, this is fantastic. I think this is going to be awesome and our audience will love it. And it’s going to be helpful, especially for younger people as they’re thinking about this and being more intentional in their lives. So appreciate you taking the time. And we’ll definitely link to Retire Often. We’ll get this out there. This will hit our newsletter of 120,000 people and all that good stuff. And so for everyone listening, I know all feedback on this podcast is welcome. All sharing is welcome. And definitely please check out Jillian’s work and we hope you enjoy it and let us know if it has a big impact on your life. And with that, Jillian, thanks again for joining us on the podcast.
Jillian Johnsrud (01:05:52):
Thank you so much for having me.