[KATHRYN]: Imperfect Thriving is a part of the Practice of the Practice podcast network, a network of podcasts seeking to help you thrive imperfectly. To hear other podcasts like the Bomb Mom podcast, Beta Male Revolution, or Empowered and Unapologetic, go to practiceofthepractice.com/network.
Welcome to the Imperfect Thriving podcast for all of us women in midlife to discover yourself limiting beliefs, determine exactly what you want your life to look like and the imperfect actions to get you there.
Hi, this is the Imperfect Thriving podcast and I’m your host, Kathryn Ely. I am so glad you are here today because I am so excited about today’s podcast. Today we have Sherry Ott. Sherry is the host of the popular travel blog Ottsworld featuring travel guides, adventure travel, ideas, photography, and so much more. But this has not always been Sherry’s life. So, you are not going to want to miss this.
But before we jump into today’s episode, if you enjoy it, please rate, review and subscribe to the podcast on iTunes. This podcast is designed for you. Let me hear from you what’s working, what you want to hear more of. And if you haven’t already done so, head on over to imperfectthriving.com/course to get your very own Blueprint to Thrive. This is a free email course I designed to guide you step by step to assess the satisfaction in your current life, determine exactly what you want your life to look like and how to take daily imperfect action to get you there. So, go to imperfectthriving.com to get yours today. You have nothing to lose and everything to gain.
Now let me tell you a little bit more about Sherry Ott. Sherry is a self-prescribed corporate runaway who has undergone an incredible career journey that is taking her all around the world and into a career people only dream of as a professional travel blogger and photographer. She is a pioneer in the emerging world of new media, writing about her travel lifestyle and around the world adventures on ottsworld.com since 2006. In her 11 years of living nomadically, she’s circled the globe multiple times, visiting all seven continents. Recently named as an influencer to follow in oprahmagazine.com, she continues to seek out epic adventures to intriguing places, inspiring people to overcome their fears and reap the benefits of travel. I don’t know about y’all, but that sounds incredibly exciting to me. Welcome to the show, Sherry.
[SHERRY]: Thank you so much for having me.
[KATHRYN]: Oh, I’m so excited to have a conversation with you. I can’t even explain.
[SHERRY]: I’m excited too.
[KATHRYN]: So, I just want to jump right in and start with sort of your journey to where you are today. Just tell us a little bit about you and your life so far.
[SHERRY]: Sure. It’s been a long journey. So, let’s see. I started in Corporate. I was working in IT for about 14 years and when I was 36 years old, I ended up leaving that job. I actually quit. I’ve been through many jobs, but I quit my current job because I wanted to go travel around the world. The idea was that I didn’t really want to wait for retirement. So, I was going to go knock off a bunch of these things that I’d always wanted to do. I took off on that. I called it a career break. I took off on the career break, I sublet my apartment in New York City and ended up traveling for a year and a half because I stretched my budget. And in that, really about in the first three months, I knew I really didn’t ever want to go back to what I was doing or I wasn’t ready to go back to what I was doing.
I stayed in this kind of travel world. Now that whole time I was keeping a little website. We didn’t even call it a blog. I kept a little website to a journal, just to share my photos, to let my family know I was okay and that was the beginning of Ottsworld. And in 2006, 2007, that was just when we started calling things a blog, we started, you know, this new media stuff started coming out. And what I ended up doing is I went home after a year and a half, I sold everything I owned and put a few things in storage and then I went and I moved to Vietnam and I taught English because that was about the only way you could make money at that time. And I kept my blog and I kept on writing and doing photography and eventually the whole world kind of changed.
We, you know, have social media and smartphones and I was in the right place at the right time with a blog that people were following and were interested in what I was doing and it became a career at that point. It did take probably five years or so for me to actually really start making money from it, but I held on and I was nomadic for 11 years. So, I didn’t have a home. I just kept on moving around and writing and doing pictures and networking with travel companies and destinations. And, I really was kind of, I suppose a pioneer in this area and now I live in Denver and I’m a professional travel blogger.
[KATHRYN]: That is amazing. You were so nonchalant and you breezed right by this chart. “At 36 years old, I basically quit my corporate job, left a steady paycheck because I wanted to travel around the world.” I mean, you said that just like it was a walk in the park, but for a lot of us, that sounds a little crazy. Like honestly, how did you get to the point where that was okay for you? Like that it wasn’t a big deal?
