How to Take a Long Vacation

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show that solves entrepreneurs' toughest problems. I'm Jason Pfeiffer, Editor-in-Chief of Entrepreneur Magazine, and each week I take a problem that you're probably dealing with and get tactical solutions from people who have been there and solved that. So, let's get solving. Imagine taking a month off. A month off, going and doing whatever you want, just leaving work behind. Sounds great, right? But also it sounds impossible. Like, that's not going to happen because you work at a company that is not going to give you a month off, or you run a company and there's not any way that you could walk away from this company for a month and it's still standing.

2:18So nice fantasy, but end of episode, right? Except that I have somebody today who is going to convince you that not only is this possible, but it is advantageous, not just because it's nice to take a month off, but because the planning that is required to take a month off makes either your company better or makes your relationship with your job better. And I know this sounds crazy. It sounded crazy the first time that I heard it. But I have to say, the more in which I have talked to this woman, the more compelling she sounds. So here she is. I'm Jillian Johnsrud, the author of Retire Often. Retire Often.

2:58It is not usually the way in which you hear the word retirement, right? We usually think of retirement as a thing that happens at the very end. You work, work, work, work, work, and then you retire into the sunset. But Jillian says we should think about this all differently. It's the idea that we don't have to just retire once. We can retire often by taking these mini retirements, which I define as a month or longer, stepping away from your nine to five to focus on something that matters to you. Jillian, as she will tell you later in the episode, just started doing this herself. And then she started to write about it.

3:36And then she started to get a lot of people who were reaching out and saying, hey, can you help me do this? And now what Jillian does for a living is help other people take a break from what they do for a living. She coaches people on how to do this, which is pretty complicated, actually, for reasons that you'll hear more in a second. It's not just about picking a location. It's about figuring out how to actually prepare your entire life for this to happen. And, you know, I know this is going to be kind of a dumb question, but it's worth asking. And so I asked her, what's the point of this? You know, it sounds good walking away for a month, But like, OK, what's the point?

4:11So they have a lot of different functions. For a lot of people, it's to recover from burnout. I think the latest stat is like 89 % of Americans have experienced burnout. But for a lot of people, it's spending time with people they care about. Or there's these cool adventures they want to do, but they don't fit into nights and weekends. If you want to go hike the Camino, you're probably not doing that over a four-day weekend. and so they either don't want to wait till they're 65 or there's some things in life that have an expiration date. Like when your kids are little, if you want to do a big road trip with them, you probably can't do that when they're like in their 40s.

4:48Or you could, but the alcohol bill is going to be a lot higher. All right, so I promised at the very beginning that Jillian is not just going to convince us that this is a good idea, that sounds pretty easy, but she has a strategy for how to actually implement it. Whether you are working at a company, and you have a boss that you got to run this whole crazy thing by, or if you are the boss, if it is your company, and you have a whole team that you need to prepare. Either way, Jillian has a plan. It is a good plan. And as you will find out, it is a plan that really helps you get everything into shape, not just to leave for a month, but because that's a better way to be.

5:28So that's what we're going to be talking about today on Problem Solvers, right after the break. All right, we're back. I'm talking with Jillian Johnsrud, author of the new book, Retire Often, about how you can do exactly that. And we're going to pick up the conversation with just getting into tactics. So I said to Jillian, how is this possible? If everyone listening thinks this is a good idea, they are probably also going to think, I can't do this. So how can you? How can you actually do this? We're going to start by talking about working at a company and being an employee. And then we'll transition into running a company and how to do this as the entrepreneur.

6:08Either way, really useful tactics. And here is where we started. So taking the nine to five employee, the reality, if I was talking to someone who was 24, starting the career, the reality of them working for the next 40 years with the same employer in the same profession, it's probably pretty slim. Like it used to be a thing. It's not really a thing anymore. So for most employees, their best chance at a significant raise, at a significant promotion is going to come by switching companies. And if they're planning on switching companies every three to five years, why not take a month off in between?

6:47Why not take three months off and then go into that next one. So by planning this. But what if I'm not interested in switching companies right now? What if I'm perfectly happy at my company, but I still want to do all the things that you just said I should do? I think most people underestimate how possible it is to negotiate a month off from your current employer. I have a lot of people are like, well, my company doesn't have that policy. Nobody does it. People would think I'm crazy. But if you put a little bit of planning and preparation into that conversation, it usually goes better than people imagine.

