Take Back Retirement
She Did It! Real Retirement Stories with Lori Osterberg
Today’s guest is Lori Osterberg. She is an author, content creator, educator, and, in her own words, a “Gen-Xer who has been setting the online world on fire for the past 20 years.”
Currently in a little town outside Portland, OR, Lori is living what she recently realized to be her dream life. She writes up to three books a year and just recently published her ninth novel.
Lori recalls how at the start of their careers she and her husband lived through several rounds of corporate downsizing. They got to a point where they decided enough was enough—it was time to take control.
Since then, Lori and her husband have been in business for themselves, bringing together their interest in computers with their artistic skills in photography. Then when their daughter was looking at colleges she first heard of the “gap year” concept. Inspired, they decided to truly maximize their freedom and explore new possibilities. As it turns out, their gap year turned into a gap rest-of-their-lives!
Listen in and learn how Lori achieved the freedom to do what she loves, and how she helps other women over 40 do the same.
How Lori’s doing right now (2:06)
Lori’s journey from corporate to business owner to globe-trotting romance novelist (4:05)
Navigating big challenges in 2020 and those lingering in 2021 (9:25)
How Lori got to the point where she could semi-retire (11:16)
What Lori knows now that she wishes she knew then (15:33)
Meeting fellow “gap year lifestyle” folks (17:15)
“There’s something freeing in letting stuff go.” (18:54)
Keeping in touch with friends and family while living a mobile life (21:14)
Has this lifestyle impacted Lori’s writing? (22:11)
Lori’s tips for people who want to have a lifestyle like hers (24:00)
How Lori got her husband, family, and friends onboard with her gap life plan (26:36)
The pros and cons of moving to or retiring in Mexico (29:42)
“It’s never been about retirement. It’s about freedom.” (33:35)
How to get in touch with Lori (36:02)
“Don’t think about your current situation. Think about where you want to go.” (36:32)
Stephanie McCul…: 00:06 Welcome to Take Back Retirement, the show for women 50 and better facing a financial future on their own. I’m Stephanie McCullough. And along with my fellow financial planner, Kevin Gaines, we’re going to tackle the myths and mysteries of quote unquote retirement, so you can make wise decisions toward a sustainable financial future. Through conversations and interviews. You’ll get the information and motivation you need to move forward with confidence, and we’ll be sure to have some fun along the way. We’re so glad you’re here. Let’s dive in.
Stephanie McCul…: 00:40 Coming to you semi live from the beautiful Westlakes Office Park in suburban Philadelphia, this is Stephanie McCullough and Kevin Gaines of Sofia Financial and American Financial Management Group. Say, ‘hello,’ Kevin.
Kevin Gaines: 00:51 Hello, Kevin.
Stephanie McCul…: 00:52 Today we have the second in our series of real retirement stories where we are asking women who have been through the quote unquote retirement door. We’ll talk about what that actually means. But, we’re inviting them to share their stories with you so that you can get some ideas, learn some lessons, get some inspiration.
Kevin Gaines: 01:14 Yeah. There’s a lot of possibilities. The world is changing. Everybody has different thoughts on what they want and don’t want to do. So, we want to bring this opportunity to hear different things that might be outside of your perception.
Stephanie McCul…: 01:30 Yeah, exactly. Open up the range of possibilities. So, today we’re excited to welcome Lori Osterberg. She is an author, content creator, educator, and as she says, ‘Gen X-er, who’s been setting the online world on fire for the past 20 years.’ We’ll hear more about her story and her history in the interview. So, let’s get to it.
Stephanie McCul…: 01:58 Lori Osterberg, welcome to Take Back Retirement. We’re thrilled to have you here. Why don’t we start out by telling us where you are today and what you’re doing.
Lori Osterberg: 02:06 Sounds good. Thank you so much for having me here. I’m excited to share my story with you. Where I’m at today. Currently we are sitting in the Pacific Northwest. I’m located in a little town outside of Portland, Oregon, and kind of living what, at least as of a few years ago, what I consider to be my dream life. I didn’t know it when I graduated college and all those other things, but it turned out that I fell in love with writing along the way. And so what I really wanted to do for a number of years was actually to write books. I wanted to create novels and even some nonfiction books. I wanted to blog.
Lori Osterberg: 02:39 I wanted just to kind of connect with the world in some different ways. But especially writing novels and getting into that. And so, that’s kind of where I’m at today. I just published last week as a matter of fact, my ninth novel. So, I’m very excited about that and pushing forward with all of that.
Stephanie McCul…: 02:54 That’s amazing. Congratulations.
Lori Osterberg: 02:56 Thank you.
Kevin Gaines: 02:57 What kind of novels are you writing?
Lori Osterberg: 02:59 Kind of across the over. When I first started, when we kind of first moved into this position, I started out more with a memoir-type thing and being a business owner, I’ve owned businesses in the past. The first thing that I did is I started doing research and started figuring out where the money was and you don’t make a lot of money in memoirs. [laughter]
Kevin Gaines: 03:18 [laughter]
Lori Osterberg: 03:18 So, I literally ripped my book apart and I said, ‘what’s the most popular category out there?’ And of course, it’s romance. Romance novels are 70% of the market. So, of course that’s where I wanted to go into. I wanted to dive into that and kind of catapult myself in there. So, it took me several years to write that first book. Like I said, I kind of transferred it in from a memoir into a romance, which is very interesting in itself. [laughter]
Stephanie McCul…: 03:41 [laughter]
Lori Osterberg: 03:41 But, I did that and now I’m up to where I can write about three books a year. So again, I just published my ninth. I’ve been doing this for coming up to a little over four years now to get all these out.