[SHERRY]: It was a big deal. It was a huge deal and you’re right; I breeze over it now, but back then it was monumental in my life. Now, I had always been someone who, I like to move around. I moved around from my career, lived in San Francisco, Minnesota, Omaha, New York City, and I had a really good career, a career that people would’ve liked to have. But you know, one of the problems was, and I think this happens to a lot of people, we get, you know, somewhere in the middle of our career and we realize, “Oh, you know what, this career chose me. I didn’t choose it.” And that was a big realization for me. I didn’t choose this. I, in fact, I told you I was an IT executive, but, I mean, I studied accounting in college. So, I did, due to timing, I fell into this career and it was a really good career. But you just come to this point and you think, is this what I want to keep doing?
At the same time, my most recent move and change into a new position had me climbing the ladder. And so, I was headed in a director level and I was, you know, mid-thirties at a big company. And I think one of the things that I was realizing after I had spent about a year in this job is that “You know what? I don’t want to climb the ladder.” It wasn’t enjoyable for me anymore. And right there that was hard because you know, we’re taught to achieve and want to get better and want to get promotions and all that. But what I was finding was I didn’t really like it because I kept on moving higher and higher and up and I got to do less of the hands-on stuff and I was just managing budgets and hiring and firing and I was away from the stuff that I really liked. And there was no creativity in my job really. So, I was at this point where I’m like, “Is this really what I want to be doing for the rest of my life, and do I want to continue climbing this ladder?”
[KATHRYN]: So, it was really a huge moment? I love exactly how you put it, that you realized that your career chose you and you didn’t choose that career. So, it was at that moment that you really started to do some more in-depth searching about how you wanted to live your life and how you wanted to spend your time?
[SHERRY]: Yes, definitely, and you know, the concept of golden handcuffs, you know, feeling like you can’t leave because maybe you lived at a certain level of lifestyle or you know, you’re used to making X amount. That was real. That was absolutely real for me. And so, there was a stage where I knew that I was unhappy with what I was doing. I knew that I wanted to make a change, but I didn’t feel like I could partially because I didn’t know if I could do anything else than what I was doing because I felt like I’d been doing it so long. You know I felt like I didn’t even think about changing industries or anything, and then partially also because I had this lifestyle that was full of a lot of stuff and expensive rent in New York City. And I kept on thinking, “Well, I have to have a job like this because how am I going to afford my lifestyle?” So, I felt very handcuffed, not only just by the job itself, but just from my own decision that I had made earlier in my life.
[KATHRYN]: Yes. Well, let me ask you about this. You said you didn’t feel like you could do anything else and that is a limiting thought that I think so many of us have. “I haven’t done anything else. Therefore, I can’t do anything else or I don’t know how to do anything else.” How did you get past that and make the link to something else, something so completely different?
[SHERRY]: You know, actually I got past it by traveling, by actually, I shouldn’t say by traveling, but it was actually more of really stepping out of my routine, and my life really, because when I traveled, I took off and my first stop was Africa. You know, and throwing myself into such a different type of routine, so it was really stepping away and getting away from my routine. At that point, you know, I was writing in this little website, I was traveling around, I was meeting new people, I was getting eight hours of sleep a day, I, you know, there was just all this newness and everything and it was pushing me in all these different ways. And I started realizing after just journaling and kind of running this little website that, oh my goodness, I had skills that had been lying dormant that I just kind of forgot I had, like marketing.
Like I was good at business and I totally had forgotten about that. And you start to see as I traveled and more and more that confidence grew in these other skills I had because I was putting all kinds of different skills to use when you travel, especially when you travel on your own and in long periods of time. It’s not a vacation. This wasn’t a vacation. This wasn’t me sitting on a beach. This was travel, and that I was putting myself in different situations every day, learning new things, seeing new things every day and it just woke up my whole self, my whole body.
[KATHRYN]: I love what you’ve said there. I think there are two really important things that I really want to shine a light on right there is that, first of all, it’s by stepping away from the things that you could do and that you knew and slowing down that your brain really got those creative juices flowing. And that’s when you realized your other gifts, your other talents that you did have that were there all along.
[SHERRY]: Yes, definitely.
[KATHRYN]: I absolutely love that. And then the second thing about just basically throwing yourself into action, you proved that you could do it to yourself by actually jumping in and doing it. There’s only so much that we can fake about things. We learn from the imperfect actions of actually doing it.
[SHERRY]: Yeah, and if we think too much, we’ll never do it. That’s, you know, it’s kind of like jumping into a pool or a lake, that’s going to be cold. If we think about it too much, we might dip our toe in, and then it’s a little bit harder to get in, but sometimes you just have to jump.
[KATHRYN]: Exactly. So, as you were getting ready to, you know, you’ve quit your job and you’re ready to go on your first trip, did any of that negative self-limiting thoughts, did that try to get in your way at all from jumping in?