7:20So what has to go into that conversation? I encourage people to find four elements of the story that they're going to pitch. So you need the story and then you need the solution. That story, it should be something positive. Don't be like, I'm just tired of y 'all's faces. I need to leave for a month. Ideally, you're doing something interesting, not just I'm going to go home and nap a lot. Something specific. It's much easier for us to connect with really specific things. So instead of I want more time with my kids, you know, I did a 10-week road trip to 10 national parks in a pop-up camper with my five kids.

7:54It's a very specific way we spent quality time together. And the last thing is make it a one-time event. Something that's not like he's going to ask for this every single year, but if you're going to hike the Camino, no, you're probably going to do that once in your lifetime. So you come up with a story, how are you going to frame this up? And then the second part is think through all of the objections, all of the concerns your employer would have, all of the logistical challenges, and come up with those solutions. Bring those to the table. And something that's a little bit counterintuitive, but articulate those challenges for your employer.

8:32Don't even put it on them to be like, well, what about A, B, and C? You kind of phrase it as, I know you might be concerned about this client. I know you might be concerned about this project. Here are some ideas I have for how we can handle that. What are you actually accomplishing through these four things that you identified? As you're talking, for example, I'm thinking that what you're really saying here with, you know, it shouldn't be some abstract thing. It should be really specific. It should feel like a one-time thing is that in some way you are trying to help your manager see you and your needs from a human lens.

9:09Is it because if it's, you know, hey, I just want some more time off. That is annoying and that's not something that as a manager I'm going to say yes to. But if you say, for example, and this is a real example from my own life as I'm now realizing it maps very well onto what you just described. If, for example, you say, hey, manager, hey, Rick, who was my manager at the time when I said this, my wife and I are a little TMI here, but are thinking about starting to have kids soon. And we want to do the kind of trip that we will not be able to do for the next 15 to 20 years of our lives. And the time to do that is right now.

9:56And what we really want to do is go to Asia and see all these places that we haven't seen. And I would like to do that for a month. So this is like the pre-baby moon or whatever. And I know that that is going to cause a hole, so I can work ahead of time and get a bunch of things done. And also just like set up who else will take care of tasks when I'm gone. But can I have this month off? Also, you don't have to pay me. That was more or less what I said a long time ago. And my boss said yes. And we did go to Asia. We went to Japan, Thailand, Cambodia, and Vietnam. And it was amazing. Yeah. When you frame it, it is the psychology of it to connect with those, create that vision.

10:41You're selling an idea. And in doing the problem solving, you know, you don't have to be heavy handed. But the reality is your job is just to make you taking a month off the easiest, quickest, simplest solution. Because replacing you might be a much more difficult and costly and time consuming proposition. And whenever I have people that I spoke in an event and a CFO was like, yeah, that's awesome. I desperately need a month off. Nobody does my job. Nobody can replace me. nobody does the things I do. I'm too important. And I'm like, awesome. Okay, cool, cool, cool. So if you left, how long would it take to replace this very important job?

11:25He's like, oh, yeah, it's a long process. It takes six months. And I'm like, uh-huh. And how long would it take that person to get up to speed to where maybe they're functioning at the level you function at now? That's a long process. It was probably another six months. And I'm like, uh-huh. So they could have an empty or underperforming role for 12 months. And if those are the two options and you give like, here's how we can navigate me being gone for a month, from an HR perspective, from a business perspective, it really is the cheapest, easiest solution. That's an interesting point. And you don't even have to verbally articulate it like that, which actually might get you shoved out the door because that's pretty obnoxious.

12:06But if people just recognize, you know, if this person is bringing me a very hyper-specific thing that they've always wanted to do, and it's like a once in a lifetime thing or whatever, and I say no to it, they're going to be bitter here. And it could change the nature of the relationship. And if they're bitter, then eventually I got to get rid of them. And if I got to get rid of them, then I got to go through the long process of replacing them. And what a pain. So the easier thing to do is actually to just let them go do this thing. Yeah. And you don't, like I said, companies know this. HR knows this.

12:39You don't have to be heavy handed with it. But if you use a little bit of the sandwich method, gosh, I've loved working here so much. I really have this cool adventure I'd like to do. I would hate to separate from the company because I'm really excited about these projects we have coming up. And it's just like you sprinkle in real light, but it changes the dynamic because they're not picking between you taking a month off and that being a hassle or just saying no and the hassle disappears, they're picking between two problems. Okay, now let's shift and you're the person running the business and you're going to say things very similar to what that executive told you, which is nobody knows how to do the thing that I'm doing.