Stephanie McCul…: 03:52 That’s great. I love that story. Tell us about this big change. A few years ago, you were not living this dream life. You were living a very different life and then what drove you to kind of uproot everything? Take us through that story.
Lori Osterberg: 04:05 Okay. I was born and raised in Denver, Colorado. Never left. We did a lot of traveling and everything, but that was my home and thought it would be my forever home. But at the same time, my husband and myself when we first got married in our twenties, we kind of went through the whole thing. We’re of the generation where we were corporate downsized several times over several years. And when that happens again, and again, you tend to start looking at your life and going, ‘okay, what do I want to do different?’ So, we kind of jumped at the opportunity of starting our own business. And my husband was very good at photography, started kind of moving into that arena. And we were also kind of computer nerds at heart. So, we jumped into that arena, started up a website in the mid to late nineties and the dot-commers found us and started flying us everywhere.
Lori Osterberg: 04:54 So, we built this wedding photography business and it was a wonderful life. Absolutely loved it. But then when we started settling down and having a kid, and when she moved into elementary, middle school, she didn’t like flying around. Because we literally, we had that lifestyle. We would do about 30 weddings a year, but she wanted to be at home. She wanted to play with her friends. She wanted soccer games. So, we kind of pulled back and I started building online businesses with that, gearing myself towards helping photographers develop the same type of a business. But that, again, it just kind of morphed and changed over the years. And when my daughter started taking a look at college and she was looking, going to career fairs and the college fairs, things like that, I remember we were kind of scanning, stuffing all the envelopes into a bag and way back in the corner was this thing called gap year.
Lori Osterberg: 05:41 And of course, my daughter just kept on going, but I was fascinated with the concept of gap year. And you could just take a year out of your life, move on and try something new. And that really appealed to me. So, even though she moved on, she went to college and did all her things, I really talked my husband into a gap year. So, we sold our house, got rid of everything. And again, I’m telling it obviously very quickly. It was a process. But, we got rid of everything, sold our house. We decided we wanted to do what we call slow travel the rest of our life. So by that, what we wanted to do is we wanted to pick out a location and then go and choose to live there for a year, two years, three years, however long we felt comfortable there to really get to know the area.
Lori Osterberg: 06:21 Because, I think if you go someplace for a couple of weeks, you tend not to see the seasons or get to know the people or everything that happens within there. And we’d never been up here to the Pacific Northwest. So, it really intrigued us. We wanted to come up here and explore, go into Canada, just kind of do this whole region. So, this was our first shot at it. We moved up here. Well, we sold our forever home, got rid of a lot of our stuff, most of our stuff. And then just moved up here and we’ve been exploring ever since and just kind of having a lot of fun with it.
Stephanie McCul…: 06:51 That’s really amazing. Somehow the gap year turned into the gap rest of your life.
Lori Osterberg: 06:56 [laughter] Exactly. That’s exactly what happened. Because once you start planning for all this, once you kind of see it all taking action, you’re like, ‘well, why do I have to go back to my old life?’ So, that really kind of became key of the whole thing. We started seeing that even before we moved, because we were like, ‘well, if we move and do this, why can’t we move to the next location and do that, too? When, not necessarily we’re sick of it or tired of it, but when we’re ready to explore a new area and we want to kind of move on.’
Stephanie McCul…: 07:25 Moving is such a hassle for a lot of people. They kind of dread it and here you are looking forward to several moves. But like you said, you downsized your stuff.
Lori Osterberg: 07:33 And I think that was key to everything. Right now we’re probably one of the few people. When last summer we had the big wildfires come through here. And we were actually in kind of the area that we could evacuate very quickly. And a lot of people around us were like panicking. ‘What do you put in your car? What do we take with us?’ And for us, it was like, literally I could leave with the clothes on my back because I digitized everything. Everything of importance is on my computer, in the cloud, obviously one of those. Yeah, I have certain things in the closet that I would miss. We all have certain things that are irreplaceable, but literally with a box I could technically leave and just walk away and that’s kind of refreshing in itself. I can replace the TV. I can replace the couch. The memories, like I said, everything’s been stored video wise, picture wise up in the cloud. So, that in itself is quite freeing.
Kevin Gaines: 08:24 So, how many times have you moved in this gap lifestyle?
Lori Osterberg: 08:28 Actually, we are currently here. We’ve had a few hiccups along the way. We got here with the intention of being here maybe two to three years. And then for various reasons, we kind of were looking at moving last year and then enter COVID. So, we kind of got stuck when we didn’t anticipate it. So, we are now, again, contemplating now that things are opening up, what we want to do. One of our goals has been even to try and live outside of the country. We’ve looked at Europe, we’ve looked at Mexico. I have a number of friends that are living down in Mexico. So, we’d love to try that at some point. Maybe within the next year or so. We’re kind of keeping an eye on that, as well. So, we’ll see.