[SHERRY]: Often, every day that I got closer to it. So, I was planning this for about two years. I mean, I should say I knew that I was going to leave, I knew that I was going to do this trip around the world, but I waited for two years for the right time financially to go, and that gave me time to save. But every day is a get closer. That fear started just taking over. In fact, I still remember having the craziest dreams and it was all like, you know, total stress dreams about leaving and so on. And that just intensified as I got closer to the date that I knew I was going to go and quit my job. You know, I was scared of what I was going to encounter. I wasn’t really even a traveler. Like I had never done anything like this before, I didn’t know anyone that had done this before. I was 30 when I got my first passport, so I wasn’t even that much of an international traveler and here I was going to go off alone. So, it was very daunting. I also had that fear of like, “Oh my goodness, I’m going to, you know, this is the first time in my whole life that I’m not going to have money going in. It’s only going to be going one way. It’s going to be going out.” But I also knew at that time I thought my whole plan was I was going to travel for one year and then I was going to come back and I was going to hope that that gave me some clarity, that year.
And then I figured I would just kind of plug back into the work in society and all of that. And so always knowing that it was like this is just a year made it easier to continue to move forward. And I think, yeah, I don’t know. It was, I didn’t even think about the fact of like, what am I really going to do when I get back? But I think there’s another aspect here at play, not only your own fears, but it’s the fear of people around you or you know, the naysayers in a way. And I remember telling people, like in my family or friends that I was going to do this and everyone’s first question was always like, “Well, that’s exciting, but what are you going to do when you get back?” And I didn’t have an answer for that and what I found is that every time someone would ask me that, I would get more anxious and stressed out about it and so I decided that’s it. I’m just going to act like I know what I’m doing. So, I decided I would just have a standard answer for people. So, they’d ask me, what are you going to do back or what are you going to do when you get back and I would just make something up. I’m like, “Oh, I’m going to find a job and do this and this and this is what I want to do.” I didn’t really know, but I had an answer and that’s all they were looking for and they would be like, “Okay, and then leave me alone.” And that was fine. It just bought me time and it bought people, not questioning me any further.
[KATHRYN]: Yes. I, that was so smart. I interviewed Karen Brown not too long ago and she said that if your dream is not big enough to make other people laugh, you need to go back to the drawing board.
[SHERRY]: That’s good.
[KATHRYN]: So that is exactly what you were doing and it’s really easy to back down from our dreams when other people heap on and act like we’re crazy for having them. Were there any other kind of societal should or norms that you felt like you were fighting by jumping into this?
[SHERRY]: Well, back then in November 2006, 2005. I mean, the idea of having any kind of gap in your resume was not a good idea. You know, most people would have said, “Oh no, you shouldn’t do that.” I think that’s changed a lot now, which I love. That was one of my goals and you know, let’s get people to think differently about career breaks. But so, there was that, a lot of it was, I was scared about what society, what the business world would say about my gap that I was going to have for a year and how was I going to explain that? And so, and I didn’t really know. As I said, I kind of threw caution to the wind and just said whatever, and at some point, you know, you have to tell yourself, “I’m a smart person. I got this far. There’s no reason why when I get back that I won’t find something and it’ll be okay.”
[KATHRYN]: That’s amazing. That is absolutely amazing. Now I know how you put together some pretty incredible tours where other people can go travel with you, right?
[SHERRY]: Yeah, I just started doing that.
[KATHRYN]: Tell us about Ottsworld Tours because that sounds so amazing.
[SHERRY]: Yeah, I’ve just started doing it. I’ve had people tell me for years like, “Oh, I wish I could travel with you.” And I thought, “Oh, I don’t know that I want to take that on.” But I’ve just started, a couple of years ago, I ran a hiking tour because I do a lot of hiking and I write a lot about long-distance hiking. So, I did a hiking tour to Ireland and had, it was actually all women that signed up and we did a week in Ireland on the West coast hiking and doing some really cultural things. We went to a part of Ireland that most people haven’t even heard of, which I love. I love to introduce people to new things and kind of those underdog areas where people you know, don’t know about because I like to get people to understand the enjoyment of being an explorer of like really exploring and feeling like you’re the first.
So, I started doing that. I did another tour to Ireland last year and this year, I’m not sure exactly what I’m going to do. Actually, just next week I’m going to be though doing a tour with women to a surf and yoga camp in El Salvador. And that’s really about, you know, really challenging ourselves through trying something new, as we get older, I’m actually celebrating my 50th birthday and as we get older, I think it’s so easy to be scared of anything new. And one of the things that I think is important is to keep challenging yourself, keep trying new things, even if you’re not good at them because that’s what keeps you young. It’s a muscle that needs to be exercised.
