Don’t wait for retirement: How career breaks enrich your life with Jillian Johnsrud
What if taking extended time off work could actually boost your lifetime earning potential? Meet Jillian Johnsrud, who by age 40 has taken over a dozen "mini retirements" — month-long career breaks that allowed her to travel to 27 countries, buy real estate, learn new skills, and completely reinvent her career.
This conversation reveals why switching jobs combined with strategic breaks often leads to bigger raises than staying loyal to one employer. Jillian shares her funding formulas, creative strategies, and why some dreams can't wait for traditional retirement.
Whether you're burned out, curious about career breaks, or just tired of postponing the life you actually want, this episode will shift your perspective on what's possible.
Episode Timestamps:
[05:00] Jillian’s very first mini retirement: the cross-country road trip that changed everything
[07:00] How mini retirements can increase your lifetime earning potential
[11:00] Signs you might need a mini retirement vs. just a vacation
[15:00] The most accessible first steps for planning a career break on any budget
[22:00] Jillian's experiences that unexpectedly changed her perspective
[24:00] How much money to save and avoiding over-preparation paralysis
[30:00] Preparing your business for a mini retirement when you're self-employed
[39:00] Designing intentional, transformative breaks (not just unstructured time off)
[46:00] What to do if you’re scared to step away for career break
[48:00] Dreams with expiration dates and the seasons of life that won't wait
[52:00] Rapid fire: packing essentials, dream locations, and money advice
Connect with Jillian:
Website: retireoften.com
Social: @jillianjohnsrud
Podcast: Retire Often Podcast
Book: "Retire Often" (launches September 9th, 2025)
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Transcript
Cassidy: [00:00:00] Hey, girlies, if you've ever dreamed about taking a break from work but not retiring exactly, just kind of recalibrating a little bit, then this episode is going to open up your mindset in the best way.
Emily: Today we're talking about mini retirements, which are actual extended breaks from work that you can take before you reach retirement age. And as somebody who intentionally tries to slow down during the summer months, I am really, really excited for this conversation.
Cassidy: Truly, Emily is the queen of scaling back in the summer so she can soak up all that Michigan has to offer during the warm season. I've been trying to follow her lead and rewire my own mindset around rest and time off. I used to think that I had to hustle year-round, but I've been so inspired by Emily and other friends that we have in the freelance copywriting community to slow down a little bit and not feel like I have to plow ahead at max capacity year-round.
Emily: And that brings us to today's guest. Jillian Johnsrud didn't expect to be able to retire early, so she hatched a plan to retire often. Inspired by the idea of sabbatical years, she set out to sprinkle retirements throughout her life. At 40, she's taken over [00:02:00] a dozen mini retirements, which allowed her to pursue dreams like living abroad, traveling to 27 countries, adopting four kids, and having two of her own, investing in real estate, and touring the U.S. in a camper.
Jillian has taught, coached, and written about mini retirements for almost a decade. She hosts the Retire Often Podcast and is a popular speaker and consultant for mini retirements, and she lives in Montana, where she spends time in the garden drinking tea, which sounds lovely.
Cassidy: Jillian is also the author of the upcoming book, Retire Often, which launches September 9th, 2025. I also saw on LinkedIn where you just finished recording the audio version, so congratulations on that. Yeah. But Jillian is here to help us all think a little differently about our careers, our rest, and how we build a life that actually feels good.
So Jillian, welcome to the Finance Girlies Podcast.
Jillian: Thank you so much for having me.
Emily: We're really excited. I guess before we get into kind of your [00:03:00] background, can you just tell us a little bit more about what you do today, and maybe how you got to where you are?
Jillian: Yeah. So, let's see. I started with like, really normal jobs. Like I worked at Starbucks and I waited tables and I worked at REI, and sold mattresses, like high-end mattresses. I sold furniture, and took mini retirements along the way as me and my spouse were building our financial independence. Like we were growing our financial freedom.
And at 32, him and I both took a year off. And we had this huge long list of things we wanted to do during our year off and like, legitimately like, 150 things, one of those lines, very unassumingly, I had written, “something to do with writing.” And so a couple months into that year off, I started writing and I started a blog and started writing about personal finance and intentional living and mini retirements.
And [00:04:00] 10 years later, I have a book coming out. So, I'm basically an overnight success.
Emily: That's awesome. Okay, let's start at the beginning because your lifestyle I think is unique for a lot of people. Can you walk us through that very first mini retirement? What prompted it? How did you plan for it and how did it just change the way you think about work and life?
Jillian: Yeah, so when I was 19 my spouse at the time and I got married and this was like a first year conversation of, hey, what if we took little career breaks? What if we took sabbaticals? And he kind of thought it was crazy and I was like, no, I think this'll be awesome. Like we'll just save a little extra money and think of all the cool dreams and goals we can accomplish during this time off.
And so those first five years when him and I finished college, we had like $55,000 of debt and we both chose low-earning professions. So that's a winning combination. [00:05:00] But we were paying off that debt. We were starting to save, building an emergency fund. And I always tell people, there's three ways you can take a mini retirement. You can negotiate the time off. You can do it in between jobs, or something unexpected might happen where you get a break from work, usually something bad. And my first one was number three. And so I always encourage people to kind of, pack a mini retirement go bag, have some plans for things you would want to do, set aside some money, and then when something unexpected happens, you can quickly pivot and go do that thing.
So for me, I was probably, I was probably 24, 23. Me and my spouse at the time were starting to kind of think about having a baby and I got pregnant and I miscarried. And for a lot of people that's like a blip. A small incident on their path to having biological children. For me, it was a lifetime [00:06:00] of trauma and pain I had never addressed, became unlocked and was like an avalanche trying to crush me. And so I was a mess and my employer was like, yeah, you need to pull it together. This is a lot. How about we just like, give you a month off paid, go sort this out, and please come back as a normal human being. And I was like, cool. Deal. Let's do it.
So my best friend and I, she had just been living abroad, had just come back to the U.S.