Kevin Gaines: 09:08 Wow.
Stephanie McCul…: 09:10 I love this. It sounds so appealing. And yet it sounds like a big process to go from, like you said, the forever home and the stuff to the more agile lifestyle. You mentioned hiccups. What kind of got in the way of that?
Lori Osterberg: 09:20 Well, probably one of the hiccups was that our daughter’s off doing her thing. And then she decided to quit school for a year. So, of course she came back here, which kids do. So, brought her back, did all those kinds of things. And then right before COVID into that I’ve had a lot of caregiving issues with my mom back in Colorado. So, it’s been a process of going back and forth and handling all those kinds of things as well. Which, that in itself is something I’m still kind of processing, too, of how you handle that, especially if you don’t live [nearby]. It’s one thing to be able to hop on a plane two hours away and fly back or something, but what about if you’re in Europe or Mexico or someplace like that and you need it? So, that’s been also something I’ve been doing a lot of research on is how you handle not only caregiving from a far, but from a different country when you might be stuck in a whole different way. So, it’s been interesting.
Stephanie McCul…: 10:17 Hmm. Yeah. I think a lot of us are in that kind of sandwich generation. We’ve got the youngers and the olders who might need us at any moment.
Lori Osterberg: 10:23 Exactly, exactly.
Kevin Gaines: 10:26 Yeah, and you don’t want to be inhibited from having to cross borders.
Lori Osterberg: 10:29 Exactly. Yeah. And I watched that, like I said, I have quite a few friends down in Mexico that I’ve been touching base with and that is a big process, at least at first with COVID. A lot of them could get back in, but then how do you get back out? And if you do, what’s the process of crossing back in and out? And obviously in Mexico, there are a lot more lenient than they are here. Just the nature of the beast. But, it’s still very interesting. And where do you want to get caught with certain things? And there’s a lot to consider. A lot of it is just obviously trust, too. You just make a jump at it and see what happens.
Kevin Gaines: 11:02 So, How long did it take you from deciding you wanted to do this to actually executing? Did you already have a big enough nest egg in savings to be able to finance these moves?
Lori Osterberg: 11:16 We did have quite a bit in savings. We’re not at the point that we want to permanently retire. We see ourselves going a long ways just because of where we are and what we want to do. But it caused us to look at our business in entirely different way. And so, we started putting some tweaks on it to the point where we could sell it. So, really it was like a two-year process. Again, my daughter was, I think she was actually a sophomore when we started doing those career fairs when I found this gap idea. And then it was a matter of starting to clear out everything in the house, finding the resources, doing things like that. And then we, like I said, actually cleaned up the business enough that we put it for sale, as well. So, that helped finance part of our move, as well. And then when she graduated we got her into college, moved her and then we started on our life. So about two and a half years, I would say is what it took.
Stephanie McCul…: 12:11 Did you have some anxieties along the way? You were jumping into a new career. Or had you already started the writing before you sold the business? Did you have some kind of proof that you could make a little bit of money in the writing before you jumped?
Lori Osterberg: 12:23 Actually, yeah, I did. So, as a photographer, again, we were very high up in wedding photography, but we got to the point where people wanted us to come in and speak to them because not a whole lot of people were doing what we were doing, especially in the nineties like that. And we were finding all our clients online, which again, in the nineties, nobody had websites at that point. So, again, we started kind of touring and speaking about this whole concept. And at one of the locations, I had a publisher come up to me and say, ‘I love your story. I want to put it in a book.’ And again, I’d never thought about a book before, but I signed on with him and created my first book called Studio Without Walls. And so from there, it just kind of morphed.
Lori Osterberg: 13:05 And we were doing about 30 weddings a year, which left a lot of opportunity, a lot of open time for me. And that’s when online sites were really starting to grow more the portal where you could do like online coaching, membership sites. So, I developed the Studio Without Walls concepts into a blog and membership sites. And I did like a coaching program and everything through there. So, that was also the time when Kindle started coming around. Amazon developed its Kindle platform. And so again, I kind of jumped in with Kindle. I had over a dozen books that sold with that particular business and they were all on producing a photography business, marketing a photography business, more of that arena. So, it sold with that business, but it gave me all the understanding of even traditional publishers working with that. Because I had done that in that beginning, as well as figuring out the Kindle platform when, trust me, it was not very user-friendly. [laughter] It’s much more user-friendly today.
Stephanie McCul…: 14:03 That’s great. And then what is your husband doing? You say you’re both not retired.
Lori Osterberg: 14:07 Well, when we first started, again, he was kind of the nerd from the beginning. He loved to design websites way back when, loved computers and everything like that. So, when I kind of did this, he jumped in and he’s actually working kind of with a startup now and we’re helping them do different things like understanding SEO. He does a lot of SEO work. Just all that kind of stuff. Because he loves being online, too. So, I’m lucky enough that he understands all this. He does all my web design work for me.
Kevin Gaines: 14:32 [laughter]
Lori Osterberg: 14:32 He handles all that. So, I keep it in-house [laughter]
Stephanie McCul…: 14:39 Yeah, handy. [laughter]
Kevin Gaines: 14:39 Makes it easy.