[KATHRYN]: Yeah. I have so many women come into my counseling and coaching practice who used to love to travel and as they get into our age, I turned 50 this year, they’re scared of getting on airplanes, they’re scared of going anywhere. And I want to do more research into that because I think it’s a very interesting phenomenon. But are you seeing that in your business?
[SHERRY]: Oh yeah. I just think that’s, you know, most of the people that I talk to or that even read my blog are people that are, you know, scared of one thing or another. And I do absolutely believe that as we get older, that gets worse. And to me, the only way to combat that is to continue to push yourself, to continue to accept change and try new things. And like I said, I’m not any good at surfing, but I’m going to go down there and try it. And my little goal is to be able to paddle out there myself, turn the board around and pick a wave to catch on my own. I might not ever stand up and that’s fine, but the fact that I just get out there and try it is the important thing.
[KATHRYN]: Oh, that sounds so much fun. I want to go.
[SHERRY]: It is fun.
[KATHRYN]: That sounds awesome. So, what is the most exciting adventure you’ve been on so far? I would love to hear about that. Because you’ve been everywhere.
[SHERRY]: Well, the most exciting adventure I’ve been on. Wow. I’m going to say, I’ve done a few of these kinds of adventure races and one of them was, well, I drove with three other people, a small car from London to Mongolia over the course of five weeks in a race.
[KATHRYN]: What?
[SHERRY]: Yeah. So, talk about things you’d never thought that you’d do. And one of my reasons for doing that, it was a charity event, but one of my reasons for even doing it was, one, it seemed really like crazy and I had never heard of anything like this before, but I was always someone who was scared to drive in other countries. It just intimidated me and so I thought, what better way to get over that fear than drive for five weeks across two continents, like 9,000 miles, and sure enough, I have no more fear.
[KATHRYN]: Oh, what are some of the amazing places you saw along the way on that drive?
[SHERRY]: Romania was really interesting through Ukraine, which is, you know, a hard place to get to now, probably. But it was gorgeous. The city of Kiev is lovely, and one of my favorites, like of course, you know, driving on the Autobahn in Germany is really fun, but one of my favorite things and the reason why I did this is I love Mongolia. It’s one of my favorite countries I’ve ever traveled to and I had been there before and then I decided to do this race. But it’s so beautiful. It is so incredible. There are no fences, there are no limits, there’s no, I mean it’s just open space, and that made me really happy because it’s, it really is like taking a step back in time there. And the culture is so interesting. So, the idea of driving across it sounded really exciting to me.
I tend to, and I started doing this. I wasn’t always like this at all, but once I started traveling and really getting into that whole thing, I tended to take all kinds of, like the thing that scared me the most, I would then find some way to do it so that I could get over that fear. I lived in Vietnam for a year and I was terrified of the traffic there and I ended up, one of the reasons why I moved there is I wanted to learn how to ride a motorbike there because I thought if I could do that, I could do that anywhere, you know, I can do anything.
[KATHRYN]: I’m going to go in on one of these adventures. That sounds like so much.
[SHERRY]: Well, in most of my, like Ottsworld Tours are going to be more, a little tamer, but you know, I do like to push people, whether that’s through hiking or maybe like a surfing thing like this, it’s important, I think. It makes us all grow and you know, these are the stories we remember the most. And when you get out the other side, there’s nothing that makes you feel more confident.
[KATHRYN]: Oh, I bet. Do you have any hiking trips coming up?
[SHERRY]: This year? Let me think about that. Oh yeah, I’m going to be doing some hiking probably in Switzerland and France, and then also I’ll be in Australia in October. So, I’m definitely doing some hiking there.
[KATHRYN]: Okay. When is Switzerland and France so it’s on my radar?
[SHERRY]: These are actually, these are more press trips than they are my Ottsworld Tours. But, I know, I know I’m thinking my next Ottsworld tour will likely be in Spain and potentially also Alaska next winter.
[KATHRYN]: Oh, Alaska in winter?
[SHERRY]: I know.
[KATHRYN]: Yeah, I’m a girl from Alabama. I get [inaudible 00:26:09] 30 degrees I can’t feel my fingers and [crosstalk. Yeah, maybe so. I’m going to keep my eye out for that. Tell me about your blog. You still chronicle your journeys to share with others and how do you do this?