We got in my green Honda Civic and we drove from D.C. to Seattle and back in a month. We slept on people's couches, and we camped, and we stayed with friends and family, and almost got trampled by bison. Like it was a really amazing trip. And it was exactly, exactly what I needed.
Cassidy: That's so beautiful. You have said something that totally caught our attention and that is that taking mini retirements can actually increase your lifetime earning potential. And that might sound backward to some people. So [00:07:00] can you explain how stepping away from work can boost your career in the long run?
Jillian: Yeah, I think it is really counterintuitive that leaving a job can be better for your career, but statistically, your best chance at getting a substantial raise, of getting a substantial promotion, comes when you switch employers.
I had a friend who, he took a year long mini retirement and when he came back to work, he got a 50% raise. Which sounds awesome. It is not. It is not, because the reason he got such a substantial raise was that he had been at his previous employer for 15 years, which means he had been underpaid. He had been under market value for a long time, and the mini retirement was the only reason he got back up to his market value.
But if you think about 15 years, let's say he was earning a hundred thousand and maybe he was underpaid for eight of those [00:08:00] years, he left $400,000 on the table. And even if his mini retirement cost him a full hundred thousand, which it didn't, but let's say it did, that's $300,000 of, of money that he gave up by not taking mini retirements. And you know, let's say he's 40 at the time, that's probably a million dollars in retirement. And your life is substantially worse because you don't have all these amazing experiences and this time to invest in hobbies and relationships and yourself.
So, being strategic, you know, especially when I talk to people who are coming out of college and that like, 22, 25 age, I'm like, just plan to switch employers at least every five years. You can negotiate a mini retirement from your current employer, let's say two years in, and then two years after that, take a three month break, take a six month break, and find your next best job. That's [00:09:00] gonna give you your best career trajectory and it's gonna give you your highest lifetime learning potential. And it makes an enormous difference in the long run.
Cassidy: Yeah, and it sounds like in the case of the guy who increased his salary by 50%, it took him thinking outside of the box and being like, I'm gonna take a mini retirement to even open up his mind to the possibility of switching jobs, returning to his market value.
Jillian: Yes. A mini retirement can be a great motivation because it's scary. It's scary to switch jobs but it can kind of be the carrot to the stick. And it does a lot of other things, like, it allows people to get additional training, or certifications, or uplevel their soft skills during their mini retirement, but they also recover from burnout and they come back refreshed and creative and excited. And there are some careers. We're being 10% better than everyone else matters a lot. You think about in like, a 400 meter [00:10:00] dash, if you're 10% faster than everyone else, you don't win 10% more races. You win all the races. And in some careers being 10% better kind of means you win all the things.
Emily: Hmm.
Cassidy: Yeah.
Emily: That’s an interesting perspective.
Cassidy: I feel like that gave me chills a little bit.
Emily: That was, like, a perfect segue into our next question, which you kind of already touched on, but talking about burnout, I think a lot of our listeners either are experiencing burnout or have in the past. How do you know when you need a mini retirement versus just like, a long weekend or a, you know, a week-long vacation?
Jillian: I mean I would try a long weekend, I would see how far you get. I think that's the beginning stage, but. You know, I encourage people, this is kind of a strange exercise, but think about before you were in this stressful situation, think about the last point in your life where you felt excited and motivated and creative and [00:11:00] like, bubbling with energy, and like, do you feel that now?
When I was younger I used to think people in middle age were boring. Like they just weren't like, excited or motivated or doing cool stuff, and then I got to be 40 and I'm like, oh, we're just tired. It's not that we're boring, we're tired.
So, there's some signs of burnout. I think, not just feeling tired, but I think it is that decreased motivation, that decreased excitement, that zest for life, that creativity, that optimism slowly goes away and it's a survival mechanism. Because burnout allows us, if, if we find ourselves in a bad situation, it gives us the energy and the focus, the narrowing of the focus to get out of that situation. So if you're in like, a wartorn country or in a famine, or you have to like, walk through a long desert, burnout gets you out of that situation. It's like running [00:12:00] away from a bear. It keeps you focused and it gives you the energy to keep going. Although you're not gonna ourtun a bear it's totally gonna eat you. I'm from Montana. You have, you have no chance, but it keeps you, it keeps you going.
And unfortunately, we've like, kind of biohacked this into be like, hey, I'm really good at trying to run away from this bear. Maybe I should do this all the time. Maybe I should just be the person who runs away from bears. 'Cause I actually, I think I'm, I'm like, thriving in this running away from bear situation. So sometimes it is really helpful to step outside of the situation that created the burnout.
You know, can you heal in a place that made you broken? You know, it's like, if you got an injury, should you keep going to the gym and working hard? Just take a break, go home, rest, heal, do some PT, and then come back at full strength.
Cassidy: Mm-hmm. [00:13:00] Okay. Have a little bit of a side question. Do you have like, a litmus test that you follow where it's like, if I'm starting to experience these signs, this is my sign to myself that maybe I need to build in a little mini retirement?
Jillian: I think it's good to know yourself. Like we all experience it different, and I think unfortunately, like, we're really good at kind of lying to ourselves like, no, no, we're fine. We're fine, we're fine. I'm fine. You know what, I'm showing up. I'm doing the thing. But there again, looking at what's the best version of me. And I think sometimes as we burn out, we associate that with age or realism. Like, well, it's not realistic that I would be that creative 'cause that's when I was younger. Or it's not realistic that I would be that optimistic. Like now I'm in the real world, so I should be a pessimist. Like it's not, it's not realistic that I should be so creative or motivated, like I'm in the grind. [00:14:00] This is how people feel. And we really try to normalize it for ourselves, but it's not normal. We're surviving. We're not thriving.
So I think having a baseline of what, who am I when I'm thriving, what does that look like? What kind of energy do I bring to things? Am I excited to go hang out with my friends after work? Am I excited to engage in my hobbies? Am I excited to take on projects? Or do those things make me feel overwhelmed and tired and like I want to want them, but I don't quite want them? Those might be your individual signs of burnout.