Stephanie McCul…: 14:39 But they’re both very mobile careers. You could kind of work from anywhere.
Lori Osterberg: 14:42 Exactly. Yeah. And we’ve tested that. We went to Europe, tested that for a while. My daughter actually did, after she graduated and stuff, went down to New Zealand. They have a one-year work visa program where kids 20 to 30, I think it is, can go down there and work in like the tourist industry. So, she did that, again, right before COVID. So, I went down there and spent a month with her and it’s just so wonderful to have that flexibility and freedom to be able to go down and, as long as there’s an internet access, I can work from anywhere.
Stephanie McCul…: 15:11 Right. I think some people call it location-independent lifestyle.
Lori Osterberg: 15:15 Exactly.
Kevin Gaines: 15:17 So, now that you’ve done this for a couple of years, what has been the biggest shock of switching to the gap lifestyle? I don’t know if that’s the term we want to use for it. But, what do you know now that you wish you knew then, so to speak?
Lori Osterberg: 15:34 Let’s see. I think a lot of what has honestly not allowed me to be as flexible is I think we tend to fall back into some of the same old patterns. So, even though we settled in a location, just a very small apartment and stuff. You tend to get comfy and that’s actually been probably one of the things. We haven’t jumped as quickly in some cases as I would’ve liked to because it’s easy just to fall back in those patterns. So, I try and keep myself out there, joining different organizations, doing different things that force me to leave my comfort zone. Even though we did tend to work from having a laptop and stuff, before I was a lot more involved with people and writing in this capacity anyway, is definitely me and my table.
Lori Osterberg: 16:23 And obviously that’s exacerbated here during COVID because you can’t get out anywhere. But, I think that networking, that getting out, that connecting with people and not even just local, because if you have hopes to move, you don’t want to get too comfortable in that local arena. So, I have tried to find like-minded people outside of this. I had prior to this and stuff, I would fly down to Austin, meet with a group down there. And so, just keeping yourself out there and if this is the life you want, you kind of have to live the life that you want. And it’s not that you can’t get close, because I’ve got a lot of great friends here, but you do have to also think a little more globally.
Kevin Gaines: 17:01 You may have referenced that you talk to other people in this lifestyle. I’m assuming there’s plenty of groups, whether it’s Facebook or whatever, networks out there of people doing what you’re doing. Do you find these groups particularly robust and helpful?
Lori Osterberg: 17:15 Oh yes, definitely. Yeah. Actually this is when I first came up with this concept, a gap year, I typed it in obviously to Google, did a bunch of research and there are so many sites. Gap year at 60, gap year…You can find this all over the place. But yeah, there’s one gentleman that, I was hoping to maybe get down there here soon. But he actually runs something down in the Baja area called the Elder Academy and stuff where 50-year-olds go and they learn how to just be flexible and to kind of switch paths.
Lori Osterberg: 17:48 So, even places like that, that they have picked up and moved from one location, say San Francisco and moved to Mexico or something, it’s just opened up their world to a whole new idea. And yeah, I have a number of friends that have created a lifestyle like this that have been out on the road for five, six, seven years or more. And literally moving every couple of months to, even sooner, every couple of weeks, even, in some cases. So, having them as kind of reference tools and following them and stuff that helps give you your motivation to keep this going.
Kevin Gaines: 18:19 Well, I know a few families that have taken advantage of COVID, so to speak, and especially with the remote learning for kids and they’re touring the country. They rent an RV, driving around since the kids aren’t in a physical school. So, I’m curious to find out 10, 15 years down the road, everybody who’s done this, if once they are ready for the second or third part of their life, if they’re going to embrace something along the lines of what you’re doing. It’ll be curious to watch.
Lori Osterberg: 18:54 Yeah. So, when you have the great big house with all the stuff in it, that very first thing that you send out the door that you put on Craigslist and that leaves, you see the memories behind and you’re like, ‘oh, did I really do the right thing?’ And, you have that. But by the time you get to the 10th or the 15th thing, you can’t get it out the door fast enough because there’s something freeing in letting stuff go. When we got down to even what we have now. Well, like I said, I could leave it without a problem. But even the stuff that we do have, I really like the stuff I have. So, I invest in high quality. If I want a blender or whatever, I have the very high quality that does what I want it to do. So, you just tend to think about stuff in a different way. And for me, right now, it’s all about experiences, where I can go and how I can grow from that experience as opposed to the stuff behind it.
Stephanie McCul…: 19:45 I think so many of us in this culture we live in, get stuck with this stuff, right? Look at all the proliferation of professional organizers, just because we have so much stuff to deal with. And I’ve gotten many friends who’ve been having to deal with parents, either passing away or falling ill and needing to relocate. And there’s just a lifetime worth of stuff in that house that someone’s going to have to deal with.