13:21Everything rides on me. There is just literally no way that I can step away for a month. I can barely step away for an hour. What do you say? It's a lot more of a hassle when you're on the show, but there's a lot more benefit because the fact that nobody can, it's a company-wide issue because that's a really fragile system. If everything hangs on one person and a mini-retirement is the perfect motivation to do the stuff you know you should be doing, to do the cross-training, to do the mentoring, to share that institutional knowledge so that you have a more resilient system. Because the reality is, at some point you might want to sell the company and you're going to have to do all the same stuff to get it ready to extract yourself.

14:07Or at some point you might want to retire for realsies, in which case you have to do all the same stuff to be able to pass this on to someone else or you're building something knowing that it will implode as soon as you're not available. As soon as you need to step away, as soon as you want to retire, as soon as you get hit by a bus, the thing that you've given so much of your life to just won't, it won't exist anymore. You know, as you're saying that, I am flashing back to a conversation I might have even had on this show, I don't remember, but it was many years ago and it was a guy who was telling me about how he unexpectedly was in the hospital for a long time, some medical emergency that came out of nowhere, and how unprepared he and his company was for him to be absent, and how it forced them to very quickly create solutions in the form of systems and distribution of responsibilities and elevating people that ultimately made the business much stronger.

15:13So that by the time he was out of the hospital, this business actually knew how to run without him, which was a far better way of operating than what had happened before where everything was centralized with him. Now, the company was more resilient. He was able to step away for longer, and he had empowered other people around him. So those people felt more ownership over the state of the company and felt more engaged and so on. And his lesson, the reason we were talking was essentially because he wanted people to think, you don't wait for something like this to get your business in order. If you are involved at every single moment of every single day and you cannot step away from your business, then you don't actually have a business.

16:03You have a job. And to have a business is to have a thing that can scale beyond you. And so what it sounds like you're saying, Jillian, is that in a way, the idea of stepping away for a month is really, or at least could really be, just a really nice excuse to get your business structured the way that it should be anyway. A hundred percent. It is a deadline and it's a motivation because this is stuff we should be doing. But there's the urgent and then there's the important and there's always more urgent things. Yes, this is important, but it's never urgent. So a mini retirement makes it urgent.

16:39Hey, in six months, I'm going to be gone for a month. So let's figure out what we need to figure out between now and then. Because you're right, it gives when you come back, you have more creativity, you have more time bandwidth, you have more mental bandwidth, and you have the ability to scale and to take on bigger projects and to take on new things. You know, even for you, I said, if I could say, hey, Jason, what if I magically could give you an extra 20 hours a week? You'd be like, oh, there's some stuff I could do. There's some cool things. Like if there's space and if you have that time and that bandwidth, like you can grow your business in ways that you can't currently because your plate's full.

17:18Yeah. We have just originally introduced you as the author of this book, but this is a thing that you help people do. You are actively coaching them on how to do this, which means really getting into the systems of their lives. So could you give me a case study, somebody off the top of your head that was running a business, thought I cannot step away, and then what did they actually do in order to be able to step away? I work with a lot of clients who run businesses, who own businesses that I know nothing about. I am not an expert in that field. But the process is the same. It really isn't as hyper industry specific as we might think it is.

17:57So I had a client who ran a training program for avalanche safety professionals. How much do I know about avalanches? Nothing. Sounds very important. Yeah. Needed, but I don't know. and not only did they want to do a mini retirement but they were thinking about selling their company and so the process is really similar there's four steps four wide ranging steps that I have people consider the first one is to simplify there is complexities in our business sometimes that's just a complicated we do the way we do things because we can do it that way because we know because we have the time and the bandwidth to do it kind of the wrong way because to fix it would take more time.

18:37But sometimes it's low performing products. Sometimes it's difficult clients or just parts of our business that aren't working well. But we keep it anyways, because we can. So you have to start with simplifying. And then it's doing some of that automation. And that might even just be understanding the steps. And maybe it's technology, but maybe it's other people that step into that. But doing a little bit more automation and then kind of like you're saying the documentation. What's our SOP? How do I do what I do? What is this process? Because you have all of that institutional knowledge in you, but you need to put it down somewhere.