Cassidy: Yeah. So it sounds like if you're gaslighting yourself into being like, I shouldn't be creative, like that was the old me, or it's okay to feel tired and not wanna work on your passions, you're living your real life, then maybe, maybe it's time. Okay. That's really great.
Let's talk real life logistics for a moment. For someone who's listening, who's thinking mini [00:15:00] retirements or a career break sound amazing, but I've got bills and responsibilities. I don't know that it's financially in the cards for me. What are the most accessible first steps toward planning for a mini retirement, even for someone who's on a budget?
Jillian: So I would start by, let's define what a mini retirement is. I've got, I've got three kind of qualifications. It's a month or longer. I find a month is like the minimum effective dose, stepping away from your nine to five to focus on something that matters to you. So if you're like, gosh, money's really tight, I would start with a shorter one. I would start with a month. You don't have to be like, I'm gonna, I'm gonna do an around the world trip and it's gonna be $80,000. Like I called the book, Retire Often instead of Take One Massive Epic Mini Retirement Throughout Your, you know, Throughout Your Entire Career. Because there is benefits to doing this over and over and over. So I would start with something shorter.
I would also kind of brainstorm like, [00:16:00] what's your bucket list? If you had 20 amazing adventures, what are they? And maybe frontload the more affordable options. This doesn't have to be expensive. Last year I took a month off to learn tango and I gave myself a budget of a thousand dollars and I wouldn't have had to spend a thousand dollars, but it was incredible and fun and energizing. And now because I made that investment of time and energy and money, I have this hobby I can enjoy for the next 40 years.
So you could, like, one year I planted a food forest in my backyard. You could have a mini retirement gardening, you could learn guitar, you could do, you could write the first draft of a book.
There's lots of super affordable things. And if money is tight and let's say you wanna travel, think about those other levers you could pull. Maybe you are in between jobs and if you don't earn a ton of money, you're like, well, that's not really the issue. Maybe you take three months and you do a road trip, you travel really [00:17:00] affordably. When we travel, we rent out our place while we're gone. And that actually covers the entire cost of our trip. So it costs us the same amount of money living at home as it does traveling full time. Like those are, those are a break even.
Cassidy: Yeah.
Jillian: And if money is really a concern, I would say, and you wanna travel, I would rent out your place, sublet your room, whatever that looks like. And then you could do like TrustedHousesitters or you could do kind of a, you know, volunteer at a farm in Italy. Like, there's a lot of really affordable ways. I know some people that traveling full-time is substantially cheaper than living at home. Like it's actually a cost-saving activity.
Emily: Yeah, I've heard that too. There's so many good ideas that you just rattled off, but one thing I came into this recording, like, needing to ask you is, can you tell me what a food forest is and how you built it? I heard you talk about it on another podcast.
Jillian: I'm so obsessed. So it's, it's like [00:18:00] a, a big garden, except you focus on perennials. So like fruit bushes, fruit trees, herbs that come back year after year. So basically, instead of like, planting annuals like tomatoes and squash and all of that, it just returns every year. So right now I have like, I have a 50-foot row of raspberries and just like buckets of raspberries everyday. I have five kids and they're like, we cannot eat any more. Like, this is, this is too much. Last year I planted like 150 strawberry plants, but then they all, like, tripled. So now I have like, 400 strawberry plants.
Cassidy: Oh my.
Jillian: And so it's really, it's fun.
Emily: That's amazing. That is something I wanna do someday for sure. That will be one of my mini retirements.
Cassidy: You are getting little glimpses into mine and Emily's personal interests because my follow-up questions are about what exactly you did when you took a month off to learn tango. Like, were you going to class every day? How many days [00:19:00] a week? I need the details because honestly it might not be tango, but like some kind of dance class, like, that would be a mini retirement idea for myself.
Jillian: I, I love it. I, so part of the motivation, I met this like, the coolest human being ever. He's like 80, and, but he knows like 15 different social dances. And when I think about 80-year-olds, like, he's the opposite of all of my assumptions. Super active. Has tons of friends, always out of the house doing stuff, really fit, really agile, like, learning, just, he, he's not like the person I'm like, I wanna be like him when I'm 80. He is outpacing me in every area of life, right now.
So. That was kind of my motivation. I was like, this is a gift to my 80-year-old self. She'll be so appreciative that I do this.
So I aimed to do 10 hours of dance a week, and it was a combination I did, in Tango you have like, group lessons, but then you also have this thing, like practica, where you just practice the stuff you learn in group lessons. [00:20:00] And then you have milongas, which is the social dance. So, I did all three of those plus private lessons. Plus I went to a Tango festival, which I had only been dancing Tango for three weeks. I do not recommend this. Give yourself a little bit longer. It was very overwhelming. I almost cried every single day 'cause it was so hard.
But yeah, then I went to like, a three-day Tango festival. So kind of a combination of all of that. And Tango's a super hard dance to learn. But by the end I was like, I, it's like passable. Like, I have a passable amount of skill that I can show up and it not be torture.
Cassidy: Mm. And you can keep building on it.
Jillian: Yes. Yep.
Cassidy: Do you still do any type of tango lessons? Post-mini retirement?
Jillian: Yes. And that this is one of the great things, like, mini retirements are so useful for different reasons, but one of 'em is you can do kind of this upfront investment in a hobby or a skill or a relationship and then maintain that [00:21:00] going forward. There are some things that are really hard to start, but if you do all the upfront work, whether it's like learning yoga or learning to meditate or writing or learning how to apologize and like communication skills or intensive therapy, I did a month of intensive therapy once, you do this huge upfront investment, but then you can just maintain that and re-, continue to receive all of those benefits for years after.
Emily: Yeah. Wow. So you have clearly done some amazing things during your breaks. So I know you did like a 10 week road trip to different national parks. You took a year off after you adopted three kids and found out you were pregnant, right?