Lori Osterberg: 20:07 Exactly. And that’s exactly where I am now with my mom, too, having to go back there. She fell in the middle of COVID. We had put her in assisted living, do all those kinds of things. But now it’s a matter of going back there to help clean out that house and to get rid of all the stuff that, and she had lived there for 40 years or something. So again, just boxes upon boxes and just having to go through all that is just, yeah, truly, it’s not something… And I’ve been hearing more about that too, that the millennial kids, they don’t want what their parents had. So it’s, if you can get rid of it on your own, and I definitely know that’s in my case, it’s just, I want to get rid of that for my daughter, so she doesn’t have to do it, knowing what I’m going through with my own mother and stuff too.
Stephanie McCul…: 20:52 Yup. Yup. The other thing that I imagine when I think about taking off on this lifestyle, and of course it’s different in COVID, because I haven’t actually seen many of my friends, but kind of leaving behind, like you said, you get comfortable, right? The networks, the neighbors and the stuff you know. Obviously that wasn’t enough to keep you rooted.
Lori Osterberg: 21:12 Right. You keep the friends that are closest to you or at least we have found that. And I can’t imagine doing it in this world without Zoom and stuff like that. Because we have Zoom calls all the time even as couples and things like that, we’ll pull out a wine bottle and have a zoom call. So, that has been just a lifesaver in so many ways to have something like that. And I think now more than ever, even my mom is open to using that, which before she didn’t even have a cell phone. So, I think it’s something that we’re now more open than ever around the world to accepting this as the way it is. And is it perfect? Of course not. But at the same time it does allow you to keep those connections. And so, I really haven’t found that I’ve missed because I’ve held onto those closest to me and we still connect in a lot of ways.
Stephanie McCul…: 22:03 That’s great.
Kevin Gaines: 22:05 Has this lifestyle impacted your writing? Has it given you a different perspective on your books?
Lori Osterberg: 22:11 Definitely. Again, like I said, I kind of started my first book as a memoir and we were actually spending the summer in Europe when I finally transferred it all in and kind of made my first book. But the concept hit me when I was over there of turning all this into, again, all my books are geared towards women over 40. I just wanted that life change. I didn’t want out of college ‘finding the perfect one’ type of a situation I wanted 40-year-olds going through death and divorce of spouses and caregiving situations, things like that. But my very first book, I came up with the concept of ‘what if you were in the airport and there was a game right there that you spun the wheel and it landed on an exotic location and wherever you went, you had to leave within an hour.
Lori Osterberg: 22:54 They were going to put you on a plane and would you be willing to do that for a week? You got a free trip if you were willing to play the game.’ And so, I have a whole series called Destination. It’s based on a destination roulette. So, there’s destination Barcelona, destination Mexico City. The whole concept was driven from the whole idea of travel. And I’ve worked with an editor throughout all of my books. She’s remained the same. And every time she gets a new one, even if I’m writing on a totally different subject, actually, I just released a Christmas one last year. And when she was editing it the first time she just laughed, she goes, ‘you cannot get away from travel’ because she traveled away for Christmas. It’s just something that’s a part of me. So, I would say that’s a huge part of what I do. [laughter]
Kevin Gaines: 23:40 [laughter]
Stephanie McCul…: 23:43 What advice would you have for say, someone of our listeners who finds this lifestyle very appealing? If they’re starting to think, ‘oh gosh, I would like to get to that point where Lori is now,’ what tips would you give them to start with?
Lori Osterberg: 24:00 From even a financial standpoint, I think a lot of people say ‘I’ll do that in retirement’ without truly defining it. Or they say, ‘when I have a million dollars, I’ll do that.’ And the thing is, once you start looking at all this, you start realizing that cashflow is everything and that freedom is everything. And a lot of what holds you down is that standard stuff. So, what comes along with owning a house with having to repair the roof and putting in a new water heater and all of those kinds of things. And when you open yourself up and you move, you can shrink your cashflow, your flow going, out very quickly. And especially even if you move to places like Mexico or anywhere in the world, really, you can reduce that so much. So, sometimes it’s, instead of just saying, ‘when I get the million dollars, when I retire,’ putting that thing that you can never grasp your head around.
Lori Osterberg: 24:54 If you actually start taking a look at the costs behind it, sometimes it’s very shocking. And I know we’ve done that numerous times. You look at what it would cost to live down in Mexico, and it almost blows your mind in some cases. But, just even moving from owning to renting was a huge eye-opening experience for us. Because, like I said, if the water heater breaks, that’s your responsibility or the furnace goes out and there goes thousands of dollars. So, sometimes just with that tweak, now when you rent, it’s on them, not on you. So, it can really open up your cashflow and make things a lot more realistic.
Stephanie McCul…: 25:29 Yeah. Or the municipality hikes your taxes for the fourth time in a decade, it happens and it not only changes your cashflow, but presumably you’re freeing up some money from the equity in your home to do something with.
Lori Osterberg: 25:42 Right. Exactly.
Stephanie McCul…: 25:42 So, it’s kind of that double benefit. And yet, I think it’s so ingrained in us as Americans, that if you don’t own a home, there’s something wrong. The American dream, I have to buy a house, I have to buy a house. And I’m often trying to have that conversation with people. ‘Do you really? Where did that message come from? That you’ve absorbed.’