19:18I was talking to someone who worked at this company that all of their executives were going to be retiring in the next five years. And she was like, I think the company is going under. Because they know how to do all the things, and it's not written down anywhere, and no one else knows how to do it. And for whatever reason, they're super resistant to documenting this process and to sharing this information. So as soon as they retire, I think we're and it was like an 80 person company. Like it was really sad that they spent their whole lives building this. So doing that documentation, because then the fourth step is being able to delegate things.

19:54If anyone has ever had an assistant and it just bombed completely, it's usually because you think they magically can simplify and automate. and document things for you, but they can't. But if you do those steps, you can start to delegate out these tasks. And it might not be to like one magical clone replacement of you, but you can break out the 20 different tasks that you do and that you're responsible for and give them to the most qualified people. How long, on average, would you say it takes for someone to prepare to walk away for a month? For an employee, I say give it about four months. Anything shorter is a little rushed.

20:35Anything longer and the company will procrastinate. They'll be like, that's tomorrow's problem. I'm not dealing with it. For your own business, usually four to 12 months, but I've seen some of them take 24 months. Yeah, it must feel really good when these people finally do step away. Oh, man, not only is it magical for them, but they come back creative, fresh, energized. They come back to this high performance business and they come back with now the space to really grow and expand their business in a way that honestly they couldn't have even imagined. I have a friend who runs this big conference and he ended up unplanned stepping away from the business for like 18 months.

21:19you know and that's hard when you do it unplanned it's a rough transition yeah but did the thing simplified things automated things documented things was able to delegate that to other people to run and then he came back so excited and refreshed and with all this bandwidth and this business that was performing much better and he bought another conference and he bought another business and i was like it's so funny to me because if i would have talked to him a year before this and been like, hey, what do you think about just like tripling the size of your business? He would have been like, Jillian, no, that's insane.

21:52My plate is 100 % full. I can't take on any other projects. Jillian, finally, how on earth did this become your thing? This is a great thing, but it's also a pretty random thing. How did this become your thing? Yeah, I loved the idea of like sabbatical years. And I went into kind of me and my spouse at the time, like low earning profession. So I thought, well, I'm never gonna be able to retire early. but I had all these dreams and ambitions and goals and things I wanted to do so how could I sprinkle in these mini retirements and then 10 years ago I started writing online and other people were like how do we do this and it was through the one-on-one coaching and just hundreds and hundreds of conversations of working this out in real time for other people that I'm like there's a system here there's a process it seems super unbelievable and random But once you see it, you really can't unsee it.

22:47What was your best mini retirement? I did that 10-week trip with my kiddos to 10 national parks in a pop-up camper. And now they're all gigantic. My oldest is like almost 6 '4", and they're high schoolers and junior hires. But we did this when they were little, like 2, 6, 7, 9. And these places are so beautiful. and it's just like national parks and kids are just like it's adventure and fun and discovering and running amok and climbing and hiking and swimming and I just look back on that trip and it's so precious and so sweet and you know many retirements are a hassle there are a lot of work up front getting ready for that trip if you ever left on vacation with your family is a hassle Leaving for a 10-week vacation is not easier.

23:34Like, so stressful. But in the rearview mirror, the hassle gets a lot smaller, and the meaningfulness and the joy of those memories expands. They get more valuable over time. That is great inspiration to try something like this. Jillian, the book is called Retire Often. People can find it, I presume, wherever they find books. How can they get in touch with you? On my website, retireoften.com, I've got an unhinged newsletter, group coaching, consulting, my podcast, and then on social media, I'm at Jillian Johnsrud. Is the name of your newsletter unhinged or are you just describing it as unhinged?

24:14No, it's just unhinged. It's just unhinged. Yeah. It's like not nearly as good as yours. Yours is like so value added. Mine's like, here's what I've been thinking about lately. Yeah. That's great. You might find it useful. Amazing. Jillian, thank you so much. Thanks so much for having me. And that's our episode. Now let's keep the conversation going. I write a newsletter called One Thing Better, where each week I offer one new way to be successful and satisfied and build a career or company you love. You can find it at onethingbetter.email. That's a web address, just plug it into a browser, onethingbetter.email.

24:54And if you get one of those emails and reply, it goes straight to my inbox and I will get back to you. Problem Solvers comes out every Monday morning, so make sure you're subscribed so you don't miss an episode. The show is produced by Emily Holmes and Money News Network. My name is Jason Pfeiffer. See you next week.