Jillian: Yes, we went from one to five in two years.
Emily: That is wild. So what is one experience that you pursued during a mini retirement that maybe changed your perspective in a way you didn't expect?
Jillian: [00:22:00] Gosh, it's so tough. Mini retirements are a little bit like a Swiss Army knife. They, it's one tool, it has many different functions. So like, in my, I'll actually, I'll do three.
So in my financial life, we did two mini retirements where we took a month off to buy real estate. And so, like, the house I'm sitting in now was a rental property that we bought, like, 12 years ago during a mini retirement. It, all in, it's appreciated like $300,000. So that was a very profitable one month off.
The year off where I started writing it completely changed my professional trajectory. Like, I reinvented entirely what I do as a profession. So massively, like, massively impacted my life.
On a personal level, they've all been really good. I would say the month of that intensive outpatient therapy, I did like, six hours of therapy a day. And it was a little [00:23:00] bit like doing a full house renovation, being like, you know, we need to fix the foundation. We need all new plumbing, all new electrical. Like, let's just get in and do the heavy lifting and then we can kind of maintain and do some of the more cosmetic things moving forward.
But when I think about my twenties, I think I was 27 when I did it. I delineate my twenties as like before the month of therapy, and after the month of therapy. 'Cause it changed the trajectory of my personal growth massively and something that continues to this day.
Emily: Wow. Yeah, those are all huge in so many different ways.
Jillian: Yeah.
Emily: So getting to more, maybe more of like the practical side, and again, you, you kind of gave some creative ideas for the financial aspect of a mini retirement, but is there like, a specific amount you recommend people saving before they take a break? And then how do you strike that balance between preparing for a mini retirement and not [00:24:00] just like, over-preparing and maybe procrastinating.
Jillian: So I would say kind of your, your largest budget would be the, your monthly cost, like your monthly take-home pay if you're gonna, you know, not get, not be earning money during your mini retirement, and then up to an additional 50% of that take-home pay. It's one of the reasons I think mini retirements are very accessible to a lot, like pretty much people in all financial levels, is because the amount you need to save is very proportionate to how much you earn.
So if you earn $2,000 a month, you should probably save $3,000 to cover that cost of your month off. Where if you're bringing home $10,000 a month, then you should probably save $15,000 to cover the cost of that month off.
But yeah, I would start there and there are lots of ways you can kind of reduce that number like we've talked about, but that's a good [00:25:00] baseline.
One of the kind of, the math formula, if you think about how much money to save to take a month off every other year, so like, a lifetime packed full of mini retirements, by that, you're saving like 150% of your take home pay, that's you're saving an additional 6.5% of whatever that take-home pay is.
So it's not, it's not substantial, and it's really different from your long-term retirement savings in that it can be so hard to be motivated when you're like, I'm not gonna go to Starbucks. And then that means when, in 40 years, like, maybe I can pay my water bill. It's just, it's so abstract and it's, it's so, it's such a long timeframe.
But if you say, you know what, I get like a Chipotle burrito bowl every lunch on Friday, and that's like $10 and it's kind of sad and I eat it at my desk at work. But if I just didn't [00:26:00] do that, if I skipped the Chipotle burrito bowl that would mean in two years. I would have enough money to pay for street tacos in Mexico and a margarita, three times a day for a month.
So I'm not really giving up sad Mexican food. I'm trading my sad Mexican food for real Mexican food in 24 months. Like an abundance of real Mexican food.
Cassidy: I was gonna say your math makes it feel so approachable and also so tangible.
Jillian: Yeah. It's one of the things in the book, I talk through coming up with like your dream price list. Don't think about it like, oh, this is gonna cost me $5,000. Write out like, how much is this museum pass? How much does it cost to like, how much is my transportation in Paris gonna be? How much is you know, how much is it gonna cost to go see the Mona Lisa and put all of those numbers out specifically because then, as you're saving money or as you're like, ah, do I really wanna take this dog sitting gig? You're like, it's 200 bucks. Like, you're like, well, it's not [00:27:00] just $200 towards a $5,000 goal, it's $200. You're like, oh, that's all of my coffee while I'm in Paris. Okay. Yeah. Like, I'll do the dog sitting, that's gonna cover every cappuccino while I'm there.
Emily: Mm.
Cassidy: I feel like you're reinventing the whole concept of a smart goal, like kind of reverse engineering it almost to be like, no, if I take this gig, like it is gonna equate to $200 worth of coffee in Paris, and then you're like, absolutely.
Emily: And like you hear financial experts do that all the time with like, skip the latte and in 40 years, it'll be this much money, you know? But yeah, I like that you're talking about, no, literally, you can do this in like one year or two years, and it's so much more tangible.
Jillian: Yeah, I don't like the idea of skipping because then we're, we're making our life smaller.
Emily: Mm-hmm.
Cassidy: Mm-hmm.
Jillian: In my mind it's like, just postpone it slightly for something [00:28:00] much better. You're still gonna have the same thing. It's a latte now. It's a latte in Paris. We're just gonna postpone it for like a little bit so that you could be having it like, while you walk around underneath the Eiffel Tower, like, we're just gonna shift this to a better version.
Cassidy: Yeah. Okay. We are so excited about your book, Retire Often, which comes out September 9th. What inspired you to write it now, and what do you hope readers take away from it?
Jillian: The inspiration, so I've done, I've done one-on-one coaching, I've done group coaching for a long time, and like I knew, okay, one-on-one, I can help people do this and like, they can take these mini retirements and it'll be awesome. But I want it to be accessible for literally everyone. I want companies to change their policies. Like, I want a massive shift in, especially, let's start in America, but worldwide, but in America, with how we approach our work culture and how we look at our work lives. [00:29:00] And I hope people take away, like, even if you're not planning a mini retirement yet, even if you're like, oh, that's a cool idea, I had no idea how I'd pull that off. I would hope that if you just read the book, like hear some of, like, your fears answered, some of your objections kind of resolved a little bit because it will naturally, whether you mean for it or not, it kind of starts you on this path and, and then opportunities arise. You know, you move across the country and you have to switch jobs and you're like, actually, why don't I just take an extra month off?