Lori Osterberg: 26:02 Exactly. And to me it’s all about freedom. Right now I can pick up and I can leave whenever I choose to leave. And there’s nothing holding me here. So, it’s my choice. Not based on, ‘can I sell my house or what’s going to happen from that? Can I make enough money from the sale of my house?’ I don’t worry about any of that right now.
Kevin Gaines: 26:20 So, when you first stumbled across this idea, how did the conversation go with your husband?
Lori Osterberg: 26:26 [laughter]
Kevin Gaines: 26:26 It sounds like this was your idea, so.
Lori Osterberg: 26:29 Correct.
Kevin Gaines: 26:29 Was it hard to get him to come along or did he say ‘that’s a brilliant idea’ and the conversation was done in five minutes?
Lori Osterberg: 26:36 Actually. Yeah, the latter. He was all on board with it. And partially because again, through our photography business, we had kind of created that virtual business anyway, and that our clients were not local. Some were, but not all of them.
Lori Osterberg: 26:51 So, we would pick up every weekend and fly to Atlanta or fly down to Florida or fly up to San Francisco. So, we were always on the go anyway. That was just a part of who we were and what we liked to do. We like to travel. So yeah, when I came home to him with this idea, of course, ‘how are we going to put this into action?’ But we did definitely work on it together and call each other crazy. And numerous times throughout that going…
All speakers: 27:15 [laughter]
Lori Osterberg: 27:15 ‘…is this really worth it?’ type of thing, but yeah. Just taking the leap. That worked every time.
Stephanie McCul…: 27:20 Did you have odd reactions from family or friends? Curious?
Lori Osterberg: 27:26 Very, very much so. Yeah.
Stephanie McCul…: 27:28 [laughter]
Lori Osterberg: 27:28 And that’s probably the other thing that I’ll say is you learn who your friends and your family are because some of them literally say, ‘don’t do this or else.’ And then that’s hard. That’s a hard thing, but you have to be true to yourself, too, and do what you need to do. Yeah, it definitely separates. And you learn who your true friends are and stuff like that through a process like this.
Stephanie McCul…: 27:50 Well, I think some people stay put, even when the kids go off to college because they feel like the kids are going to want to come home and see their friends. And that keeps them rooted.
Lori Osterberg: 27:59 Exactly.
Stephanie McCul…: 27:59 Did you have that feeling with your daughter?
Lori Osterberg: 28:02 Somewhat, but I would say all of her friends’ families are still in their original home, what they kind of grew up in, but her friends as a whole, for whatever reason, her friends are all over the world. They’re going to school over in Italy. There’s one who studied abroad and now got married and lives in the UK.
Lori Osterberg: 28:21 So again, they’re all over. A couple of them have gone down to New Zealand in same program she has and lived and worked for a year. So, I think that whole generation, they’re so much more open to the concept. And we’ve definitely, at least in my friend base, they were all more the professional types, the lawyers, the doctors, the accountants, things like that. And then there’s us who were starting businesses and flying over. So, I think they kind of learned to be shocked about our lifestyle a way long time ago.
All speakers: 28:53 [laughter]
Stephanie McCul…: 28:53 You were both creatives from the start, right, if you’re a photographer?
Lori Osterberg: 28:56 Exactly. Right.
Stephanie McCul…: 28:58 That’s great.
Kevin Gaines: 28:59 So, going back to the thought of you moving to Mexico, what are the pros and cons that you’ve come across on that one so far? And the reason I ask is because the whole concept of retiring into the ex-pat lifestyle is growing. I think the last number I saw is like five, 6% of retirees go ex-pat, which doesn’t sound like a big number. But, when you look at the number of people retiring, there’s a lot of people moving to Mexico, Costa Rica, wherever. So, what are the conversations or what are the thoughts that you’re having on that particular idea?
Lori Osterberg: 29:42 Well, and I think once that idea hits you, then you start finding people that are doing it and they’re everywhere. You literally find so many stories. I have so many books and things from people that have written that have done this lifestyle. So, one of the writing clubs that I belong to down in Austin, that’s been several years now, since I joined that one, there was a gentleman there from San Miguel in Mexico. And he had worked and lived in San Francisco his whole life. And he knew that there was no way he could retire and sustain his lifestyle. So they picked up and they moved to San Miguel. And he’s been there now, geez, at this point probably 10 years. But then he picked up his writing business and wanted to write novels as well and that’s how I met him, was at this novel-writing convention and absolutely loved it.
Lori Osterberg: 30:27 So, I’ve kind of stayed in touch with him a little bit. And obviously a place like San Miguel, that’s a big artist community down there. There’s a ton of ex-pats. That’s probably one of the most popular towns down in Mexico for ex-pats and just the lifestyle. When he comes back up for things like that, he can’t wait to go home because it’s slower, it’s slower paced. As far as the home that he has, he couldn’t even touch something like that in San Francisco. And that comes with maid service. And just the number of amenities that you can get on a salary based from here down there is incredible. Plus, the other thing that we’ve looked at is even medical. For him medical insurance down there is virtually nothing when you compare it to places like this.