[SHERRY]: Yes, it’s my full-time job. I run my blog; it’s still called Ottsworld. That’s what it started as back in 2006. You know, how I write is very different than how I started, but all of that is still the same. The one thing people want to know is, well, how do you make money? But you know, that’s done through advertising, it’s done through affiliate revenue, I do speaking engagements, I run tours, there’s sell photography, all kinds of things. You become a hustler when you run your own business, and that’s what I also love about running a blog; is that it keeps me in this world of like technology and new things that, if I had not taken, if I had not gone on and done this, I would have never been this comfortable with technology.
I just know me. Like, I wouldn’t even be this comfortable with like a smartphone or, you know, internet and all that kind of junk. But being in this field really keeps me up to date and I like that. It takes a lot of work because it’s not just, I mean, the writing part is such a small part of it. So much of it is just about how to run a blog, how to run a website, understanding how the internet works, marketing, and pitching yourself constantly. You know, it really keeps all those skills active.
[KATHRYN]: Yes, absolutely. Well, I’ll tell you what, Sherry, I love me some Sherry Ott and I can talk to you all day long, but I know that you are about to pack up and hit the road again. So, I think I’ve learned so much from you today, but one big thing and, I tried to do this on my own, it’s not to the scale that you’re doing it is the more we stretch outside of our comfort zone, the more things we become comfortable with.
[SHERRY]: Yes.
[KATHRYN]: And if you stay comfortable all of the time, there’s no growth in that, right?
[SHERRY]: I can’t agree more.
[KATHRYN]: So, Sherry, obviously you step out of your comfort zone and into your fears often. What piece of advice can you give our listeners about that?
[SHERRY]: Yeah, I think fear is completely normal. It happens to everyone; it doesn’t matter who you are. And I’m not going to tell you not to worry or not to have fear because it’s just a human trait that we all have. So, my advice though is to counteract that fear by, you know, give an equal amount of time in thinking about what could go right. We spend so much time thinking about all the scenarios of what could go wrong. And I did that a lot when I was, you know, leading up to leaving, but I think we owe it to ourselves to spend that equal amount of time about what could go right. What, you know, just let yourself dream, be crazy about it and think about the scenarios that could go right.
[KATHRYN]: Okay, that is absolute gold. So instead of spending all of our time on the what-ifs, what can go wrong, spend more time on the positive what ifs, what could go right and what do I, what would be the greatest thing in the world?
[SHERRY]: Yeah.
[KATHRYN]: Dreaming big. I love that. So, Sherry, where can people go to find out more about you?
[SHERRY]: They can find me in a few different places. They can find me ottsworld.com, which is my blog and I do updates on there about every week or so. Also, if they want to kind of like follow my live travels, you can follow me on social media. I do a lot on Instagram with Instagram Stories, I am at Ottsworld on Instagram and then I do quite a bit also on Facebook and I do updates all the time from there. And I am at Ottsworld travel on Facebook. And then I would say if you’re interested in learning more about the Ottsworld Tours, just head to my website, you’ll see some information about it. There’s a place where you can sign up for a newsletter to learn more about it, so you’ll be the first to know when I announced new tours. And I think, you said Kathryn, that you would go ahead and put that in the show notes too?
[KATHRYN]: Yes, I will. Absolutely, I’ll put a link to your newsletter in the show notes for sure.
[SHERRY]: Thank you.
[KATHRYN]: So, knowing that, what is the one imperfect action you would suggest our listeners take today that will bring them closer to their best lives, the lives that they really want?
[SHERRY]: I have had a couple, but the first thing that comes to mind is, I have magnets on my refrigerator, even though it says this, you know, do one thing that scares you every day. And that does not have to be driving a car across two continents. It can be very, I mean, like every day you should do something. That might be trying different food, it might be walking to the store instead of driving, it might be signing yourself up for a new hobby. I mean, it can be anything and it can be small and that’s how you start building upon that.
[KATHRYN]: Absolutely. I could not agree more. That’s awesome. Sherry I’ve had so much fun with you today. I can’t even tell you.
[SHERRY]: Thank you. I’ve had a good time too.
[KATHRYN]: It’s been awesome. So y’all listen. The one imperfect action I encourage you to do today is to go figure out one thing that you can do that scares you. And I don’t mean something scary like jumping off of a building. I mean one thing that you can do to stretch yourself outside of that comfort zone because the more you stretch out of that comfort zone, the more comfortable you’re going to be with doing more and more things. And don’t think about it for too long. Just go do it because your brain will try to talk you out of it. And when you do that, pat yourself on the back, hear the trumpets, save the confetti, and celebrate the fact that you took action toward the life that you want.
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