Like, hey, I remember I read that mini retirement idea like four years ago. Like, this could be a cool opportunity. Or you get laid off and you get six months of severance and you're like, actually, I remember reading this book and I had all these cool ideas of things I wanted to do. Like, maybe now's the time.
And I think people will see it's, it's so much more possible than you think kind of upfront. And if you [00:30:00] just move in that direction a little bit, ah, it'll happen.
Emily: Yeah. I already feel like my perspective on this has dramatically changed in just the short time we've been talking. Like, it feels so much more attainable. I thought of a question that I kind of wish I had asked earlier, and I'm not sure it, it's kind of like a change in direction. But, Cassidy and I are both like, freelance writers, so we are self-employed. If you don't have the ability, or it's just not realistic for you to be switching jobs, like you work for yourself and you have to kind of define your own breaks, how can you like, intentionally build a mini retirement into your own business?
Jillian: Yeah, I put a whole separate chapter about self-employed in the book 'cause it's such a different beast. And I've been self-employed for 10 years, and so sometimes people have nine to five jobs, they're like, oh well, [00:31:00] like, it's like so much easier for you now 'cause like, you're your own boss. And I'm like, oh sweetie, it's not, that's not it at all. It's so much more work upfront and for a lot of people it's much scarier because you've put so much time and effort into building this thing, and it feels like there's a real risk of, if you leave, it might burn down. Where like, if you work at Google and you take a month off, like Google will continue to exist without you, you'll come back and Google will still be there in the universe. Our businesses there's, there's a possibility it might disappear.
So in the book, I kind of outline four things to do to prepare your business. And these can honestly, it might take a couple months. I've seen it take 18 months to really help prepare, and you have to adjust your expectations a little bit.
The one encouragement I have is that doing these things in your business, it's a little bit like, like doing a deep clean of your house. Before we would go on [00:32:00] these long trips, when we rented out our house, you have to clean every single thing. You have to clean the light fixtures, you have to clean behind the fridge. Like, you have to deep clean everything. And you have to organize every cupboard, every closet, like you have to declutter everything. And it's so much work, and it's so stressful. But one of the benefits is when you come home from the trip, you come home to this really clean, organized, tidy home. And your business is the same.
It's gonna be so much more work upfront, but you come back to a more streamlined, efficient, organized business that honestly, you know, if you typically work 40 hours a week, when people come back, they might be like, huh, actually it only takes me like, 30 hours a week to do this now. Huh. So it goes one or two ways. They're like, actually I think I'm gonna start doing that yoga class and I wanna take up journaling. Or they're like, oh, all those cool ideas I had about how I could expand this and how I could [00:33:00] grow and like new projects I could take on, totally doing that. 'Cause now you have the time and the bandwidth and the emotional energy and you're not burned out. So you're like, all excited and buzzing with creativity and motivation.
But the four things that can be helpful, the first one is to simplify. Sometimes there is complexity in our business because we can deal with it and we can handle it, and it's like, kind of faster to put up with than not put up with. And if you, if you're a freelancer, part of that simplicity is the clients that are a total pain in the butt, but you just deal with them. It might be a good motivation to be like, actually we could simplify this a little bit and maybe get rid of those ones.
The second one is to start to automate things. It takes so much work upfront and it's such a hassle, but if you do the work now, like, you come back to a better business.
The third one, and there can be a lot of [00:34:00] emotional baggage around all four of these, but the third one is to document things. We know we should document more, what our process is, how we go about it, kind of creating that. But it's a little bit of ego. Like nobody can really do what I do. Like, I just bring magic and innovation to every single thing. Like there is no, there is no template. But creating that template so that the fourth one, which is delegation. If you've ever tried to hire an assistant and it was a disaster, typically 'cause you didn't do the first three things. Like you were hoping they could come in and like, simplify things and automate things and document things and they can't 'cause they're not you. So we have to do those first three and then we can really start to delegate.
So a couple concessions though. If it's your first one, just do a month. Like, don't make this like, I'm gonna leave for a year. It is too much risk. Start with a month. [00:35:00] And the second concession is, I encourage people to still work about 10% of the amount of time they normally work. So if you typically work 40 hours a week. Check in for four hours a week. 'Cause there's a couple things, a couple clients, a couple tasks that like you don't really feel great delegating. And I find for most entrepreneurs, business owners, those four hours where they check in and they make sure everything's smooth and they do the most critical tasks, actually helps them pivot and enjoy their time off and be more fully present while they're doing their fun, relaxing things, versus just being like, don't look, don't look, don't look, don't look at the email, don't look, like, it's probably fine. It might be burning down, but it's probably fine. Just don't look. It's better to take 30 minutes, take an hour, double-check everything, and then go off and like, have fun for the day.
Cassidy: Yeah. I also had this thought while listening to some of your other Retire Often podcast episodes that like, the first time you do a mini retirement, it might be [00:36:00] a little messy and things might be a little wobbly, but it's not like that's the only chance that you're gonna get to retire. Like, you can take what you've learned from that first one, and then whenever you do one again, it'll be theoretically a little bit smoother, a little bit better, and then that, you know, it'll just continue to get better.
And that's kind of how it is with anything, at least in my experience. I try for the first time, even if it goes off without a hitch, it's kind of just a little bit based on luck, you know, because it's messy, you've never done it before, so just reminding yourself that like, it will get better and this isn't your only chance to do this thing.
Jillian: One of the benefits is that you can see what will actually break when you're gone. Like, where are you kind of the bottleneck? And what actually needs to be fixed and like, adjusted when you come back. Like, you'll see the weak points in your business. And one extra little tip for people who have client work, you know, you want to kind of, obviously, like, give them lots of heads up, kind of, pick the right time of year, like, [00:37:00] be really strategic about this.