Lori Osterberg: 31:09 And I have done research on that even, and you can get policies as an American for outside of America that are so far beyond what you can get here in America. It’s unbelievable. It’s like, you can get a whole year’s policy for like a one month payment here in some cases. It’s just phenomenal, the difference. Plus then you pick up things. If you live there, you can pick up things there, too. But even a lot of their hospitals and stuff, they train here in the States. So, if you watch where you’re going, you’re comfortable with it and you really do your research, you can find great lifestyles. You just have to kind of be aware and go out there and find it.
Kevin Gaines: 31:44 And not be trapped by the stereotypes or preconceptions of what this stuff is like. Only from what I’ve read, Belize or Costa Rica, Mexico, there are communities of American ex-pats, so it’s not even necessarily a language issue that you’re the only one who’s going to be speaking English and you’ve got to take a crash course in Spanish to figure out what’s going on. You may actually be able to live in existence and not really pick up much of the language.
Lori Osterberg: 32:16 Exactly. You find that all the time. And it was like that again with the friend that I have down in San Miguel. It’s not just Americans, it’s UK. There’s a lot of Brits that go there and from different places and stuff, but you pick up enough of the Spanish to communicate and to do what you need to do, which even coming from Colorado and now on the West coast, I have enough Spanish that I can communicate very mildly, but I can pick up some words and stuff. So, it is something that I want, which sounds kind of weird, but I do want some people that I can communicate with regularly and then obviously living somewhat of the culture too. I want both. I want to immerse in the culture because I think that’s fun, too, just seeing how other people live.
Stephanie McCul…: 33:03 Yeah, we have clients who visited Panama and Costa Rica when they were thinking about a retirement destination. And I think they’re still pondering which one they want to go to, but they met all kinds of great people in both locations.
Lori Osterberg: 33:15 Exactly, exactly. Yeah. Once you open yourself up, it’s amazing the number of people that are doing this.
Kevin Gaines: 33:21 So, here’s a question for you. Are you ever going to be retired, given your lifestyle and what you’re doing?
Stephanie McCul…: 33:28 The stereotypical retire.
Kevin Gaines: 33:30 Yeah. There is no retirement, as in sitting in the rocking chair. Right?
Lori Osterberg: 33:35 Correct. Yeah. I think that’s something that, being a Gen X, again, I’m kind of at the upper end. I’m in my fifties already. But, that was something that throughout my life, everyone always said, ‘social security is never going to be there for you. You’re not going to have it. You better do it on your own or else.’ That was kind of always in the back of my mind. So, I’ve always kind of worked for that and planned for that and programs for that. So for me, it’s never been really about retirement. It’s been more about freedom. So, what can I do to enjoy my life today? I love writing. I would never give up writing. And with the tools that are in place today to share my writing, I can blog, which I do every week. In some cases I love to write novels. I love to teach. I love to do things like this. So, I don’t see myself giving most of this up for a very long time because I just enjoy it. I have so much fun with it.
Stephanie McCul…: 34:26 I think that’s the key we’d all like to get to, somewhere where we’re doing things that we enjoy that bring us fulfillment. And if they bring us some dollars too, that’s great.
Lori Osterberg: 34:36 Exactly. Exactly. Yeah.
Stephanie McCul…: 34:38 That’s kind of my definition of retirement.
Lori Osterberg: 34:40 I agree.
Kevin Gaines: 34:41 I was going to say, that’s one of the cliches that we use or that we created ourselves is retirement being not so much stopping working, but it’s the thing of doing what you want to do instead of what you have to do. It definitely sounds like you’ve reached that point.
Lori Osterberg: 34:55 Exactly, exactly. And it’s just, it’s nice. When I get up in the morning, I don’t have an alarm clock. I still get up at five o’clock, but that’s because I choose to.
All speakers: 35:03 [laughter]
Lori Osterberg: 35:03 I just love that time in the morning. It’s still dark. Nobody else is up. It’s really quiet. And that’s when I can get my best writing in. So, I can sit down for three hours and pound out several thousand words very quickly. So, that’s something I choose to do. And then I’m very conscious of where I live. Even during COVID here and stuff, I live right by the river. So, I have a river walk. I can go out and walk for a couple of miles, which I do every day, but it brings me energy. So, after three hours of writing, when I go out there, I get my mindset back and I can come back in and write for a couple hours more.
Lori Osterberg: 35:33 So, every day, every part of day is planned. Obviously I’m not tied down or anything like that, but I enjoy what I do. And so, every piece of it has been planned over the course of the last, however long, 30 years or whatever, to get me to where I’m at today. And I love it. I love every moment of it.
Stephanie McCul…: 35:53 That’s wonderful. You’re definitely a role model on that score.
Lori Osterberg: 35:57 [laughter] Thank you.
Stephanie McCul…: 35:58 Lori, thanks so much for being with us. How can people find you and find your work?
Lori Osterberg: 36:02 I actually have two websites. I kind of write on reinvention itself. Which is that visionofsuccess.com. And then all my novels are listed on my website, which is Loriosterberg.com.
Stephanie McCul…: 36:15 Awesome. I want to check out the Destination series.
All speakers: 36:19 [laughter]
Stephanie McCul…: 36:19 Travel, at least in my mind.
Lori Osterberg: 36:22 Exactly. Especially right now, right?
Stephanie McCul…: 36:24 Exactly. Polishing up my passport.
Lori Osterberg: 36:29 Exactly.