But I found, and this is just a little like, psych hack, but if you say, if there's any emergency, if anything comes up, I won't be on my email. Here's my cell phone. Just give me a call. If you need anything, if there's an emergency, just call me. I will have my cell phone on.
If people know they can email you, they'll email you with all sorts of random crap, whether it's important or not. But this filter, especially in a culture where we like, are hesitant to call people, if they know they're going to call you on vacation while you're like, traveling in Europe, they will self-filter. How important is this? And it's funny, when you give them their, your phone number, they're like, I can wait. It's just, you know, she'll be back in three weeks. Like, it's not that big a deal. Where they would email you all sorts of crap.
Emily: I can see how that would deter people.
Jillian: If not, you know, they're the bad client. If they call you three [00:38:00] times a day, then maybe they're the one that you're like, I knew I should have simplified them, they're, I, in step one, but I just gave them a chance and now I know what I need to do when I get home.
Cassidy: Yep. You're like, you'll not be making the second cut.
Jillian: Yes. Because even then you come back and you've gotten rid of the bad clients and you've kept the ones that are great and you've kind of trained them how to like, survive without you for a month and everything's okay. You have more space and you have more time and you have more energy for better clients. Because it's the bad ones who require a disproportionate amount of our time and energy and it, just, they take up space that we can't like, find the ones that we should be working with, that align more.
Emily: Mm-hmm. Yeah. That is a lesson that I think both of us have learned over and over again in our years of freelancing.
Cassidy: Mm-hmm.
Emily: So, you've said that mini retirements aren't like just about [00:39:00] escaping. They're more intentional than that. So how can somebody design a mini retirement that is restorative and transformative, but not just a bunch of like, unstructured time where you're like, twiddling your thumbs and you don't know what to do with yourself?
Jillian: One of the exercises that I have clients do, and I put it in the book, is to write out your ideal day. If you could, if you could create any sort of day and your ideal week, what would that look like? And one of the reasons I like this exercise is that it usually reveals what people really value. They end up allocating more time to the things that are important to them, whether that's time with people they love, or their hobbies, or their health, or whatever that is, you see that show up in the schedule. And you're like, okay, so here's some of your values.
And then the second thing it reveals is what do they need right now? If there's a disproportionate amount of [00:40:00] time going towards like, I'm gonna sleep nine hours a night and I'm gonna nap, you're like, they're tired, they need rest. Because if they did this in three years, it might look different. There might be no mention of sleep 'cause they just don't feel tired. Maybe it's more like, I'm gonna go running and walking and workout and get in shape because that's really what their body's craving is more physical activity.
So it kind of shows like, what are the things you value, and what are the things that you know you need right now? And, and those kind of pop up in that.
And so during your mini retirement, even if it doesn't look exactly like your ideal day or your ideal week, making sure you prioritize those things that you value and those things that feel urgent and important right now.
Cassidy: Yeah, I am someone who has, for better or for worse, like, deeply intertwined my identity with my work. And I think that work is a coping mechanism that I rely on a lot. Like, [00:41:00] if I feel like my personal life is hard, I will just throw myself into more work. If I'm feeling a little bit depressed, I will numb that depression by just working more. If I know I need to sit with my feelings and really don't want to, I will just take on more work, and that's really easy to do when you do work for yourself, because you just have to say yes as the work comes, and then the work will pile on and then all of a sudden all you're doing is working.
And I know that that's unhealthy. This is something that I'm trying to unravel, but it does make me think like, if I am someone who is deeply interested in the idea of a mini retirement, I still feel like I would struggle with the idea of like, what do I do if I'm just sitting still and like, work isn't an option. And it sounds like you kind of alluded to that with the like, what do you need in this moment kind of thing, but is there anything else that pops up?
Jillian: Yes, I, I always encourage people to like, split the difference. So whatever level of like, structure and busyness you [00:42:00] have, there's a temptation to go to the other extreme. Don't, don't, don't do it. It's not gonna go well. It's gonna be a disaster. So wherever you're at, split the difference. And pick half as much structure, half as much routine, half as much busyness, because you just legitimately don't have the skillset yet.
It's like saying, hey, I've been sitting at my desk 60 hours a week. I think I wanna, I think I wanna try running. Maybe I'll start sprints, or maybe I'll start with a marathon. Like, just don't. Like, start with walking. Start with like, jogging, like, let's, let's warm into this because your, your muscles and your tendons and your body just aren't ready for that.
So if you're like, yeah, I work 60 hours a week, I think I'll just like, chill at my house. Oh, it'll go so badly, so, so, so badly. So pick something halfway in between. Create some sort of structure, have some, especially, if you're a person who likes to use work as a [00:43:00] coping skill, don't go cold turkey. This is like, like, like use the nicotine patch. 'Cause it's just gonna be a lot less painful. Find hobbies, find activities, find things that are really engaging. So when you're like, I can't sit with these emotions anymore, I need to like, occupy my body and my mind, you have really good, healthy things that are engaging. You know, like go play pickleball, like, whatever it is for you. But yeah, split the difference from kind of whatever your schedule is now to between that and nothing.
Cassidy: Yeah, that's a good tip. This reminds me, one of my only business goals that I set in 2024, which, I have been freelancing full time since the beginning of 2019. And usually my goals were like, really aggressive, really like, growth-oriented. But my only business goal for 2024 was to pick up a hobby so that I had a reason to like, look forward to not working.
And the hobby that I picked up was crocheting and I loved [00:44:00] it. So I feel like that was kind of my first step into being like, yeah, let's go 50/50. Yeah. And now I'm in a position where, kind of going through some life transitions, I imagine similar to you, just moved to a new state. And I'm also like, I could see myself having a little mini retirement to take care of myself emotionally, work on some hobbies, get to know myself a little bit more, maybe do some therapy. So yeah, that's good advice.
Emily: Cassidy, I wonder for you, something I've done, not in the context of like a mini retirement, but just in my free time, over the past couple of years, is taking like, community college classes and things I'm interested in, Cassidy, I wonder if that would be something that would like, be a good structure for you. 'Cause I know you're like, star student, I wonder if you would like, thrive in that kind of environment.
Cassidy: I feel like I would, and now that I've, now that I've just moved to a new area, you've presented this idea to me before and [00:45:00] I did look up community college classes back when I was still in Washington State and I didn't really see anything in my area, but I bet there would be a lot of options now. Gonna add that to my to-do list.
Jillian: Well, I'm gonna add another plug for social dancing. If you're new to an area, it's such a good way to meet a really diverse group of people, like all ages, all kind of demographics. And yeah, you get to like stand in front of another human for like three minutes at a time. So you really get to, you really get to know people. So yeah, that added benefit.
Cassidy: Yeah. You just wait. I might show up on your podcast one day and be like, Jillian, let me tell you all about my mini retirement.
Jillian: Yay! I love it.
Cassidy: Okay. For anyone listening who feels stuck in a job but is terrified to step away, what's something you wish more people knew about what's waiting for them on the other side of a break?
Jillian: Oh, well. Okay. So two things. If you're terrified to step away, [00:46:00] I would try to negotiate, I, I would negotiate a month, a mini retirement. Like you don't have to step away. And I think negotiating a month off or three months off is a wonderful first step because it removes one of those hesitations and one of those fears of like, you know, what if I can't find my next job? Like, what if I'm gonna be stressed about this? What about the financials? So I would encourage people like that, that is an option. And even when people are like, oh, but you don't understand my workplace, like, no one ever does this. Like, we don't have that kind of policy.
If you and I, I go into like an extreme amount of detail in the book, like, exactly how to have these conversations, exactly how to structure the story, what emails to send, like full scripts, because I've done so much one-on-one coaching, and you can't just, like, when another human sitting in front of you, you can't just be like, yeah, just go talk to your boss. It'll be great. They're like, exactly what do I say? What are the exact words? Like, let me write [00:47:00] this down. I'm gonna write a script. So I've gotten really used to like, giving people the exact things to say.
So that would be one side. The other side of, kind of, the potential like, oh man, there's so many things that don't fit into nights and weekends, and if you're gonna do these things, you're gonna have to create more time.
Like, you can't hike the Camino on a four day weekend. You can't do a 10-week road trip to 10 national parks with your kids on a four day weekend. Like, so either, either say, you know what? I'm gonna figure out how to make the time, or just come to terms with yourself. Make peace with the fact you're never gonna do this in this life and grieve it now, regret it now. Like, feel those emotions now when maybe you could still do something about it. Versus getting to 65 and being like, well, nothing I can do except feel sad and like, full of regret that I didn't do those things with my kids when they were really [00:48:00] young. Or, I didn't do this big physical activity when I had the energy and the physicality and the motivation to do it.
Because that second thing is, there's seasons in life with expiration dates. Not everything can nicely sit on a shelf for the next 40 years. You know, I think about actually before our interview, I was thinking about that road trip that I did, that very first mini retirement and all the people that I got to see. And I'm like, we stayed, me and my friends stayed with my in-laws. We stayed at their place and they've both passed away now. And I went to visit my grandmother, and she's passed away now. And I got to see my great-grandpa, who I lived with when I was younger and I was so close with, and he's passed away now.
And I'm like, I, and nowhere in my mind did I think when I was doing that trip, I'm going to go see the people that I have such a finite amount of time with. But now, 20 years later, looking back, I'm like, oh, I had such a finite amount of time with [00:49:00] those people. And there are expiration dates for when our kids are young or our parents are healthy, or you know, we're with our partner. Like you don't always know when things are gonna change, and you don't always know when things are gonna end or when an opportunity will have passed you by sometimes until it's too late.
Emily: Yeah, I was listening to, I think it was your recent episode with J.L. Collins. You were talking about how people who are really invested in financial independence will say things like, yeah, but if I take a mini retirement, then it'll delay my financial independence by a year or 18 months or something. And you said kind of like, but would you rather have, the life now where you're able to go on that road trip with your kids, or I think you said, go hiking with your, with your parent while they're still able. And just hearing you say [00:50:00] that was like such a good reframe in my brain that I think people don't always think like that. But if you just take, like, a few moments to think about, what do I dream about that I won't be able to do, potentially, when I'm traditional retirement age, it just changes your whole perspective on that.
Jillian: Not everything, not everything's gonna wait for you. And I think something that I, something I did not fully appreciate when I was in my twenties was that my preferences changed. And so I'm so happy, I'm so grateful that I leaned in hard to like, every decade of life. And I did the things that, that were amazing in that decade. And now I'm like, yep, not doing that again. Like that, that cross country road trip, we, me and my best friend, we stayed in Yellowstone. And we were tent camping and it, like, it snowed, like, blizzard, it snowed, and our tent collapsed three times due [00:51:00] to the weight of the snow. And we ended up sleeping in our car. And the next night, it's like just sleeping on the frozen ground, then the next night, we woke up and our tent was surrounded by a herd of bison which is how we almost got like, trampled like a peanut butter jelly sandwich in a Ziploc bag. Like, this is almost what happened. And it was amazing. And there's no way I'm sleeping on the frozen ground anymore. Like it's, I'm 42. This season of life has passed, you know, and I, I was thinking about it the other day, like, we're, I'm getting ready to sell our camper. And someone was like, are you, are you sad about it? And I'm like, kind of like, it was such a big part of our life doing these huge road trips. We did three to six month road trips every winter with our kids when there were itsy bitsy and, and I'm a little sad because that season of life is over and now they're in high school and junior high and they have friends and hobbies and they're in school and the whole thing. I was like, but on the other hand, [00:52:00] there's no way we could have done more. Like we went so hard. Literally hundreds of days we traveled in this camper all over the U.S. Like we had so many memories, so many experiences. Like, so while I'm sad it's over, I can't, like, there's no regret. Like there's no way we could have done more amazing things with our kids.