Stephanie McCul…: 36:29 Awesome. Any last words of wisdom?
Lori Osterberg: 36:32 I think, again, just don’t think about your current situation. Think about where you want to go and kind of work towards that freedom. What’s it going to take to get you there? And don’t keep something so generalized. It’s not just about hitting retirement age or a certain cashflow. ‘I need a million dollars.’ Actually take a look at it. And there are so many resources online. Whatever you can think of Google, because you’re going to find someone doing the lifestyle you’re dreaming about. And once you do, you kind of have a role model that you can follow.
Stephanie McCul…: 37:01 Yeah, exactly. And even if you don’t go precisely and follow what they’re doing, it gives you more ideas. Like you said, opening up your mind to what you might be able to build.
Lori Osterberg: 37:10 Exactly.
Kevin Gaines: 37:11 Great. Well, I’ve got to say it’s exciting that you embraced what you wanted to do, not what you felt you had to do. So, not only that has got to be freeing.
Lori Osterberg: 37:20 Thank you. Exactly. Yup, yup. I, for the most part, have fun every day.
Stephanie McCul…: 37:23 Can’t ask for more than that.
Lori Osterberg: 37:26 Exactly.
Stephanie McCul…: 37:27 All right. Thanks so much, Lori.
Lori Osterberg: 37:29 Yeah. Thank you for having me on.
Kevin Gaines: 37:32 We appreciate you joining us.
Stephanie McCul…: 37:37 I really enjoyed hearing Lori’s story and having her be so open with us about the journey of creating this very intentional life they’re living.
Kevin Gaines: 37:47 It was interesting to hear somebody, again, living the retirement defined as doing what they want to do, not what they have to do. But their version of that doesn’t mean that they’re stuck in one place just doing the same thing day after day, sitting in the rocking chair or whatever. Now again, that’s what they want to do. There’s plenty of people, plenty of us would be happy to sit around, play golf every day and hang out with the grandkids or whatever.
Stephanie McCul…: 38:16 Yes.
Kevin Gaines: 38:16 The point is. It’s what you want to do. Not what you have to do.
Stephanie McCul…: 38:20 Exactly. Not what society tells you. Not what the conventional vision of retirement is. Give yourself permission to question those things. She was inspired by hearing this idea of a gap year and thought, ‘oh my gosh, that sounds like a lot of fun. How can we create that?’ And then they went and did it and it took a few years to create it, but they did.
Kevin Gaines: 38:40 And it turned out she was not the first person on this planet to think of it. There is a community. And that’s one of the big things that she said was go out onto the internet, Google or the social media, whatever. Chances are there’s other people that are at least having the same ideas that you’re having.
Stephanie McCul…: 38:56 Yeah. We’ll link to some of the things that she mentioned in the show notes. I loved her concept of it’s about more than quote unquote retirement. It’s about freedom for her. She said, freedom is everything. And from the financial standpoint, in this phase of life, cash flow is everything, not assets, cash flow. So, having money to pay the bills and understanding your costs of living. Can you reduce them in some way to give you more freedom?
Kevin Gaines: 39:23 It’s an equation. It’s what you do with the assets you have and how you control the liabilities and expenses that you have. You can play with both sides to get to the point you want to be.
Stephanie McCul…: 39:37 I’m just really inspired by it, personally. I love the idea of checking out a new place for more than a week or two weeks at a time, and really living it, absorbing it, understanding it. And then, we’re not stuck here forever. We can move on.
Kevin Gaines: 39:52 No. And with technology, it’s easier to stay in contact with people. Silver lining of the last year has introduced people more to ways to use technology or other methods to stay in contact with friends and family and such. And maybe it doesn’t work for everybody, but I suspect that more than a few people have had their eyes opened to the possibilities.
Stephanie McCul…: 40:17 Yep. Yep. More things are possible than maybe we’ve been led to believe. So I enjoyed it. We’re definitely going to be working to bring you more real retirement stories. If you or someone you know, a woman has gone through some big, I always say, quote, unquote, retirement. I’m going to have to find a better phrase than that and is willing to share their story with us, we would love to hear from them.
Kevin Gaines: 40:39 It’s always exciting to hear new ideas and the process behind those ideas. It’s not just doing it, but what was involved because that’s the hurdle most of us have to deal with is ‘how do I get started?’
Stephanie McCul…: 40:51 Yes. It might feel impossible. ‘How the heck could I transform the life I’m living right now into that?’ But it’s doable. Thanks for being with us. Talk to you next time. It’s goodbye from me.
Kevin Gaines: 41:02 And it’s goodbye from her.
Stephanie McCul…: 41:07 Be sure to subscribe to the show and please share it with your friends. Show notes and more information available at TakeBackRetirement.com. Huge thanks for the original music by the one and only Raymond Loewy through New Math in New York. See you next time.
Disclaimer: 41:21 Investment advice offered through Private Advisor Group, LLC, a registered investment advisor. Private Advisor Group, American Financial Management Group, and Sofia Financial are separate entities. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual security. To determine which investments may be appropriate for you consult your financial advisor prior to investing. This information is not intended to be substitute for individualized tax advice. Please consult your tax advisor regarding your specific situation.