Emily: Well, before we wrap up, we have just kind of a handful of some fun rapid-fire questions that we'd like to ask.
What is one non-negotiable item you always pack for a mini retirement?
Jillian: For me, it would be like, a journal, or even just a pen. I love to write on the back of postcards just like a little journal entry of like, what we did that day and what we saw and, 'cause it's easy to forget, but I have like, literally hundreds of postcards from places we've been that each have their own little journal entry. So I like things to, to kind of document what I'm learning and thinking and feeling and experiencing.
Emily: [00:53:00] I love that idea.
Cassidy: What is the most unexpected place you fell in love with during your travels?
Jillian: Croatia. It, I'm from Montana, I still live in Montana, but it felt like home. It was so beautiful, like just the agriculture and the people and the, the nature there. But it also has this, has this amazing Roman architecture. And I smuggled a cat across international borders um, which is a whole ‘nother story. I don't recommend it, but I, I love Croatia.
Emily: Okay. Current dream mini retirement location.
Jillian: So I think because I'm really obsessed with Tango I might, and I dance Argentine Tango, I might do like a month or three months in Argentina at some point. And I kind of, I'm really nervous about it though, honestly, like it would be very intimidating. But I think in another year or two I'll, I'll feel confident enough to, to, [00:54:00] to dance in the, the birthplace of Tango.
Cassidy: I was gonna say, I think the future version of you that's like just days away from that trip might still be a little nervous, is, but is gonna be very prepared.
Jillian: For sure.
Cassidy: She's gonna be ready to show off those skills. What's a mini retirement activity that costs $0 that brings you major joy?
Jillian: So $0 is tough. I would say gardening for me, but it can be super expensive, but I kind of have everything planted. But I love, I love doing like, walking tours, just walking around towns. Of course I like to get a coffee, so there's a couple dollars there. But writing is is really great. And, and time with my friends. Like I, I really appreciate those relationships and investing in those relationships. I feel like they've made my life substantially better, so.
Emily: Do you have a piece of money or financial advice you'd give to your like, early career self?
Jillian: I would put as much or more [00:55:00] into an opportunity fund as I did an emergency fund. I think I over-indexed towards safety and under-indexed towards potential opportunity.
Emily: Hmm. And by opportunity fund, do you mean specifically money to put toward mini retirement or just kind of whatever comes your way?
Jillian: Any opportunity. Yeah. I think, I think sometimes we see cool, cool opportunities and it's really easy to very quickly say, nope, can't afford that. Nope, I can't do that. Nope. That's not realistic. And keep moving. And I think just having, if I would've had five, 10, $20,000 sitting there, just waiting, waiting, it would kind of, it opened that mental loop to look for opportunities.
Like what are cool things that I'm seeing. It's like when you start looking to buy like, a Toyota Camry and then you see them everywhere, I think if I [00:56:00] had all this money waiting for a cool opportunity, I would've seen a lot more and been willing to act on them.
Cassidy: That is so good. Last rapid fire question. Who is someone real or fiction you'd love to take a career break with.
Jillian: Oh, Taylor Tomlinson, celebrity crush, like, and she's so hardworking. She needs a break, right? Road trip, maybe a European vacation. We would have so much fun.
Cassidy: I hope she reads your book and is inspired.
Jillian: Come on. Come on, girl. Slide in my DMs. Let, let's go to, let's go to Europe.
Cassidy: Have you been to one of her live shows?
Jillian: haven't, I live in Montana. We've got nothing. Well, we have lots of mountains and lots of hiking. We have lots of cool stuff. We have lots of nature. Big venues, not so much.
Cassidy: Yeah. Quick side story, two weeks ago I moved from the Seattle area to Minneapolis, so I did the road trip across Montana, North Dakota. And my mom flew out and did [00:57:00] the road trip with me, and she grew up in Georgia, lives in Tennessee, hasn't really seen much of the West coast at all, and I kid you not, she snapped over 600 photos driving through Montana because literally every single thing, she was like, oh my gosh, that's so beautiful. Wow. That's gorgeous. She was the cutest person ever driving across Montana.
Jillian: I just, I just drove Kalispell to Spokane and then Kalispell to Billings. So I, in the last, in the last week, I've done 24 hours of driving. But it is just so beautiful everywhere in like, in a, this is just what it is. But also I don't if you remember that little stretch of road around Butte, where it's like, a really steep hill and a really steep, hilly, but there's just like mountain, like big boulders all along. And I was with my 9-year-old, he's like, I think this is where the rock giant sleeps. And I'm like, it looks like that, doesn't it?
Cassidy: It does. That's so [00:58:00] cute.
Emily: Jillian, this has been so inspiring and just fun, as well. And for our listeners who think the same and want to learn more about this lifestyle and about you, where can they find you online and how can they get your book?
Jillian: Pretty much everything lives at retireoften.com. So you can find the book there. The podcast, coaching. I have a really unhinged newsletter, so if that's your sort of thing, I don't know when, when does it get sent? It's a surprise to us all. What's it about? Surprise to us all. I think I have a really high open rate just 'cause people are like, I wonder what's in here? And no one knows. On social media, I'm @jillianjohnsrud. So yeah, that's it.
Cassidy: And we will be sure to link all the things in the show notes below. But girlies, I hope this convo expanded what you think is possible in terms of taking mini retirements and career breaks and just taking care of yourself and enjoying your life a little bit more, and not feeling like you [00:59:00] have to postpone that until you reach traditional retirement age.
We all deserve rest, we all deserve joy, and we all deserve goals that aren't tied to a paycheck, which I think is the biggest takeaway for me personally here.
Emily: Mm-hmm. I think this is the perfect episode to send to a friend, so please do that. And maybe they'll be inspired to start thinking about their own mini retirement.
Cassidy: Yeah, we will be back next week with a brand new episode. See you then.
